Didehydro Atovaquone is a fully conjugated hydroxynaphthoquinone derivative characterized by a 2-chloro-3-(4-nitrophenyl)-1,4-naphthoquinone core, featuring a fully oxidized quinone moiety and a para-nitrophenyl substituent. Its structure lacks the 1,4-dihydroxy substitution of the parent drug, replacing it with a fully conjugated 1,4-quinone system, while retaining a chloromethyl group at the naphthoquinone ring. This compound arises as a synthetic byproduct during atovaquone oxidation processes, resulting from over-oxidation of the hydroxyl groups. Serves as an HPLC reference standard for atovaquone impurity profiling in pharmaceutical quality control.
On RequestC1CC(=CCC1C2=C(C3=CC=CC=C3C(=O)C2=O)O)C4=CC=C(C=C4)Cl
InChI=1S/C22H17ClO3/c23-16-11-9-14(10-12-16)13-5-7-15(8-6-13)19-20(24)17-3-1-2-4-18(17)21(25)22(19)26/h1-5,9-12,15,24H,6-8H2
HZBPGPKKLODCKG-UHFFFAOYSA-N