JP7420633B2 - fragrance composition - Google Patents
fragrance composition Download PDFInfo
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- JP7420633B2 JP7420633B2 JP2020073320A JP2020073320A JP7420633B2 JP 7420633 B2 JP7420633 B2 JP 7420633B2 JP 2020073320 A JP2020073320 A JP 2020073320A JP 2020073320 A JP2020073320 A JP 2020073320A JP 7420633 B2 JP7420633 B2 JP 7420633B2
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- fragrance
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- 239000000203 mixture Substances 0.000 title claims description 396
- 239000003205 fragrance Substances 0.000 title claims description 75
- 239000000796 flavoring agent Substances 0.000 claims description 81
- 235000019634 flavors Nutrition 0.000 claims description 81
- 150000001875 compounds Chemical class 0.000 claims description 52
- 238000004519 manufacturing process Methods 0.000 claims description 29
- 235000013305 food Nutrition 0.000 claims description 16
- 235000019505 tobacco product Nutrition 0.000 claims description 9
- 238000009472 formulation Methods 0.000 description 58
- 238000011156 evaluation Methods 0.000 description 45
- 230000001953 sensory effect Effects 0.000 description 44
- -1 1a Chemical compound 0.000 description 43
- 239000002304 perfume Substances 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 235000015203 fruit juice Nutrition 0.000 description 22
- 239000000047 product Substances 0.000 description 21
- 235000013361 beverage Nutrition 0.000 description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 15
- 239000007968 orange flavor Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- 244000269722 Thea sinensis Species 0.000 description 13
- 239000000344 soap Substances 0.000 description 13
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- 235000009508 confectionery Nutrition 0.000 description 12
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 11
- 241000951471 Citrus junos Species 0.000 description 11
- 235000005979 Citrus limon Nutrition 0.000 description 11
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- 240000006909 Tilia x europaea Species 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
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- 238000003786 synthesis reaction Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
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- XMGQYMWWDOXHJM-SNVBAGLBSA-N (-)-α-limonene Chemical compound CC(=C)[C@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-SNVBAGLBSA-N 0.000 description 4
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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- 235000013615 non-nutritive sweetener Nutrition 0.000 description 4
- 125000001131 obtusiloyl group Chemical group O=C([*])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 235000015040 sparkling wine Nutrition 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 240000007651 Rubus glaucus Species 0.000 description 3
- 240000000851 Vaccinium corymbosum Species 0.000 description 3
- 235000019568 aromas Nutrition 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
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- 239000003921 oil Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
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- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- WBZFUFAFFUEMEI-UHFFFAOYSA-M Acesulfame k Chemical compound [K+].CC1=CC(=O)[N-]S(=O)(=O)O1 WBZFUFAFFUEMEI-UHFFFAOYSA-M 0.000 description 2
- 108010011485 Aspartame Proteins 0.000 description 2
- 239000001512 FEMA 4601 Substances 0.000 description 2
- 244000307700 Fragaria vesca Species 0.000 description 2
- 240000009088 Fragaria x ananassa Species 0.000 description 2
- 241000234295 Musa Species 0.000 description 2
- 240000008790 Musa x paradisiaca Species 0.000 description 2
- HELXLJCILKEWJH-SEAGSNCFSA-N Rebaudioside A Natural products O=C(O[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1)[C@@]1(C)[C@@H]2[C@](C)([C@H]3[C@@]4(CC(=C)[C@@](O[C@H]5[C@H](O[C@H]6[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O6)[C@@H](O[C@H]6[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O6)[C@H](O)[C@@H](CO)O5)(C4)CC3)CC2)CCC1 HELXLJCILKEWJH-SEAGSNCFSA-N 0.000 description 2
- 239000004376 Sucralose Substances 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000000619 acesulfame-K Substances 0.000 description 2
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 2
- 235000013334 alcoholic beverage Nutrition 0.000 description 2
- 235000015197 apple juice Nutrition 0.000 description 2
- 239000000605 aspartame Substances 0.000 description 2
- 235000010357 aspartame Nutrition 0.000 description 2
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 2
- 229960003438 aspartame Drugs 0.000 description 2
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- 235000015218 chewing gum Nutrition 0.000 description 2
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- 210000003298 dental enamel Anatomy 0.000 description 2
- 235000011850 desserts Nutrition 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- HELXLJCILKEWJH-UHFFFAOYSA-N entered according to Sigma 01432 Natural products C1CC2C3(C)CCCC(C)(C(=O)OC4C(C(O)C(O)C(CO)O4)O)C3CCC2(C2)CC(=C)C21OC(C1OC2C(C(O)C(O)C(CO)O2)O)OC(CO)C(O)C1OC1OC(CO)C(O)C(O)C1O HELXLJCILKEWJH-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
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- 235000019674 grape juice Nutrition 0.000 description 2
- 235000015201 grapefruit juice Nutrition 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 235000015110 jellies Nutrition 0.000 description 2
- 239000008274 jelly Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 235000013336 milk Nutrition 0.000 description 2
- 239000008267 milk Substances 0.000 description 2
- 210000004080 milk Anatomy 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- PAXWQLGKYISPNH-UHFFFAOYSA-N octane-2,7-diol Chemical compound CC(O)CCCCC(C)O PAXWQLGKYISPNH-UHFFFAOYSA-N 0.000 description 2
- 235000015205 orange juice Nutrition 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- HELXLJCILKEWJH-NCGAPWICSA-N rebaudioside A Chemical compound O([C@H]1[C@H](O)[C@@H](CO)O[C@H]([C@@H]1O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HELXLJCILKEWJH-NCGAPWICSA-N 0.000 description 2
- 235000019203 rebaudioside A Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 235000019408 sucralose Nutrition 0.000 description 2
- BAQAVOSOZGMPRM-QBMZZYIRSA-N sucralose Chemical compound O[C@@H]1[C@@H](O)[C@@H](Cl)[C@@H](CO)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 BAQAVOSOZGMPRM-QBMZZYIRSA-N 0.000 description 2
- 230000001256 tonic effect Effects 0.000 description 2
- 239000000341 volatile oil Substances 0.000 description 2
- UFDULEKOJAEIRI-UHFFFAOYSA-N (2-acetyloxy-3-iodophenyl) acetate Chemical compound CC(=O)OC1=CC=CC(I)=C1OC(C)=O UFDULEKOJAEIRI-UHFFFAOYSA-N 0.000 description 1
- AMKGKYQBASDDJB-UHFFFAOYSA-N 9$l^{2}-borabicyclo[3.3.1]nonane Chemical compound C1CCC2CCCC1[B]2 AMKGKYQBASDDJB-UHFFFAOYSA-N 0.000 description 1
- FEJUGLKDZJDVFY-UHFFFAOYSA-N 9-borabicyclo[3.3.1]nonane Substances C1CCC2CCCC1B2 FEJUGLKDZJDVFY-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- ZBNWEDACYZPATD-UHFFFAOYSA-N C12OC3CCC(CC31)C2 Chemical compound C12OC3CCC(CC31)C2 ZBNWEDACYZPATD-UHFFFAOYSA-N 0.000 description 1
- VHXVIBGILAKCSU-UHFFFAOYSA-N CC1C2CCC3(C)OC1C3C2 Chemical compound CC1C2CCC3(C)OC1C3C2 VHXVIBGILAKCSU-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 244000183685 Citrus aurantium Species 0.000 description 1
- 235000007716 Citrus aurantium Nutrition 0.000 description 1
- 244000276331 Citrus maxima Species 0.000 description 1
- 235000001759 Citrus maxima Nutrition 0.000 description 1
- 240000002319 Citrus sinensis Species 0.000 description 1
- 235000005976 Citrus sinensis Nutrition 0.000 description 1
- 241001137251 Corvidae Species 0.000 description 1
- 239000004278 EU approved seasoning Substances 0.000 description 1
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 1
- 241001236294 Hebe Species 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 244000179970 Monarda didyma Species 0.000 description 1
- 235000010672 Monarda didyma Nutrition 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
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- 244000235659 Rubus idaeus Species 0.000 description 1
- FWXMGTAGQIUBJN-UHFFFAOYSA-J S(=O)([O-])[O-].[Th+4].S(=O)([O-])[O-] Chemical compound S(=O)([O-])[O-].[Th+4].S(=O)([O-])[O-] FWXMGTAGQIUBJN-UHFFFAOYSA-J 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 244000077233 Vaccinium uliginosum Species 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 230000001166 anti-perspirative effect Effects 0.000 description 1
- 239000003213 antiperspirant Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000013040 bath agent Substances 0.000 description 1
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- 239000007844 bleaching agent Substances 0.000 description 1
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- 235000013736 caramel Nutrition 0.000 description 1
- 235000014171 carbonated beverage Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229940112822 chewing gum Drugs 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 235000019504 cigarettes Nutrition 0.000 description 1
- 235000013409 condiments Nutrition 0.000 description 1
- 235000014510 cooky Nutrition 0.000 description 1
- 235000012495 crackers Nutrition 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
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- 239000000839 emulsion Substances 0.000 description 1
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- 239000002979 fabric softener Substances 0.000 description 1
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- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000006197 hydroboration reaction Methods 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 239000007934 lip balm Substances 0.000 description 1
- 229940039092 medicated shampoos Drugs 0.000 description 1
- 235000020124 milk-based beverage Nutrition 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
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- 238000000746 purification Methods 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
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- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Cosmetics (AREA)
- Detergent Compositions (AREA)
- Fats And Perfumes (AREA)
- Tea And Coffee (AREA)
- Cigarettes, Filters, And Manufacturing Of Filters (AREA)
- Seasonings (AREA)
- Non-Alcoholic Beverages (AREA)
- Epoxy Compounds (AREA)
Description
本発明は、調合香料原料などとして有用な化合物および香料組成物に関する。 TECHNICAL FIELD The present invention relates to compounds and perfume compositions useful as raw materials for prepared perfumes and the like.
近年、消費者の嗜好性が多様化したことにより、飲食品等に使用される香料においては、果実感、天然感の高い香味や、他と差別化された香味を強く求められている。しかしながら、従来の香料原料の組み合わせではこうした要求に対応が難しい場合もあり、新たな香料素材が強く求められている。 In recent years, as consumer tastes have diversified, there has been a strong demand for flavorings used in foods and beverages to have fruity, natural flavors, and flavors that are differentiated from others. However, it is sometimes difficult to meet these demands with conventional combinations of fragrance materials, and new fragrance materials are strongly sought after.
本発明は、調合香料原料などとして有用な香気を持つ新規な化合物および該化合物を含有する香料組成物、飲食品等を提供することにある。 An object of the present invention is to provide a novel compound having an aroma useful as a raw material for a mixed flavor, and a flavor composition, food/beverage, etc. containing the compound.
本発明者らは、種々の化合物を合成し、その香気について検討したところ、オキサトリシクロ構造を有する化合物が、優れた香気を有することを見出した。 The present inventors synthesized various compounds and studied their aromas, and found that compounds having an oxatricyclo structure have excellent aromas.
すなわち本発明は以下の［１］～［５］に関する。
［１］ 下記式（１）で表される化合物。
That is, the present invention relates to the following [1] to [5].
[1] A compound represented by the following formula (1).
［２］ ［１］に記載の化合物を含有する香料組成物。
［３］ 飲食品用である［２］に記載の香料組成物。
［４］ ［１］に記載の化合物または［２］もしくは［３］に記載の香料組成物を含有する飲食品、口腔用組成物、たばこ製品、または消費者製品。
［５］ ［１］に記載の化合物または［２］もしくは［３］に記載の香料組成物を添加することを特徴とする飲食品、口腔用組成物、たばこ製品、または消費者製品の製造方法。
[2] A fragrance composition containing the compound according to [1].
[3] The fragrance composition according to [2], which is used for food and drink products.
[4] A food or drink, an oral composition, a tobacco product, or a consumer product containing the compound according to [1] or the flavor composition according to [2] or [3].
[5] A method for producing a food or drink, an oral composition, a tobacco product, or a consumer product, which comprises adding the compound described in [1] or the flavor composition described in [2] or [3]. .
本発明によれば、調合香料原料などとして有用な香気を持つ新規な化合物および該化合物を含有する香料組成物が提供できる。 According to the present invention, it is possible to provide a novel compound having an aroma that is useful as a raw material for a prepared perfume, and a perfume composition containing the compound.
以下、本発明について詳細に説明する。
本発明における３，９－ジメチル－２－オキサトリシクロ［４．２．１．０３，８］ノナン（以下、本発明化合物とも記載する）は、下記式（１ａ）、（１ｂ）、（１ｃ）、（１ｄ）で表される４つの異性体が存在する。
The present invention will be explained in detail below.
The 3,9-dimethyl-2-oxatricyclo[4.2.1.0 3,8 ]nonane (hereinafter also referred to as the compound of the present invention) in the present invention has the following formulas (1a), (1b), ( There are four isomers represented by 1c) and (1d).
