Perfume compositions – Perfume compositions – Ring containing active ingredient
Patent
1994-07-05
1995-11-07
Reamer, James H.
Perfume compositions
Perfume compositions
Ring containing active ingredient
549302, A61K 746
Patent
active
054648246
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP93/03164, Nov. 11, 1993.
TECHNICAL FIELD
The present invention relates to the perfume industry. More particularly, it concerns the use of a furanone of formula ##STR2## wherein symbols R.sup.1 and R.sup.2, taken separately, are identical and represent each a methyl radical, or are different and represent each a hydrogen atom or a methyl radical, or, taken together, represent a methylene radical.
PRIOR ART
Formula (I) furanones are homologues of 5,6,7,7a-tetrahydro-7a-methoxy-3,6-dimethyl-2(4H)-benzo[b]furanone, also known under the name of mintlactone, a natural component of peppermint essential oil, and the use of which in perfumery and the flavor industry is described in the prior art [see U.S. Pat. No. 4,407,740].
On the other hand, U.S. Pat. No. 5,114,493 describes the use of lactones of formula ##STR3## wherein R is a C.sub.1 a C.sub.6 alkyl radical, a C.sub.1 -C.sub.4 alkylphenyl radical or a C.sub.1 -C.sub.4 alkoxyphenyl radical, for flavoring tobacco.
The structures of furanones (I) are also known from the prior art. For example, the synthesis of perhydro-6-methyl-3-methylene-2-benzo[b]furanone has been the object of several publications [see, for example, J. M. Fang et al., Proc. Nat. Sci. Counc. ROC(A) 9, 95 (1985)], while perhydro-3,6-dimethyl-2-benzo[b]furanone was described in European patent EP 219 199, relating to a process for the preparation of lactones. Although this patent makes no reference to any particular properties of this furanone, the use of this compound as an insect repellent is known--see European patent application EP 167 265-.
The synthesis of perhydro-3,3,6-trimethyl-2-benzo[b]furanone has also been described by I. Yoshihiko et al. in J. Org. Chem. 47, 741 (1982).
On the other hand, several optically active isomers of compounds (I), the structure of which comprises several chiral centers, have been described in the literature, their characterization being however often deficient [see, for example, J. M. Fang et al., cited ref.; M. Carda et al., Tetrahedron Lett. 32, 5191 (1991); I. Kitagawa et al., Chem. Pharm. Bull. 31, 2639 (1983); E. J. Corey et al., J. Am. Chem. Soc. 111, 5472 (1989); C. W. Jefford et al., J. Chem. Soc. Chem. Comm. 1988, 634].
Despite the abundance of synthetical and structural descriptions, and the chemical similarity between furanones (I) and their homologues known from U.S. Pat. Nos. 4,407,740 and 5,114,493, to our knowledge the odor properties of these furanones (I) have gone unnoticed heretofore. We have been unable to find in the cited prior art any reference, or even suggestion, of the eventual usefulness of these furanones, or of any isomer thereof, as perfuming ingredients.
DESCRIPTION OF THE INVENTION
We have now discovered that these compounds possess surprising odor properties in view of the prior art, which render their use in perfumery very advantageous.
For example, perhydro-6-methyl-3-methylene-2-benzo[b]furanone possesses a very powerful odor of the coumarinic, fat, lactonic type, with a balsamic bottom note reminiscent of the odor of daffodil. This is an odor note which is very dose to that of coumarine and which is best represented in (+)-(3aS,6R,7aR)-perhydro-6-methyl-3-methylene-2-benzo[b ]furanone, a preferred compound of the invention.
As for perhydro-3,6-dimethyl-2-benzo[b]furanone, it possesses a very powerful coumarine type note, with a hay-like aspect which is reminiscent of the odor of flouve and Florex.RTM.[5 and 6-ethylideneoctahydro-5,8 -methane-2H-l-benzopyran-2-one; origin: Firmenich SA, Geneva, Switzerland], as well as a fruity-balsamic undernote reminiscent of the odor of tonka and liquorice.
We have discovered unexpectedly that the odor of this compound is particularly useful since, according to the perfumers, it is olfactively the closest note to that of coumarine known to this day. This is dearly seen from the comparaison examples presented further on, wherein this furanone is evaluated against the compounds presently available on the market and whose odors are related to t
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patent: 5137035 (1992-08-01), Podraza
Database WPI, Section Ch, Week 8213, Derwent Publications Ltd., London, GB; Class D18, AN 82-24625E & JP, A, 57 029 279 (Japan Tobacco & Salt), Feb. 17, 1982.
Agricultural and Biological Chemistry, vol. 37, No. 10, 1973, Tokyo, JP, pp. 2441-2442, I. Sakata et al., "Isolation and Identification of 2,3-Dimethyl-4-hydroxy-2-nonenoic Acid Lactone from Shubi".
Food Technologists, vol. 44, No. 2, Feb. 1990, Chicago, U.S., G. A. Burdock et al., "15. GRAS Substances", pp. 78, 80, 83, 84, 86.
Journal of the American Chemical Society, vol. 111, 1989, Washington, D.C., U.S., pp. 5472-5474, E. J. Corey et al., "Enantiospecific Total Synthesis of Pseudopterosins A and E".
Tetrahedron Letters, vol. 32, No. 38, 1991, Oxford, GB, pp. 5191-5192, M. Carda et al., "Total Synthesis of (-)--Mintlactone".
Chemical and Pharmaceutical Bulletin, vol. 31, No. 8, 1983, Tokyo, JP, pp. 2639-2651, I. Kitagawa et al., "Chemical Transformation of Terpenoids. V. Acidic Conversions of 10--Hydroxygeraniol and 10--Hydroxynerol Derivatives Leading to Cyclic Monoterpenoids".
Journal of Organic Chemisty, vol. 47, 1982, Easton, U.S., pp. 741-743, Y. Ito et al., "A New Approach for Stereoselective Synthesis of Gama-Butyrolactones".
Firmenich SA
Reamer James H.
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