67516-56-7

Basic information

• Product Name: (20S)-3-oxopregna-1,4-diene-20-carboxylic acid
• CAS NO: 67516-56-7
• Molecular Weight: 342.478
• Mol File: 67516-56-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (20S)-3-oxopregna-1,4-diene-20-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (20S)-3-oxopregna-1,4-diene-20-carboxylic acid(67516-56-7)
• EPA Substance Registry System: (20S)-3-oxopregna-1,4-diene-20-carboxylic acid(67516-56-7)

Safety Data

• Hazardous Substances Data: 67516-56-7(Hazardous Substances Data)

Upstream product

• 35525-27-0 22-hydroxy-23,24-bis-norchola-1,4-diene-3-one 
• 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 

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

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.

Synthesis of 20-Carbaldehydes and 20-Carbonitriles of the Pregnane Series Starting with (20S)-20-Hydroxymethylpregna-1,4-dien-3-one

An efficient six-step approach to 3-protected (20S)-3β-hydroxypregna-1,5-diene-20-carbaldehydes 8 with potential importance in the synthesis of vitamin D analogues was developed starting with (20S)-20-hydroxymethylpregna-1,4-dien-3-one (1).Oxidation of the 22-hydroxy group of 1 by means of periodinane 2 (Dess-Martin reagent) furnished the aldehyde 3 without epimerization. 3 was protected selectively at C-22 as dimethyl acetal 5.Isomerization to 6 and subsequent reduction of the 3-carbonyl group with calcium borohydride furnished the 3β-alcohol 7a with high stereoselectivity.Cleavage of the acetal to 8a occurred in a homogeneous solution of acetic acid in the presence of small amounts of water and trifluoroacetic acid.After protection of the 3-OH group 8b-d were obtained in 54percent overall yield.The in situ generated aldehyde N,N-dimethylhydrazones of 3, 8a, and 8b were converted in high yields with excellent chemoselectivity into the nitriles 12, 15a, and 15b with magnesium monoperoxyphthalate hexahydrate.The uniform (20S) stereochemistry of 3 and 8a-d was elucidated by 1H-NMR investigations. - Key Words: Pregnanes / Steroids

Microbial production of 3-oxobisnorchola-1,4-dien-22-oic acid

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