Drug – bio-affecting and body treating compositions – Topical sun or radiation screening – or tanning preparations – Aromatic acid or derivative containing
Patent
1997-03-14
2000-05-23
Killos, Paul J.
Drug, bio-affecting and body treating compositions
Topical sun or radiation screening, or tanning preparations
Aromatic acid or derivative containing
424 59, 560 38, 560 60, 560 75, A01K 744, C07C22900
Patent
active
060663111
DESCRIPTION:
BRIEF SUMMARY
THIS INVENTION relates to the production and uses of caffeic acid and derivatives thereof, and more particularly to a method of producing caffeic acids and derivatives from chlorogenic acid and uses of caffeic acid and derivatives thereof as sunscreen additives.
As the harmful effects of strong sunlight become more widely publicized and concern grows over the depletion of the ozone layer, the general public is becoming more aware of the harmful effects of atmospheric ultra-violet radiation. In particular, the identification of atmospheric radiation as a major causative agent in skin cancers has increased the demand for effective and economic protection against atmospheric ultra-violet radiation.
Of the three types of ultraviolet radiation, uvA, uvB and uvC, uvC does not penetrate the earth's atmosphere, being absorbed by the ozone layer. Of the two types of ultraviolet radiation that reach the earth's surface, uvB has been identified as the causative agent of skin cancer. Accordingly, the majority of sunscreens currently available concentrate on the reduction of uvB rays contacting the skin. However, uvA has now been identified as a cause of ageing of skin and wrinkling. As such, it is considered preferable to provide sunscreen agents which reduce the harmful effects of both uvA and uvB in sunlight.
Furthermore, with the increase in environmental awareness in the general public, there is an increased requirement for "natural" products, notably biodegradable products, to avoid environmental damage. There is, therefore, a need for such biodegradable "natural" products for use in sunscreens.
Finally, there is a desire in the art to produce sunscreens which not only have the primary function of blocking ultraviolet light but also have the secondary function of caring for the skin to which they are applied. Thus many sunscreens also contain moisturisers and antioxidants as skin care additives.
One of the most used sunscreen agents is octyl methoxycinnamate (p-methoxycinnamate-2-ethylhexylester). This is an oil soluble uvB absorber having a .lambda. max of 308 nms. The majority of commercial sunscreen agents are also oil soluble uvB absorbers.
A water soluble uvB absorber is phenylbenzimadazole sulphonic acid which has a .lambda. max of 302 nms. One of the few known uvA absorbing agents which is commercially used is the oil-soluble menthylanthranilate. Others include the Parsol range (Givaudan-Roure) for example.
At present sunscreens intended to block uvA and uvB light comprise a combination of two different molecules, one to block uvA light and one to block uvB light. This presents great difficulty in formulation because the two different molecules often have very different physico--chemical properties.
Caffeic acid is a molecule of the formula: ##STR1## This molecule is known per se but is only of use as a research chemical. It is a natural molecule being found in plants such as coffee. It is extremely difficult and expensive to produce and is available only in very small quantities. At present the method of production of caffeic acid is by solvent extraction from plant tissue and column chromatography. This molecule has now been found to absorb both uvA and uvB. The molecule is, further, biodegradable and has excellent antioxidant properties.
The present invention provides a novel inexpensive method for producing caffeic acid and derivatives thereof. The present invention further allows the use of caffeic acid and derivatives thereof as sunscreen agents.
According to the present invention there is provided a compound of the formula: ##STR2## or a salt thereof, wherein R.sub.1 is H, OH or NH.sub.2, R.sub.2 is H, OH or NH.sub.2 or R.sub.1 and R.sub.2 form a double bond, R.sub.3 is H, a straight or branched chain, substituted or unsubstituted C.sub.1 -C.sub.16 alkyl, alkylene, or alkylyne, a substituted or unsubstituted homocyclic or heterocyclic aromatic group; or a group having a uv absorption extinction coefficient of 2,000 or more, R.sub.4, R.sub.5 and R.sub.6 are H, or an electron donating group, such as O
REFERENCES:
patent: 2213717 (1940-09-01), Poizat et al.
Ellis, B. E., and Amrhein, N., The `NIH-Shift` During Aromatic OrthoHydroxylation in Higher Plants, Phytochemistry, 10, pp. 3069-3072, 1971, Pergamon Press.
Freudenberg Karl, Berichte der Deutschen Chemischen Gesellschaft, vol. 53, No. 1, 1920 Weinheim DE, pp. 232-239. In German--See Ref. AK.
Gestentner B., and Conn, Eric E., "The 2-Hydroxylation of trans-Cinnamic Acid by Chloroplasts from Melilotus alba Desr." Archives of Biochemistry and Biophysics, 163, pp. 617-624, 1974, Academic Press.
Sripad, G., Prakash, V., Narasinga Rao, M.S. "Extractability of polyphenols of sunflower seed in various solvents.", J. Biosci, 4, No. 2, pp. 145-152, 1982.
Tranchino L., Constantino R., and Sodini G., "Food grade oilseed protein processing; sunflower and rapeseed.", Qual.Plant Foods Hum. Nutr., 32, pp. 305-334, 1983.
International Search Report for PCT GB95/01324. which cites References AA, AB, AE, AG and which is in the possession of the USPTO per attached Form PCT/DO/EO/903 dated Jun. 18, 1997.
CA 108:19241 (1987).
Shaku, M. et al. "Efficacy of Sodium Isoferulate as a New Sunscreen Agent", J. SCCJ, 26 (1), pp 8-17, (1992).
Banister Nigel E.
Cheetham Peter S. J.
Killos Paul J.
Zylepsis Limited
LandOfFree
Production and uses of caffeic acid and derivatives thereof does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Production and uses of caffeic acid and derivatives thereof, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Production and uses of caffeic acid and derivatives thereof will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1834996