21-Hemiacetal Dexamethasone is a structurally modified derivative of the corticosteroid dexamethasone, characterized by a hemiacetal linkage at the C21 hydroxyl position. This impurity arises from the reaction of the C21 hydroxyl group with an adjacent carbonyl moiety, forming a five-membered hemiacetal ring. The molecule retains the core cyclopentanoperhydrophenanthrene scaffold with hydroxyl groups at C17 and C11, and a fluorine substituent at C9. The hemiacetal functionality introduces stereochemical complexity, distinguishing it from the parent drug. It serves as an HPLC reference standard for quantifying dexamethasone impurities in pharmaceutical formulations.
On RequestC[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)C(O)OC)O)C)O)F)C
InChI=1S/C23H31FO6/c1-12-9-16-15-6-5-13-10-14(25)7-8-20(13,2)22(15,24)17(26)11-21(16,3)23(12,29)18(27)19(28)30-4/h7-8,10,12,15-17,19,26,28-29H,5-6,9,11H2,1-4H3/t12-,15+,16+,17+,19?,20+,21+,22+,23+/m1/s1
UCCNAQVBEVBWAA-HIAQARTRSA-N