Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing heterocyclic carbon compound having only o – n – s,...
Reexamination Certificate
2002-01-07
2004-08-17
Saucier, Sandra E. (Department: 1651)
Chemistry: molecular biology and microbiology
Micro-organism, tissue cell culture or enzyme using process...
Preparing heterocyclic carbon compound having only o, n, s,...
Reexamination Certificate
active
06777211
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a process for producing [n-5]-hydroxy fatty acids (n is an even number of 10 or more) wherein the [n-6]-position is a single bond from straight-chain fatty acids having n carbon atoms wherein at least the [n-6]-position is a double bond. The present invention also relates to a process for producing &bgr;-lactones from the fatty acids and compositions containing &dgr;-lactones.
BACKGROUND ART
Lactones are important compounds which are widely used as food additives because of their property of imparting preferable flavors such as a fruit flavor and a milk flavor. However, as lactones are contained in natural materials only at low concentrations, chemically synthesized products are generally used.
As for the process for producing lactones using microorganisms, it is known that 10-hydroxyoctadecanoic acid, a precursor of &dgr;-dodecalactone, is formed from oleic acid by the activity of microorganisms such as lactic acid bacteria and bifidobacteria.[Gastroenterology, 62, 430(1972)], bacteria belonging to the genus Corynebacterium [Agricultural and Biological Chemistry, 45, 2025(1981)] and bacteria belonging to the genus Pseudomonas [Archives of Biochemistry and Biophysics, 99, 249(1962)]. It is also known that hydroxylated fatty acids such as 10-hydroxyoctadecanoic acid and ricinoleic acid in castor oil can be converted into &dgr;-lactones by the activity of yeasts (Japanese Published Unexamined Patent Application Nos. 66991/85 and 100508/85).
Sporobolomyces odorus
, a yeast which produces lactones, is known to produce &dgr;-decalactone from linoleic acid. From the fact that &dgr;-decalactone is produced from 13-hydroxy-9Z,11E-octadecadienoic acid (coriolic acid), it is presumed that the yeast produces coriolic acid as an intermediate [ACS SYMPOSIUM SERIES, Flavor Precursors, 490, 46(1992)].
A method is known for converting coriolic acid as a precursor obtained by reduction of hydroperoxide obtained by subjecting linoleic acid to photooxidation or treatment with soybean lipoxygenase into &dgr;-decalactone by the activity of bacteria belonging to the genus Cladosporium or yeasts (Japanese Published Unexamined Patent Application No. 187387/91). Also known is a method for converting coriolic acid contained in seed oil of
Coriaria nepalencis
and 11-hydroxypalmitic acid extracted from the roots of Mexican jalap as precursors into &dgr;-decalactone by the activity of bacteria belonging to the genus Cladosporium [Journal of organic Chemistry, 54, 4979 (1989)] or yeasts [Journal of organic Chemistry, 57, 1954(1992) and Japanese Published Unexamined Patent Application No. 219886/91].
However, there has not been reported a process for producing &dgr;-decalactone and jasmine lactone respectively from 13-hydroxy-9-ocatadecenoic acid and 13-hydroxy-9,15-octadecadienoic acid formed respectively from linoleic acid and &agr;-linolenic acid by the activity of microorganisms.
DISCLOSURE OF THE INVENTION
An object of the present invention is to provide a process for producing [n-5]-hydroxy fatty acids (n is an even number of 10 or more) wherein the [n-6]-position is a single bond from straight-chain fatty acids having n carbon atoms wherein at least the [n-6]-position is a double bond using a microorganism. Another object of the present invention is to provide a process for producing &dgr;-lactones from the fatty acids using a microorganism and to provide compositions containing &dgr;-lactones.
