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 PDF

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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
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Prior art keywords
tricyclo
decane
esters
mixture
carboxylic acids
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German (de)
French (fr)
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EP0008103B1 (en
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Ulf-Armin Dr. Schaper
Klaus Dr. Bruns
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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    • 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.

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

Figure imgb0001
in denen R einen gesättigten oder ungesättigten, geradkettigen oder verzweigten aliphatischen Kohlenwasserstoffrest mit 1 - 5 Kohlenstoffatomen darstellt, in vorteilhafter Weise als Riechstoffe in Kompositionen zur Parfümierung technischer und kosmetischer Präparate verwendet werden können. /2It was found that esters of the mixture of tricyclo [5.2.1.0 2.6 ] decane-3 (4) -carboxylic acids of the general formulas
Figure imgb0001
 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. / 2nd

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:

Figure imgb0002
Das auf diesem Wege gewonnene Gemisch der Tricyclo-[5.2.1.02.6] -decan-3(4)-carbonsäuren ist unter dem Namen TCD-Carbonsäure S Handelsprodukt.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:
Figure imgb0002
 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.

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:

Figure imgb0003
Führt man die Reaktion in Alkohol anstatt in wäßrigem Milieu durch, so gelangt man direkt zu den entsprechenden Estern. Die auch hierbei erhaltenen Säuren bzw. Ester sind ein Gemisch verschiedener Stereoisomerer der Tricyclo [5.2.1.02.6]decan-3(4)carbonsäuren bzw. deren Estern. Dieses Gemisch wird nicht aufgetrennt, sondern bildet als solches den erfindungsgemäß zu verwendenden interessanten Riechstoff.Another way to get to the 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:
Figure imgb0003
 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.

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.

BeispieleExamples

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°

Figure imgb0004
1,506 Geruch: Maggi-Walnuß-Note Tricyclo [5.2.,1.0 2.6]decan-3(4)-carbonsäure- allylester Kp0,07 mbar 74 - 81°
Figure imgb0005
1,497Tricyclo [5.2.1.0 2.6 ] decane-3 (4) -carboxylic acid-propargylester bp 0.013 mbar 100-110 °
Figure imgb0004
 1,506 Odor: Maggi walnut note tricyclo [5.2., 1.0 2.6 ] decane-3 (4) -carboxylic acid allyl ester bp 0.07 mbar 74 - 81 °
Figure imgb0005
 1,497

Geruch: Ocimen-, Styrolyl-Note Tricyclo[5.2.1.02.6]decan-3(4)-carbonsäure- ethylester Kp0,013 mbar 60 - 63°

Figure imgb0006
1,489Odor: Ocimen, styrolyl note tricyclo [5.2.1.0 2.6 ] decane-3 (4) -carboxylic acid ethyl ester bp 0.013 mbar 60 - 63 °
Figure imgb0006
 1,489

Lit:

  • Kp4 mbar 103°
    Figure imgb0007
    1,486
  • Geruch: fruchtig, Marmeladen-Note
  • Tricyclo [5.2.1.02.6]decan-3(4)-carbonsäuren-propylester
  • Kp0,015 mbar 94 - 100°
    Figure imgb0008
    1,488
  • Geruch: technisch, Maggi-Note
  • Tricyclo [5.2.1.02.6]decan-3(4)-carbonsäure- iso-propylester
  • Kp0,07 mbar 67 - 72°
    Figure imgb0009
    1,483
  • Geruch: Himbeer-Note /6 Tricyclo [5.2.1.02.6]decan-3(4)-carbonsäuren-butylester
  • Kp0,07 mbar 78-80°
    Figure imgb0010
    1,484
  • Geruch: schwach fruchtig
Lit:
  • Kp 4 mbar 103 °
    Figure imgb0007
     1,486
  • Smell: fruity, jam note
  • Tricyclo [5.2.1.0 2.6 ] decane-3 (4) -carboxylic acid propyl ester
  • Kp 0.015 mbar 94 - 100 °
    Figure imgb0008
     1,488
  • 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 °
    Figure imgb0009
     1.483
  • Smell: raspberry note / 6 Tricyclo [5.2.1.0 2.6 ] butyl decane-3 (4) -carboxylic ester
  • Kp 0.07 mbar 78-80 °
    Figure imgb0010
     1,484
  • Smell: slightly fruity

