EP0056109B1 - Verwendung des Methylesters der 2,6,6-Trimethyl-cyclohex-2-ene-1-yl-carbonsäure als Riechstoff - Google Patents

Verwendung des Methylesters der 2,6,6-Trimethyl-cyclohex-2-ene-1-yl-carbonsäure als Riechstoff Download PDF

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Publication number
EP0056109B1
EP0056109B1 EP81109812A EP81109812A EP0056109B1 EP 0056109 B1 EP0056109 B1 EP 0056109B1 EP 81109812 A EP81109812 A EP 81109812A EP 81109812 A EP81109812 A EP 81109812A EP 0056109 B1 EP0056109 B1 EP 0056109B1
Authority
EP
European Patent Office
Prior art keywords
cyclohex
trimethyl
damascone
ene
methyl
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
EP81109812A
Other languages
English (en)
French (fr)
Other versions
EP0056109A3 (en
EP0056109A2 (de
Inventor
Karl-Heinrich Schulte-Elte
Dietrich Kastner
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.)
Firmenich SA
Original Assignee
Firmenich SA
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 Firmenich SA filed Critical Firmenich SA
Publication of EP0056109A2 publication Critical patent/EP0056109A2/de
Publication of EP0056109A3 publication Critical patent/EP0056109A3/fr
Application granted granted Critical
Publication of EP0056109B1 publication Critical patent/EP0056109B1/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
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • 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
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms

Definitions

  • the invention relates to a new fragrance ingredient, in the specific case to an alicyclic ester of formula or methyl 2,6,6-trimethyl-cyclohex-2-ene-1-yl-carboxylate, also known as methyl a-cyclogeraniate.
  • the subject of the invention is the use of said compound (I) as a perfuming ingredient, in particular its use in the pure state or as a mixture with at least one perfuming ingredient below: a-damascone, ⁇ -damascone, y-damascone, ⁇ -damascone, s-damascone, a-damascenone, ⁇ -damascenone, y-damascenone and 8-damascenone
  • the subject of the invention is also a perfume composition containing said compound (1), in particular a perfume composition containing said compound (1) pure or in mixture with at least one of the perfume ingredients defined above.
  • Methyl 2,6,6-trimethyl-cyclohex-2-ene-1-yl-carboxylate (1) is a known compound [see for example Helv. Chim. Acta 42, 2597 (1959)]; its olfactory properties have not been described so far, however.
  • Compound (I) indeed develops an original olfactory note that can be described as both fruity and floral, accompanied by a fresh tone of the citrus genus. This fact is all the more remarkable since these olfactory characters only develop fully when the compound (I) is used in diluted form, in particular in the form of a 10, 5 or 1% solution, or even less.
  • the compound (I) can be advantageously used for perfuming products such as soaps, liquid or solid detergents, cosmetic products or cleaning products for example. It can also be used just as advantageously in fine perfumery, in particular for the preparation of perfuming compositions of the fruity, floral, rosé, woody, spicy, chypre or citrus type, for example.
  • the compound (I) can be used pure or in mixture with one or more perfuming ingredients, a solvent or a usual support.
  • the compound (I) is preferably used in an amount of 0.1 to 5, or even 10% approximately relative to the weight of said composition. Proportions greater than 10% can also be considered, in particular when preparing bases or hearts for perfumes. Proportions less than 0.1% can also be envisaged, in particular when perfuming products such as soaps, detergents or cosmetic products for example.
  • methyl 2,6,6-trimethyl-cyclohex-2-ene-1-yl-carboxylate (I) could have a particularly advantageous action in terms of the effects olfactory agents of certain perfume ingredients, in particular those of the series of damascones and damascenones.
  • Damascones and damascenones are very popular ingredients both in fine perfumery and during the perfuming of technical products: they are characterized in particular by a remarkably radiant rosy and woody olfactory note, even fruity like apple, or mint depending on the case.
  • compound (I) has, among other things, the advantage of combining in a very harmonious manner with said damascones and damascenones, contributing to give them even more richness and roundness.
  • Compound (I) also has the particularity of significantly lowering the level of olfactory perception of the aforementioned ingredients: we can speak in this connection of synergistic effect.
  • methyl 2,6,6-trimethyl-cyclohex-2-ene-1-yl-carboxylate (I) is used in mixture with one or more of said damascones or damascenones, olfactory effects such as those mentioned above can be obtained by using mixtures of compound (I) / damascone or damascenone in which the proportions of each of the constituents are most generally between 20: 1 and 1:20.
  • the proportions given above are not, however, to be considered as absolute limits.
  • Methyl 2,6,6-trimethyl-cyclohex-2-ene-1-yl-carboxalate (I) can be easily obtained according to the methods described in the literature, for example by esterification of the corresponding cyclogeranic acid or by cyclization of methyl geraniate [see for example Helv. Chim. Acta 42, 2597 (1959) and Chem. Abstr. 57, 11239; (1962)].
  • a basic perfuming composition was prepared as follows:
  • the basic composition thus obtained has a relatively ill-defined floral-green odor.
  • the new perfuming composition thus obtained is particularly suitable for perfuming products such as soaps or shampoos
  • a basic "rose” type perfuming composition was prepared as follows:
  • the base thus prepared has a "red rose” odor.
  • a new perfuming composition is obtained, the odor of which has become fresher and more promising. and more elegant than that of said base; it can now be defined as "tea rose”.
  • a basic "rose” type perfuming composition was prepared as follows:
  • the base has a 'pink' type odor. This odor becomes clearly more characteristic after addition to said base of 15 parts of a 0.01% solution of ⁇ -damascenone in ethyl alcohol.
  • talc 100 g was perfumed at 0.15% using a 50:50 mixture of p-damascone and 2,6,6-trimethyl methyl thyl-cyclohex-2-ene-1-yl-carboxylate. This gives a powder giving off a particularly pleasant rosé, fruity and fresh odor.
  • a concentrated liquid detergent was perfumed at 0.15% using a 1:10 mixture of ⁇ -damascenone and 2,6,6-trimethyl-cyclohex-2-ene-1-yl-carboxylate. It now develops a particularly pleasant fruity and fresh rosé-like odor.