化合物（１ａ）：（１Ｓ，３Ｒ，６Ｓ，８Ｒ，９Ｒ）体
化合物（１ｂ）：（１Ｒ，３Ｓ，６Ｒ，８Ｓ，９Ｓ）体
化合物（１ｃ）：（１Ｓ，３Ｒ，６Ｓ，８Ｒ，９Ｓ）体
化合物（１ｄ）：（１Ｒ，３Ｓ，６Ｒ，８Ｓ，９Ｒ）体
本発明の化合物の製造方法について、化合物（１ａ）及び化合物（１ｃ）を例に説明する。
ｌ－リモネンをハイドロボレーションによりヒドロキシ化した後に酸化反応を行いカルボン酸とする。続いて、無水トリフルオロ酢酸を反応させて二環性化合物を合成し、ＮａＢＨ４を作用させ閉環反応を行うことで、化合物（１ａ）及び化合物（１ｂ）の混合物が得られる。
Compound (1a): (1S,3R,6S,8R,9R) Compound (1b): (1R,3S,6R,8S,9S) Compound (1c): (1S,3R,6S,8R,9S) Compound (1d): (1R,3S,6R,8S,9R) The method for producing the compound of the present invention will be explained using Compound (1a) and Compound (1c) as examples.
After l-limonene is hydroxylated by hydroboration, an oxidation reaction is performed to form a carboxylic acid. Subsequently, a bicyclic compound is synthesized by reacting with trifluoroacetic anhydride, and a ring-closing reaction is performed by reacting with NaBH 4 to obtain a mixture of compound (1a) and compound (1b).
化合物（１ｂ）及び化合物（１ｄ）は、化合物（１ａ）及び化合物（１ｃ）を合成する際の出発原料であるｌ－リモネンを、ｄ－リモネンに替えることによって同様に合成することができる。 Compound (1b) and compound (1d) can be synthesized in the same manner by replacing l-limonene, which is the starting material for synthesizing compound (1a) and compound (1c), with d-limonene.
本発明の香料組成物における本発明化合物の含有量は、香料組成物の重量を基準として好ましくは０．００００１～１００００ｐｐｍ、より好ましくは０．０００１～１０００ｐｐｍ、さらに好ましくは０．００１～１００ｐｐｍである。
また、本発明化合物の４種の異性体は、いずれも香気成分として有用であり、任意の異性体及び異性体混合物を本発明の香料組成物に用いることができる。
The content of the compound of the present invention in the perfume composition of the present invention is preferably 0.00001 to 10000 ppm, more preferably 0.0001 to 1000 ppm, even more preferably 0.001 to 100 ppm, based on the weight of the perfume composition. .
All of the four isomers of the compound of the present invention are useful as aroma components, and any isomer or mixture of isomers can be used in the perfume composition of the present invention.
本発明化合物及び本発明の香料組成物は、そのまま、飲食品、口腔用組成物、たばこ製品、消費者製品に極微量配合して、柑橘様の香気・香味を付与又は増強することができる。
飲食品の具体例としては、例えば、炭酸飲料、清涼飲料、果汁飲料類、乳飲料類、乳酸菌飲料類、ドリンク剤類、豆乳、茶飲料などの飲料類；チューハイ、カクテルドリンク、発泡酒、果実酒、薬味酒などのアルコール飲料類；アイスクリーム、アイスミルク、ラクトアイス、氷菓、ヨーグルト、プリン、ゼリー、デイリーデザートなどのデザート類；キャラメル、キャンディー、錠菓、クラッカー、ビスケット、クッキー、パイ、チョコレート、スナック、チューインガムなどの菓子類；和風スープ、洋風スープなどのスープ類；ジャム類；風味調味料類；各種インスタント飲料類；各種インスタント食品類などを挙げることができる。この中でも、飲料類又はアルコール飲料類が好ましい。
The compound of the present invention and the flavor composition of the present invention can be added to foods and drinks, oral compositions, tobacco products, and consumer products in extremely small amounts to impart or enhance citrus-like aromas and flavors.
Specific examples of food and beverages include carbonated drinks, soft drinks, fruit juice drinks, milk drinks, lactic acid bacteria drinks, drink preparations, soy milk, tea drinks, and other drinks; chu-hi, cocktail drinks, low-malt beer, and fruits. Alcoholic beverages such as sake and condiments; Desserts such as ice cream, ice milk, lacto ice, frozen confectionery, yogurt, pudding, jelly, and daily desserts; Caramels, candies, candy tablets, crackers, biscuits, cookies, pies, chocolates, Examples include confectionery such as snacks and chewing gum; soups such as Japanese soup and Western soup; jams; flavor seasonings; various instant beverages; and various instant foods. Among these, beverages and alcoholic beverages are preferred.
本発明の化合物の飲食品への添加量は、飲食品の重量に対して各々０．００００１～１００００ｐｐｂ、好ましくは０．０００１～１０００ｐｐｂ、より好ましくは０．００１～１００ｐｐｂの濃度範囲とすることができる。
香料組成物の飲食品への添加量は、製品の種類や形態に応じて異なるが、通常、香料組成物を添加する前の飲食品の質量を基準として０．００１～１０質量％、好ましくは０．０１～５質量％の濃度範囲とすることができる。
口腔用組成物としては、例えば、歯磨き剤、口腔洗浄料、マウスウオッシュ、トローチ、チューインガム類などを挙げることができる。
The amount of the compound of the present invention added to the food or drink may be within a concentration range of 0.00001 to 10000 ppb, preferably 0.0001 to 1000 ppb, more preferably 0.001 to 100 ppb, based on the weight of the food or drink. can.
The amount of the flavoring composition added to the food/beverage product varies depending on the type and form of the product, but is usually 0.001 to 10% by mass, preferably 0.001 to 10% by mass based on the mass of the food/beverage product before adding the flavoring composition. Concentrations can range from 0.01 to 5% by weight.
Examples of oral compositions include toothpastes, mouthwashes, mouthwashes, troches, and chewing gums.
本発明の化合物の口腔用組成物への添加量は、口腔用組成物の重量に対して各々０．０００１～１０００００ｐｐｂ、好ましくは０．００１～１００００ｐｐｂ、より好ましくは０．０１～１０００ｐｐｂの濃度範囲とすることができる。
香料組成物の口腔用組成物への添加量は、製品の種類や形態に応じて異なるが、通常口腔用組成物の全質量に対して、好ましくは０．０１～５質量％、より好ましくは０．１～３質量％とすることができる。
The amount of the compound of the present invention added to the oral composition is in the concentration range of 0.0001 to 100000 ppb, preferably 0.001 to 10000 ppb, more preferably 0.01 to 1000 ppb, based on the weight of the oral composition. It can be done.
The amount of the fragrance composition added to the oral composition varies depending on the type and form of the product, but is usually preferably 0.01 to 5% by mass, more preferably 0.01 to 5% by mass, based on the total mass of the oral composition. It can be 0.1 to 3% by mass.
たばこ製品としては、紙巻きたばこ、電子たばこなどを挙げることができる。
本発明の化合物のたばこ製品への添加量は、たばこ製品の重量に対して各々０．０００１～１００ｐｐｍ、好ましくは０．００１～１０ｐｐｍ、より好ましくは０．０１～１ｐｐｍの濃度範囲とすることができる。
香料組成物のたばこ製品への添加量は、製品の種類や形態に応じて異なるが、例えばたばこの葉の部分の全質量に対して、好ましくは０．００００１～９０質量％、より好ましくは０．０００１～５０質量％とすることができる。
Tobacco products include cigarettes, electronic cigarettes, and the like.
The amount of the compound of the present invention added to the tobacco product may be in the concentration range of 0.0001 to 100 ppm, preferably 0.001 to 10 ppm, more preferably 0.01 to 1 ppm, based on the weight of the tobacco product. can.
The amount of flavor composition added to tobacco products varies depending on the type and form of the product, but for example, it is preferably 0.00001 to 90% by mass, more preferably 0.00001% to 90% by mass, based on the total mass of tobacco leaves. It can be .0001 to 50% by mass.
消費者製品の具体例としては、香水、オードパルファム、オードトワレ、オーデコロンなどのフレグランス製品；
洗顔クリーム、クレンジングクリーム、乳液、化粧水、美容液などの基礎化粧品；
口紅、リップクリーム、アイライナー、マスカラ、アイシャドゥ、眉墨、アイパック、ネイルエナメル、エナメルリムーバなどの仕上げ化粧品；
ポマード、ブリランチン、セットローション、ヘアースティック、ヘアーソリッド、ヘアーオイル、ヘアートリートメント、ヘアークリーム、ヘアートニック、ヘアーリキッド、ヘアースプレー、バンドリン、養毛剤、染毛剤などの頭髪化粧品；
サンタン製品、サンスクリーン製品などの日焼け化粧品；
制汗剤、アフターシェービングローション及びジェル、パーマネン卜ウェーブ剤、薬用石鹸、薬用シャンプー、薬用皮膚化粧料などの薬用化粧品；
シャンプー、リンス、リンスインシャンプー、コンディショナー、トリートメン卜、ヘアーパックなどのヘアケア製品；
化粧石鹸、浴用石鹸、香水石鹸、透明石鹸、合成石鹸などの石鹸；
ボディソープ、ボディシャンプー、ハンドソープ、フェースクリームなどの身体洗浄剤；
入浴剤（バスソルト、バスタブレット、バスリキッド、等）、フォームバス（バブルバス、等）、バスオイル（バスパヒューム、バスカプセル、等）、ミルクバス、バスジェリー、バスキューブなどの浴用剤；
衣料用重質洗剤、衣料用軽質洗剤、液体洗剤、洗濯石鹸、コンパクト洗剤、粉石鹸などの洗剤；
ソフナー、ファーニチァケアーなどの柔軟仕上げ剤；
クレンザー、ハウスクリーナー、トイレ洗浄剤、浴室用洗浄剤、ガラスクリーナー、カビ取り剤、排水管用洗浄剤などの洗浄剤；
台所用石鹸、台所用合成石鹸、食器用洗剤などの台所用洗剤；
酸化型漂白剤（塩素系漂白剤、酸素系漂白剤、等）、還元型漂白剤（硫黄系漂白剤、等）、光学的漂白剤などの漂白剤；
スプレータイプ、パウダースプレーなどのエアゾール剤；
固形状タイプ、ゲル状タイプ、リキッドタイプ（水性、油性）などの消臭・芳香剤；
ティッシュペーパー、トイレットペーパーなどの日用・雑貨品；
液体入浴剤、洗口液、忌避剤（ミストスプレータイプ、水性液体タイプ）などの医薬部外品、薬用化粧品、薬用ローションなどの医薬品、などを挙げることができる。
Examples of consumer products include fragrance products such as perfumes, eau de parfum, eau de toilette, and cologne;
Basic cosmetics such as face wash creams, cleansing creams, emulsions, lotions, and serums;
Finishing cosmetics such as lipstick, lip balm, eyeliner, mascara, eye shadow, eyebrow ink, eye pack, nail enamel, and enamel remover;
Hair cosmetics such as pomade, Brilantine, setting lotion, hair stick, hair solid, hair oil, hair treatment, hair cream, hair tonic, hair liquid, hair spray, Bandolin, hair tonic, hair dye;
Suntan cosmetics such as suntan products and sunscreen products;
Medicinal cosmetics such as antiperspirants, aftershave lotions and gels, permanent waving agents, medicated soaps, medicated shampoos, and medicated skin cosmetics;
Hair care products such as shampoo, conditioner, conditioner-in-shampoo, conditioner, treatment, hair pack;
Soaps such as toilet soaps, bath soaps, perfume soaps, transparent soaps, synthetic soaps;
Body cleansers such as body soap, body shampoo, hand soap, and face cream;
Bath agents such as bath salts (bath salts, bath tablets, bath liquids, etc.), foam baths (bubble baths, etc.), bath oils (bath perfume, bath capsules, etc.), milk baths, bath jelly, bath cubes, etc.;
Detergents such as heavy laundry detergent, light laundry detergent, liquid detergent, laundry soap, compact detergent, powder soap;
Fabric softeners such as softeners and furniture care;
Cleaners such as cleansers, house cleaners, toilet cleaners, bathroom cleaners, glass cleaners, mold removers, drain cleaners;
Kitchen detergents such as kitchen soap, synthetic kitchen soap, and dish detergent;
Bleaching agents such as oxidizing bleaches (chlorine bleaches, oxygen bleaches, etc.), reducing bleaches (sulfur bleaches, etc.), optical bleaches;
Aerosol agents such as spray type and powder spray;
Deodorants and fragrances such as solid types, gel types, and liquid types (aqueous and oil-based);
Daily necessities and miscellaneous goods such as tissue paper and toilet paper;
Examples include quasi-drugs such as liquid bath salts, mouth washes, and repellents (mist spray type, aqueous liquid type), and pharmaceuticals such as medicated cosmetics and medicated lotions.
