Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1997-05-29
1999-10-12
Owens, Amelia
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C07F 906
Patent
active
059657502
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to highly purified tocopheryl phosphates which are soluble in water at about neutrality, a process for producing the same and a method of analyzing tocopheryl phosphates. The present invention also relates to cosmetics containing the above tocopheryl phosphates.
BACKGROUND ART
The tocopherol is generally well known as vitamin E. The tocopherol is much contained in vegetable oils such as peanut oil and soybean oil.
The vitamin E, i.e., tocopherol has been studied for the elucidation of the antisterile effect thereof. What has attracted the greatest interest during the study is the antioxidant effect of tocopherol. Further, extensive biologic effects have recently been recognized of tocopherols inclusive of tocopherol and salts thereof.
These effects of the tocopherols have been noted and, now, the tocopherols are used in a wide range of application fields such as not only pharmaceutical preparations, cosmetic ingredients and livestock feed additives but also food, health food and plastic additives.
However, the tocopherols have drawbacks in that they are insoluble in water although being soluble in fats and oils and organic solvents such as acetone and ethanol and are viscous and oily, so that the handling thereof is restricted and that they are easily oxidized by the action of light, heat, alkali, etc. in the air.
Accordingly, in recent years, extensive studies are made on, for example, converting the tocopherol to derivatives in order to increase the hydrophilicity thereof. Examples of such attempts to increase hydrophilicity of the tocopherol include the synthesis of a phosphoric diester of tocopherylglycerol and a salt thereof (see Japanese Patent Laid-open Publication No. 6(1994)-87875), the synthesis of a tocopherol glycoside (see, for example, Japanese Patent Laid-open Publication No. 60(1985)-56994) and the synthesis of an ethylene glycol derivative of tocopheryl phosphate (see Yakugaku Zasshi, 75, 1322 (1955) and Chem. Pharm. Bull., 19, 687 (1971)). Further, examples of the above attempts include the synthesis of a phosphoric diester of L-ascorbic acid/dltocopherol (see Japanese Patent Laid-open Publication Nos. 59(1984)-219295, 62(1987)-205091 and 02(1990)-111722).
However, all the tocopherol derivatives disclosed in the above literature must be synthesized through multiple stages of reactions, so that the problems are encountered that the production involves difficulty and the cost is high.
Moreover, an aqueous emulsion composition containing a tocopherol in high concentration has been proposed in Japanese Patent Publication No. 7(1995)-037381, which specifically contains an alkali metal salt of hemisuccinic ester of tocopheryl phosphate but contains none of a dissolution auxiliary and an emulsifier. Further, tocopheryl nicotinates have been proposed (see, for example, Japanese Patent Publication No. 55(1980)-049074).
However, the compounds described in these literature, like those described in the above literature, must be synthesized through multiple stages of reactions, so that the problems are encountered that the production involves difficulty and the cost is high. Further, they are scarcely soluble in water, so that the problem is encountered that the addition thereof to a wide variety of cosmetic preparations is difficult.
It has been reported that a sodium salt of tocopheryl phosphate is a hydrophilic tocopherol derivative whose synthesis is relatively easy (see Yakugaku Zasshi, 75, 1322 (1955), Japanese Patent Publication Nos. 37(1962)-1737 and 03(1991)-32558 and Khim.-Fram. Zh., 17(7), 840 (1983)).
However, Nakagawa et al. have described in the pharmaceutical journal (Yakugaku Zasshi, 75(11), 1322 (1955)) that an aqueous solution of tocopheryl phosphate obtained by the reaction of tocopherol with an oxyphosphorus trichloride is emulsified, when brought into about neutrality, or form precipitates, which are not readily soluble in water.
E. E. Zhukova et al. have described in the journal (Khim.-Fram. Zh., 17(7), 840 (1983)) that a tocopher
REFERENCES:
Yakugaku Zasshi, "Synthesis of Water-soluble Vitamin E Derivatives," Nakagawa et al., 75(11), 1322, 1955, pp. 1322-1325.
Chemical Pharmacy Bulletin, "A New Phosphorylating Reagent., The Preparation of the Mixed phosphoric . . . " Mushika et al., vol. 19, No. 4. 1971, pp. 687-695.
Pharmaceutical Chemistry Journal, (Khim. Farm. Zh. 17(7), 840, 1983), "Methods of Synthesis and Technology of Drug Production," 1797), 501, 1983 (English Trans.) pp. 501-504.
Bioact. Mol 3., "Synthesis of Vitamin E Phosphate and Vitamin K.sub.1 Phosphate," from 2nd Intern' Symposium on Phosphrus Chemistry Directed Towards Biology., 1987, pp. 235-246.
Ito Shinobu
Kurata Yohei
Mano Keisuke
Misu Naoaki
Nozawa Tsutomu
Owens Amelia
Showa Denko K.K.
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