Adduct of cinnamic acid and glycerin, ultraviolet absorbent and

Details Adduct of cinnamic acid and glycerin, ultraviolet absorbent and Adduct of cinnamic acid and glycerin, ultraviolet absorbent and

1993-03-05

1995-06-20

Killos, Paul J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

424 60, 562465, C07C 6976, A61K 744

Patent

active

054262100

DESCRIPTION:

BRIEF SUMMARY
[TECHNICAL FIELD]

This invention relates to an adduct of cinnamic acid and glycerin, an ultraviolet absorbent and an external preparation for skin and more particularly, a cinnamic acid derivative having ultraviolet absorbancy, and an ultraviolet absorbent and an external preparation for skin using the same.


[BACKGROUND ART]

Various influences of ultraviolet rays to skin, such as rapid aging of the skin, are recently well known. The ultraviolet rays included in sunlight are classified into a long wavelength ultraviolet ray having a wavelength from 400 nm to 320 nm as UV-A, a medium wavelength ultraviolet ray having a wavelength from 320 nm to 290 nm as UV-B, and a short wavelength ultraviolet ray having a wavelength of not more than 290 nm as UV-C in a field of skin science.
Since most of the ultraviolet rays usually irradiated human body originate in sunlight, the UV-C are absorbed by the ozonosphere and the body is mainly influenced by the UV-A and UV-B.
Among these, the UV-B forms erythema or blister and causes aggravation of melanin formation and chromatosis when the skin is irradiated with the UV-B over a certain level.
In order to prevent aging of human skin and generation or increase of blots and flecks thereon, it is very important to protect human skin from the UV-B, and various types of UV-B absorbent have been developed.
The prior UV-B absorbents used for practical application include a PABA derivative, a cinnamic acid derivative, a salicylic acid derivative, a benzophenone derivative, an urocanine derivative, a camphor derivative, and a heterocyclic derivatives.
These types of UV-B absorbents are generally mixed in external preparations for skin such as cosmetics or quasi drugs.
The prior types of UV-B absorbents, however, are oil soluble in most cases and their solubility in water is very low, so their applications have been limited to a narrow area. As a water soluble UV-B absorbent, only 2-hydroxy-4-methoxy-5-sulfoxonium benzophenone sodium salt has been known, however this had not enough ultraviolet ray absorptivity.


[DISCLOSURE OF THE INVENTION]

Accordingly, it is an object of the present invention to eliminate the above-described problems in the prior art and to provide a water soluble material having a high ultraviolet ray absorptivity.
As a result of studies undertaken by the inventors so as to attain this aim, and it has been found that a new adduct of cinnamic acid and glycerin had an excellent ultraviolet ray absorptivity as well as a solubility in water. The present invention has been achieved on the bases of this finding.
The adduct of cinnamic acid and glycerin according to this invention is represented by the following general structural formula (1), ##STR2## (In the general structural formula (1) above, G represents 1 mole of glycerin, and e represents average mole number of addition and at least 1. R represents hydrogen or fatty chain. n and k are identified by (n+k) is 1 to 3, and n and k are 0 to 3 respectively. X represents hydrogen, ion, fatty chain or Gm, and the G represents 1 mole of glycerin, and m represents average number of addition and at least 1.)
The ultraviolet absorbent according to claim 2 is characterized in that the ultraviolet absorbent is the adduct of cinnamic acid and glycerin represented by the general structural formula (1).
The external preparation for skin according to claim 3 is characterized in that at least one of the adducts of cinnamic acid and glycerin represented by the general structural formula (1) are contained.
Detail structures of this invention will be explained hereinafter.
In the general structural formula (1), R represents a hydrogen or fatty chain. In the case of fatty chain, total number of carbon atoms is preferably 1 to 4. The fatty chain may be any of a straight chain alkyl group, a branched chain alkyl group, an unsaturated alkyl group and a cycloalkyl group. As an example of the R, a methyl group, an ethyl group, an acetylenyl group, a propyl group, an isopropyl group, a propenyl group, a butyl group, an isobutyl group, a

REFERENCES:
Chemical Abstracts, vol. 106, No. 15, Abstract No. 105(15); 119004c, 1984; F. Clouet, et al. "J. Chromatogrphy".
Tetrahedron Letters, Oct. 1970, vol. 49, W. Oppolzer, et al.; "Intramolekulare Cycloadditionen von N-Alkyl-C-Phenoxymethyl-Nitronen an Ortho-Staendige C=C-Doppelbindungen"; pp. 4313-4314.
France, 6380M; Laboratories Anphar, Nov. 1967.
Chemical & Pharmaceutical Bulletin, vol. 39, No. 9, Sep. 1991; Y. Sashida, et al.; "Studies on the Chemical Constituents of the Bulbs of Lilium Machliniae"; pp. 2362-2368.
Chemical Abstracts, vol. 107, No. 12, Abstract No. 107(12); Sep. 1987; Obata Yasuo; "Fragrance J.," 15(3).
Chemical Abstracts, vol. 99, No. 6, Abstract No. 99(6); 43309u, 1983; R. Roelandts, et al., "Int. J. Dermatology".

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