Stabilization of polyunsaturates

Details Stabilization of polyunsaturates Stabilization of polyunsaturates

1996-10-16

1999-02-16

Venkat, Jyothsna

Drug, bio-affecting and body treating compositions

Preparations characterized by special physical form

Cosmetic, antiperspirant, dentifrice

514549, 426651, 4241951, A61K 748, A61K 3578

Patent

active

058717579

DESCRIPTION:

BRIEF SUMMARY
The invention relates to the stabilisation of polyunsaturates, that is to say triply or more highly ethylenically unsaturated organic materials, and especially to essential fatty acids of this class.
Essential fatty acids (EFAS) are nutrients, which are essential for health and well being, and like vitamins must be ingested, since they cannot be synthesised in the body. They are found in vegetable seed oils, fish oils and other natural sources and are readily susceptible to spoilage by mild oxidation conditions such as by contact with atmospheric oxygen at ambient temperature. Antioxidants are required to protect these sensitive and labile materials.
Most vegetable oils which contain an n-6 EFA contain only linoleic acid which has two double bonds. However, some oils of vegetable, fungal or algal origin contain other, more unsaturated fatty acids such as gamma-linolenic acid (18:3 n-6, GLA), dihomo-gamma-linolenic acid (20:3 n-6, DGLA) and arachidonic acid (20:4 n-6, AA). Since susceptibility to oxidation is related to the number of double bonds, oils or purified compounds containing GLA. DGLA, or AA are highly susceptible to oxidation.
Oils from various sources frequently contain highly unsaturated fatty acids of the n-3 series, such as eicosapentaenoic acid (EPA. 20:5 n-3), docosapentaenoic-acid (DPA. 22:5 n-3) and docosahexaenoic acid (DHA, 22:6 n-3). These fatty acids are particularly susceptible to oxidation.
Most oils of natural occurrence, especially vegetable seed oils already contain antioxidants, most commonly phenolic compounds such as tocopherols. In some cases however, especially when the levels of natural antioxidants have been reduced by refining, by purifying or by other processing, it is advantageous to supplement residual antioxidants by the addition of like compounds of natural or synthetic origin. This is particularly important with natural vegetable, fungal or algal oils containing polyunsaturated fatty acids such as GLA and/or AA, and with marine oils containing EPA, DPA and DHA.
A quite different class of oils is formed by essential oils, extracted from a wide range of culinary and medicinal plants. They have been known from antiquity to possess important biological effects, and are principally known for their antifungal and antibacterial properties. Their defining characteristics are steam distillability and lipophilicity, and they are, usually, odorous mixtures of esters, aldehydes, alcohols, ketones and mono- and sesqui-terpenes of which the terpenes are particularly significant.
Recently it has been reported that whole essential oils have antioxidant effects in vivo (Deans, Noble & Svoboda, 1992). It has also been reported that specific methanolic extracts from some herbs can stabilise lard at 75.degree. C. (Economou, Oreopoulou, Thomopoulas, 1991). Such extracts correspond only in part to essential oils, and the paper is primarily concerned in any case with stability in high temperature use, as in cooking oils. Furthermore it does not concern the triply and more highly ethylenically unsaturated fatty acids that are particularly valuable components in many natural oils and are highly susceptible to oxidation even at room temperature.
Another publication, in JP 5-255692 (Furn Seiyu KK), is of fats showing low absorption from the gut, in which the fatty acids comprise polyunsaturates, and among possible antioxidants is rosemary oil. This is no doubt one of the many processed and fractionated extracts available for use in foods and cooking oils. A still further report, by Toyama et al Bull.Jap.Soc. Sci. Fisheries 39 891-898(1973) is of fractionated citrus fruit oils containing above 90% terpenes being fairly effective in room temperature storage tests in flat fish off.
These publications, and for example others using citrus fruit oils for flavour masking in fish oil products, are unspecific. We have now however found that for the particular problem of long-term, ambient-temperature stabilisation of triply and more highly unsaturated materials, especially in pharmaceuticals where par

REFERENCES:
Lofty, M. et al. "The antioxidant properties of Garden Cress . . . " The Journal of the American Oil Chemists' Society, vol. 34, pp. 96-100.
Toyama, K. et al. "The protection of marine products from deterioration due to the oxidation . . . " Bulletin of the Japanese Society of Scientific Fisheries, 39(8) (1973), pp. 891-898.
Deans, S.G. et al. "Promotional effects of plant volatile oils . . . " Age, vol. 16, 1993, pp. 71-74.
Database WPI Week 9344, Derwent Publications Ltd., London, GB, An 9303486685 & JP, A, 5 255 692 (Fuji Oil Co Ltd) 5 Oct. 1993, abstract.
Wada, S. et al. "The synergistic antioxidant effect of rosemary extract and . . . " Journal of Food Processing and Preservation, vol. 16, No. 4, 1992, Trumbull, US, pp. 263-274.
Revankar, G.D. et al. "Anti-oxidant effect of a spice mixture . . . ", vol. 11, No. 1, 1974, pp. 31-32.

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