JP2018121599A - カプサイシノイド含有油脂組成物用辛味増強剤 - Google Patents
カプサイシノイド含有油脂組成物用辛味増強剤 Download PDFInfo
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- JP2018121599A JP2018121599A JP2017018258A JP2017018258A JP2018121599A JP 2018121599 A JP2018121599 A JP 2018121599A JP 2017018258 A JP2017018258 A JP 2017018258A JP 2017018258 A JP2017018258 A JP 2017018258A JP 2018121599 A JP2018121599 A JP 2018121599A
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- Prior art keywords
- capsaicinoid
- oil
- acid
- fatty acid
- acid ester
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- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 title claims abstract description 66
- 239000000203 mixture Substances 0.000 title claims abstract description 53
- 235000019633 pungent taste Nutrition 0.000 title claims abstract description 27
- 239000003623 enhancer Substances 0.000 title claims abstract description 22
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 48
- 229930195729 fatty acid Natural products 0.000 claims abstract description 48
- 239000000194 fatty acid Substances 0.000 claims abstract description 48
- -1 diglycerol fatty acid ester Chemical class 0.000 claims abstract description 46
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000004480 active ingredient Substances 0.000 claims abstract description 6
- 229940105990 diglycerin Drugs 0.000 claims description 29
- 235000011187 glycerol Nutrition 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 11
- 230000002708 enhancing effect Effects 0.000 claims description 4
- 239000003921 oil Substances 0.000 description 42
- 235000019198 oils Nutrition 0.000 description 42
- 239000003925 fat Substances 0.000 description 40
- 235000019197 fats Nutrition 0.000 description 34
- 229930003231 vitamin Natural products 0.000 description 16
- 229940088594 vitamin Drugs 0.000 description 16
- 235000013305 food Nutrition 0.000 description 12
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 11
- 235000011194 food seasoning agent Nutrition 0.000 description 8
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 8
- 150000004665 fatty acids Chemical class 0.000 description 7
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 6
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 6
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 6
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 6
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 6
- 235000021355 Stearic acid Nutrition 0.000 description 5
- 229930014626 natural product Natural products 0.000 description 5
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 5
- 150000007524 organic acids Chemical class 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 239000008117 stearic acid Substances 0.000 description 5
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 4
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- 239000005642 Oleic acid Substances 0.000 description 4
- 235000021314 Palmitic acid Nutrition 0.000 description 4
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 4
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 4
- 229960002504 capsaicin Drugs 0.000 description 4
- 235000017663 capsaicin Nutrition 0.000 description 4
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 4
- 229960004488 linolenic acid Drugs 0.000 description 4
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- 235000021313 oleic acid Nutrition 0.000 description 4
- 150000004671 saturated fatty acids Chemical class 0.000 description 4
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 4
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 4
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 4
- 235000015112 vegetable and seed oil Nutrition 0.000 description 4
- 239000008158 vegetable oil Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 235000021357 Behenic acid Nutrition 0.000 description 3
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 3
- 235000002568 Capsicum frutescens Nutrition 0.000 description 3
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 3
- 239000005639 Lauric acid Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000010775 animal oil Substances 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 229940116226 behenic acid Drugs 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 235000019871 vegetable fat Nutrition 0.000 description 3
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 2
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 2
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 2
- 239000004278 EU approved seasoning Substances 0.000 description 2
- AKDLSISGGARWFP-UHFFFAOYSA-N Homodihydrocapsaicin Chemical compound COC1=CC(CNC(=O)CCCCCCCC(C)C)=CC=C1O AKDLSISGGARWFP-UHFFFAOYSA-N 0.000 description 2
- 240000008415 Lactuca sativa Species 0.000 description 2
- 235000021353 Lignoceric acid Nutrition 0.000 description 2
- CQXMAMUUWHYSIY-UHFFFAOYSA-N Lignoceric acid Natural products CCCCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 CQXMAMUUWHYSIY-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- VQEONGKQWIFHMN-UHFFFAOYSA-N Nordihydrocapsaicin Chemical compound COC1=CC(CNC(=O)CCCCCC(C)C)=CC=C1O VQEONGKQWIFHMN-UHFFFAOYSA-N 0.000 description 2
