Optically active esters and their use as perfuming ingredients

Details Optically active esters and their use as perfuming ingredients Optically active esters and their use as perfuming ingredients

1999-06-25

2000-12-12

Warden, Jill

Perfume compositions

Perfume compositions

Oxygen containing active ingredient

512 1, 512 25, 512 27, 424401, 424 764, A61K 746, A61K 600, A61K 700, A61L 904

Patent

active

061599298

DESCRIPTION:

BRIEF SUMMARY
BRIEF SUMMARY OF THE INVENTION

The invention belongs to the field of perfumery. It relates more particularly to a compound of formula ##STR3## wherein X represents a C.dbd.O group or a CH--OH group, in the form of an optically active isomer or of a mixture of isomers, and its use as a perfuming ingredient.


BACKGROUND OF THE INVENTION

The structure of the esters of formula (I) in racemic form is known. Several references have disclosed it, either mentioning only the molecule, or describing its preparation in detail. In this context, the following references can be cited for their mention of the compound of formula (I) wherein X represents a C.dbd.O group, namely 3-methyl-2-oxo-ethyl pentanoate: R. Kozlowski et al., Org. Prep. Proceed. lnt., 21(1), 75-82 (1989); Y. Akiyama et al., Chem. Pharm. Bull. 32(5), 1800-1807 (1984); Y. Akiyama et al., Chem. Lett. 8, 1231-1232 (1983); P. Yates et al., Can. J. Chem. 61(7), 1397-1404 (1983); H. M. Walborsky et al., J. Org. Chem. 39(5), 604-607 (1974); L. N. Akimova et al., Zh Org. Khim. 5(9), 1569-1571 (1969). However none of these references either describes the odor of said ester or suggests its utilization in the field of perfumery.
Moreover, the acids of formula ##STR4## wherein R can be hydrogen or represents a great variety of alkyl radicals, saturated or unsaturated, linear or branched, and namely 3-methyl-2-oxopentanoic acid, are known to be used in the field of flavors. The international application WO 96/10927 describes the utilization of this group of compounds in a variety of foods, to which they impart an enhanced impact in the mouth. The C.sub.1 to C.sub.4 alkyl esters of said acids are also mentioned as useful flavoring ingredients in a general manner, without however giving any concrete example of preparation or even of application of these alkyl esters. Once again there is no description of the odor characteristics of said esters.
On the other hand, the racemic compound of formula (I) wherein X represents a CH--OH group, namely ethyl 2-hydroxy-3-methylpentanoate is described in the following articles: R. Kaiser, J. Ess. Oil Res. (1991), 3, 129-146 or R. Kozlowski, Z. Kubica, B. Rzeszotarska, L. Smelka, G. Pietrzynski, Org. Prep. Proced. Int. (1989), 21(1), 75-82. Moreover, the synthesis of one of the four optically active isomers of this compound, namely ethyl (2S,3S)-2-hydroxy-3-methylpentanoate has been described by D. Wistuba, O. Trager and V. Schurig in Chirality (1992), 4(3), 185-92. However, this article does not include any description of the organoleptic properties of said isomer and generally speaking, the prior art never suggests any possible usefulness of the isomers of 2-hydroxy-3-methyl-pentanoate from an olfactory point of view.


DETAILED DESCRIPTION OF THE INVENTION

Surprisingly, we have now been able to establish that the esters of formula (I) in the form of an optically active isomer or of a mixture of isomers, are very useful perfuming ingredients, having an original and unusual odor, which is a combination of fresh and fruity notes with a walnut type odor character.
The invention is thus related to a method to confer, improve, enhance or modify the odor properties of a perfuming composition or a perfumed product, which method comprises adding as perfuming ingredient to said composition or product, a compound of formula ##STR5## wherein X represents a C.dbd.O group or a CH--OH group, in the form of an optically active isomer of formula ##STR6## wherein X has the meaning indicated above and when X is a CH--OH group, the asymmetric carbon (2) has an R configuration, or in the form of a mixture of isomers.
More particularly, the esters of the invention present a complex odor note of the walnut type, that can be described as being reminiscent of the odor of a fresh walnut, together with a walnut husk character. This note is surprisingly fruity; moreover; there is also a hazelnut connotation. The characteristic walnut-fresh hazelnut note is accompanied by an odor which is reminiscent of that of rhum. In sum, the odor is very natural,

REFERENCES:
R. Kozlowski et al., "Lower Aliphatic 2-Oxoacids and their Ethyl Esters From Ethyl Esters of 2-Hydroxy Acids", Organic Preparations and Procedures Inc. 21(1), 75-82 (1989).
Y. Akiyama et al., "Studies on Conjugated Nitriles. IV.", Chem. Pharm. Bull. 32 (5) 1800-1807 (1984).
Y. Akiyama et al., "Reaction of Organocadmium Reagents with Ethyl Cyanoformate: preparation of .alpha.-Keto Esters", Chemistry Letters, pp. 1231-1232, 1983.
P. Yates et al., "Synthesis of piperazine-2,5-diones related to bicyclomycin; 1,4-dibenzyl-3-hydroxy-3-[1-(2-methoxyethyl) ethenyl] piperzaine-2,5-dione, 2. Route via cyclic intermediates". Can. J. Chem. 61970, 1397-1404 (1983).
H.M. Walborsky, "Partial Asymmetric Syntheses of Amino Acids Using Lithium Aldimine Precursors", J. Org. Chem., vol. 39, (5), 604-607, 1974.
L.N. Akimova. "Preparation of Estes of .alpha.-Keto Acids by the Actions of Grignard Reagents of Oxalic Esters". Zhurnal Organicheskoi Khimii 5(9) pp. 1569-1571, Sep. 1969.
Kaiser, "New Volatile Constituents of the Flower Concrete of Michelia champaca L.", J. Ess. Oil Res., 3:129-146 (May/Jun. 1991).
Kozlowski et al., "Lower Aliphatic 2-Oxoacids and Their Ethyl Esters From Ethyl Esters of 2-Hydroxy Acids", Org. Prep. Proceed. Int., 21:75-82 (1989).
Wistuba et al., "Enantio- and Regioselectivity in the Epoxide-Hydrolase-Catalyzed Ring Opening of Aliphatic Oxiranes: Part II: Dialkyl- and Trialkylsubstituted Oxiranes", Chirality, 4:185-192 (1992).

Affiliated with

Also associated with

Rating

Optically active esters and their use as perfuming ingredients does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Optically active esters and their use as perfuming ingredients, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Optically active esters and their use as perfuming ingredients will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-217003