7-Dehydrocholesterol (7-DHC) can be converted to Vitamin D3 inside the skin by sunlight and heat, in which Vitamin D3 has been used to treat osteoporosis patients via strengthening action of bone density by stimulus of calcium absorption. 7-DHC has been also applied as an bioactive ingredient for functional cosmetics having strong function of wrinkle improvement and antioxidant, and also showed the possibility as a medicine for the childhood atopic dermatitis which is a common chronic allergic disease, but it is very unstable against light source except skin in vivo system and is converted to several undesirable side products which are very difficult to generate a Vitamin D3, and thus decrease the activity. Although many efforts to overcome the unstability of 7-DHC and the barrier of its penetration into the skin have been devoted, the study on tetraethylene glycol succinate 7-DHC 1 has not been studied yet. We introduced tetraethylene glycol succinate group to increase the stability and water solubility of 7-DHC. Herein, we wish to report on the synthesis of tetraethylene glycol succinate 7-DHC 1 from the reaction of 7-DHC with succinic anhydride in the presence of triethylamine and 4-dimethylaminopyridine, followed by treatment with tetraethylene glycol in the presence of 4-dimethylaminopyridine and N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide, and its physical properties as well as its biological properties such as wrinkle improvement, better skin absorption and antioxidantal activity.

Tetraethylene glycol succinate 7-dehydrocholesterol derivative as vitamin D3 precursor

254th National Meeting (2017)

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