Mupirocin Impurity D
Mupirocin Impurity D is a sodium carboxylate derivative arising from partial hydrolysis of the parent compound’s methyl ester moiety. It retains the core structure of mupirocin, featuring two thiazole rings and a furan ring linked via a branched aliphatic chain, but exhibits a de-esterified carboxylic acid group complexed with sodium. This impurity forms during synthetic processes due to incomplete esterification or hydrolytic degradation under basic conditions. Its distinct ionic character and altered hydrophilicity differentiate it from the parent API. It serves as an HPLC reference standard for quantifying process-related ester hydrolysis byproducts in mupirocin formulations.
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Molecular Formula
C26H43NaO9
Molecular Weight
522.6000
CAS Number
116182-43-5
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PubChem CID
23662786 ↗
IUPAC Name
sodium 9-[(E)-4-[(2R,3aS,6S,7S,7aR)-2-[(1S,2S,3S)-1,3-dihydroxy-2-methylbutyl]-7-hydroxy-3,3a,4,6,7,7a-hexahydro-2H-furo[3,2-c]pyran-6-yl]-3-methylbut-2-enoyl]oxynonanoate
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📝 Synonyms
116182-43-5
4H-Furo[2,3-c]pyranyl Mupirocin Sodium Impurity
Mupirocin EP Impurity D Sodium Salt
🔬 Chemical Identifiers
C[C@@H]([C@H](C)O)[C@@H]([C@H]1C[C@H]2CO[C@H]([C@@H]([C@@H]2O1)O)C/C(=C/C(=O)OCCCCCCCCC(=O)[O-])/C)O.[Na+]
InChI=1S/C26H44O9.Na/c1-16(13-23(30)33-11-9-7-5-4-6-8-10-22(28)29)12-20-25(32)26-19(15-34-20)14-21(35-26)24(31)17(2)18(3)27;/h13,17-21,24-27,31-32H,4-12,14-15H2,1-3H3,(H,28,29);/q;+1/p-1/b16-13+;/t17-,18-,19-,20-,21+,24-,25-,26+;/m0./s1
WGWNMOGICRTCLI-BWHRDUBESA-M
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