Spiranolactone Impurity E
Spiranolactone Impurity E is a sulfur-substituted spirolactone derivative characterized by a tetrahydrofuran ring fused to a γ-lactone core, with a methylthio group at the C-17 position. The thioether functionality introduces steric hindrance and alters hydrogen bonding compared to the parent compound, resulting in distinct chromatographic behavior. This impurity forms via side-chain oxidation during Spiranolactone synthesis, yielding a stable, non-reactive byproduct. It functions as an HPLC reference standard for quantifying process-related impurities in pharmaceutical formulations.
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Molecular Formula
C24H32O4S
Molecular Weight
416.6000
CAS Number
33784-05-3
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PubChem CID
11509929 ↗
IUPAC Name
S-[(7S,8R,9S,10R,13S,14S,17R)-10,13-dimethyl-3,5'-dioxospiro[2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17,2'-oxolane]-7-yl] ethanethioate
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📝 Synonyms
33784-05-3
7b-Spironolactone
7-Beta-Spironolactone
SC 11940
Spironolactone EP Impurity E
7beta-Spironolactone
8NK6P5VN96
A-Spironolactone
S-[(7S,8R,9S,10R,13S,14S,17R)-10,13-dimethyl-3,5'-dioxospiro[2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17,2'-oxolane]-7-yl] ethanethioate
3'-(3-Oxo-7beta-acetylthio-17beta-hydroxyandrost-4-en-17alpha-yl)-propionic acid lactone
🔬 Chemical Identifiers
CC(=O)S[C@H]1CC2=CC(=O)CC[C@@]2([C@@H]3[C@@H]1[C@@H]4CC[C@]5([C@]4(CC3)C)CCC(=O)O5)C
InChI=1S/C24H32O4S/c1-14(25)29-19-13-15-12-16(26)4-8-22(15,2)17-5-9-23(3)18(21(17)19)6-10-24(23)11-7-20(27)28-24/h12,17-19,21H,4-11,13H2,1-3H3/t17-,18-,19-,21+,22-,23-,24+/m0/s1
LXMSZDCAJNLERA-KVXIHFSQSA-N
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