Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing oxygen-containing organic compound
Patent
1994-01-21
1995-11-07
Naff, David M.
Chemistry: molecular biology and microbiology
Micro-organism, tissue cell culture or enzyme using process...
Preparing oxygen-containing organic compound
435134, 435155, 435171, C12P 724, C12P 764, C12P 702, C12P 102
Patent
active
054647614
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to the field of organic synthesis, more particularly, it provides an enzymatic process allowing the preparation of aldehydes and alcohols having six carbon atoms, namely n-hexanal, 3-(Z)-hexen-1-al, 2-(E)-hexen-1-al and their corresponding alcohols. These are oxygen-containing compounds of current use in the flavor industry, namely as a result of their fruity and green type organoleptic characters. There are many studies described in the literature related to a variety of synthetic methods for preparing these compounds, which are known to be constituents of several flavors of natural origin.
Given the legal prescriptions presently in force in most countries with regard to the use of food additives, it becomes imperative to have at one's disposal the above-mentioned alcohols and aldehydes in a quality capable of fulfilling the established criteria as regards their natural origin character.
Although, in principle, one could imagine obtaining these compounds via extraction of the natural origin products which contain them, it is quite obvious that, given their proportions, such a method is hardly economical.
PRIOR ART
Amongst the studies described in the literature relating to methods for synthesizing the above-mentioned compounds, one should cite that described in French patent application no. 2652587, published on Apr. 5, 1991, which relates to a biological process for the preparation of 3-(Z)-hexen-1-ol, starting from unsaturated fatty acid. The described process resorts to the combined action of a natural enzymatic system, put in under the form of radish or Rumex stalks, and of a yeast capable of promoting the reduction of 3-(Z)-hexen-1-al into 3-(Z)-hexen-1-ol. According to the authors, such a process made it possible to improve the yields in desired alcohol relative to the results obtained with previously used biological processes, such as for example those described in U.S. Pat. Nos. 4,769,243 or 4,806,379.
Although we have been able to ascertain the validity of this claim, parallel studies carried out by us have shown that it was possible to go substantially beyond the efficiency coefficients indicated in the cited patent application, thanks to the process which is the object of the present invention.
BRIEF DESCRIPTION OF THE DRAWINGS
FIG. 1 is the reaction scheme for the production and isolation of 3-(Z)-hexen-1-al, 3-(Z)-hexen-1-ol, 2-(E)-hexen-1-al, and 2-(E)-hexen-1-ol from linoleic acid or precursor in hydrolysate form.
FIG. 2 is the reaction scheme for the production and isolation of n-hexanal and n-hexanol from linoleic acid or precursor in hydrolysate form.
FIG. 3 is a graph of the relationship between the yield of 3-(Z)-hexen-1-ol and the pH in steps b) and c) of the present invention.
DESCRIPTION OF THE INVENTION
The present invention provides a method for the preparation of aldehydes and alcohols having 6 carbon atoms, which, on the one hand, satisfies the natural origin legal requirements and, on the other hand, fulfills the criteria of economic profitability.
We have, in fact, discovered that it was now possible to obtain n-hexanal, 3-(Z)-hexen-1-al and 2-(E)-hexen-1-al, as well as their corresponding alcohols, through an enzymatic process starting from linoleic or linolenic acid, or from a natural origin precursor of said acid in the form of a hydrolysate, which process comprises the following discrete reaction steps: in hydrolysate form, to the action of a lipoxygenase in an appropriate culture medium to obtain 13-hydroperoxy-octadeca-9,11-dienoic acid ("C.sub.13 HDPO"), respectively 13-hydroperoxy-octadeca-9,11,15-trienoic acid ("C.sub.13 HDPOT"); HDPOT", into n-hexanal, respectively into 3-(Z)-hexen-1-al, by means of a lyase; of a yeast to obtain n-hexanol, respectively 3-(Z)-hexen-1-ol; or temperature and pH conditions to obtain 2-(E)-hexen-1-al, and 2-(E)-hexen-1-ol.
As is apparent from the preceding comments, the aldehydes are obtained by stopping the process at step b) or c'), thus before beginning their reduction by the yeas
REFERENCES:
patent: 4769243 (1988-09-01), Kanisawa et al.
patent: 4806379 (1989-02-01), Goers et al.
Luckner, In: "Secondary Metabolism Microorganisms, Plants, and Animals", Publisher: Springer-Verlag pp. 146-147, 1990.
Piazza, G. J., "Lipoxygan Lipoxygenase Cataling & Hydroperoxide Formation in Microemulsion Containing Nonionic Surfactant," Biotechnol Letters, vol. 14, No. 12, pp. 1153-1158 1992.
Zhang, P. et al., "Enzymatic Asymmetric Hydrozation of Pentadiamo Using System Liporganic", J. Am Chem Soc., vol. 111, pp. 9241-9242 1989.
"Chemistry and Physics of Lipids, vol. 44, Nos. 2-4, Jul.-Sep. 1987, 341-361, :Biosynthetic pathway for C6-Aldehydes Formation From Linolenic Acid in Green Leaves", Akikazu Hatanaka et al.
Agric. Biol. Chem., 43(5), 969-980, 1979, "Volatile C6-Aldehyde Formation via Hydroperoxides from C18-Unsaturated Fatty Acids in Etiolated Alfalfa and Cucumber Seedlings", Jiro Sekiya, et al.
Chemical Abstracts, vol. 111, 1989, Columbus, Ohi, abstract No. 74853n, Hatakaka, Akikazu et al., "Biogeneration of green odor (I). Enzymic oxygen-active-cleavage reaction of linolenic acid in leaves", p. 455; column L.
Dean Christopher
Gautier Antoine
Kuhn Jean-Charles
Muller Bernard
Firmenich S.A.
Naff David M.
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