EP0008103A1 - Application of esters of the mixture tricyclo-(5.2.1.0)decane-3- and tricyclo(5.2.1.0)decane-4-carboxylic acids as perfumes; perfuming compositions containing them - Google Patents
Application of esters of the mixture tricyclo-(5.2.1.0)decane-3- and tricyclo(5.2.1.0)decane-4-carboxylic acids as perfumes; perfuming compositions containing them Download PDFInfo
- Publication number
- EP0008103A1 EP0008103A1 EP79102824A EP79102824A EP0008103A1 EP 0008103 A1 EP0008103 A1 EP 0008103A1 EP 79102824 A EP79102824 A EP 79102824A EP 79102824 A EP79102824 A EP 79102824A EP 0008103 A1 EP0008103 A1 EP 0008103A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- tricyclo
- decane
- esters
- mixture
- carboxylic acids
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 29
- 150000002148 esters Chemical class 0.000 title claims abstract description 19
- 239000002304 perfume Substances 0.000 title description 2
- 239000003205 fragrance Substances 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 1
- 230000035943 smell Effects 0.000 description 7
- 239000002253 acid Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 2
- -1 aliphatic hydrocarbon radical Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241001632578 Hyacinthus orientalis Species 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- 240000007651 Rubus glaucus Species 0.000 description 1
- 235000011034 Rubus glaucus Nutrition 0.000 description 1
- 235000009122 Rubus idaeus Nutrition 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- GVRWIAHBVAYKIZ-UHFFFAOYSA-N dec-3-ene Chemical compound CCCCCCC=CCC GVRWIAHBVAYKIZ-UHFFFAOYSA-N 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- DITHIFQMPPCBCU-UHFFFAOYSA-N propa-1,2-diene Chemical compound [CH]=C=C DITHIFQMPPCBCU-UHFFFAOYSA-N 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
Definitions
- esters of the mixture of tricyclo [5.2.1.0 2.6 ] decane-3 (4) -carboxylic acids of the general formulas in which R represents a saturated or unsaturated, straight-chain or branched aliphatic hydrocarbon radical having 1 to 5 carbon atoms, can advantageously be used as fragrances in compositions for perfuming technical and cosmetic preparations.
- esters to be used according to the invention can be prepared by generally known methods by reacting the tricyclo [5.2.1.0 2.6 ] decane-3 (4) carboxylic acids or their acid chlorides with the corresponding alcohols.
- the mixture of acids is obtained by hydroformylation of tricyclo [5.2.1.0 2.6 ] dec-3-ene with subsequent oxidation, according to the following scheme:
- the mixture of tricyclo- [5.2.1.0 2.6 ] -decane-3 (4) -carboxylic acids obtained in this way is a commercial product under the name TCD-carboxylic acid S.
- esters to be used according to the invention or the acids on which they are based is provided by the carbonylation reactions according to Reppe or Koch.
- the reaction proceeds as follows: If the reaction is carried out in alcohol instead of in an aqueous medium, the corresponding esters are obtained directly.
- the acids or esters also obtained here are a mixture of different stereoisomers of tricyclo [5.2.1.0 2.6 ] decane-3 (4) carboxylic acids or their esters. This mixture is not separated, but as such forms the interesting fragrance to be used according to the invention.
- esters covered by the aforementioned general formula the methyl ester and ethyl ester are known from the literature as such, but their suitability as a fragrance has not been recognized.
- the much more interesting esters of unsaturated alcohols are new compounds.
- the mixtures of the esters of tricyclo [5.2.1.0 2.6 ] decane-3 (4) -carboxylic acids to be used according to the invention are valuable fragrances with characteristic odor notes. They can be combined very well to create new and interesting smells. Among the products, the allyl and propargyl ester mixtures are of the greatest importance due to their special smell notes.
- the Propargylester have an interesting Maggi-Walnut note, while the Allylestern can be attributed an Ocimen, Styrolyl note. Such olfactory notes are particularly suitable for the development of novel fragrance compositions.
- the esters of the mixture of tricyclo [5.2.1.0 2.6 ] decane-3 (4) -carboxylic acids to be used as fragrances according to the invention can be mixed with other fragrances in a wide variety of proportions to give new fragrance compositions.
- the proportion of the esters of the mixture of tricyclo- [5.2.1.0 2.6 ] decane-3 (4) -carboxylic acids in the fragrance move compositions in amounts of 1 - 50 percent by weight, based on the entire composition.
- Such compositions can be used to perfume cosmetics such as creams, lotions, aerosols, toilet soaps, technical articles such as washing and cleaning agents, disinfectants and textile treatment agents.
