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...
Reexamination Certificate
2002-11-13
2003-08-05
Wong, Leslie (Department: 1761)
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...
C426S003000, C426S536000, C426S538000, C426S590000
Reexamination Certificate
active
06602535
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to novel styralyl alcohol isomer mixtures and novel sytralyl acetate isomer mixtures, fermentation processes for preparing same and organoleptic uses for same as aroma or food flavor ingredients.
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 certain alcohol and acetate derivatives which can properly be called “natural.”
Furthermore, in today's market, a trend is developing whereby it is now determined to be desirable to identify fragrance ingredients of fragrance compositions as being “natural fragrance ingredients.” It is generally recognized in the industry that a fragrance compound having been prepared by microbial processes can be designated as a natural product and therefore have an important place in the commercialization of perfumes and perfumed articles containing them. As a result, the industry has devoted considerable time and effort to develop methods for the production of fragrance components and in particular for the production of alcohols and esters which can be called “natural fragrance ingredients.”
It is also well known in the flavor and fragrance industry that particular stereoisomers of specific ingredients are, in many instances, more advantageous than their corresponding opposite stereoisomers. Accordingly, a significant amount of research has been carried out covering the formation of such stereoisomers using, for example, microbial reduction.
Thus, Simon, et al,
Angew. Chem. Int. Ed. Engl
. 24 (1985), pages 539-553 (title: “Chiral Compounds Synthesized by Biocatalytic Reductions”) discloses at section 3.2 on page 545 the hydrogenation of ketones to form chiral secondary alcohols using Clostridia such as
Clostridium kluyveri
and specifically sets forth the production of &agr;-phenylethyl alcohol stereoisomers having the structure:
with an enantiomeric excess of 94%.
Adlercreutz,
Biotechnology Letters
, Volume 13, No. 4 at pages 229-234 (1991) (title: “ASYMMETRIC REDUCTION OF KETONES WITH ENZYMES FROM ACETIC ACID BACTERIA”) shows production of &agr;-phenylethyl alcohol at page 233 using
G. oxydans
(an enantiomeric excess of 99%);
A. aceti
(an enantiomeric excess of 92%);
G. oxydans
(an enantiomeric excess of 75%);
A. aceti
(an enantiomeric excess of 86%);
A. pasteurianus
(an enantiomeric excess of 94%); and
A. peroxydans
(an enantiomeric excess of 66%)
Nakamura, et al,
Tetrahedron: Asymmetry
, Volume 7, No. 10, at: pages 3021-3024, 1996, published by Elsevier Science Ltd. (title: “Asymmetric Synthesis of (S)-Arylalkanols by Microbial Reduction”) sets forth the production of the isomers having the structures:
using acetophenone as a starting material in accordance with the reaction:
using
Geotrichum candidum
IFO 4597, but only shows the production of a stereoisomer mixture having 28% enantiomeric excess.
Vicenzi, et al,
Enzyme and Microbial Technology
, 20: pages 494-499, 1997, published by Elsevier Science Inc. (title: “Large-scale stereoselective enzymatic ketone reduction with in situ product removal via polymeric adsorbent resins”) discloses the stereoselective enzymatic reduction of 3,4-methylene-dioxyphenyl acetone to the corresponding S-3,4-methylene-dioxyphenyl isopropanol utilizing
Zygosaccharomyces rouxii.
Sorrilha, et. al,
Organic
&
Medicinal Chemistry Letters
, Volume 2, No. 2 at pages 191-196, 1992, published by Pergamon Press plc (title: “REDUCTION OF PHENYLKETONES BY IMMOBILIZED BAKER'S YEAST”) discloses a process wherein baker's yeast immobilized on chrysotile and montmorillonite causes stereoselective reduction of 1-phenyl-1,2-propanedione to the corresponding (1R,2S)-diol.
Nothing in the prior art, however, discloses the production of the stereoisomeric mixture of the compounds having the structures:
having an
α
D
20
=
-
38.6
°
with an enantiomeric excess percent of 87.5 ([&egr;&egr;%=87.5]) and furthermore, nothing in the prior art discloses the production of the stereoisomeric mixture of esters having the structures:
having
(
α
D
20
=
+
73.06
°
)
with an enantiomeric excess percent of 79.2, [&egr;&egr;%=79.21] or
α
D
20
=
-
102.7
°
with an enantiomeric excess percent of 89.15, [&egr;&egr;%=89.15], which materials have been found by us to have unexpected, unobvious and advantageous properties insofar as their organoleptic (flavor and fragrance) utilities are concerned.
SUMMARY OF THE INVENTION
The above and other objects and features of the invention are obtained in accordance with the present invention by carrying out a process using (i) reductive reaction techniques to produce and recover certain naturally occurring alcohols and (ii) esterification reaction techniques to produce and recover certain naturally occurring esters, found to be useful for their organoleptic properties in augmenting or enhancing the aroma or taste of consumable materials such as foodstuffs, chewing, gums, toothpastes, oral care 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.
The reductive reaction products are styralyl alcohol stereoisomer mixtures containing compounds having the structures:
produced according to a fermentation reaction whereby acetophenone is reduced according to the reaction:
using a culture of
Kluyveromyces polysporus
ATCC 22028.
The resulting products may be used as is for their organoleptic properties or may be further reacted by means of esterification with acetic acid according to the reaction:
The aforementioned esterification reaction may take place using such esterification catalysts as citric acid or may take, place by means of a fermentation reaction using an ester-forming enzyme, preferably
Candida antarctica
esterase expressed in
Asperigilus orzae
, for example NOVOZYM® 435, a triacylglycerol hydrolase (E.C. No.3.1.1.3) acting as an effective carboxylesterase. NOVOZYM® is a trademark of the Novo Nordisk A/S Organization of Novo Alle, 2880Bagsvaerd, Denmark.
When carrying out the reductive fermentation reaction, to wit:
the resulting product has an optical rotation of −38.6°, [&agr;=−38.6°] and an enantiomeric excess percent of about 87.5, [&egr;&egr;%=87.5±0.5].
When carrying out the esterification reaction, to wit:
using a citric acid catalyst, the resultant stereoisomer mixture has an optical activity of −102.7°, [&agr;=−102.7°] with an enantiomeric excess percent of about 78.31, [&egr;&egr;%=78.31±0.5].
When carrying out the estenfication reaction, to wit:
using the enzyme
Candida antarctica
esterase expressed in Asperigilus orzae, specifically NOVOZYM® 435, a triacylglycerol hydrolase (E.C. No. 3.1.1.3) acting as an effective carboxylesterase, a mixture of stereoisomers having an optical activity of +73.06° is produced ([&agr;=+73.06°]) with an enantiomeric excess percent of about 81.1, [&egr;&egr;%=81.1±0.5].
The mixture of optical isomers of the styralyl alcohol having the structures:
produced as set forth above having an optical rotation of −38.6°, [&agr;=−38.6°] with an enantiomeric excess percent of about 87.5, [&egr;&egr;%=87.5±0.5] has a mild hyacinth, gardenia aroma with strawberry nuances. It is, accordingly, useful in augm
Arvizzigno Joseph
Blocker Robert W.
Farbood Mohamad I.
Muralidhara Ranya
International Flavors & Fragrances Inc.
Leightner Joseph F.
Wong Leslie
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