Tricyclo [5.2.1.02.6] decan-3(4)-carbonsäure- tert.-butylester Kp0,07 mbar 92 - 95°

Figure imgb0011
1,481 Geruch: schwach fruchtigTricyclo [5.2.1.0 2.6 ] decane-3 (4) -carboxylic acid tert-butyl ester bp 0.07 mbar 92-95 °
Figure imgb0011
 1,481 smell: slightly fruity

Beispiel 1example 1 Hyazinthe-KomplexHyacinth complex

Figure imgb0012
Figure imgb0012

Beispiel 2Example 2 Chypre-BaseChypre base

Figure imgb0013
Figure imgb0013

Claims (4)

1. Verwendung der Ester des Gemisches der Tricyclo-[5.2.1.02.6]decan-5(4)-carbonsäuren der allgemeinen Formeln 1
Figure imgb0014
in denen R einen gesättigten oder ungesättigten, geradkettigen oder verzweigten aliphatischen Kohlenwasserstoffrest mit 1 - 5 Kohlenstoffatomen darstellt, als Riechstoffe.1. Use of the esters of the mixture of tricyclo- [5.2.1.0 2.6 ] decane-5 (4) -carboxylic acids of the general formulas 1
Figure imgb0014
 in which R represents a saturated or unsaturated, straight-chain or branched aliphatic hydrocarbon radical with 1-5 carbon atoms, as fragrances. 2. Verwendung des Estergemisches gemäß Anspruch 1, dadurch gekennzeichnet, daß Allyl- und/oder Propargylester des Gemisches der Tricyclo [5.2.1.02.6]decan-3(4)-carbonsäuren verwendet werden.2. Use of the ester mixture according to claim 1, characterized in that allyl and / or propargyl esters of the mixture of tricyclo [5.2.1.0 2.6 ] decane-3 (4) -carboxylic acids are used. 3. Riechstoffkompositionen, gekennzeichnet durch einen Gehalt an Estern des Gemisches der Tricyclo-[5.2.1.02.6] decan-3(4)-carbonsäuren nach Anspruch 1 und 2.3. fragrance compositions, characterized by a content of esters of the mixture of tricyclo- [5.2.1.0 2.6 ] decane-3 (4) -carboxylic acids according to claim 1 and 2. 4. Riechstoffkompositionen nach Anspruch 3, dadurch gekennzeichnet, daß sie die Ester des Gemisches der Tricyclo [5.2.1.02.6] decan-3(4)-carbonsäuren in einer Menge von 1 bis 50 Gewichtsprozent, bezogen auf die gesamte Komposition, enthalten.4. fragrance compositions according to claim 3, characterized in that they contain the esters of the mixture of tricyclo [5.2.1.0 2.6 ] decane-3 (4) -carboxylic acids in an amount of 1 to 50 percent by weight, based on the overall composition.
EP79102824A 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 Expired EP0008103B1 (en)

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

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EP0008103A1 true EP0008103A1 (en) 1980-02-20
EP0008103B1 EP0008103B1 (en) 1981-05-20

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US (2) US4311616A (en)
EP (1) EP0008103B1 (en)
JP (1) JPS5527188A (en)
BR (1) BR7905147A (en)
CA (1) CA1126165A (en)
DE (1) DE2835445C2 (en)

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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
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

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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
CN105431126A (en) * 2013-07-22 2016-03-23 高砂香料工业株式会社 Derivatives of 2,2,6-trimethylcyclohexane-carboxylate
EP3098216B1 (en) * 2014-01-20 2019-11-06 Kokyu Alcohol Kogyo Co., Ltd. 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
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

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
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

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EP0008103B1 (en) 1981-05-20
DE2835445A1 (en) 1980-02-28
US4311616A (en) 1982-01-19
JPS5527188A (en) 1980-02-27
CA1126165A (en) 1982-06-22
BR7905147A (en) 1980-05-06
JPS622564B2 (en) 1987-01-20
US4289660A (en) 1981-09-15
DE2835445C2 (en) 1986-12-11

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