本発明の化合物の消費者製品への添加量は、消費者製品の重量に対して各々０．０００１～１０００００ｐｐｂ、好ましくは０．００１～１００００ｐｐｂ、より好ましくは０．０１～１０００ｐｐｂの濃度範囲とすることができる。
香料組成物の消費者製品への添加量は、製品の種類や形態に応じて異なるが、通常、香料組成物を添加する前の消費者製品の質量を基準として、各々０．００１～９０質量％、好ましくは０．０１～５０質量％、より好ましくは０．１～２５質量％とすることができる。
The amount of the compounds of the present invention added to consumer products is in the concentration range of 0.0001 to 100000 ppb, preferably 0.001 to 10000 ppb, more preferably 0.01 to 1000 ppb, based on the weight of the consumer product. be able to.
The amount of the fragrance composition added to the consumer product varies depending on the type and form of the product, but is usually 0.001 to 90% by weight each based on the weight of the consumer product before adding the fragrance composition. %, preferably 0.01 to 50% by weight, more preferably 0.1 to 25% by weight.
また、本発明の化合物または香料組成物を、他の香料成分と混合して上記の各製品及び組成物に添加し、柑橘様の香気・香味を付与又は増強することもできる。他の香料成分としては、各種の合成香料、天然香料、天然精油、植物エキスなどを挙げることができ、例えば、「特許庁公報、周知・慣用技術集（香料）第ＩＩ部食品香料，Ｐ８８－１３１，平成１２年１月１４日発行」に記載されている天然精油、天然香料、合成香料などを挙げることができる。 Furthermore, the compound or flavor composition of the present invention can be mixed with other flavor ingredients and added to each of the above-mentioned products and compositions to impart or enhance citrus-like aroma and flavor. Other fragrance ingredients include various synthetic fragrances, natural fragrances, natural essential oils, plant extracts, etc. For example, "Patent Office Publication, Collection of Well-known and Commonly Used Techniques (Fragrances) Part II Food Flavors, P88- 131, published January 14, 2000", natural essential oils, natural fragrances, synthetic fragrances, and the like.
本発明において付与又は増強される柑橘様香気・香味の柑橘類としては、グレープフルーツ、オレンジ、レモン、ライム、ユズ、ブラッドオレンジ、ビターオレンジ、タンジェリン、マンダリンオレンジ、みかん、甘夏、ナツミカン、ハッサク、ブンタン、カボス、スダチ、ヘベス、ベルガモット、スウィーティー（オロブロンコ）等が好ましいが、ここに記載した柑橘類に限定されるものではない。 Examples of citrus fruits with a citrus-like aroma/flavor to be imparted or enhanced in the present invention include grapefruit, orange, lemon, lime, yuzu, blood orange, bitter orange, tangerine, mandarin orange, mandarin orange, sweet summer, nut mandarin, hassaku, buntan, Kabosu, sudachi, hebes, bergamot, sweetie (orobronco), etc. are preferred, but are not limited to the citrus fruits listed here.
以下、実施例により本発明をさらに具体的に説明するが、本発明はこれら実施例に限定されるものではない。
実施例において使用した分析機器は以下の通りである。
EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to these Examples.
The analytical instruments used in the examples are as follows.
ＮＭＲ測定装置：ＡＶＡＮＣＥＩＩＩ ５００（ブルカーバイオスピン社製）
ガスクロマトグラフ質量分析計：ＧＣＭＳ‐ＱＰ２０１０（島津製作所社製）
ガスクロマトグラフ‐オービトラップ型質量分析計：ＴＲＡＣＥ１３１０（ＧＣ）＋ Ｅｘａｃｔｉｖｅ ＧＣ（質量分析計）（サーモフィッシャーサイエンティフィック社製）
高速液体クロマトグラフ
ポンプ：ＬＣ－２０Ａ（島津製作所社製）
検出器：ＳＰＤ－Ｍ２０Ａ（ジーエルサイエンス社製）
分離カラム：ＹＭＣ－ＴｒｉａｒｔＣ１８ ＥｘＲＳ（ＹＭＣ社製）
（実施例１）化合物（１ａ）および化合物（１ｃ）の合成
NMR measurement device: AVANCE III 500 (manufactured by Bruker Biospin)
Gas chromatograph mass spectrometer: GCMS-QP2010 (manufactured by Shimadzu Corporation)
Gas chromatograph-orbitrap mass spectrometer: TRACE1310 (GC) + Exactive GC (mass spectrometer) (manufactured by Thermo Fisher Scientific)
High performance liquid chromatograph pump: LC-20A (manufactured by Shimadzu Corporation)
Detector: SPD-M20A (manufactured by GL Sciences)
Separation column: YMC-TriartC18 ExRS (manufactured by YMC)
(Example 1) Synthesis of compound (1a) and compound (1c)
（ａ）（Ｓ）－２－（４－メチル－３－シクロヘキセン－１－イル）プロパン－１－オールの合成 (a) Synthesis of (S)-2-(4-methyl-3-cyclohexen-1-yl)propan-1-ol
ｌ－リモネン（４．８２ｇ）のＴＨＦ溶液（１４．５ｍＬ）に、９－ＢＢＮ（０．５Ｍ／ＴＨＦ溶液、９６．０ｍＬ）を５℃にて滴下した。滴下終了後、２０℃にて１時間反応させることで、中間体化合物を得た。その後、１０％水酸化ナトリウム水溶液（１２．０ｍＬ）およびの過酸化水素水（１３．０ｍＬ）を加え、４０℃にて２時間反応させた後、ジエチルエーテル（２０ｍＬ）を加え分液した。
続いて、得られた有機層を濃縮し、シリカゲルカラムクロマトグラフィー(ヘキサン：酢酸エチル＝５：１)により精製を行うことで、（Ｓ）－２－（４－メチル－３－シクロヘキセン－１－イル）プロパン－１－オールが５．１６ｇ（収率：９３．０％、ＧＣ純度：９５．１％）得られた。
9-BBN (0.5M/THF solution, 96.0 mL) was added dropwise to a THF solution (14.5 mL) of l-limonene (4.82 g) at 5°C. After the dropwise addition was completed, an intermediate compound was obtained by reacting at 20° C. for 1 hour. Thereafter, a 10% aqueous sodium hydroxide solution (12.0 mL) and a hydrogen peroxide solution (13.0 mL) were added, and the mixture was reacted at 40°C for 2 hours, followed by addition of diethyl ether (20 mL) and the mixture was separated.
Subsequently, the obtained organic layer was concentrated and purified by silica gel column chromatography (hexane: ethyl acetate = 5:1) to obtain (S)-2-(4-methyl-3-cyclohexene-1- 5.16 g (yield: 93.0%, GC purity: 95.1%) of propan-1-ol (yield: 93.0%) was obtained.
（ｂ）（Ｓ）－２－（４－メチル－３－シクロヘキセン－１－イル）－１－プロパナールの製造 (b) Production of (S)-2-(4-methyl-3-cyclohexen-1-yl)-1-propanal
（ａ）で得られた（Ｓ）－２－（４－メチル－３－シクロヘキセン－１－イル）プロパン－１－オール（２．０４ｇ）のトルエン（２．７ｍＬ）溶液に、１６．０ｍｇのＡＺＡＤＯＬ（１６．０ｍｇ）およびジアセトキシヨードベンゼン（４．５ｇ）を加え、１５℃にて１時間反応させた。この反応液にトルエン（３０．０ｍＬ）および５％亜硫酸差トリウム水溶液（４５．０ｍＬ）を加え反応をクエンチした後、有機層を分液した。
続いて、得られた有機層を濃縮し、シリカゲルカラムクロマトグラフィー(ヘキサン：酢酸エチル＝１２：１)により精製を行うことで、（Ｓ）－２－（４－メチル－３－シクロヘキセン－１－イル）－１－プロパナールが１．２６ｇ（収率：６４．７％、ＧＣ純度：９９．３％）得られた。
In a toluene (2.7 mL) solution of (S)-2-(4-methyl-3-cyclohexen-1-yl)propan-1-ol (2.04 g) obtained in (a), 16.0 mg of AZADOL (16.0 mg) and diacetoxyiodobenzene (4.5 g) were added and reacted at 15°C for 1 hour. Toluene (30.0 mL) and 5% thorium sulfite aqueous solution (45.0 mL) were added to this reaction solution to quench the reaction, and then the organic layer was separated.
Subsequently, the obtained organic layer was concentrated and purified by silica gel column chromatography (hexane:ethyl acetate = 12:1) to obtain (S)-2-(4-methyl-3-cyclohexene-1- 1.26 g (yield: 64.7%, GC purity: 99.3%) of yl)-1-propanal was obtained.
（ｃ）（Ｓ）－２－（４－メチル－３－シクロヘキセン－１－イル）プロピオン酸の合成 (c) Synthesis of (S)-2-(4-methyl-3-cyclohexen-1-yl)propionic acid
（ｂ）で合成した（Ｓ）－２－（４－メチル－３－シクロヘキセン－１－イル）－１－プロパナール（２．１２ｇ）の蒸留水（１２．ｍＬ）およびｔｅｒｔ－ブタノール（１２．６ｍＬ）溶液に、リン酸二水素ナトリウム（２．３２ｇ）および７等量の２－メチル－２－ブテンを順次加え、反応液を２０℃に保温した。続いて、１．０Ｍ次亜塩素酸ナトリウム水溶液（１５．０ｍＬ）を滴下し、室温にて３０分間反応させた。この反応液にヘキサン（５０．０ｍＬ）および１０％水酸化ナトリム水溶液（２５．０ｍＬ）を滴下後、１規定塩酸をｐＨ＝１になるまで加えた後、有機層を分液した。
続いて、得られた有機層を濃縮し、シリカゲルカラムクロマトグラフィー(ヘキサン：酢酸エチル＝２：１)により精製を行うことで、（Ｓ）－２－（４－メチル－３－シクロヘキセン－１－イル）プロピオン酸が収量１．５４ｇ（収率：７１．０％、ＧＣ純度：１００％）得られた。
(S)-2-(4-methyl-3-cyclohexen-1-yl)-1-propanal (2.12 g) synthesized in (b) in distilled water (12.mL) and tert-butanol (12. Sodium dihydrogen phosphate (2.32 g) and 7 equivalents of 2-methyl-2-butene were sequentially added to the 6 mL) solution, and the reaction solution was kept at 20°C. Subsequently, a 1.0 M aqueous sodium hypochlorite solution (15.0 mL) was added dropwise, and the mixture was allowed to react at room temperature for 30 minutes. Hexane (50.0 mL) and 10% aqueous sodium hydroxide solution (25.0 mL) were added dropwise to this reaction solution, and then 1N hydrochloric acid was added until pH=1, and the organic layer was separated.
Subsequently, the obtained organic layer was concentrated and purified by silica gel column chromatography (hexane: ethyl acetate = 2:1) to obtain (S)-2-(4-methyl-3-cyclohexene-1- 1.54 g (yield: 71.0%, GC purity: 100%) of propionic acid was obtained.
（ｄ）（１Ｓ，５Ｓ）－２，６－ジメチル－７－オキソビシクロ[３，２，１]オクタン－２－イル－トリフルオロアセテートの合成 (d) Synthesis of (1S,5S)-2,6-dimethyl-7-oxobicyclo[3,2,1]octan-2-yl-trifluoroacetate
（ｃ）で合成した（Ｓ）２－（４－メチル－３－シクロヘキセン－１－イル）プロピオン酸（１．５０ｇ）のトルエン（４５．０ｍＬ）溶液に、トリフルオロ酢酸無水物（７．４９ｇ）を加え、２０℃にて２時間反応させることで、（１Ｓ、５Ｓ）－２，６－ジメチル－７－オキソビシクロ[３，２，１]オクタン－２－イル－トリフルオロアセテートを得た。この時、副生成物として（１Ｓ，５Ｓ）－４，７－ジメチルビシクロ[３，２，１]オクタン－３－エン－６－オンが３３．６％生成した。続いて、この反応液に１０％水酸化ナトリウム水溶液（２８．０ｍＬ）を滴下後、有機層を分液した。
得られた有機層を濃縮し、シリカゲルカラムクロマトグラフィー(ヘキサン：酢酸エチル＝１０：１)を用いて精製を行うことで、（１Ｓ，５Ｓ）－２，６－ジメチル－７－オキソビシクロ[３，２，１]オクタン－２－イル－トリフルオロアセテートが、副生成物の（１Ｓ、５Ｓ）－４，７－ジメチルビシクロ[３，２，１]オクタン－３－エン－６－オンとの混合物として１．４６ｇ得られた。
Trifluoroacetic anhydride (7.49 g) was added to a toluene (45.0 mL) solution of (S) 2-(4-methyl-3-cyclohexen-1-yl)propionic acid (1.50 g) synthesized in (c). ) and reacted at 20°C for 2 hours to obtain (1S,5S)-2,6-dimethyl-7-oxobicyclo[3,2,1]octan-2-yl-trifluoroacetate. . At this time, 33.6% of (1S,5S)-4,7-dimethylbicyclo[3,2,1]octan-3-en-6-one was produced as a by-product. Subsequently, a 10% aqueous sodium hydroxide solution (28.0 mL) was added dropwise to this reaction solution, and then the organic layer was separated.
