Perfume compositions – Perfume compositions – Oxygen containing active ingredient
Reexamination Certificate
1999-10-04
2001-02-13
Warden, Jill (Department: 1743)
Perfume compositions
Perfume compositions
Oxygen containing active ingredient
C512S011000, C512S026000, C435S255300, C435S125000, C435S135000, C435S147000, C435S911000, C426S650000
Reexamination Certificate
active
06187741
ABSTRACT:
The present invention relates to a two phase microbial process for the preparation of compositions containing certain saturated lactones. In a further aspect, the present invention relates to products produced by the microbial process.
In a still further aspect, the present invention relates to organoleptic uses of said products.
In today's market, it is frequently desirable to identify flavor components of food items as being “natural flavors”. It is generally recognized in the industry that a flavor compound having been prepared by microbial processes can be designated as a natural product and therefore have an important place in the commercialization of products containing them. As a result, the industry has devoted considerable time and effort to develop methods for the production of flavoring components and, in particular, for the production of lactones which can be called “natural”.
Thus, as an example of such prior developments a method for preparing certain optically active delta lactones and the corresponding hydroxy carboxylic acids by microbial reduction of ketocarboxylic acids is shown in U.S. Pat. No. 3,076,750.
Investigations reported in the
Journal of Biochemistry,
54, pages 536-540 (1963) relate to metabolism of ricinoleic acid by some Candida strains and show that gamma hydroxydecanoic acid is an intermediate in the oxidative degradation of ricinoleic acid. In a number of such prior disclosed methods, the processes were not entirely satisfactory because of the toxicity of certain components to the microorganism.
A method of producing optically active gamma hydroxydecanoic acid by culturing or incubating a microorganism capable of hydrolyzing castor oil and effecting beta oxidation of the resulting hydrolysate in the presence of castor oil to produce gamma hydroxydecanoic acid is shown in U.S. Pat. No. 4,560,656.
This reference also discloses a method of producing optically active gamma hydroxydecanoic acid by enzymatically hydrolyzing castor oil using lipase to form an enzymatic hydrolyzate and culturing a microorganism capable of effective beta-oxidation of the enzymatic hydrolyzate in the presence of the hydrolyzate to produce gamma hydroxydecanoic acid. Similarly, a way of culturing or incubating the microorganism capable of hydrolyzing castor oil and a microorganism capable of affecting beta oxidation of the castor oil hydrolyzate in the presence of the castor oil to produce gamma hydroxydecanoic acid is also shown in that document.
European published patent application 258993 of Apr. 9, 1988 discloses a process for the production of optically active gamma hydroxydecanoic acid suitable for conversion to optically active gamma decalactone.
Microbial production of natural &dgr;-dodecalactone from Massoi bark oil was discussed by van der Shaft et al. in
Applied Microbiology and Biotechnology
(1992) Vol. 36, pages 712-716.
The usefulness of yeast for reduction reactions in general, including conversion of Massoi lactone is referred to by N. J. Turner in
Chemistry & Industry
, Aug. 1, 1994 pages 592 et seq.
Japanese application 09 031071-A discloses production of (R)-(−)-massoi lactone by incubating a microorganism.
More recently, in U.S. Pat. No. 5,128,261, 5-decanolide and 5-dodecanolide have been shown to be produced from a series of strains of yeast in a fermentation reaction by carrying out a biocatalytic reduction of the corresponding natural unsaturated 5-olides. such prior methods are said to be economically attractive but there is a constant need for improvement of yields and conversion which is addressed in this invention.
In the flavor and fragrance art the need has risen for the development of more efficient production of naturally occurring lactones which have heretofore been found to be useful and necessary in the creation of flavor formulation used in augmenting or enhancing the aroma or taste of such items as foodstuffs, chewing gums and toothpastes, and also useful in augmenting or enhancing the aroma of perfume compositions such as colognes, perfumed articles either in solid or liquid state as, for example, ionic, cationic, nonionic or zwitterionic detergents, perfumed polymers, fabric softener compositions, fabric softener articles, hair preparations and cosmetic powders.
It is therefore an object of the present invention to provide a new and improved method for preparing certain saturated naturally occurring lactones found to be suitable for a wide variety of purposes in a more efficient manner to produce a higher yield and greater conversion.
SUMMARY OF THE INVENTION
The above and other objects and features of the invention are obtained in accordance in the present invention by carrying out a process using oxidative reaction techniques to produce and recover certain naturally occurring saturated lactones found to be useful for their organoleptic properties in augmenting or enhancing the aroma or taste of consumable materials such as foodstuffs, chewing gums, toothpaste, additional products, chewing tobaccos, smoking tobaccos, perfume compositions, colognes and perfumed articles such as solid or liquid detergents, perfumed polymers, fabric softener compositions, fabric softener articles, cosmetic powders, hair preparations and the like, which saturated lactones are defined according to the structure:
wherein R is a member selected from the group consisting of methyl and n-propyl. These compounds are &dgr;-decalactone and &dgr;-dodecalactone, respectively.
The process to produce the lactone compositions of the invention are carried out under oxidative growth conditions by preparing (1) an aqueous nutrient medium including a source of sugar in a first aqueous liquid phase, and (2) a second non-aqueous, organic liquid phase (which is the “organic” phase) containing a significant concentration of the unsaturated 5-olide compound represented by the structural formula:
wherein R is a member selected from a group consisting of methyl and n-propyl. The starting materials thus can be a natural 2-decen-1,5-olide or a natural 2-dodecen-1,5-olide compound.
The first aqueous liquid phase and the second organic liquid phase are mixed together with agitation to form a two-phase system while (i) maintaining sufficiently low dextrose levels and (ii) aerating with an oxygen-containing gas such as air or oxygen, whereby oxidative growth is achieved with surprisingly high conversion of the unsaturated 5-olide compound into the corresponding saturated 5-olide compound. The reaction is carried out in the presence of a selected yeast capable of producing the natural &dgr;-lactone.
A further feature of the present invention resides in the products produced by the present invention characterized by the GLC profiles which accompany this application.
Still further, another feature of the invention resides in the flavor and fragrance compositions containing the &dgr;-decalactone and &dgr;-dodecalactone products produced by the present invention.
REFERENCES:
patent: 5128261 (1992-07-01), Maria de Laat et al.
patent: 5763233 (1998-06-01), Gocho et al.
patent: 5849551 (1998-12-01), Kümin et al.
patent: 4401388A1 (1995-07-01), None
patent: 0952226A1 (1999-10-01), None
patent: 09182598A (1997-07-01), None
Farbood Mohamad I.
Harris Gail
Kizer Laura E.
McLean Lynda B.
Morris James
Cole Monique T.
International Flavors & Fragrances Inc.
Liberman Arthur L.
Warden Jill
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