- 235000019484 Rapeseed oil Nutrition 0.000 description 2
- 235000019485 Safflower oil Nutrition 0.000 description 2
- 235000019486 Sunflower oil Nutrition 0.000 description 2
- 229930003268 Vitamin C Natural products 0.000 description 2
- 229930003427 Vitamin E Natural products 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 235000005687 corn oil Nutrition 0.000 description 2
- 239000002285 corn oil Substances 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- XJQPQKLURWNAAH-UHFFFAOYSA-N dihydrocapsaicin Chemical compound COC1=CC(CNC(=O)CCCCCCC(C)C)=CC=C1O XJQPQKLURWNAAH-UHFFFAOYSA-N 0.000 description 2
- RBCYRZPENADQGZ-UHFFFAOYSA-N dihydrocapsaicin Natural products COC1=CC(COC(=O)CCCCCCC(C)C)=CC=C1O RBCYRZPENADQGZ-UHFFFAOYSA-N 0.000 description 2
- FARYTWBWLZAXNK-WAYWQWQTSA-N ethyl (z)-3-(methylamino)but-2-enoate Chemical compound CCOC(=O)\C=C(\C)NC FARYTWBWLZAXNK-WAYWQWQTSA-N 0.000 description 2
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
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- 229960002446 octanoic acid Drugs 0.000 description 2
- 229940049964 oleate Drugs 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
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- 235000019154 vitamin C Nutrition 0.000 description 2
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- 229940046009 vitamin E Drugs 0.000 description 2
- 239000011709 vitamin E Substances 0.000 description 2
- DNISEZBAYYIQFB-PHDIDXHHSA-N (2r,3r)-2,3-diacetyloxybutanedioic acid Chemical compound CC(=O)O[C@@H](C(O)=O)[C@H](C(O)=O)OC(C)=O DNISEZBAYYIQFB-PHDIDXHHSA-N 0.000 description 1
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical class O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 1
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
- FKOKUHFZNIUSLW-UHFFFAOYSA-N 2-Hydroxypropyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(C)O FKOKUHFZNIUSLW-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
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- 240000008574 Capsicum frutescens Species 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
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- 235000019482 Palm oil Nutrition 0.000 description 1
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- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
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- 241001247145 Sebastes goodei Species 0.000 description 1
- NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
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- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
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- 230000000694 effects Effects 0.000 description 1
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
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- JKIHLSTUOQHAFF-UHFFFAOYSA-N homocapsaicin Natural products COC1=CC(CNC(=O)CCCCCC=CC(C)C)=CC=C1O JKIHLSTUOQHAFF-UHFFFAOYSA-N 0.000 description 1
- MLJGZARGNROKAC-VQHVLOKHSA-N homocapsaicin Chemical compound CCC(C)\C=C\CCCCC(=O)NCC1=CC=C(O)C(OC)=C1 MLJGZARGNROKAC-VQHVLOKHSA-N 0.000 description 1
- JZNZUOZRIWOBGG-UHFFFAOYSA-N homocapsaicin-II Natural products COC1=CC(CNC(=O)CCCCC=CCC(C)C)=CC=C1O JZNZUOZRIWOBGG-UHFFFAOYSA-N 0.000 description 1
- GOBFKCLUUUDTQE-UHFFFAOYSA-N homodihydrocapsaicin-II Natural products CCC(C)CCCCCCC(=O)NCC1=CC=C(O)C(OC)=C1 GOBFKCLUUUDTQE-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Seasonings (AREA)
- Edible Oils And Fats (AREA)
Abstract
Description
(1)ジグリセリン脂肪酸エステル及び/又はグリセリン有機酸脂肪酸エステルを有効成分とすることを特徴とするカプサイシノイド含有油脂組成物用辛味増強剤。
(2)カプサイシノイドを含有する油脂組成物にジグリセリン脂肪酸エステル及び/又はグリセリン有機酸脂肪酸エステルを添加することを特徴とするカプサイシノイドの辛味増強方法。
本発明の辛味増強剤を添加したカプサイシノイド含有油脂組成物は、カプサイシノイドの含有量が比較的少量でも十分な辛味を呈する。
(1)原材料
1)菜種サラダ油(商品名;ボーソー油脂社製)
2)唐辛子抽出物製剤(商品名:オレオレジンカプシカム#62;カプサイシン濃度約1%;高田香料社製)
3)ジグリセリンオレイン酸エステル(商品名:ポエムDO−100V;理研ビタミン社製)
4)ジグリセリンパルミチン酸エステル(商品名:ポエムDP−95RF;理研ビタミン社製)
5)グリセリンクエン酸脂肪酸エステル(商品名:ポエムK−37V;理研ビタミン社製)
6)グリセリンジアセチル酒石酸脂肪酸エステル(商品名:ポエムW−60;理研ビタミン社製)
7)グリセリン酢酸脂肪酸エステル(商品名:ポエムG−002;理研ビタミン社製)
8)グリセリンオレイン酸エステル(商品名:ポエムOL−200V;理研ビタミン社製)
9)トリグリセリンパルミチン酸エステル(商品名:ポエムTRP−97RF;理研ビタミン社製)
10)ヘキサグリセリン縮合リシノール酸エステル(商品名:ポエムPR−300;理研ビタミン社製)
11)プロピレングリコールステアリン酸エステル(商品名:リケマールPS−100;理研ビタミン社製)
12)ソルビタンオレイン酸エステル(商品名:ポエムO−80V;理研ビタミン社製)
上記原材料を用いて調製したカプサイシノイド含有油脂組成物1〜12の配合組成を表1に示した。これらの内、カプサイシノイド含有油脂組成物1〜6は本発明の辛味増強剤を添加した実施例であり、カプサイシノイド含有油脂組成物7〜11は本発明の辛味増強剤以外の乳化剤を添加した比較例である。また、対照としてカプサイシノイド含有油脂組成物12は乳化剤を一切添加せずに調製した。
表1に示した配合割合に従って、200ml容量のビーカーに原材料を合計100gとなるように量りとり、60℃に加熱しながらよく撹拌して混合し、常温まで放冷してカプサイシノイド含有油脂組成物1〜12各100gを得た。
得られたカプサイシノイド含有油脂組成物1〜12について、辛味に関しての官能評価を、表2に示す評価基準に従い10名のパネラーで行った。結果はそれぞれ10名の評点の平均値を求め、下記基準にて記号化した。結果を表3に示す。
<記号化基準>
◎:極めて良好 平均値3.5以上
○:良好 平均値2.5以上、3.5未満
△:やや悪い 平均値1.5以上、2.5未満
×:悪い 平均値1.5未満
Claims (2)
- ジグリセリン脂肪酸エステル及び/又はグリセリン有機酸脂肪酸エステルを有効成分とすることを特徴とするカプサイシノイド含有油脂組成物用辛味増強剤。
- カプサイシノイドを含有する油脂組成物にジグリセリン脂肪酸エステル及び/又はグリセリン有機酸脂肪酸エステルを添加することを特徴とするカプサイシノイドの辛味増強方法。
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JP2021058176A (ja) * | 2019-10-09 | 2021-04-15 | 学校法人神奈川大学 | 調味料、食品、刺激成分による刺激の増加方法及び刺激成分による刺激の増加剤 |
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