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 ⁇ -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, ⁇ -damascone, ⁇ -damascone, ⁇ -damascone, a-damascenone, ⁇ -damascenone, y-damascenone and ⁇ -damascenone.
• the subject of the invention is also a perfume composition containing said compound (I), in particular a perfume composition containing said compound (I) 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 (I) 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, per 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 when perfuming technical products: they are characterized in particular by a remarkably radiant pink 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-3-yl-carboxatalate (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) 7.
• 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 ⁇ -damascone and 2,6,6-trimethyl-cyclohex-2-ene-1-yl-carboxylate methyl. A powder is thus obtained which gives 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 rosé, fruity and fresh smell.

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)

Applications Claiming Priority (2)

Publications (3)

Family

ID=4181015

Family Applications (1)

Country Status (4)

Cited By (2)

Families Citing this family (56)

Family Cites Families (14)

• 1981
  • 1981-11-21 EP EP81109812A patent/EP0056109B1/de not_active Expired
  • 1981-11-21 DE DE8181109812T patent/DE3173535D1/de not_active Expired
  • 1981-12-15 US US06/331,013 patent/US4411829A/en not_active Expired - Lifetime
• 1982
  • 1982-01-13 JP JP57002920A patent/JPS57139010A/ja active Pending

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