The obtained organic layer was concentrated and purified using silica gel column chromatography (hexane:ethyl acetate = 10:1) to obtain (1S,5S)-2,6-dimethyl-7-oxobicyclo[3 ,2,1]octan-2-yl-trifluoroacetate with the by-product (1S,5S)-4,7-dimethylbicyclo[3,2,1]octan-3-en-6-one. 1.46g of the mixture was obtained.
（ｅ）（１Ｒ，５Ｓ，６Ｒ，７Ｓ）－２，６－ジメチルビシクロ[３，２，１]オクタン－２，７－ジオーおよび（１Ｒ，５Ｓ，６Ｓ，７Ｓ）－２，６－ジメチルビシクロ[３，２，１]オクタン－２，７－ジオールの合成 (e) (1R,5S,6R,7S)-2,6-dimethylbicyclo[3,2,1]octane-2,7-dio and (1R,5S,6S,7S)-2,6-dimethylbicyclo Synthesis of [3,2,1]octane-2,7-diol
（ｄ）で合成した（１Ｓ，５Ｓ）－２，６－ジメチル－７－オキソビシクロ[３，２，１]オクタン－２－イル－トリフルオロアセテートおよび副生成物の混合物（０．４０ｇ）のメタノール（６．０ｍＬ）溶液を５℃に冷却し、水素化ホウ素ナトリウム（０．２８ｇ）を加え２時間反応させた後、ジエチルエーテル（１２．０ｍＬ）および水（６．０ｍＬ）を加えて、有機層を分液した。
続いて、得られた有機層を濃縮し、シリカゲルカラムクロマトグラフィー(ヘキサン： 酢酸エチル＝５：１)を用いて精製することで、目的の（１Ｒ，５Ｓ，６Ｒ，７Ｓ）－２，６－ジメチルビシクロ[３，２，１]オクタン－２，７－ジオールを３６．０ｍｇ、収率２８．０％にて、（１Ｒ，５Ｓ，６Ｓ，７Ｓ）－２，６－ジメチルビシクロ[３，２，１]オクタン－２，７－ジオールを８０．０ｍｇの収率４１．０％にて得た。
(1S,5S)-2,6-dimethyl-7-oxobicyclo[3,2,1]octan-2-yl-trifluoroacetate synthesized in (d) and the mixture of by-products (0.40 g). A methanol (6.0 mL) solution was cooled to 5°C, sodium borohydride (0.28 g) was added, and the mixture was reacted for 2 hours, followed by addition of diethyl ether (12.0 mL) and water (6.0 mL). The organic layer was separated.
Subsequently, the obtained organic layer was concentrated and purified using silica gel column chromatography (hexane: ethyl acetate = 5:1) to obtain the desired (1R,5S,6R,7S)-2,6- (1R,5S,6S,7S)-2,6-dimethylbicyclo[3,2 ,1]octane-2,7-diol was obtained in a yield of 41.0% (80.0 mg).
（ｆ）（１Ｓ，３Ｒ，６Ｓ，８Ｒ，９Ｒ）－３，９－ジメチル－２－オキサトリサイクロ［４．２．１．０３，８］ノナン（１ａ）および（１Ｓ，３Ｒ，６Ｓ，８Ｒ，９Ｓ）－３，９－ジメチル－２－オキサトリサイクロ［４．２．１．０３，８］ノナン（１ｃ）の合成 (f) (1S,3R,6S,8R,9R)-3,9-dimethyl-2-oxatricyclo[4.2.1.0 3,8 ]nonane (1a) and (1S,3R,6S, Synthesis of 8R,9S)-3,9-dimethyl-2-oxatricyclo[4.2.1.0 3,8 ]nonane (1c)
（ｅ）で合成した６５．０ｍｇの（１Ｒ，５Ｓ，６Ｒ，７Ｓ）－２，６－ジメチルビシクロ[３，２，１]オクタン－２、７－ジオールおよび（１Ｒ，５Ｓ，６Ｓ，７Ｓ）－２，６－ジメチルビシクロ[３，２，１]オクタン－２，７－ジオールの混合物(８：９２)を、ジクロロメタン（２．０ｍＬ）溶液を５℃に冷却し、２．０ｍＬの１規定塩酸を加え５時間反応させた後、有機層を分液した。分液した有機層を濃縮することにより、（１Ｓ，３Ｒ，６Ｓ，８Ｒ，９Ｒ）－３，９－ジメチル－２－オキサトリシクロ［４．２．１．０３，８］ノナン（１ａ）および（１Ｓ，３Ｒ，６Ｓ，８Ｒ，９Ｓ）－３，９－ジメチル－２－オキサトリシクロ［４．２．１．０３，８］ノナン（１ｃ）の混合物を得た。続いて、高速液体クロマトグラフィー（水：アセトニトリル＝３５：６５（容積比））により精製を行い、目的の（１Ｓ，３Ｒ，６Ｓ，８Ｒ，９Ｒ）－３，９－ジメチル－２－オキサトリシクロ［４．２．１．０３，８］ノナン（１ａ）（ＧＣ純度１００％）および（１Ｓ，３Ｒ，６Ｓ，８Ｒ，９Ｓ）－３，９－ジメチル－２－オキサトリシクロ［４．２．１．０３，８］ノナン（１ｃ）（ＧＣ純度１００％）を得た。 65.0 mg of (1R,5S,6R,7S)-2,6-dimethylbicyclo[3,2,1]octane-2,7-diol and (1R,5S,6S,7S) synthesized in (e) A mixture of -2,6-dimethylbicyclo[3,2,1]octane-2,7-diol (8:92) in dichloromethane (2.0 mL) was cooled to 5°C, and 2.0 mL of 1N After adding hydrochloric acid and reacting for 5 hours, the organic layer was separated. By concentrating the separated organic layer, (1S,3R,6S,8R,9R)-3,9-dimethyl-2-oxatricyclo[4.2.1.0 3,8 ]nonane (1a) and (1S,3R,6S,8R,9S)-3,9-dimethyl-2-oxatricyclo[4.2.1.0 3,8 ]nonane (1c) was obtained. Subsequently, purification was performed by high performance liquid chromatography (water:acetonitrile = 35:65 (volume ratio)) to obtain the desired (1S,3R,6S,8R,9R)-3,9-dimethyl-2-oxatricyclo [4.2.1.0 3,8 ] Nonane (1a) (GC purity 100%) and (1S,3R,6S,8R,9S)-3,9-dimethyl-2-oxatricyclo[4.2 .1.0 3,8 ]nonane (1c) (GC purity 100%) was obtained.
＜（１Ｓ，３Ｒ，６Ｓ，８Ｒ，９Ｒ）－３，９－ジメチル－２－オキサトリシクロ［４．２．１．０３，８］ノナンの物理的データ＞
１Ｈ ＮＭＲ（５００ＭＨｚ，ａｃｅｔｏｎｅ－ｄ６）δ：
４．３１（ｄｄ，Ｊ＝５．５Ｈｚ，１．２６Ｈｚ，１Ｈ），２．９０（ｄｄ，Ｊ＝５．５０Ｈｚ，４．１０Ｈｚ，１Ｈ），１．９７（ｍ，１Ｈ），１．９３（ｍ，１Ｈ），１．９０（ｑ，Ｊ＝７．５０Ｈｚ，１Ｈ），１．６８（ｍ，１Ｈ），１．６１（ｄ，Ｊ＝１２．５０Ｈｚ，１Ｈ），１．４９（ｄｔ，Ｊ＝１２．５０Ｈｚ，４．１０Ｈｚ，１Ｈ），１．４８（ｄｔ，Ｊ＝１４．７０Ｈｚ，１．０７Ｈｚ，１Ｈ），１．４３（ｄｄｄ，Ｊ＝１４．７０Ｈｚ，９．５０Ｈｚ，１．０７Ｈｚ，１Ｈ），１．１９（ｓ，３Ｈ），０．７３（ｄ，Ｊ＝７．５０Ｈｚ，３Ｈ）
１３Ｃ ＮＭＲ（１２５ＭＨｚ，ＣＤＣｌ３）δ：
８５．６８，８５．１０，５０．１３，４５．７８，４１．１６，３１．９８，２９．６７，２８．８２，２７．９５，１７．１９
ＨＲＭＳ（ＣＩ＋）：ｃａｌｃｄ Ｃ１０Ｈ１７Ｏ（［Ｍ＋Ｈ］＋）１５３．１２７４；ｆｏｕｎｄ，１５３．１２７３
<Physical data of (1S,3R,6S,8R,9R)-3,9-dimethyl-2-oxatricyclo[4.2.1.0 3,8 ]nonane>
1H NMR (500MHz, acetone-d6) δ:
4.31 (dd, J=5.5Hz, 1.26Hz, 1H), 2.90 (dd, J=5.50Hz, 4.10Hz, 1H), 1.97 (m, 1H), 1.93 (m, 1H), 1.90 (q, J = 7.50Hz, 1H), 1.68 (m, 1H), 1.61 (d, J = 12.50Hz, 1H), 1.49 (dt , J=12.50Hz, 4.10Hz, 1H), 1.48 (dt, J=14.70Hz, 1.07Hz, 1H), 1.43 (ddd, J=14.70Hz, 9.50Hz, 1 .07Hz, 1H), 1.19 (s, 3H), 0.73 (d, J=7.50Hz, 3H)
13C NMR (125MHz, CDCl3) δ:
85.68, 85.10, 50.13, 45.78, 41.16, 31.98, 29.67, 28.82, 27.95, 17.19
HRMS (CI+): calcd C10H17O ([M+H]+) 153.1274; found, 153.1273
＜（１Ｓ，３Ｒ，６Ｓ，８Ｒ，９Ｓ）－３，９－ジメチル－２－オキサトリシクロ［４．２．１．０３，８］ノナンの物理的データ＞
１Ｈ ＮＭＲ（５００ＭＨｚ，ＣＤＣｌ３）δ：
４．４７（ｔ，Ｊ＝５．００Ｈｚ，１Ｈ），２．８３（ｄｄ，Ｊ＝５．３０Ｈｚ，４．７５Ｈｚ，１Ｈ），２．０４（ｑ，Ｊ＝５．００Ｈｚ，１Ｈ），１．８１（ｍ，１Ｈ），１．６７（ｍ，１Ｈ），１．５９（ｄ，１２．４５Ｈｚ，１Ｈ），１．５７（ｄｔ，Ｊ＝１３．９５Ｈｚ，８．５０Ｈｚ，１Ｈ），１．４３（ｄｄ，Ｊ＝１４．３５Ｈｚ，８．６０Ｈｚ，１Ｈ），１．３４（ｄｔ，Ｊ＝１４．３５Ｈｚ，９．５０Ｈｚ，１Ｈ），１．２４（ｓ，３Ｈ），１．２４（ｍ，１Ｈ），１．０１（ｄ，Ｊ＝６．９５Ｈｚ，３Ｈ）
１３Ｃ ＮＭＲ（１２５ＭＨｚ，ＣＤＣｌ３）δ：
８５．２４，８１．２１，４４．８６，４２．８６，３６．６６，３０．１０，２９．６５，２８．７１，１９．１０，８．８０
ＨＲＭＳ（ＣＩ＋）：ｃａｌｃｄ Ｃ１０Ｈ１７Ｏ（［Ｍ＋Ｈ］＋）１５３．１２７４；ｆｏｕｎｄ，１５３．１２７４
<Physical data of (1S,3R,6S,8R,9S)-3,9-dimethyl-2-oxatricyclo[4.2.1.0 3,8 ]nonane>
1H NMR (500MHz, CDCl3) δ:
4.47 (t, J=5.00Hz, 1H), 2.83 (dd, J=5.30Hz, 4.75Hz, 1H), 2.04 (q, J=5.00Hz, 1H), 1 .81 (m, 1H), 1.67 (m, 1H), 1.59 (d, 12.45Hz, 1H), 1.57 (dt, J=13.95Hz, 8.50Hz, 1H), 1 .43 (dd, J = 14.35Hz, 8.60Hz, 1H), 1.34 (dt, J = 14.35Hz, 9.50Hz, 1H), 1.24 (s, 3H), 1.24 ( m, 1H), 1.01 (d, J=6.95Hz, 3H)
13C NMR (125MHz, CDCl3) δ:
85.24, 81.21, 44.86, 42.86, 36.66, 30.10, 29.65, 28.71, 19.10, 8.80
HRMS (CI+): calcd C10H17O ([M+H]+) 153.1274; found, 153.1274
（実施例２）（１Ｒ，３Ｓ，６Ｒ，８Ｓ，９Ｓ）－３，９－ジメチル－２－オキサトリシクロ［４．２．１．０３，８］ノナン（化合物（１ｂ））および（１Ｒ，３Ｓ，６Ｒ，８Ｓ，９Ｒ）－３，９－ジメチル－２－オキサトリシクロ［４．２．１．０３，８］ノナン（化合物（１ｄ））の合成
実施例１におけるｌ－リモネンをｄ－リモネンに変更した以外は実施例１と同様に行い、（１Ｒ，３Ｓ，６Ｒ，８Ｓ，９Ｓ）－３，９－ジメチル－２－オキサトリシクロ［４．２．１．０３，８］ノナン（ＧＣ純度１００％）および（１Ｒ，３Ｓ，６Ｒ，８Ｓ，９Ｒ）－３，９－ジメチル－２－オキサトリシクロ［４．２．１．０３，８］ノナン（ＧＣ純度１００％）を得た。
(Example 2) (1R,3S,6R,8S,9S)-3,9-dimethyl-2-oxatricyclo[4.2.1.0 3,8 ]nonane (compound (1b)) and (1R ,3S,6R,8S,9R)-3,9-dimethyl-2-oxatricyclo[4.2.1.0 3,8 ]nonane (compound (1d)) Synthesis of l-limonene in Example 1 The same procedure as in Example 1 was carried out except that d-limonene was used, and (1R,3S,6R,8S,9S)-3,9-dimethyl-2-oxatricyclo[4.2.1.0 3,8 ]nonane (GC purity 100%) and (1R,3S,6R,8S,9R)-3,9-dimethyl-2-oxatricyclo[4.2.1.0 3,8 ]nonane (GC purity 100%) ) was obtained.