- esters were prepared from the commercially available TCD carboxylic acid S, which, as stated above, are mixtures.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
Abstract
Verwendung der Ester des Gemisches der Tricyclo[5,2,1,0²,<6>]decan-3(4)-carbonsäuren der allgemeinen Formeln <IMAGE> denen R einen aliphatischen Kohlenwasserstoffrest mit 1-5 Kohlenstoffatomen darstellt, als Riechstoffe, sowie diese enthaltende Riechstoffkompositionen.Use of the esters of the mixture of tricyclo [5,2,1,0², <6>] decane-3 (4) -carboxylic acids of the general formulas <IMAGE> to which R represents an aliphatic hydrocarbon radical with 1-5 carbon atoms, as fragrances, and fragrance compositions containing them.
Description
Es wurde gefunden, daß Ester des Gemisches der Tricyclo[5.2.1.02.6]decan-3(4)-carbonsäuren der allgemeinen Formeln
Von besonderem Interesse ist dabei das Gemisch der Ester, in denen R den Allylrest -CH2-CH=CH2 oder den Propargylrest -CH2-C=CH darstellt.Of particular interest is the mixture of esters in which R represents the allyl radical -CH 2 -CH = CH 2 or the propargyl radical -CH 2 -C = CH.
Die Herstellung der erfindungsgemäß zu verwendenden Ester kann nach allgemein bekannten Methoden durch Umsetzung der Tricyclo[5.2.1.02.6]decan-3(4)carbonsäuren oder deren Säurechloriden mit den entsprechenden Alkoholen erfolgen.The esters to be used according to the invention can be prepared by generally known methods by reacting the tricyclo [5.2.1.0 2.6 ] decane-3 (4) carboxylic acids or their acid chlorides with the corresponding alcohols.
Das Gemisch der Säuren wird durch Hydroformylierung von Tricyclo[5.2.1.02.6] dec-3-en mit nachfolgender Oxidation erhalten, entsprechend folgendem Schema:
Eine andere Möglichkeit zu den erfindungsgemäß zu verwendenden Estern bzw. den ihnen zugrundeliegenden Säuren zu gelangen, bieten die Carbonylierungsreaktionen nach Reppe oder Koch. Die Reaktion verläuft dabei nach folgendem Schema:
Von den unter vorgenannte allgemeine Formel fallenden Estern sind bisher der Methylester und Äthylester als solche literaturbekannt, ohne daß jedoch ihre Eignung als Riechstoff erkannt worden wäre. Die wesentlich interessanteren Ester ungesättigter Alkohole stellen neue Verbindungen dar.Of the esters covered by the aforementioned general formula, the methyl ester and ethyl ester are known from the literature as such, but their suitability as a fragrance has not been recognized. The much more interesting esters of unsaturated alcohols are new compounds.
Die erfindungsgemäß zu verwendenden Gemische der Ester der Tricyclo[5.2.1.02.6] decan-3(4)-carbonsäuren sind wertvolle Riechstoffe mit charakteristischen Geruchsnoten. Sie lassen sich sehr gut zu neuartigen und interessanten Geruchsnuancen kombinieren. Unter den Produkten kommt den Allyl- und Propargylestergemischen aufgrund ihrer besonderen Geruchsnoten die größte Bedeutung zu. Die Propargylester besitzen eine interessante Maggi-Walnuß-Note,während den Allylestern eine Ocimen-, Styrolyl-Note zuzuschreiben ist. Derartige Geruchsnoten sind für die Entwicklung neuartiger Riechstoffkompositionen besonders geeignet.The mixtures of the esters of tricyclo [5.2.1.0 2.6 ] decane-3 (4) -carboxylic acids to be used according to the invention are valuable fragrances with characteristic odor notes. They can be combined very well to create new and interesting smells. Among the products, the allyl and propargyl ester mixtures are of the greatest importance due to their special smell notes. The Propargylester have an interesting Maggi-Walnut note, while the Allylestern can be attributed an Ocimen, Styrolyl note. Such olfactory notes are particularly suitable for the development of novel fragrance compositions.
Die erfindungsgemäß als Riechstoffe zu verwendenden Ester des Gemisches der Tricyclo[5.2.1.02.6]decan-3(4)-carbonsäuren können mit anderen Riechstoffen in den verschiedensten Mengenverhältnissen zu neuen Riechstoffkompositionen gemischt werden. Im allgemeinen wird sich der Anteil der Ester des Gemisches der Tricyclo-[5.2.1.02.6]decan-3(4)-carbonsäuren in den Riechstoffkompositionen in den Mengen von 1 - 50 Gewichtsprozent, bezogen auf die gesamte Komposition, bewegen. Derartige Kompositionen können zur Parfümierung von Kosmetika wie Cremes, Lotionen, Aerosolen, Toiletteseifen, technischen Artikeln wie Wasch- und Reinigungsmitteln, Desinfektionsmitteln und Textilbehandlungsmitteln dienen.The esters of the mixture of tricyclo [5.2.1.0 2.6 ] decane-3 (4) -carboxylic acids to be used as fragrances according to the invention can be mixed with other fragrances in a wide variety of proportions to give new fragrance compositions. In general, the proportion of the esters of the mixture of tricyclo- [5.2.1.0 2.6 ] decane-3 (4) -carboxylic acids in the fragrance move compositions in amounts of 1 - 50 percent by weight, based on the entire composition. Such compositions can be used to perfume cosmetics such as creams, lotions, aerosols, toilet soaps, technical articles such as washing and cleaning agents, disinfectants and textile treatment agents.
