ABC01197LA

3-Formyl Rifampicin

3-Formyl Rifampicin is a structurally modified rifamycin derivative featuring a formyl group at the 3-position of the naphthopyran core, replacing the native hydroxyl moiety. This oxidation product retains the macrocyclic anhydride and enolic side chain characteristic of Rifampicin but exhibits altered electrophilic reactivity due to the aldehyde functionality. The substitution disrupts hydrogen bonding patterns while preserving chromophore conjugation, leading to distinct UV spectral properties. Synthetically, it arises as a side product during oxidative functionalization of Rifampicin precursors. Analytically, it serves as a critical HPLC reference standard for impurity profiling in rifamycin-based pharmaceuticals.

On Request
Molecular Formula C38H47NO13
Molecular Weight 725.8000
CAS Number 13292-22-3 โœ“ Verified
PubChem CID 6438444 โ†—
Purity N/A
Product Type API Impurity
Parent Drug Rifampicin
Lead Time On Request
IUPAC Name [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-26-formyl-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl] acetate

๐Ÿ“ Synonyms

3-Formylrifamycin Rifaldehyde 13292-22-3 Rifamycin AF 3-Formylrifamycin SV 3-Formylrifampicin SV Rifamycin, 3-formyl- NCI 145-635 C87UV623UL 2,7-(Epoxypentadeca(1,11,13)trienimino)naphtho(2,1-b)furan-8-carboxaldehyde, 1,2-dihydro-5,6,9,17,19,21-hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-1,11-dioxo-, 21-acetate

๐Ÿ”ฌ Chemical Identifiers

C[C@H]1/C=C/C=C(\C(=O)NC2=C(C(=C3C(=C2O)C(=C(C4=C3C(=O)[C@](O4)(O/C=C/[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]1O)C)O)C)OC(=O)C)C)OC)C)C)O)O)C=O)/C
InChI=1S/C38H47NO13/c1-16-11-10-12-17(2)37(48)39-28-23(15-40)32(45)25-26(33(28)46)31(44)21(6)35-27(25)36(47)38(8,52-35)50-14-13-24(49-9)18(3)34(51-22(7)41)20(5)30(43)19(4)29(16)42/h10-16,18-20,24,29-30,34,42-46H,1-9H3,(H,39,48)/b11-10+,14-13+,17-12-/t16-,18+,19+,20+,24-,29-,30+,34+,38-/m0/s1
BBNQHOMJRFAQBN-UPZFVJMDSA-N

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