＜（１Ｒ，３Ｓ，６Ｒ，８Ｓ，９Ｓ）－３，９－ジメチル－２－オキサトリシクロ［４．２．１．０３，８］ノナンの物理的データ＞
１Ｈ ＮＭＲ（５００ＭＨｚ，ａｃｅｔｏｎｅ－ｄ６）δ：
４．３１（ｄｄ，Ｊ＝５．５Ｈｚ，１．２６Ｈｚ，１Ｈ），２．９０（ｄｄ，Ｊ＝５．５０Ｈｚ，４．１０Ｈｚ，１Ｈ），１．９７（ｍ，１Ｈ），１．９３（ｍ，１Ｈ），１．９０（ｑ，Ｊ＝７．５０Ｈｚ，１Ｈ），１．６８（ｍ，１Ｈ），１．６１（ｄ，Ｊ＝１２．５０Ｈｚ，１Ｈ），１．４９（ｄｔ，Ｊ＝１２．５０Ｈｚ，４．１０Ｈｚ，１Ｈ），１．４８（ｄｔ，Ｊ＝１４．７０Ｈｚ，１．０７Ｈｚ，１Ｈ），１．４３（ｄｄｄ，Ｊ＝１４．７０Ｈｚ，９．５０Ｈｚ，１．０７Ｈｚ，１Ｈ），１．１９（ｓ，３Ｈ），０．７３（ｄ，Ｊ＝７．５０Ｈｚ，３Ｈ）
１３Ｃ ＮＭＲ（１２５ＭＨｚ，ＣＤＣｌ３）δ：
８５．６８，８５．１０，５０．１３，４５．７８，４１．１６，３１．９８，２９．６７，２８．８２，２７．９５，１７．１９
ＨＲＭＳ（ＣＩ＋）：ｃａｌｃｄ Ｃ１０Ｈ１７Ｏ（［Ｍ＋Ｈ］＋）１５３．１２７４；ｆｏｕｎｄ，１５３．１２７４
<Physical data of (1R,3S,6R,8S,9S)-3,9-dimethyl-2-oxatricyclo[4.2.1.0 3,8 ]nonane>
1H NMR (500MHz, acetone-d6) δ:
4.31 (dd, J=5.5Hz, 1.26Hz, 1H), 2.90 (dd, J=5.50Hz, 4.10Hz, 1H), 1.97 (m, 1H), 1.93 (m, 1H), 1.90 (q, J = 7.50Hz, 1H), 1.68 (m, 1H), 1.61 (d, J = 12.50Hz, 1H), 1.49 (dt , J=12.50Hz, 4.10Hz, 1H), 1.48 (dt, J=14.70Hz, 1.07Hz, 1H), 1.43 (ddd, J=14.70Hz, 9.50Hz, 1 .07Hz, 1H), 1.19 (s, 3H), 0.73 (d, J=7.50Hz, 3H)
13C NMR (125MHz, CDCl3) δ:
85.68, 85.10, 50.13, 45.78, 41.16, 31.98, 29.67, 28.82, 27.95, 17.19
HRMS (CI+): calcd C10H17O ([M+H]+) 153.1274; found, 153.1274
＜（１Ｒ，３Ｓ，６Ｒ，８Ｓ，９Ｒ）－３，９－ジメチル－２－オキサトリシクロ［４．２．１．０３，８］ノナンの物理的データ＞
１Ｈ ＮＭＲ（５００ＭＨｚ，ＣＤＣｌ３）δ：
４．４７（ｔ，Ｊ＝５．００Ｈｚ，１Ｈ），２．８３（ｄｄ，Ｊ＝５．３０Ｈｚ，４．７５Ｈｚ，１Ｈ），２．０４（ｑ，Ｊ＝５．００Ｈｚ，１Ｈ），１．８１（ｍ，１Ｈ），１．６７（ｍ，１Ｈ），１．５９（ｄ，１２．４５Ｈｚ，１Ｈ），１．５７（ｄｔ，Ｊ＝１３．９５Ｈｚ，８．５０Ｈｚ，１Ｈ），１．４３（ｄｄ，Ｊ＝１４．３５Ｈｚ，８．６０Ｈｚ，１Ｈ），１．３４（ｄｔ，Ｊ＝１４．３５Ｈｚ，９．５０Ｈｚ，１Ｈ），１．２４（ｓ，３Ｈ），１．２４（ｍ，１Ｈ），１．０１（ｄ，Ｊ＝６．９５Ｈｚ，３Ｈ）
１３Ｃ ＮＭＲ（１２５ＭＨｚ，ＣＤＣｌ３）δ：
８５．２４，８１．２１，４４．８６，４２．８６，３６．６６，３０．１０，２９．６５，２８．７１，１９．１０，８．８０
ＨＲＭＳ（ＣＩ＋）：ｃａｌｃｄ Ｃ１０Ｈ１７Ｏ（［Ｍ＋Ｈ］＋）１５３．１２７４；ｆｏｕｎｄ，１５３．１２７４
<Physical data of (1R,3S,6R,8S,9R)-3,9-dimethyl-2-oxatricyclo[4.2.1.0 3,8 ]nonane>
1H NMR (500MHz, CDCl3) δ:
4.47 (t, J=5.00Hz, 1H), 2.83 (dd, J=5.30Hz, 4.75Hz, 1H), 2.04 (q, J=5.00Hz, 1H), 1 .81 (m, 1H), 1.67 (m, 1H), 1.59 (d, 12.45Hz, 1H), 1.57 (dt, J=13.95Hz, 8.50Hz, 1H), 1 .43 (dd, J = 14.35Hz, 8.60Hz, 1H), 1.34 (dt, J = 14.35Hz, 9.50Hz, 1H), 1.24 (s, 3H), 1.24 ( m, 1H), 1.01 (d, J=6.95Hz, 3H)
13C NMR (125MHz, CDCl3) δ:
85.24, 81.21, 44.86, 42.86, 36.66, 30.10, 29.65, 28.71, 19.10, 8.80
HRMS (CI+): calcd C10H17O ([M+H]+) 153.1274; found, 153.1274
（実施例３）オレンジ香料組成物の製造
実施例１で製造した化合物（１ａ）を用いて、下記処方に従って、オレンジ香料組成物（Ａ）を調製した。比較として、下記処方に従いオレンジ香料組成物（Ｂ）を調製した。
(Example 3) Production of Orange Flavor Composition Using the compound (1a) produced in Example 1, an orange flavor composition (A) was prepared according to the following formulation. For comparison, an orange flavor composition (B) was prepared according to the following formulation.
上記処方で調製したオレンジ香料組成物（Ａ）および（Ｂ）をそれぞれ水に０．１％添加し、１１名の専門パネラーによる官能試験を行ったところ、香料組成物（Ａ）の方が、香料組成物（Ｂ）よりも、本物らしい果汁感、瑞々しさ、フレッシュさが付与され、格段に優れていると全員が指摘した。香料組成物（Ａ）中の化合物（１ａ）については、化合物（１ｃ）に置き換えた場合も同様の評価であった。 Orange flavor compositions (A) and (B) prepared according to the above formulation were each added to water at 0.1%, and a sensory test was conducted by 11 expert panelists. Everyone pointed out that it was much better than the fragrance composition (B), giving a real fruit juice feel, freshness, and freshness. Regarding compound (1a) in perfume composition (A), similar evaluations were obtained when compound (1c) was substituted.
（実施例４）オレンジ香料組成物の製造
実施例２で製造した化合物（１ｂ）を用いて、下記処方に従って、オレンジ香料組成物（Ｃ）を調製した。比較として、下記処方に従いオレンジ香料組成物（Ｄ）を調製した。
(Example 4) Manufacture of orange flavor composition Using the compound (1b) produced in Example 2, an orange flavor composition (C) was prepared according to the following formulation. For comparison, an orange flavor composition (D) was prepared according to the following formulation.
上記処方で調製したオレンジ香料組成物（Ｃ）および（Ｄ）をそれぞれ水に０．１％添加し、１１名の専門パネラーによる官能試験を行ったところ、香料組成物（Ｃ）の方が、香料組成物（Ｄ）よりも、本物らしいグリーン感やフレッシュ感が強化され、格段に優れていると全員が指摘した。香料組成物（Ｃ）中の化合物（１ｂ）については、化合物（１ｄ）に置き換えた場合も同様の評価であった。 Orange flavor compositions (C) and (D) prepared according to the above formulation were each added to water at 0.1%, and a sensory test was conducted by 11 expert panelists. All the members pointed out that it was much better than the fragrance composition (D), with an enhanced authentic green feeling and fresh feeling. Regarding compound (1b) in perfume composition (C), similar evaluations were obtained when compound (1d) was substituted.
（実施例５）オレンジ香料組成物の製造
実施例１で製造した化合物（１ａ）と化合物（１ｃ）の混合物（以下、実施例１の混合物という）を用いて、下記処方に従って、オレンジ香料組成物（１）を調製した。比較として、下記処方に従いオレンジ香料組成物（２）を調製した。
(Example 5) Production of orange flavor composition Using the mixture of compound (1a) and compound (1c) produced in Example 1 (hereinafter referred to as the mixture of Example 1), an orange flavor composition was prepared according to the following recipe. (1) was prepared. For comparison, an orange flavor composition (2) was prepared according to the following formulation.
上記処方で調製したオレンジ香料組成物（１）および（２）をそれぞれ水に０．１％添加し、１１名の専門パネラーによる官能試験を行ったところ、香料組成物（１）の方が、香料組成物（２）よりも、本物らしい果汁感、瑞々しさ、フレッシュさが付与され、格段に優れていると全員が指摘した。香料組成物（１）中の実施例１の混合物については、４種の異性体のいずれであっても、化合物（１ｂ）と化合物（１ｄ）の混合物（以下、実施例２の混合物という）に置き換えた場合も同様の評価であった。 Orange fragrance compositions (1) and (2) prepared according to the above formulation were each added to water at 0.1%, and a sensory test was conducted by 11 expert panelists. Everyone pointed out that it was much better than fragrance composition (2), giving a real fruit juice feel, freshness, and freshness. Regarding the mixture of Example 1 in the fragrance composition (1), any of the four isomers may be added to the mixture of compound (1b) and compound (1d) (hereinafter referred to as the mixture of Example 2). The same evaluation was obtained when the product was replaced.
（実施例６）オレンジ香料組成物の製造
実施例１の混合物を用いて、下記処方に従って、オレンジ香料組成物（３）を調製した。比較として、下記処方に従いオレンジ香料組成物（４）を調製した。
(Example 6) Manufacture of orange flavor composition Using the mixture of Example 1, an orange flavor composition (3) was prepared according to the following recipe. For comparison, an orange flavor composition (4) was prepared according to the following formulation.