Die nachfolgenden Beispiele sollen den Gegenstand der Erfindung näher erläutern, ohne ihn jedoch hierauf zu beschränken.The following examples are intended to explain the subject matter of the invention in more detail, but without restricting it thereto.
Nach allgemein bekannten Veresterungsverfahren wurden aus der als Handelsprodukt erhältlichen TCD-Carbonsäure S folgende Ester hergestellt, wobei es sich, wie vorstehend ausgeführt, um Gemische handelt.According to generally known esterification processes, the following esters were prepared from the commercially available TCD carboxylic acid S, which, as stated above, are mixtures.
Tricyclo [5.2.1.02.6]decan-3(4)-carbonsäure-propargylester Kp0,013 mbar 100 - 110°
Geruch: Ocimen-, Styrolyl-Note Tricyclo[5.2.1.02.6]decan-3(4)-carbonsäure- ethylester Kp0,013 mbar 60 - 63°
Lit:
- Kp4 mbar 103°
- Geruch: fruchtig, Marmeladen-Note
- Tricyclo [5.2.1.02.6]decan-3(4)-carbonsäuren-propylester
- Kp0,015 mbar 94 - 100°
- Geruch: technisch, Maggi-Note
- Tricyclo [5.2.1.02.6]decan-3(4)-carbonsäure- iso-propylester
- Kp0,07 mbar 67 - 72°
- Geruch: Himbeer-Note /6 Tricyclo [5.2.1.02.6]decan-3(4)-carbonsäuren-butylester
- Kp0,07 mbar 78-80°
- Geruch: schwach fruchtig
- Kp 4 mbar 103 °
- Smell: fruity, jam note
- Tricyclo [5.2.1.0 2.6 ] decane-3 (4) -carboxylic acid propyl ester
- Kp 0.015 mbar 94 - 100 °
- Smell: technical, maggi note
- Tricyclo [5.2.1.0 2.6 ] decane-3 (4) -carboxylic acid iso-propyl ester
- Kp 0.07 mbar 67 - 72 °
- Smell: raspberry note / 6 Tricyclo [5.2.1.0 2.6 ] butyl decane-3 (4) -carboxylic ester
- Kp 0.07 mbar 78-80 °
- Smell: slightly fruity
Tricyclo [5.2.1.02.6] decan-3(4)-carbonsäure- tert.-butylester Kp0,07 mbar 92 - 95°
Claims (4)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2835445A DE2835445C2 (en) | 1978-08-12 | 1978-08-12 | Use of esters of the mixture of tricyclo- [5.2.1.0 → 2 → →. → → 6 →] decane-3 and tricyclo [5.2.1.0 → 2 → →. → → 6 →] decane-4-carboxylic acid as fragrances, and fragrance compositions containing them |
| DE2835445 | 1978-08-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0008103A1 true EP0008103A1 (en) | 1980-02-20 |
| EP0008103B1 EP0008103B1 (en) | 1981-05-20 |
Family
ID=6046925
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP79102824A Expired EP0008103B1 (en) | 1978-08-12 | 1979-08-06 | Application of esters of the mixture tricyclo-(5.2.1.0)decane-3- and tricyclo(5.2.1.0)decane-4-carboxylic acids as perfumes; perfuming compositions containing them |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US4311616A (en) |
| EP (1) | EP0008103B1 (en) |
| JP (1) | JPS5527188A (en) |
| BR (1) | BR7905147A (en) |
| CA (1) | CA1126165A (en) |
| DE (1) | DE2835445C2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2477874A1 (en) * | 1980-03-14 | 1981-09-18 | Kao Corp | FRAGRANCE COMPOSITION BASED ON TRICYCLO (5.2.1.0.2.6) METHYL DECANE-2-CARBOXYLATE AND PROCESS FOR PREPARING THE SAME |
| FR2478084A1 (en) * | 1980-03-14 | 1981-09-18 | Kao Corp | NOVEL ESTERS OF TRICYCLO (5.2.1.02,6) DECANE-2-CARBOXYLIC ACID, PROCESSES FOR THEIR PREPARATION AND THEIR USE IN PERFUMERY |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4311852A (en) * | 1978-07-05 | 1982-01-19 | Firmenich Sa | Oxygen containing derivatives of tricyclo[6.2.1.02,7 ]undecane |
| JPS56128710A (en) * | 1980-03-14 | 1981-10-08 | Kao Corp | Perfume composition |
