Food or edible material: processes – compositions – and products – Products per se – or processes of preparing or treating... – Flavor per se – or containing flavor or flavor improver of...
Patent
1996-04-29
1997-12-16
Mosley, Terressa
Food or edible material: processes, compositions, and products
Products per se, or processes of preparing or treating...
Flavor per se, or containing flavor or flavor improver of...
131276, 252522, 560 1, A23L 122
Patent
active
056982534
DESCRIPTION:
BRIEF SUMMARY
This is a 371 of PCT/EP93/03548 filed Dec. 9, 1993.
The present invention relates to the use of certain dimethyl-cyclohexanecarboxylic acid esters as fragrance materials and to perfumes and perfumed products containing these compounds.
Many synthetic perfume components have been developed, especially in the last decades to substitute known perfume materials of natural origin. Nevertheless there is a constant need for new synthetic perfume components which are more stable than those previously developed and/or have additional or more delicate odour notes to further complete the fragrance palette from which the perfumer can chose in composing perfumes which are suitable also for various agressive environments.
Various substituted cyclohexene- and cyclohexadienecarboxylic acid esters are known as fragrance materials in the art of perfumery. The majority of them are of the 2,6,6-trimethyl- or the 2-ethyl-6,6-dimethyl-substituted type and were developed in analogy to various compounds found in nature possessing the 2,6,6-trimethylcyclohexene moiety. Such compounds, with the double bond in the 1- or 2-position and sometimes containing an additional methyl group in the 3-position are described e.g. in EP-A-0 056 109, GB 1 497 498 and U.S. Pat. No. 4,375,001 and various other patents and patent applications mentioned therein. In EP-A-0 053 704 corresponding 2,3,6,6-tetramethyl- and 2-ethyl-6,6-dimethyl-cyclohexane-1-carboxylic acid esters are described. Thus, these compounds are all heavily substituted with methyl and ethyl groups. The odors reported may vary considerably although in many cases fruity and floral, especially roselike dours are reported.
In EP-A-0 199 330 1,4,6-trimethylcyclohex-3-ene derivatives, including methyl 1,4,6-trimethylcyclohex-3-ene-1-carboxylate, are reported to be of use in perfumery. They appear to have mostly herbal woody, even patchouli-like, odors and thus appear to be distincty different in odour character from the 2,6,6- and 2,3,6,6-substituted cyclohexenecarboxylic acid esters reported above. In EP-A-0 199 330 this is attributed to the presence of the quaternary carbon atom in the 1-position. Nevertheless, methyl 1-methylcyclohex-3-ene-1-carboxylate, which is marketed as a fragrance material, has a predominantly fruity odour, which seems to be in contradiction with this rule.
Ethyl 2,4-dimethyl-cyclohexane-1- carboxylate, on the other hand, is also marketed as a fragrance material, but with a distinctly floral odour.
Methyl and butyl 1,4-dimethylcyclohex-3-ene-1-carboxylate stereoisomers have been descibed in CH-A-680 853. The (-)-S methylester is described to have a rather uninteresting herbal, humus and woody and also slightly chemical type of odour whereas the (+)-R isomer has an agreeable fresh fruity-menthol-anis-like odour. The racemic mixture is describes as being spoiled from a perfumery point of view by the odour contribution of the (-)-S isomer.
Finally, in U.S. Pat. No. 4,392,976 4-methyl-cyclohex-3-ene-1-carboxylic acid is reported to have a cumin-like odour. No mention is made of any esters of this acid.
It has now been found that 1,4-dimethylcyclohexane-1-carboxylic acid esters of the general formula: ##STR1## wherein R is an alk(en)yl group having 1-4 carbon atoms, are valuable fragrance materials having very agreeable fresh herbal odours with green and floral notes. The methyl esters are especially preferred. Although the methyl esters are known as such, e.g. from H. van Bekkum et al, Recl. Tray. Chim. Pays-Bas, 88(3) 301-6, 1969 and from W. G. Schindel, R. E. Pincock, J. Org. Chem., 35960, 1789-94, 1970, no mention is made of any organoleptic property.
The compounds may be prepared by methods known in the art, particularly by Diels-Alder reaction of the corresponding methacrylate ester with isoprene, followed by hydrogenation and separation of the 1,3-dimethyl from the 1,4-dimethyl esters. A mixture of cis-dimethyl and trans-dimethyl esters is thus obtained which may be separated into its components by methods described in the art, e.g. by W. G. Schindel, vide su
REFERENCES:
patent: 3910963 (1975-10-01), Souma et al.
patent: 4439353 (1984-03-01), Schenk
de Bruine Johan L.
Dekker Enno E. J.
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