上記処方で調製したオレンジ香料組成物（３）および（４）をそれぞれ水に０．１％添加し、１１名の専門パネラーによる官能試験を行ったところ、香料組成物（３）の方が、香料組成物（４）よりも、本物らしい果汁感、瑞々しさ、フレッシュさが付与され、格段に優れていると全員が指摘した。香料組成物（３）中の実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。 Orange flavor compositions (3) and (4) prepared according to the above formulation were each added to water at 0.1%, and a sensory test was conducted by 11 expert panelists. Everyone pointed out that it was much better than fragrance composition (4), giving a real fruit juice feel, freshness, and freshness. Regarding the mixture of Example 1 in perfume composition (3), the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例７）レモン香料組成物の製造
実施例１の混合物を用いて、下記処方に従って、レモン香料組成物（５）を調製した。比較として、下記処方に従いレモン香料組成物（６）を調製した。
(Example 7) Manufacture of lemon flavor composition Using the mixture of Example 1, a lemon flavor composition (5) was prepared according to the following recipe. For comparison, a lemon flavor composition (6) was prepared according to the following formulation.
上記処方で調製したレモン香料組成物（５）および（６）をそれぞれ水に０．１％添加し、１１名の専門パネラーによる官能試験を行ったところ、香料組成物（５）の方が、香料組成物（６）よりも、フレッシュさ、瑞々しい甘い香りが付与され、格段に優れていると全員が指摘した。香料組成物（５）中の実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。 Lemon fragrance compositions (5) and (6) prepared according to the above formulation were each added at 0.1% to water, and a sensory test was conducted by 11 expert panelists. Everyone pointed out that it was much better than fragrance composition (6) in that it imparted a fresher, fresher, and sweeter scent. Regarding the mixture of Example 1 in perfume composition (5), the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例８）レモン香料組成物の製造
実施例１の混合物を用いて、下記処方に従って、レモン香料組成物（７）を調製した。比較として、下記処方に従いレモン香料組成物（８）を調製した。
(Example 8) Manufacture of lemon flavor composition Using the mixture of Example 1, a lemon flavor composition (7) was prepared according to the following recipe. For comparison, a lemon flavor composition (8) was prepared according to the following formulation.
上記処方で調製したレモン香料組成物（７）および（８）をそれぞれ水に０．１％添加し、１１名の専門パネラーによる官能試験を行ったところ、香料組成物（７）の方が、香料組成物（８）よりも、フレッシュさ、瑞々しい甘い香りが付与され、格段に優れていると全員が指摘した。香料組成物（７）中の実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。 Lemon fragrance compositions (7) and (8) prepared according to the above formulation were each added at 0.1% to water, and a sensory test was conducted by 11 expert panelists. Everyone pointed out that it was much better than fragrance composition (8) in that it imparted a fresher, fresher, and sweeter scent. Regarding the mixture of Example 1 in perfume composition (7), the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例９）グレープフルーツ香料組成物の製造
実施例１の混合物を用いて、下記処方に従って、グレープフルーツ香料組成物（９）を調製した。比較として、下記処方に従いグレープフルーツ香料組成物（１０）を調製した。
(Example 9) Production of grapefruit flavor composition Using the mixture of Example 1, a grapefruit flavor composition (9) was prepared according to the following recipe. For comparison, a grapefruit flavor composition (10) was prepared according to the following formulation.
上記処方で調製したグレープフルーツ香料組成物（９）および（１０）をそれぞれ水に０．１％添加し、１１名の専門パネラーによる官能試験を行ったところ、香料組成物（９）の方が、香料組成物（１０）よりも、本物らしい果汁感、瑞々しさ、フレッシュさが付与され、格段に優れていると全員が指摘した。香料組成物（９）中の実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。 Grapefruit flavor compositions (9) and (10) prepared according to the above formulation were each added to water at 0.1%, and a sensory test was conducted by 11 expert panelists. All of them pointed out that it was much better than the fragrance composition (10), giving it a real fruit juice feel, freshness, and freshness. Regarding the mixture of Example 1 in perfume composition (9), the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例１０）グレープフルーツ香料組成物の製造
実施例１の混合物を用いて、下記処方に従って、グレープフルーツ香料組成物（１１）を調製した。比較として、下記処方に従いグレープフルーツ香料組成物（１２）を調製した。
(Example 10) Production of grapefruit flavor composition Using the mixture of Example 1, a grapefruit flavor composition (11) was prepared according to the following recipe. For comparison, a grapefruit flavor composition (12) was prepared according to the following formulation.
上記処方で調製したグレープフルーツ香料組成物（１１）および（１２）をそれぞれ水に０．１％添加し、１１名の専門パネラーによる官能試験を行ったところ、香料組成物（１１）の方が、香料組成物（１２）よりも、本物らしい果汁感、瑞々しさ、フレッシュさが付与され、格段に優れていると全員が指摘した。香料組成物（１１）中の実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。 Grapefruit flavor compositions (11) and (12) prepared according to the above formulation were each added to water at 0.1%, and a sensory test was conducted by 11 expert panelists. Everyone pointed out that it was much better than the fragrance composition (12), giving a real fruit juice feel, freshness, and freshness. Regarding the mixture of Example 1 in perfume composition (11), the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例１１）ライム香料組成物の製造
実施例１の混合物を用いて、下記処方に従って、ライム香料組成物（１３）を調製した。比較として、下記処方に従いライム香料組成物（１４）を調製した。
(Example 11) Production of lime flavor composition Using the mixture of Example 1, a lime flavor composition (13) was prepared according to the following recipe. For comparison, a lime flavor composition (14) was prepared according to the following formulation.
上記処方で調製したライム香料組成物（１３）および（１４）をそれぞれ水に０．１％添加し、１１名の専門パネラーによる官能試験を行ったところ、香料組成物（１３）の方が、香料組成物（１４）よりも、瑞々しい甘い香りが付与され、格段に優れていると全員が指摘した。香料組成物（１３）中の実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。 Lime fragrance compositions (13) and (14) prepared according to the above formulation were each added at 0.1% to water, and a sensory test was conducted by 11 expert panelists. All of them pointed out that it imparted a fresh, sweet scent and was much superior to fragrance composition (14). Regarding the mixture of Example 1 in perfume composition (13), the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例１２）ライム香料組成物の製造
実施例１の混合物を用いて、下記処方に従って、ライム香料組成物（１５）を調製した。比較として、下記処方に従いライム香料組成物（１６）を調製した。
(Example 12) Production of lime flavor composition Using the mixture of Example 1, a lime flavor composition (15) was prepared according to the following recipe. For comparison, a lime flavor composition (16) was prepared according to the following formulation.
上記処方で調製したライム香料組成物（１５）および（１６）をそれぞれ水に０．１％添加し、１１名の専門パネラーによる官能試験を行ったところ、香料組成物（１５）の方が、香料組成物（１６）よりも、瑞々しい甘い香りが付与され、格段に優れていると全員が指摘した。香料組成物（１７）中の実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。 Lime fragrance compositions (15) and (16) prepared according to the above formulation were each added to water at 0.1%, and a sensory test was conducted by 11 expert panelists. All of the respondents pointed out that it imparted a fresh, sweet scent and was much superior to fragrance composition (16). Regarding the mixture of Example 1 in perfume composition (17), the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例１３）ユズ香料組成物の製造
実施例１の混合物を用いて、下記処方に従って、ユズ香料組成物（１７）を調製した。比較として、下記処方に従いユズ香料組成物（１８）を調製した。
(Example 13) Production of Yuzu Flavor Composition Using the mixture of Example 1, a Yuzu flavor composition (17) was prepared according to the following recipe. For comparison, a yuzu fragrance composition (18) was prepared according to the following formulation.
上記処方で調製したユズ香料組成物（１７）および（１８）をそれぞれ水に０．１％添加し、１１名の専門パネラーによる官能試験を行ったところ、香料組成物（１７）の方が、香料組成物（１８）よりも、瑞々しい甘い香りが付与され、格段に優れていると全員が指摘した。香料組成物（１７）中の実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。 Yuzu fragrance compositions (17) and (18) prepared according to the above formulation were each added to water at 0.1%, and a sensory test was conducted by 11 expert panelists. All of them pointed out that it imparted a fresh, sweet scent and was much superior to fragrance composition (18). Regarding the mixture of Example 1 in perfume composition (17), the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例１４）ユズ香料組成物の製造
実施例１の混合物を用いて、下記処方に従って、ユズ香料組成物（１９）を調製した。比較として、下記処方に従いユズ香料組成物（２０）を調製した。
(Example 14) Production of Yuzu Flavor Composition Using the mixture of Example 1, a Yuzu flavor composition (19) was prepared according to the following recipe. For comparison, a yuzu fragrance composition (20) was prepared according to the following formulation.
上記処方で調製したユズ香料組成物（１９）および（２０）をそれぞれ水に０．１％添加し、１１名の専門パネラーによる官能試験を行ったところ、香料組成物（１９）の方が、香料組成物（２０）よりも、瑞々しい甘い香りが付与され、格段に優れていると全員が指摘した。香料組成物（１９）中の実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。 Yuzu fragrance compositions (19) and (20) prepared according to the above formulation were each added at 0.1% to water, and a sensory test was conducted by 11 expert panelists. All of them pointed out that it imparted a fresh, sweet scent and was much superior to fragrance composition (20). Regarding the mixture of Example 1 in perfume composition (19), the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例１５）サイダー香料組成物の製造
実施例１の混合物を用いて、下記処方に従って、サイダー香料組成物（２１）を調製した。比較として、下記処方に従いサイダー香料組成物（２２）を調製した。
(Example 15) Production of cider flavor composition A cider flavor composition (21) was prepared using the mixture of Example 1 according to the following recipe. For comparison, a cider flavor composition (22) was prepared according to the following formulation.
上記処方で調製したサイダー香料組成物（２１）および（２２）をそれぞれ水に０．１％添加し、１１名の専門パネラーによる官能試験を行ったところ、香料組成物（２１）の方が、香料組成物（２２）よりも、シトラス様の瑞々しい甘さ、炭酸感が付与され、格段に優れていると全員が指摘した。香料組成物（２１）中の実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。 Cider flavor compositions (21) and (22) prepared according to the above formulation were each added to water at 0.1%, and a sensory test was conducted by 11 expert panelists. All of them pointed out that it was much better than the fragrance composition (22), giving it a citrus-like fresh sweetness and carbonic acidity. Regarding the mixture of Example 1 in perfume composition (21), the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例１６）アップル香料組成物の製造
実施例１の混合物を用いて、下記処方に従って、アップル香料組成物（２３）を調製した。比較として、下記処方に従いアップル香料組成物（２４）を調製した。
(Example 16) Manufacture of apple flavor composition Using the mixture of Example 1, an apple flavor composition (23) was prepared according to the following recipe. For comparison, an apple flavor composition (24) was prepared according to the following formulation.
上記処方で調製したアップル香料組成物（２３）および（２４）をそれぞれ水に０．１％添加し、１１名の専門パネラーによる官能試験を行ったところ、香料組成物（２３）の方が、香料組成物（２４）よりも、自然な果汁感が付与され、格段に優れていると全員が指摘した。香料組成物（２３）中の実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。 Apple fragrance compositions (23) and (24) prepared according to the above formulation were each added to water at 0.1%, and a sensory test was conducted by 11 expert panelists. All of the respondents pointed out that it imparted a natural fruit juice feel and was much better than the fragrance composition (24). Regarding the mixture of Example 1 in perfume composition (23), the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例１７）グレープ香料組成物の製造
実施例１の混合物を用いて、下記処方に従って、グレープ香料組成物（２５）を調製した。比較として、下記処方に従いグレープ香料組成物（２６）を調製した。
(Example 17) Production of grape flavor composition Using the mixture of Example 1, a grape flavor composition (25) was prepared according to the following recipe. For comparison, a grape flavor composition (26) was prepared according to the following formulation.
上記処方で調製したグレープ香料組成物（２５）および（２６）をそれぞれ水に０．１％添加し、１１名の専門パネラーによる官能試験を行ったところ、香料組成物（２５）の方が、香料組成物（２６）よりも、自然な果汁感が付与され、格段に優れていると全員が指摘した。香料組成物（２５）中の実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。 Grape fragrance compositions (25) and (26) prepared according to the above formulation were each added to water at 0.1%, and a sensory test was conducted by 11 expert panelists. All of the respondents pointed out that it imparted a natural fruit juice feel and was much better than the fragrance composition (26). Regarding the mixture of Example 1 in perfume composition (25), the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例１８）ピーチ香料組成物の製造
実施例１の混合物を用いて、下記処方に従って、ピーチ香料組成物（２７）を調製した。比較として、下記処方に従いピーチ香料組成物（２８）を調製した。
(Example 18) Manufacture of peach flavor composition Using the mixture of Example 1, a peach flavor composition (27) was prepared according to the following recipe. For comparison, a peach fragrance composition (28) was prepared according to the following formulation.
