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E-mail: anna@molcoo.comProduct Information
Product Code: C098018
English Name: 3-Oxo Deoxycholic Acid
English Alias: (R)-4-((5R,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dihydroxy-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid
CAS Number: 2304-89-4
Molecular Formula: C24H38O5
Molecular Weight: 406.56
Advantages：As a reference standard for 3-Oxo Deoxycholic Acid, its structure is confirmed by 1H-NMR, 13C-NMR, HRMS, and X-ray single-crystal diffraction, with ≥99.0% purity (HPLC). Stored at 2-8°C in a dry, light-protected environment, it has a shelf life of 36 months with batch-to-batch purity variation <0.5%, suitable for highly sensitive analysis. Its stability and precise structural characterization meet the control requirements of pharmacopoeias such as USP and EP for steroid impurities.
Applications：
Steroid Drug Impurity Detection: Used for HPLC/LC-MS detection of 3-Oxo Deoxycholic Acid in API and formulations of deoxycholic acid, ursodeoxycholic acid, etc., controlling impurity content ≤0.2% (refer to ICH Q3A).
Synthesis Process Optimization: In the production of cholic acid drugs, monitor the generation of this impurity during the oxidation stage (e.g., generation increases 2-fold at temperatures >60°C), and reduce its content to below 0.1% by adjusting oxidant dosage (e.g., controlling H2O2 molar ratio 1:1.5).
Stability-Indicating Studies: As a degradation product standard in acid/alkali stress tests, it validates method specificity and evaluates drug degradation pathways in pH 1.2/6.8 buffers.
Biological Sample Analysis: As an internal standard for LC-MS/MS detection of cholic acid metabolites in serum, with a LOQ of 0.5 ng/mL, supporting pharmacokinetic research.
Background Description：3-Oxo Deoxycholic Acid is a 3-keto derivative of deoxycholic acid, produced by excessive oxidation or isomerization side reactions in cholic acid drug synthesis. This impurity may affect the binding activity of bile acid receptors (e.g., FXR, TGR5), interfering with hepatic lipid metabolism. The FDA's 2022 updated guidelines for bile acid drugs require genotoxicity screening for such keto impurities, driving demand for high-purity reference standards.
Research Status：
Detection Technology: UPLC-MS/MS is used with a C18 column (1.7μm, 2.1×100mm) and 0.1% formic acid water-acetonitrile gradient elution, completing separation within 1.8 minutes with a detection limit of 0.01 ng/mL, 5 times more efficient than traditional HPLC.
Formation Mechanism: Mainly originates from the oxidation of 3-hydroxy group of deoxycholic acid under acidic conditions (pH <3) or incomplete hydrolysis of intermediate 3-acetoxy compounds. Selective reduction with NaBH4 converts the 3-keto group to hydroxyl, reducing impurity content from 0.8% to 0.05%.
Safety Evaluation: In vitro experiments show the impurity has an IC50 of 25μM on HepG2 cells, with long-term exposure potentially inducing endoplasmic reticulum stress. EMA requires its permissible daily exposure (PDE) ≤1.5μg, leading to a regulatory limit of ≤0.15% in drug standards (calculated based on a 10mg daily dose).
NOTE！
We can also customize related analogues and modified peptides including HPLC, MS, 1H-NMR, MS, HPLC, IR, UV, COA, MSDS.
This product is intended for laboratory use only!
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E-mail: anna@molcoo.com
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