| US4529599A (en) * | 1982-12-16 | 1985-07-16 | Kao Corporation | Tricyclic carboxylate ester and insecticide containing the same |
| EP3024427B1 (en) * | 2013-07-22 | 2019-10-09 | Takasago International Corporation | Derivatives of 2,2,6-trimethylcyclohexane-carboxylate |
| JP5580947B1 (en) * | 2014-01-20 | 2014-08-27 | 高級アルコール工業株式会社 | Novel ester compound and cosmetics and cosmetics containing the same |
| KR101801648B1 (en) | 2014-01-20 | 2017-11-27 | 고큐 아르코르 고교 가부시키가이샤 | Novel ester compound, and cosmetic component and cosmetic product each containing same |
| JP5663111B1 (en) * | 2014-07-08 | 2015-02-04 | 高級アルコール工業株式会社 | Novel ester compound and cosmetics and cosmetics containing the same |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2334343A1 (en) * | 1975-12-08 | 1977-07-08 | Firmenich & Cie | USE OF TRICYCLO-DECANE DERIVATIVES AS PERFUMING INGREDIENTS |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2688627A (en) * | 1952-05-08 | 1954-09-07 | Standard Oil Dev Co | Dicyclopentadiene carboxylic acids |
| US3679749A (en) * | 1968-06-10 | 1972-07-25 | Int Flavors & Fragrances Inc | Perhydro 1,4,9,9-tetramethyl-4,7-methandazulenones |
| US3598745A (en) * | 1968-10-31 | 1971-08-10 | Universal Oil Prod Co | Substituted 4,7-methanoindenes perfume compositions |
| CH529214A (en) * | 1970-04-06 | 1972-10-15 | Roure Bertrand Dupont Sa | Fragrance compositions |
-
1978
- 1978-08-12 DE DE2835445A patent/DE2835445C2/en not_active Expired
-
1979
- 1979-08-06 EP EP79102824A patent/EP0008103B1/en not_active Expired
- 1979-08-09 JP JP10080479A patent/JPS5527188A/en active Granted
- 1979-08-10 US US06/065,606 patent/US4311616A/en not_active Expired - Lifetime
- 1979-08-10 BR BR7905147A patent/BR7905147A/en unknown
- 1979-08-13 CA CA333,647A patent/CA1126165A/en not_active Expired
-
1980
- 1980-07-21 US US06/170,914 patent/US4289660A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2334343A1 (en) * | 1975-12-08 | 1977-07-08 | Firmenich & Cie | USE OF TRICYCLO-DECANE DERIVATIVES AS PERFUMING INGREDIENTS |
Non-Patent Citations (1)
| Title |
|---|
| FETTE, SEIFEN, ANSTRICHMITTEL; Band 67, Nr. 4, 1965, Hamburg, DE H.P. KAUFMANN und B. GROTHUES: "Abkommlinge des Tricyclodecans auf dem Fettgebeit I: Tricyclodecamethanal als Ausgangsmaterial". Seiten 249-257. * Seite 251, Formel IX; Seite 253, "Methylester der Siruposen beta. Tricyclodecylacrylsaure" und "Tricyclodecylglylcolsaure-Methylester"; Seite 254, "Gemisch der Isomeren Tricyclodecylsauren" und Tricyclodecylalcohol-Isomerengemisch" * * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2477874A1 (en) * | 1980-03-14 | 1981-09-18 | Kao Corp | FRAGRANCE COMPOSITION BASED ON TRICYCLO (5.2.1.0.2.6) METHYL DECANE-2-CARBOXYLATE AND PROCESS FOR PREPARING THE SAME |
| FR2478084A1 (en) * | 1980-03-14 | 1981-09-18 | Kao Corp | NOVEL ESTERS OF TRICYCLO (5.2.1.02,6) DECANE-2-CARBOXYLIC ACID, PROCESSES FOR THEIR PREPARATION AND THEIR USE IN PERFUMERY |
Also Published As
| Publication number | Publication date |
|---|---|
| BR7905147A (en) | 1980-05-06 |
| DE2835445A1 (en) | 1980-02-28 |
| JPS622564B2 (en) | 1987-01-20 |
| US4289660A (en) | 1981-09-15 |
| EP0008103B1 (en) | 1981-05-20 |
| JPS5527188A (en) | 1980-02-27 |
| CA1126165A (en) | 1982-06-22 |
| US4311616A (en) | 1982-01-19 |
| DE2835445C2 (en) | 1986-12-11 |
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