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3-Epi empagliflozin Impurity

3-Epi empagliflozin Impurity is a stereoisomer of empagliflozin, characterized by an inversion of configuration at the C-3 position of the glucosidic moiety. It retains the core 1,5-dihydroxy-2-methylpyrrolidin-3-yl scaffold and 4-chlorobenzyl substituent but exhibits altered glycosidic stereochemistry. The molecule contains multiple hydroxyl groups, an ether linkage, and a chloride moiety, contributing to its distinct chromatographic behavior. This impurity arises during synthetic processes due to partial epimerization at the anomeric center. It serves as a critical HPLC reference standard for quantifying stereoisomeric impurities in empagliflozin formulations.

On Request
Molecular Formula C23H27ClO7
Molecular Weight 450.9000
CAS Number 864070-43-9 โœ“ Verified
PubChem CID 11949687 โ†—
Purity N/A
Product Type API Impurity
Parent Drug Empagliflozin
Lead Time On Request
IUPAC Name (2S,3R,4R,5S,6R)-2-[4-chloro-3-[[4-[(3R)-oxolan-3-yl]oxyphenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol

๐Ÿ“ Synonyms

864070-43-9 (1S)-1,5-Anhydro-1-C-[4-chloro-3-[[4-[[(3R)-tetrahydro-3-furanyl]oxy]phenyl]methyl]phenyl]-D-glucitol DTXSID701113221 (1S)-1,5-Anhydro-1-C-(4-chloro-3-((4-(((3R)-tetrahydro-3-furanyl)oxy)phenyl)methyl)phenyl)-D-glucitol RefChem:1049487 DTXCID001544815 3'-Epi Empagliflozin 3'''-Epi-Empagliflozin Empagliflozin Impurity C (2S,3R,4R,5S,6R)-2-(4-Chloro-3-(4-(((R)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

๐Ÿ”ฌ Chemical Identifiers

C1COC[C@@H]1OC2=CC=C(C=C2)CC3=C(C=CC(=C3)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)Cl
InChI=1S/C23H27ClO7/c24-18-6-3-14(23-22(28)21(27)20(26)19(11-25)31-23)10-15(18)9-13-1-4-16(5-2-13)30-17-7-8-29-12-17/h1-6,10,17,19-23,25-28H,7-9,11-12H2/t17-,19-,20-,21+,22-,23+/m1/s1
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