上記処方で調製したピーチ香料組成物（２７）および（２８）をそれぞれ水に０．１％添加し、１１名の専門パネラーによる官能試験を行ったところ、香料組成物（２７）の方が、香料組成物（２８）よりも、自然な果汁感が付与され、格段に優れていると全員が指摘した。香料組成物（２７）中の実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。 Peach fragrance compositions (27) and (28) prepared according to the above formulation were each added to water at 0.1%, and a sensory test was conducted by 11 expert panelists. All of the respondents pointed out that it imparted a natural fruit juice feel and was much better than the fragrance composition (28). Regarding the mixture of Example 1 in perfume composition (27), the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例１９）パイナップル香料組成物の製造
実施例１の混合物を用いて、下記処方に従って、パイナップル香料組成物（２９）を調製した。比較として、下記処方に従いパイナップル香料組成物（３０）を調製した。
(Example 19) Manufacture of pineapple flavor composition Using the mixture of Example 1, a pineapple flavor composition (29) was prepared according to the following recipe. For comparison, a pineapple flavor composition (30) was prepared according to the following formulation.
上記処方で調製したパイナップル香料組成物（２９）および（３０）をそれぞれ水に０．１％添加し、１１名の専門パネラーによる官能試験を行ったところ、香料組成物（２９）の方が、香料組成物（３０）よりも、自然な果汁感が付与され、格段に優れていると全員が指摘した。香料組成物（２９）中の実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。 Pineapple fragrance compositions (29) and (30) prepared according to the above formulation were each added to water at 0.1%, and a sensory test was conducted by 11 expert panelists. All of the respondents pointed out that it imparted a natural fruit juice feel and was much better than the fragrance composition (30). Regarding the mixture of Example 1 in perfume composition (29), the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例２０）バナナ香料組成物の製造
実施例１の混合物を用いて、下記処方に従って、バナナ香料組成物（３１）を調製した。比較として、下記処方に従いバナナ香料組成物（３２）を調製した。
(Example 20) Manufacture of Banana Flavor Composition Using the mixture of Example 1, a banana flavor composition (31) was prepared according to the following recipe. For comparison, a banana flavor composition (32) was prepared according to the following formulation.
上記処方で調製したバナナ香料組成物（３１）および（３２）をそれぞれ水に０．１％添加し、１１名の専門パネラーによる官能試験を行ったところ、香料組成物（３１）の方が、香料組成物（３２）よりも、自然な果汁感が付与され、格段に優れていると全員が指摘した。香料組成物（３１）中の実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。 Banana flavor compositions (31) and (32) prepared according to the above formulation were each added to water at 0.1%, and a sensory test was conducted by 11 expert panelists. All of them pointed out that it imparted a natural fruit juice feel and was much better than the fragrance composition (32). Regarding the mixture of Example 1 in perfume composition (31), the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例２１）ストロベリー香料組成物の製造
実施例１の混合物を用いて、下記処方に従って、ストロベリー香料組成物（３３）を調製した。比較として、下記処方に従いストロベリー香料組成物（３４）を調製した。
(Example 21) Production of Strawberry Flavor Composition Using the mixture of Example 1, a strawberry flavor composition (33) was prepared according to the following recipe. For comparison, a strawberry flavor composition (34) was prepared according to the following formulation.
上記処方で調製したストロベリー香料組成物（３３）および（３４）をそれぞれ水に０．１％添加し、１１名の専門パネラーによる官能試験を行ったところ、香料組成物（３３）の方が、香料組成物（３４）よりも、自然な果汁感が付与され、格段に優れていると全員が指摘した。香料組成物（３３）中の実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。 Strawberry flavor compositions (33) and (34) prepared according to the above formulation were each added to water at 0.1%, and a sensory test was conducted by 11 expert panelists. All of the respondents pointed out that it imparted a natural fruit juice feel and was much better than the fragrance composition (34). Regarding the mixture of Example 1 in perfume composition (33), the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例２２）ラズベリー香料組成物の製造
実施例１の混合物を用いて、下記処方に従って、ラズベリー香料組成物（３５）を調製した。比較として、下記処方に従いラズベリー香料組成物（３６）を調製した。
(Example 22) Production of raspberry flavor composition Using the mixture of Example 1, a raspberry flavor composition (35) was prepared according to the following recipe. For comparison, a raspberry flavor composition (36) was prepared according to the following formulation.
上記処方で調製したラズベリー香料組成物（３５）および（３６）をそれぞれ水に０．１％添加し、１１名の専門パネラーによる官能試験を行ったところ、香料組成物（３５）の方が、香料組成物（３６）よりも、自然な果汁感が付与され、格段に優れていると全員が指摘した。香料組成物（３５）中の実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。 Raspberry flavor compositions (35) and (36) prepared according to the above formulation were each added to water at 0.1%, and a sensory test was conducted by 11 expert panelists. All of the respondents pointed out that it imparted a natural fruit juice feel and was much better than the fragrance composition (36). Regarding the mixture of Example 1 in perfume composition (35), the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例２３）ブルーベリー香料組成物の製造
実施例１の混合物を用いて、下記処方に従って、ブルーベリー香料組成物（３７）を調製した。比較として、下記処方に従いブルーベリー香料組成物（３８）を調製した。
(Example 23) Production of blueberry flavor composition A blueberry flavor composition (37) was prepared using the mixture of Example 1 according to the following recipe. For comparison, a blueberry flavor composition (38) was prepared according to the following formulation.
上記処方で調製したブルーベリー香料組成物（３７）および（３８）をそれぞれ水に０．１％添加し、１１名の専門パネラーによる官能試験を行ったところ、香料組成物（３７）の方が、香料組成物（３８）よりも、自然な果汁感が付与され、格段に優れていると全員が指摘した。香料組成物（３７）中の実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。 Blueberry flavor compositions (37) and (38) prepared according to the above formulation were each added at 0.1% to water, and a sensory test was conducted by 11 expert panelists. All of the respondents pointed out that it imparted a natural fruit juice feel and was much better than the fragrance composition (38). Regarding the mixture of Example 1 in perfume composition (37), the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例２４）スパークリングワイン香料組成物の製造
実施例１の混合物を用いて、下記処方に従って、スパークリングワイン香料組成物（３９）を調製した。比較として、下記処方に従いスパークリングワイン香料組成物（４０）を調製した。
(Example 24) Production of sparkling wine flavor composition Using the mixture of Example 1, a sparkling wine flavor composition (39) was prepared according to the following recipe. For comparison, a sparkling wine flavor composition (40) was prepared according to the following formulation.
上記処方で調製したスパークリングワイン香料組成物（３９）および（４０）をそれぞれ水に０．１％添加し、１１名の専門パネラーによる官能試験を行ったところ、香料組成物（３９）の方が、香料組成物（４０）よりも、発泡感を伴う軽やかなアルコール感が付与され、格段に優れていると全員が指摘した。香料組成物（３９）中の実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。 Sparkling wine flavor compositions (39) and (40) prepared according to the above formulation were each added to water at 0.1%, and a sensory test was conducted by 11 expert panelists. , all of them pointed out that it was much better than perfume composition (40), giving a light alcoholic feel accompanied by a foaming feeling. Regarding the mixture of Example 1 in perfume composition (39), the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例２５）ビール香料組成物の製造
実施例１の混合物を用いて、下記処方に従って、ビール香料組成物（４１）を調製した。比較として、下記処方に従いビール香料組成物（４２）を調製した。
(Example 25) Manufacture of Beer Flavor Composition Using the mixture of Example 1, a beer flavor composition (41) was prepared according to the following recipe. For comparison, beer flavor composition (42) was prepared according to the following formulation.
上記処方で調製したビール香料組成物（４１）および（４２）をそれぞれ水に０．１％添加し、１１名の専門パネラーによる官能試験を行ったところ、香料組成物（４１）の方が、香料組成物（４２）よりも、発泡感を伴う軽やかなアルコール感が付与され、格段に優れていると全員が指摘した。香料組成物（４１）中の実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。 Beer flavor compositions (41) and (42) prepared according to the above formulation were each added at 0.1% to water, and a sensory test was conducted by 11 expert panelists. All of the respondents pointed out that it was much better than perfume composition (42), giving a light alcoholic feel accompanied by a foaming feeling. Regarding the mixture of Example 1 in perfume composition (41), the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例２６）グリーンティー香料組成物の製造
実施例１の混合物を用いて、下記処方に従って、グリーンティー香料組成物（４３）を調製した。比較として、下記処方に従いグリーンティー香料組成物（４４）を調製した。
(Example 26) Production of green tea fragrance composition A green tea fragrance composition (43) was prepared using the mixture of Example 1 according to the following formulation. For comparison, a green tea fragrance composition (44) was prepared according to the following formulation.
上記処方で調製したグリーンティー香料組成物（４３）および（４４）をそれぞれ水に０．１％添加し、１１名の専門パネラーによる官能試験を行ったところ、香料組成物（４３）の方が、香料組成物（４４）よりも、広がりのある自然な甘い香りが付与され、格段に優れていると全員が指摘した。香料組成物（４３）中の実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。 Green tea fragrance compositions (43) and (44) prepared according to the above formulation were each added to water at 0.1%, and a sensory test was conducted by 11 expert panelists. , all of them pointed out that it was much better than the perfume composition (44), giving a broader and naturally sweet fragrance. Regarding the mixture of Example 1 in perfume composition (43), the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例２７）ブラックティー香料組成物の製造
実施例１の混合物を用いて、下記処方に従って、ブラックティー香料組成物（４５）を調製した。比較として、下記処方に従いブラックティー香料組成物（４６）を調製した。
(Example 27) Production of black tea fragrance composition A black tea fragrance composition (45) was prepared using the mixture of Example 1 according to the following formulation. For comparison, a black tea fragrance composition (46) was prepared according to the following formulation.
