Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing heterocyclic carbon compound having only o – n – s,...
Patent
1995-06-12
1998-01-06
Lilling, Herbert J.
Chemistry: molecular biology and microbiology
Micro-organism, tissue cell culture or enzyme using process...
Preparing heterocyclic carbon compound having only o, n, s,...
435 67, 435125, 435126, 435147, 435148, C12P 2300, C12P 1702, C12P 1706, C12P 724
Patent
active
057053723
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to a novel enzymatic process for the preparation of flavours, in particular of the ionones and C.sub.6 to C.sub.10 aldehydes. It relates more particularly to a process for the preparation of optically active alpha ionone, beta ionone, C.sub.6 aldehydes such as n-hexanal, trans-2-hexenal, C.sub.10 aldehydes such as trans-2, cis-4-decadienal and trans-2, trans-4-decadienal.
The production of flavouring additives presents complex problems since in most foodstuffs the natural flavour, which one attempts to reconstitute by means of flavourings, is the resultant of a mixture of many chemical compounds which it is most often difficult to define with precision.
It is known that two routes are open for the search for flavourings:
i) the production of synthetic molecules strictly identical with the natural molecules;
ii) the implementation of biotechnological processes such as micropropagation techniques, cell culture, microbial fermentations, enzymatic engineering.
It is this last procedure which is used in the present invention.
It is known that ionones, more particularly alpha-ionone and beta-ionone are found in many fruit flavours such as the raspberry, blackberry, blackcurrant, peach, apricot, melon, tomato, in the odour of plants such as the violet, Boronia megastigma in the flavour of transformed plants such as black tea, tobacco, carrot, vanilla or even in mushrooms such as the chanterelle.
Although they are present at very low concentrations, these substances play an important role in the flavour of these plants.
Moreover, the "green tones" which are due for example to n-hexanal having a green apple aroma or to trans-2-hexenal (odour of freshly cut grass) are extremely widespread among plants. Their contribution to the freshness tone of the products makes them flavouring substances of prime importance.
Other compounds, like the ionones, are derived from oxidative degradation of alpha- and beta-carotene by the same enzymatic pathways. Among others, the following compounds will be selected which can be obtained according to the process which is the object of the present invention:
dihydroactinidiolide, which is a lactone whose powerful odour recalls that of tea. This compound thus presents an interest for the flavouring industry;
5,6-epoxy-beta-ionone, which possesses a flavour similar to that of cedar wood, is more woody than that of beta-ionone. This substance thus also presents an interest for the flavouring industry.
Attempts to produce all of these compounds from natural sources in which they are usually present in minute quantities, which makes their extraction unattractive for economic reasons, have been abandoned.
Various studies including those of GROSCH et al. (J. Agric Food Chem. 24, 456-459, 1976) describe an enzymatic mechanism for the production of the ionones by means of lipoxygenases and unsaturated fatty adds, through co-oxidation of the carotenoids.
Furthermore, FISCHER and GROSCH (Z Lebenson, Unters.-Forsch, 165, 137-139, 1977) have obtained various aldehydes such as hexanal, 2,4-decadienal (two diastereoisomers), trans-2-hexenal and trans-2-octenal by placing together lipoxygenase L.sub.2 of soya and linoleic acid.
Moreover, the American U.S. Pat. No. 4,769,243 describes a process for the preparation of green tones such as n-hexanal, 1-penten-3-ol, trans-2-hexenal and cis-2-pentenol (Ex. 1 and 2, column 5). by using a mixture constituted by ground soya seeds and unsaturated fatty adds in the presence of water (in the proportion of 3 to 20 times the weight of the soya seeds) and an addition of lipase. The reaction temperature is situated between 5.degree. and 60.degree. C. (preferably between 25.degree. and 50.degree. C.). The mixture is stirred for a period extending from 5 minutes to 24 hours (preferably 30 minutes to 10 hours) while a supply of air or oxygen is maintained throughout the reaction.
Finally, let us note that CHAN et al. (Biochim. Biophys. Acta, 398, 347-350, 1975) show that if oxygen is limiting, the formation of the long chain aldehydes such a
REFERENCES:
patent: 100790 (1870-03-01), Gru et al.
patent: 4769243 (1988-09-01), Kanisawa et al.
patent: 5464761 (1995-11-01), Muller et al.
Almosnino et al., "Apple pomace: an enzyme system for producing aroma compounds from polyunsaturated fatty acids", Biotechnology Letters, vol. 13, No. 12 (Dec. 1991).
Grosch et al., "Formation of volatile carbonyl compounds and cooxidation of beta-carotene by lipooxygenase from wheat, potato, flax and beans", J. Agr. Food Chem., 24:456-459 (Jun. 1976).
Belin Jean-Marc
Dumont Benoit
Ropert Fran.cedilla.oise
BFA Laboratories
Lilling Herbert J.
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