8-Epi-cyanocobalamin is a stereoisomeric impurity of cyanocobalamin generated via epimerization at the 8-hydroxyl position of the corrin macrocycle. This structural variant retains the cyanide coordination, propionyl substituents, and dimethylbenzimidazole nucleotide but exhibits inverted stereochemistry at C8, altering its diastereomeric profile. The compound's distinct conformation affects its chromatographic behavior and enantioselective detection, necessitating its use as a reference standard for HPLC method validation in quantifying epimeric impurities during cyanocobalamin synthesis and stability testing.
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InChI=1S/C62H90N13O14P.CN.Co/c1-29-20-39-40(21-30(29)2)75(28-70-39)57-52(84)53(41(27-76)87-57)89-90(85,86)88-31(3)26-69-49(83)18-19-59(8)37(22-46(66)80)56-62(11)61(10,25-48(68)82)36(14-17-45(65)79)51(74-62)33(5)55-60(9,24-47(67)81)34(12-15-43(63)77)38(71-55)23-42-58(6,7)35(13-16-44(64)78)50(72-42)32(4)54(59)73-56;1-2;/h20-21,23,28,31,34-37,41,52-53,56-57,76,84H,12-19,22,24-27H2,1-11H3,(H15,63,64,65,66,67,68,69,71,72,73,74,77,78,79,80,81,82,83,85,86);;/q;-1;+3/p-2/t31-,34+,35-,36-,37+,41-,52-,53-,56?,57+,59-,60+,61+,62+;;/m1../s1
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