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)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (4)

1. Verwendung von Methyl 2,6,6-Trimethyl-cyclohex-2-en-1-yl Carboxylat als Parfümbestandteil.
2. Verwendung gemäss Anspruch 1 von reinem Methyl 2,6,6-Trimethyl-cyclohex-2-en-1-yl Carboxylat oder dessen Mischung mit einem oder mehreren Parfümbestandteilen, einem Lösungsmittel oder einem Träger.
3. Verwendung gemäss Anspruch 1 von Methyl 2,6,6-Trimethyl-cyclohex-2-en-1-yl Carboxylat in einer Mischung mit mindestens einem der folgenden Parfümbestandteile: a-Damascon, β-Damascon, y-Damascon, 8-Damascon, s-Damascon, a-Damascenon, β-Damascenon, y-Damascenon und 8-Damascenon.
4. Parfümkomposition, dadurch gekennzeichnet, dass sie Methyl 2,6,6-Trimethyl-cyclohex-2-en-1-yl Carboxylat in einer Mischung mit mindestens einem der folgenden Parfümbestandteile enthält: a-Damascon, β-Damascon, y-Damascon, 8-Damascon, ε-Damascon, a-Damascenon, β-Damascenon, y-Damascenon und 8-Damascenon.
EP81109812A 1981-01-13 1981-11-21 Verwendung des Methylesters der 2,6,6-Trimethyl-cyclohex-2-ene-1-yl-carbonsäure als Riechstoff Expired EP0056109B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH17781 1981-01-13
CH177/81 1981-01-13

Publications (3)

Publication Number Publication Date
EP0056109A2 EP0056109A2 (de) 1982-07-21
EP0056109A3 EP0056109A3 (en) 1983-08-31
EP0056109B1 true EP0056109B1 (de) 1986-01-15

Family

ID=4181015

Family Applications (1)

Application Number Title Priority Date Filing Date
EP81109812A Expired EP0056109B1 (de) 1981-01-13 1981-11-21 Verwendung des Methylesters der 2,6,6-Trimethyl-cyclohex-2-ene-1-yl-carbonsäure als Riechstoff

Country Status (4)

Country Link
US (1) US4411829A (de)
EP (1) EP0056109B1 (de)
JP (1) JPS57139010A (de)
DE (1) DE3173535D1 (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7196050B2 (en) 2001-12-05 2007-03-27 Firmenich Sa Unsaturated ester as perfuming ingredient

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Also Published As

Publication number Publication date
US4411829A (en) 1983-10-25
EP0056109A3 (en) 1983-08-31
DE3173535D1 (en) 1986-02-27
JPS57139010A (en) 1982-08-27
EP0056109A2 (de) 1982-07-21

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