EP0008103B1 - Verwendung von Estern des Gemisches der Tricyclo-(5.2.1.0)decan-3- und Tricyclo(5.2.1.0)decan-4-carbonsäure als Riechstoffe, sowie diese enthaltende Riechstoffkompositionen - Google Patents

Verwendung von Estern des Gemisches der Tricyclo-(5.2.1.0)decan-3- und Tricyclo(5.2.1.0)decan-4-carbonsäure als Riechstoffe, sowie diese enthaltende Riechstoffkompositionen Download PDF

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Publication number
EP0008103B1
EP0008103B1 EP79102824A EP79102824A EP0008103B1 EP 0008103 B1 EP0008103 B1 EP 0008103B1 EP 79102824 A EP79102824 A EP 79102824A EP 79102824 A EP79102824 A EP 79102824A EP 0008103 B1 EP0008103 B1 EP 0008103B1
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.)
Expired
Application number
EP79102824A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0008103A1 (de
Inventor
Ulf-Armin Dr. Schaper
Klaus Dr. Bruns
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0008103A1 publication Critical patent/EP0008103A1/de
Application granted granted Critical
Publication of EP0008103B1 publication Critical patent/EP0008103B1/de
Expired legal-status Critical Current

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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 with 1-5 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:
  • 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 general formula mentioned above the methyl ester and ethyl ester are known from the literature as such, but their suitability as a fragrance was not 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.O 2.6 ] decane-3 (4) -carboxylic acids to be used according to the invention as fragrances can be mixed with other fragrances in various 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 compositions will range from 1-50 percent by weight, based on the overall 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 by generally known Ahren f Verest fürsver from the available as a commercial product TCD-carboxylic acid S, which is as stated above, is to 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)
EP79102824A 1978-08-12 1979-08-06 Verwendung von Estern des Gemisches der Tricyclo-(5.2.1.0)decan-3- und Tricyclo(5.2.1.0)decan-4-carbonsäure als Riechstoffe, sowie diese enthaltende Riechstoffkompositionen Expired EP0008103B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2835445A DE2835445C2 (de) 1978-08-12 1978-08-12 Verwendung von Estern des Gemisches der Tricyclo-[5.2.1.0↑2↑↑.↑↑6↑]decan-3- und Tricyclo [5.2.1.0↑2↑↑.↑↑6↑]decan-4-carbonsäure als Riechstoffe, sowie diese enthaltende Riechstoffkompositionen
DE2835445 1978-08-12

Publications (2)

Publication Number Publication Date
EP0008103A1 EP0008103A1 (de) 1980-02-20
EP0008103B1 true EP0008103B1 (de) 1981-05-20

Family

ID=6046925

Family Applications (1)

Application Number Title Priority Date Filing Date
EP79102824A Expired EP0008103B1 (de) 1978-08-12 1979-08-06 Verwendung von Estern des Gemisches der Tricyclo-(5.2.1.0)decan-3- und Tricyclo(5.2.1.0)decan-4-carbonsäure als Riechstoffe, sowie diese enthaltende Riechstoffkompositionen

Country Status (6)

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

Families Citing this family (9)

* Cited by examiner, † Cited by third party
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
US4411828A (en) * 1980-03-14 1983-10-25 Kao Corporation Fragrant tricyclic carboxylates
CH654204A5 (it) * 1980-03-14 1986-02-14 Kao Corp Composizioni di profumo e procedimento per la loro preparazione.
US4529599A (en) * 1982-12-16 1985-07-16 Kao Corporation Tricyclic carboxylate ester and insecticide containing the same
CN105431126A (zh) * 2013-07-22 2016-03-23 高砂香料工业株式会社 2,2,6-三甲基环己烷羧酸酯的衍生物
WO2015108176A1 (ja) 2014-01-20 2015-07-23 高級アルコール工業株式会社 新規エステル化合物ならびにこれを含む化粧料および化粧品
JP5663111B1 (ja) * 2014-07-08 2015-02-04 高級アルコール工業株式会社 新規エステル化合物ならびにこれを含む化粧料および化粧品
JP5580947B1 (ja) * 2014-01-20 2014-08-27 高級アルコール工業株式会社 新規エステル化合物ならびにこれを含む化粧料および化粧品

Family Cites Families (5)

* Cited by examiner, † Cited by third party
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 (de) * 1970-04-06 1972-10-15 Roure Bertrand Dupont Sa Riechstoffkompositionen
CH602111A5 (enrdf_load_stackoverflow) * 1975-12-08 1978-07-31 Firmenich & Cie

Also Published As

Publication number Publication date
DE2835445A1 (de) 1980-02-28
US4311616A (en) 1982-01-19
DE2835445C2 (de) 1986-12-11
EP0008103A1 (de) 1980-02-20
JPS5527188A (en) 1980-02-27
CA1126165A (en) 1982-06-22
JPS622564B2 (enrdf_load_stackoverflow) 1987-01-20
US4289660A (en) 1981-09-15
BR7905147A (pt) 1980-05-06

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