上記処方で調製したブラックティー香料組成物（４５）および（４６）をそれぞれ水に０．１％添加し、１１名の専門パネラーによる官能試験を行ったところ、香料組成物（４５）の方が、香料組成物（４６）よりも、広がりのある自然な甘い香りが付与され、格段に優れていると全員が指摘した。香料組成物（４５）中の実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。 Black tea fragrance compositions (45) and (46) prepared according to the above formulation were each added to water at 0.1%, and a sensory test was conducted by 11 expert panelists. , all of them pointed out that it was much better than the fragrance composition (46), giving a broader and naturally sweet fragrance. Regarding the mixture of Example 1 in perfume composition (45), the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例２８）市販オレンジ果汁飲料への添加
市販オレンジ果汁飲料に実施例１の混合物を０．０１ｐｐｍ添加し、１１名の専門パネラーによる官能試験を行ったところ、３，９－ジメチル－２－オキサトリサイクロ［４．２．１．０３，８］ノナンを添加することにより、本物らしい果汁感、瑞々しさ、フレッシュさが付与され、格段に優れていると全員が指摘した。実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。
(Example 28) Addition to a commercially available orange juice beverage 0.01 ppm of the mixture of Example 1 was added to a commercially available orange juice beverage, and a sensory test was conducted by 11 expert panelists. All of them pointed out that the addition of oxatricyclo[4.2.1.0 3,8 ]nonane imparted a real fruit juice feel, freshness, and freshness, and that it was significantly superior. Regarding the mixture of Example 1, the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例２９）市販レモン果汁飲料への添加
市販レモン果汁飲料に実施例１の混合物を０．０１ｐｐｍ添加し、１１名の専門パネラーによる官能試験を行ったところ、実施例１の混合物を添加することにより、フレッシュさ、瑞々しい甘い香りが付与され、格段に優れていると全員が指摘した。実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。
(Example 29) Addition to a commercially available lemon juice drink 0.01 ppm of the mixture of Example 1 was added to a commercially available lemon juice drink, and a sensory test was conducted by 11 expert panelists, and it was found that the mixture of Example 1 was added. All of them pointed out that this imparted a freshness, a juicy, and sweet aroma, and that it was significantly superior. Regarding the mixture of Example 1, the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例３０）市販グレープフルーツ果汁飲料への添加
市販グレープフルーツ果汁飲料に実施例１の混合物を０．０１ｐｐｍ添加し、１１名の専門パネラーによる官能試験を行ったところ、実施例１の混合物を添加することにより、本物らしい果汁感、瑞々しさ、フレッシュさが付与され、格段に優れていると全員が指摘した。実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。
(Example 30) Addition to a commercially available grapefruit juice drink 0.01 ppm of the mixture of Example 1 was added to a commercially available grapefruit juice drink, and a sensory test was conducted by 11 expert panelists, and it was found that the mixture of Example 1 was added. All of them pointed out that this gave the fruit a real fruit juice feel, freshness, and freshness, making it extremely superior. Regarding the mixture of Example 1, the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例３１）市販ライム果汁飲料への添加
市販ライム果汁飲料に実施例１の混合物を０．０１ｐｐｍ添加し、１１名の専門パネラーによる官能試験を行ったところ、実施例１の混合物を添加することにより、瑞々しい甘い香りが付与され、格段に優れていると全員が指摘した。実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。
(Example 31) Addition to a commercially available lime juice drink 0.01 ppm of the mixture of Example 1 was added to a commercially available lime juice drink, and a sensory test was conducted by 11 expert panelists, and it was found that the mixture of Example 1 was added. All of them pointed out that this imparted a fresh and sweet fragrance, which was extremely superior. Regarding the mixture of Example 1, the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例３２）市販ユズ果汁飲料への添加
市販ユズ果汁飲料に実施例６で製造した実施例１の混合物を０．０１ｐｐｍ添加し、１１名の専門パネラーによる官能試験を行ったところ、実施例１の混合物を添加することにより、瑞々しい甘い香りが付与され、格段に優れていると全員が指摘した。実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。
(Example 32) Addition to a commercially available yuzu fruit juice drink 0.01 ppm of the mixture of Example 1 produced in Example 6 was added to a commercially available yuzu fruit juice drink, and a sensory test was conducted by 11 expert panelists. All of the participants pointed out that the addition of the mixture No. 1 imparted a fresh and sweet fragrance, which was significantly superior. Regarding the mixture of Example 1, the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例３３）市販サイダー飲料への添加
市販サイダー飲料に実施例１の混合物を０．１ｐｐｍ添加し、１１名の専門パネラーによる官能試験を行ったところ、実施例１の混合物を添加することにより、シトラス様の瑞々しい甘さ、炭酸感が付与され、格段に優れていると全員が指摘した。実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。
(Example 33) Addition to commercially available cider beverages 0.1 ppm of the mixture of Example 1 was added to commercially available cider beverages, and a sensory test was conducted by 11 expert panelists. , everyone pointed out that it was extremely excellent, with a fresh citrus-like sweetness and carbonic acidity. Regarding the mixture of Example 1, the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例３４）市販アップル果汁飲料への添加
市販アップル果汁飲料に実施例６で製造した実施例１の混合物を０．１ｐｐｍ添加し、１１名の専門パネラーによる官能試験を行ったところ、実施例１の混合物を添加することにより、自然な果汁感が付与され、格段に優れていると全員が指摘した。実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。
(Example 34) Addition to a commercially available apple juice drink 0.1 ppm of the mixture of Example 1 produced in Example 6 was added to a commercially available apple juice drink, and a sensory test was conducted by 11 expert panelists. All of the respondents pointed out that the addition of the mixture No. 1 imparted a natural fruit juice feel, which was significantly superior. Regarding the mixture of Example 1, the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例３５）市販グレープ果汁飲料への添加
市販グレープ果汁飲料に実施例１の混合物を０．１ｐｐｍ添加し、１１名の専門パネラーによる官能試験を行ったところ、実施例１の混合物を添加することにより、自然な果汁感が付与され、格段に優れていると全員が指摘した。実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。
(Example 35) Addition to a commercially available grape juice drink 0.1 ppm of the mixture of Example 1 was added to a commercially available grape juice drink, and a sensory test was conducted by 11 expert panelists, and it was found that the mixture of Example 1 was added. All of them pointed out that this imparted a natural fruity taste, which was extremely superior. Regarding the mixture of Example 1, the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例３６）市販ピーチ果汁飲料への添加
市販ピーチ果汁飲料に実施例１の混合物を０．１ｐｐｍ添加し、１１名の専門パネラーによる官能試験を行ったところ、実施例１の混合物を添加することにより、自然な果汁感が付与され、格段に優れていると全員が指摘した。実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。
(Example 36) Addition to commercially available peach fruit juice drink 0.1 ppm of the mixture of Example 1 was added to a commercially available peach fruit juice drink, and a sensory test was conducted by 11 expert panelists, and it was found that the mixture of Example 1 was added. All of them pointed out that this imparted a natural fruity taste, which was extremely superior. Regarding the mixture of Example 1, the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例３７）市販スパークリングワインテイスト飲料への添加
市販スパークリングワインテイスト飲料に実施例１の混合物を０．０１ｐｐｍ添加し、１１名の専門パネラーによる官能試験を行ったところ、実施例１の混合物を添加することにより、発泡感を伴う軽やかなアルコール感が付与され、格段に優れていると全員が指摘した。実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。
(Example 37) Addition to a commercially available sparkling wine-taste beverage 0.01 ppm of the mixture of Example 1 was added to a commercially available sparkling wine-taste beverage, and a sensory test was conducted by 11 expert panelists. All the members pointed out that the addition imparted a light alcoholic feel accompanied by a foaming feeling, which was extremely superior. Regarding the mixture of Example 1, the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例３８）市販ビールテイスト飲料への添加
市販ビールテイスト飲料に実施例１の混合物を０．０１ｐｐｍ添加し、１１名の専門パネラーによる官能試験を行ったところ、実施例１の混合物を添加することにより、発泡感を伴う軽やかなアルコール感が付与され、格段に優れていると全員が指摘した。実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。
(Example 38) Addition to a commercially available beer-taste beverage 0.01 ppm of the mixture of Example 1 was added to a commercially available beer-taste beverage, and a sensory test was conducted by 11 expert panelists, and it was found that the mixture of Example 1 was added. All of them pointed out that this imparted a light alcoholic feel with a foamy feel, which was extremely superior. Regarding the mixture of Example 1, the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例３９）市販緑茶飲料への添加
市販緑茶飲料に実施例１の混合物を０．０１ｐｐｍ添加し、１１名の専門パネラーによる官能試験を行ったところ、実施例１の混合物を添加することにより、広がりのある自然な甘い香りが付与され、格段に優れていると全員が指摘した。実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。
(Example 39) Addition to commercially available green tea beverages 0.01 ppm of the mixture of Example 1 was added to commercially available green tea beverages, and a sensory test was conducted by 11 expert panelists. , all of them pointed out that it imparted a broad, natural, sweet fragrance, which was significantly superior. Regarding the mixture of Example 1, the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例４０）市販紅茶飲料への添加
市販紅茶飲料に実施例１の混合物を０．０１ｐｐｍ添加し、１１名の専門パネラーによる官能試験を行ったところ、実施例１の混合物を添加することにより、広がりのある自然な甘い香りが付与され、格段に優れていると全員が指摘した。実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。
(Example 40) Addition to commercially available black tea beverages 0.01 ppm of the mixture of Example 1 was added to a commercially available black tea beverage, and a sensory test was conducted by 11 expert panelists. , all of them pointed out that it imparted a broad, natural, sweet fragrance, which was significantly superior. Regarding the mixture of Example 1, the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例４１）歯磨き粉賦香評価
実施例１の混合物を用いて、下記処方に従って、歯磨き粉向けグレープフルーツ様香料組成物（４７）を調製した。比較として、下記処方に従い歯磨き粉向けグレープフルーツ様香料組成物（４８）を調製した。
(Example 41) Toothpaste Flavoring Evaluation Using the mixture of Example 1, a grapefruit-like flavoring composition (47) for toothpaste was prepared according to the following formulation. For comparison, a grapefruit-like fragrance composition (48) for toothpaste was prepared according to the following formulation.
また、歯磨き粉基材の処方は以下の通りである。 Further, the formulation of the toothpaste base material is as follows.
上記処方で調製した香料組成物および歯磨き用基材を用い、下記歯磨き粉（４９）、（５０）を調整し、官能評価を行った。
（４９）歯磨き粉基材９９０ｇ ＋ 香料組成物（４７） １０ｇ
（５０）歯磨き粉基材９９０ｇ ＋ 香料組成物（４８） １０ｇ
これらについて１１名の専門パネラーによる官能試験を行ったところ、香料組成物（４７）を使用した歯磨き粉（４９）の方が、香料組成物（４８）を使用した歯磨き粉（５０）よりも、本物らしい果汁感、瑞々しさ、フレッシュさが付与され、格段に優れていると全員が指摘した。香料組成物（４７）中の実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。
The following toothpastes (49) and (50) were prepared using the fragrance composition and toothpaste base material prepared according to the above formulation, and subjected to sensory evaluation.
(49) Toothpaste base material 990g + fragrance composition (47) 10g
(50) Toothpaste base material 990g + fragrance composition (48) 10g
When 11 expert panelists conducted a sensory test on these, it was found that the toothpaste (49) using the fragrance composition (47) seemed more authentic than the toothpaste (50) using the fragrance composition (48). All of them pointed out that the taste was much better, with a sense of fruit juice, freshness, and freshness. Regarding the mixture of Example 1 in perfume composition (47), the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例４２）高甘味度甘味料（レバウディオサイドＡ）水溶液への添加
０．０２８質量％レバウディオサイドＡ水溶液に実施例１の混合物を０．０００１ｐｐｍ添加し、１１名の専門パネラーによる官能試験を行ったところ、実施例１の混合物を添加することにより、不快な風味が弱まり、格段に優れていると全員が指摘した。実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。
(Example 42) Addition of high intensity sweetener (rebaudioside A) to aqueous solution 0.0001 ppm of the mixture of Example 1 was added to a 0.028 mass% rebaudioside A aqueous solution, and 11 expert panelists When a sensory test was conducted, all of the respondents pointed out that the addition of the mixture of Example 1 weakened the unpleasant flavor and was significantly superior. Regarding the mixture of Example 1, the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例４３）高甘味度甘味料（アスパルテーム）水溶液への添加
０．０４質量％アスパルテーム水溶液に実施例１の混合物を０．０００１ｐｐｍ添加し、１１名の専門パネラーによる官能試験を行ったところ、実施例１の混合物を添加することにより、後半に膨らみが付与され、格段に優れていると全員が指摘した。実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。
(Example 43) Addition to high-intensity sweetener (aspartame) aqueous solution 0.0001 ppm of the mixture of Example 1 was added to a 0.04 mass% aspartame aqueous solution, and a sensory test was conducted by 11 expert panelists. All the members pointed out that the addition of the mixture of Example 1 gave the second half a bulge, which was much better. Regarding the mixture of Example 1, the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例４４）高甘味度甘味料（スクラロース）水溶液への添加
０．０１３質量％スクラロース水溶液に実施例１の混合物を０．０００１ｐｐｍ添加し、１１名の専門パネラーによる官能試験を行ったところ、実施例１の混合物を添加することにより、味の厚み・甘味の膨らみが付与され、格段に優れていると全員が指摘した。実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。
(Example 44) Addition of high intensity sweetener (sucralose) to aqueous solution 0.0001 ppm of the mixture of Example 1 was added to a 0.013% by mass sucralose aqueous solution, and a sensory test was conducted by 11 expert panelists. All the members pointed out that the addition of the mixture of Example 1 imparted a richer taste and a richer sweetness, which was significantly superior. Regarding the mixture of Example 1, the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
（実施例４５）高甘味度甘味料（アセスルファムＫ）水溶液への添加
０．０４質量％アセスルファムＫ水溶液に実施例１の混合物を０．０００１ｐｐｍ添加し、１１名の専門パネラーによる官能試験を行ったところ、実施例１の混合物を添加することにより、味の厚み・甘味の膨らみが付与され、格段に優れていると全員が指摘した。実施例１の混合物については、４種の異性体のいずれであっても、実施例２の混合物に置き換えた場合も同様の評価であった。
(Example 45) Addition of high intensity sweetener (acesulfame K) to aqueous solution 0.0001 ppm of the mixture of Example 1 was added to a 0.04% by mass acesulfame K aqueous solution, and a sensory test was conducted by 11 expert panelists. However, all the participants pointed out that the addition of the mixture of Example 1 imparted a richer taste and a richer sweetness, which was significantly superior. Regarding the mixture of Example 1, the same evaluation was obtained when any of the four isomers was replaced with the mixture of Example 2.
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| US20060040849A1 (en) | 2004-08-20 | 2006-02-23 | Narula Anubhav P | Novel methanoazuenofurans and methanoazulenone compounds and uses of these compounds as fragrance materials |
| WO2018155720A1 (en) | 2017-02-27 | 2018-08-30 | 高砂香料工業株式会社 | Novel spirosesquiterpene compound, flavoring composition and food/drink containing said compound, and method for producing said food/drink |
| JP6600116B1 (en) | 2019-07-19 | 2019-10-30 | 高砂香料工業株式会社 | Fragrance composition |
| KR102066966B1 (en) | 2018-09-20 | 2020-01-16 | 대구가톨릭대학교산학협력단 | A pharmaceutical composition comprising compounds isolated from the root bark of Morus alba L. for preventing or treating diabetes mellitus |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US20060040849A1 (en) | 2004-08-20 | 2006-02-23 | Narula Anubhav P | Novel methanoazuenofurans and methanoazulenone compounds and uses of these compounds as fragrance materials |
| WO2018155720A1 (en) | 2017-02-27 | 2018-08-30 | 高砂香料工業株式会社 | Novel spirosesquiterpene compound, flavoring composition and food/drink containing said compound, and method for producing said food/drink |
| KR102066966B1 (en) | 2018-09-20 | 2020-01-16 | 대구가톨릭대학교산학협력단 | A pharmaceutical composition comprising compounds isolated from the root bark of Morus alba L. for preventing or treating diabetes mellitus |
| JP6600116B1 (en) | 2019-07-19 | 2019-10-30 | 高砂香料工業株式会社 | Fragrance composition |
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