Abstract:

3,8-Bis-(1-hydroxyethyl)deuteroporphyrin dimethyl ester(Ⅲ) was prepared from hemin(I) by the ways of HBr-H3CCOOH addition reaction, OH- nucleophilic substitution reaction and anhydrous hydrogen chloride catalyzed esterification. It was then oxidized by Jones reagent to form 3,8-bisacetyl deuteroporphyrin dimethyl ester(Ⅳ). The effects of reaction temperature and reaction time on the yield of 3,8-bis-(1-hydroxy-ethyl) deuteroporphyrin dimethyl ester(Ⅱ) were studied. The conditions of esterification reaction were modified. A cheaper and selective oxidant was used in the synthesization of 3,8-bisacetyl deuteroporphyrin dimethyl ester(Ⅳ). The results showed that the yield of hematoporphyrin(Ⅱ) reaches to the highest of 98.5% when the temperature is 35 ℃ and the reaction time is 25 h. The yield of hematoporphyrin dimethyl ester is 72.1% when the catalyst is anhydrous hydrogen chloride. The cost of 3,8-bisacetyl deuteroporphyrin dimethyl ester(Ⅳ) was decreased greatly when the oxidant is Jones reagent. The target products were characterized with 1H NMR, IR and MS.

Key words: hemin, hematoporphyrin, porphyrin derivatives, synthesis