Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing oxygen-containing organic compound
Patent
1996-07-31
1997-09-16
Lilling, Herbert J.
Chemistry: molecular biology and microbiology
Micro-organism, tissue cell culture or enzyme using process...
Preparing oxygen-containing organic compound
435136, 435142, 435143, 435148, 435280, 435830, 435911, 560122, C12P 740
Patent
active
056679955
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to the field of biorganic synthesis. It concerns, more particularly, a process for the preparation of cyclic ketones of formula ##STR2## optionally having a double bond in one of the positions indicated by the dotted lines and wherein: m represents an integer from 0 to 3 and n an integer from 0 to 10; each of the symbols R, which can be identical or different, stands for hydrogen or for a saturated or unsaturated, linear or branched, alkyl radical having 1 to 6 carbon atoms; and each of the substituent groups can be located in any available position of the ring; the process being characterized in that a substrate containing one or several cyclic carboxylic derivatives of formula ##STR3## wherein the dotted lines and the symbols R and m have the meaning indicated in formula (I), p>n+2 and is defined as being an even integer when n is even and an odd number when n is odd, is added to a culture of a microorganism capable of .beta.-oxidising the fatty acid chain of said derivatives to form at least one of the desired ketones, which is then extracted from the reaction medium.
PRIOR ART
Microbiological processes involving .beta.-oxidation of substrates derived from fatty acids are known in the prior art. For example, U.S. Pat. No. 5,168,054 discloses a process of this type for the preparation of lactones starting from derivatives of linolenic, linoleic and oleic acids. However, to our knowledge, such processes have never been applied to cyclic carboxylic derivatives such as those presently used.
DESCRIPTION OF THE INVENTION
We have now discovered that the process according to the present invention makes it possible to prepare a great variety of cyclopentenone and cyclopentanone derivatives, in industrially applicable conditions and very advantageous yields. The process of the invention is in fact of very wide application, both as regards the nature of the substrates and the variety of microorganisms which can be used.
It has been established that one can use with equal success substrates wherein the fatty acid chain is located in the .alpha. or .beta. position of the ring, with respect to the ketonic group, and that said ring can further carry other substituent R groups, identical to or distinct from each other.
Thus, according to a preferred and particularly advantageous embodiment of the invention, there is used a substrate of formula ##STR4## wherein the dotted lines indicate the location of a single or double bond and p>n+2 and is an odd number. According to this preferred embodiment, there can thus be obtained compounds of formula ##STR5## n being an odd integer, which compounds include cyclopentanone derivatives useful for the synthesis of fragrant molecules. For example, 3-oxo-2-(2-pentenyl)-1-cyclopentaneacetic acid, or jasmonic acid, is a precursor of methyl jasmonate, a compound much appreciated in perfumery and a natural component of jasmine essential oil.
Likewise, 3-oxo-2-pentyl-1-cyclopentaneacetic acid, or dihydrojasmonic acid, is a precursor of Hedione.RTM. (methyl 3-oxo-2-pentyl-1-cyclopentaneacetate; origin: Firmenich SA, Geneva, Switzerland), a perfuming ingredient much valued for its floral, jasmine-like fragrance and its exhalting odor effect.
In addition to their use fullness in perfumery, these acids and their methyl esters are also useful for the flavor industry, in the preparation of edible products, and there is therefore a real need for a bioorganic process allowing their preparation via a microbiological pathway.
Furthermore, it is also known that several varieties of plants are capable of producing these compounds and that jasmonic acid and methyl jasmonate in particular play an important role in the metabolism of such plants, namely as growth regulators. This has prompted the interest of several investigators to study their biosynthesis, occurring via the action of enzymes present in the corresponding vegetable tissues (see for example, B. A. Vick et al., Plant Physiol. 1984, 75, 458-61). However, it is clear that the isolat
REFERENCES:
patent: 5168054 (1992-12-01), Cardillo et al.
B.A. Vick et al., "Biosynthesis of Jasmonic Acid by Several Plant Species", Plant Physiol. (1984) 75, 454-462.
P.A. Grieco et al., "Cycloalkenone Synthesis via Lewis Acid Catalyzed Retro Diels-Alder Reactions of Norbornene Derivsatives: Synthesis of 12-Oxophytodienoic Acid", J. Org. Chem. (1989) 54, 6008-6010.
Firmenich SA
Lilling Herbert J.
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