71154-85-3

Basic information

• Product Name: 3-oxopregna-1,4-diene-20-carboxylic acid
• Synonyms: 3-oxopregna-1,4-diene-20-carboxylic acid
• CAS NO: 71154-85-3
• Molecular Formula: C₂₂H₃₀O₃
• Molecular Weight: 342.4718
• EINECS: 275-222-6
• Mol File: 71154-85-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 507.8°C at 760 mmHg
• Flash Point: 275°C
• Appearance: /
• Density: 1.15g/cm³
• Vapor Pressure: 1.1E-11mmHg at 25°C
• Refractive Index: 1.568
• PKA: 4.68±0.10(Predicted)
• CAS DataBase Reference: 3-oxopregna-1,4-diene-20-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-oxopregna-1,4-diene-20-carboxylic acid(71154-85-3)
• EPA Substance Registry System: 3-oxopregna-1,4-diene-20-carboxylic acid(71154-85-3)

Safety Data

• Hazardous Substances Data: 71154-85-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C22H30O3/c1-13(20(24)25)17-6-7-18-16-5-4-14-12-15(23)8-10-21(14,2)19(16)9-11-22(17,18)3/h8,10,12-13,16-19H,4-7,9,11H2,1-3H3,(H,24,25)/t13?,16-,17+,18-,19-,21-,22+/m0/s1

Upstream product

• 5779-62-4 β-sitosterol 
• 3614-61-7 23,24-Bisnorchola-1,4-dien-3-one-22-carboxylic acid 
• 1380518-01-3 3-oxo-23,24-bisnorchol-4-en-22-oyl-coenzyme A 
• 81201-82-3 (20S)-3-oxopregna-1,4-diene-20-carboxaldehyde 
• 35525-27-0 22-hydroxy-23,24-bis-norchola-1,4-diene-3-one 

Downstream Products

• 115208-40-7 2-((8R,9S,10S,13S,14S)-10,13-Dimethyl-3-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-propionic acid 
• 3614-61-7 3-Keto-bis-norchol-4-enoic acid 

Relevant articles and documents

COMPOSITION OF MEDIA FOR CULTIVATION OF MYCOBACTERIA SPLITTING THE SIDE CHAIN OF SITOSTEROL

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Isolation, biological significance, synthesis, and cytotoxic evaluation of new natural parathiosteroids A-C and analogues from the soft coral Paragorgia sp

(Chemical Equation Presented) Three unusual new steroid thioesters, parathiosteroids A-C (1a-3a), were isolated from the 2-propanol extract of the soft coral Paragorgia sp. collected in Madagascar. Their structures, determined by detailed spectroscopic analysis, were confirmed by synthesis and represent the first isolation of natural steroids bearing a C22 thioester in their side chain. These compounds displayed cytotoxicity against a panel of three human tumor cell lines at the micromolar level. The preparation of several analogues revealed structure/activity relationships in this type of steroids, for example, that the XCH2CH2NHCOCH3 moiety (X = S, O, NH) in the side chain is essential for the antiproliferative activity, and a low degree of oxidation in the A-ring results in higher bioactivity. These natural products could be biosynthetic intermediates in the steroid side chain degradation pathway involving activation with CoA and β-oxidations.

BIODEGRADATION OF CHOLESTEROL BY A MUTANT OF THE Mycobacterium SPECIES

The biodegradation of cholesterol by the Mycobacterium mutant CCM 3528 gave rise to 22-hydroxy-23,24-bisnorchola-1,4-diene-3-one (I) as the main product.The identified by-products were 24-norchola-1,4-diene-3,22-dione (IX), androsta-1,4-diene-3,17-dione (XV) and their unsaturated analogues, X and XVI respectively.