The present invention relates to a process for producing an [n-5]-hydroxy fatty acid (n is an even number of 10 or more) wherein the [n-6]-position is a single bond, which comprises causing cells or a culture of a microorganism having the activity to introduce hydroxy into the [n-5]-position and hydrogen into the [n-6]-position of a straight-chain fatty acid having carbon atoms wherein at least the [n-6]-position is a double bond to make the [n-6]-position a single bond (hereinafter referred to as the first microorganism) or a treated matter thereof to act on a straight-chain fatty acid having n carbon atoms wherein at least the [n-6]-position is a double bond or a composition containing the fatty acid to form the [n-5]-hydroxy fatty acid wherein the [n-6]-position is a single bond, and recovering the formed [n-5]-hydroxy fatty acid wherein the [n-6]-position is a single bond.
The present invention also relates to 13-hydroxy-6,9-octadecadienoic acid represented by the following formula (I):
The present invention also relates to a process for producing a &dgr;-lactone, which comprises causing cells or a culture of the first microorganism or a treated matter thereof to act on a straight-chain fatty acid having n carbon atoms (n is an even number of 10 or more) wherein at least the [n-6]-position is a double bond or a composition containing the fatty acid to form an [n-5]-hydroxy fatty acid wherein the [n-6]-position is a single bond, then causing cells or a culture of a microorganism having the activity to &bgr;-oxidize an [n-5]-hydroxy fatty acid wherein the [n-6]-position is a single bond (hereinafter referred to as the second microorganism) or a treated matter thereof to act on the formed [n-5]-hydroxy fatty acid, and recovering the formed &dgr;-lactone.
The present invention also relates to a process for producing a composition containing a &dgr;-lactone, which comprises causing cells or a culture of the first microorganism or a treated matter thereof to act on a composition containing a straight-chain fatty acid having n carbon atoms (n is an even number of 10 or more) wherein at least the [n-6]-position is a double bond to form an [n-5]-hydroxy fatty acid wherein the [n-6]-position is a single bond in the composition, and then causing cells or a culture of the second microorganism or a treated matter thereof to act on the formed [n-5]-hydroxy fatty acid.
The present invention further relates to a process for producing a food containing a &dgr;-lactone, which comprises adding the &dgr;-lactones or the composition containing the &dgr;-lactones produced by the above process to a food.
In the present invention, the expression “the [n-m]-position is a double bond” means that the [n-m]-position and the [n-(m-l)]-position are bonded by a double bond.
The straight-chain fatty acids having n carbon atoms (n is an even number of 10 or more) wherein at least the [n-6]-position is a double bond of the present invention include monoenoic fatty acids, dienoic fatty acids and trienoic fatty acids wherein the [n-6]-position is a double bond, preferably a cis-form double bond.
Preferred polyenoic fatty acids (e.g., dienoic fatty acids and trienoic fatty acids) are nonconjugated polyenoic fatty acids wherein the [n-9]-position is a double bond, specifically a cis-form double bond. When n is 12 or more, fatty acids wherein the [n-10]- and lower positions are single bonds are desirable for the formation of &dgr;-lactones.
There is no upper limit to n insofar as n is an even number of 10 or more, but n is preferably 10 to 32, more preferably 12 to 26, and most preferably 16 to 22.
Examples of the monoenoic fatty acids include decenoic acid, dodecenoic acid, tetradecenoic acid, hexadecenoic acid, octadecenoic acid, eicosenoic acid, docosenoic acid, tetracosenoic acid, hexacosenoic acid, octacosenoic acid, triacontenoic acid, dotriacontenoic acid and tetratriacontenoic acid.
Examples of the dienoic fatty acids include decadienoic acid, dodecadienoic acid, tetradecadienoic acid, hexadecadienoic acid, octadecadienoic acid, eicosadienoic acid, docosadienoic acid, tetracosadienoic acid, hexacosadienoic acid, octacosadienoic acid, triacontadienoic acid, dotriacontadienoic acid and tetratri
Ishiguro Hiroki
Masuda Yukiko
Saitoh Chiaki
Yashiro Atsushi
Antonelli Terry Stout & Kraus LLP
Kyowa Hakko Kogyo Co. Ltd.
Saucier Sandra E.
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