1452-29-5

Basic information

• Product Name: 4-Cholenic acid-3-one
• Synonyms: 3-oxochol-4-en-24-oic acid
• CAS NO: 1452-29-5
• Molecular Formula: C₂₄H₃₆O₃
• Molecular Weight: 0
• Mol File: 1452-29-5.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 526.7°Cat760mmHg
• Flash Point: 286.4°C
• Appearance: /
• Density: 1.11g/cm³
• Vapor Pressure: 1.68E-12mmHg at 25°C
• Refractive Index: 1.546
• CAS DataBase Reference: 4-Cholenic acid-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Cholenic acid-3-one(1452-29-5)
• EPA Substance Registry System: 4-Cholenic acid-3-one(1452-29-5)

Safety Data

• Hazardous Substances Data: 1452-29-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C24H36O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h14-15,18-21H,4-13H2,1-3H3,(H,26,27)/t15-,18+,19-,20+,21+,23+,24-/m1/s1

Upstream product

• 110-86-1 pyridine 
• 104825-76-5 4β-bromo-3-oxo-5β-cholan-24-oic acid 
• 151592-49-3 26-hydroxy-24-ethylcholest-4-en-26-oic acid 
• 601-57-0 Cholest-4-en-3-one 
• 64-19-7 acetic acid 
• 5255-17-4 3β-hydroxy-5-cholenoic acid 
• 1553-56-6 dehydrolithocholic acid 
• 20231-57-6 methyl 5-cholenoate 
• 112018-64-1 (R)-4-((5S,8S,9S,10R,13R,14S,17R)-4-Bromo-10,13-dimethyl-3-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester 
• 1173-32-6 methyl 3-oxo-5β-cholan-24-oate 
• 1249-75-8 methyl lithocholate 
• 434-13-9 Lithocholic acid 
• 1857-80-3 5α,6β-dibromocholestan-3β-ol 
• 127-09-3 sodium acetate 

Downstream Products

• 473462-29-2 24-(benzoyloxy)-4-oxachol-5-en-3-one 
• 473462-28-1 24-(benzoyloxy)-chol-4-en-3-one 
• 1025965-86-9 Benzoic acid (R)-4-[(3R,3aR,5aS,6R,9aS,9bS)-6-(2-carboxy-ethyl)-3a,6-dimethyl-7-oxo-dodecahydro-cyclopenta[a]naphthalen-3-yl]-pentyl ester 
• 20231-57-6 methyl 5-cholenoate 
• 288099-95-6 6-{(4aR,4bS,6aR,7R,9aS,9bS,11aR)-7-[(R)-4-(4-Cyano-benzyloxy)-1-methyl-butyl]-4a,6a-dimethyl-hexadecahydro-indeno[5,4-f]quinolin-1-yl}-hexanoic acid tert-butyl ester 
• 1452-33-1 methyl 3-oxo-4-cholenolate 
• 1452-33-1 (R)-4-((8S,9S,10R,13R,14S)-10,13-Dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester 

Relevant articles and documents

Microbial Degradation of the Phytosterol Side Chain. 1. Enzymatic Conversion of 3-Oxo-24-ethylcholest-4-en-26-oic Acid into 3-Oxochol-4-en-24-oic Acid and Androst-4-ene-3,17-dione

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Synthesis of esters of bile acids and avermectin B1

Esters of bile acids and avermectin B1 were obtained for the first time by the reaction of avermectin B1 with bile acid anhydrides.

Synthesis and in vitro biological activity of 4α(2-propenyl)-5α- cholest-24-en-3α-ol: A 24,25-dehydro analog of the hypocholesterolemic agent 4α-(2-propenyl)-5α-cholestan-3α-ol

4α-(2-Propenyl)-5α-cholestan-3α-ol (LY295427) was previously identified from a Chinese hamster ovary (CHO) cell-based low density lipoprotein receptor/luciferase (LDLR/Luc) assay to be a potent transcriptional activator of the LDL receptor promoter in the presence of 25- hydroxycholesterol. To investigate the effect of the 24,25-unsaturation in the D-ring side chain (desmosterol D-ring side chain) on antagonizing the repressing effect of 25-hydroxycholesterol, 4α-(2-propenyl)-5α-cholest-24- en-3α-ol (17), a 24,25-dehydro analog of LY295427, was thus synthesized from lithocholic acid via the formation of 3α-[[(1,1- dimethylethyl)dimethylsilyl]oxy]-4α-(2-propenyl)5α-cholan-24-al (15). Test results showed that 17 had an EC(30) value of 2.6 (max)M, comparable to 2.9 (max)M of LY295427, in the CHO cell-based LDLR/Luc assay in the presence of 25-hydroxycholesterol. Apparently, the built-in 24,25-unsaturation in the D- ring side chain of 17 had added little effect to antagonizing the repressing effect of 25-hydroxycholesterol. In the [1-14C-acetate]cholesterol biosynthesis inhibition assay, 17 at 10 μg/ml (23 μM) has been shown to inhibit the cholesterol biosynthesis in CHO cells by 38% relative to the vehicle control; whereas LY295427 showed no inhibition in the same assay in our previous studies. In contrast to LY295427, the built-in 24,25- unsaturation in the D-ring side chain of 17 has conferred an inhibitory effect on cholesterol biosynthesis in CHO cells. In summary, the observed LDL receptor promoter activity of 17 is related to its ability to prevent 25- hydroxycholesterol from exerting the repressing effect via an undetermined mechanism and, in part, to inhibit the cholesterol biosynthesis.

SYNTHETIC STUDIES ON VITAMIN D ANALOGUES VI. A NEW SYNTHESIS OF 25-HYDROXYCHOLESTEROL FROM LITHOCHOLIC ACID

The conversion of lithocholic acid (1) into 25-hydroxycholesterol (10) via methyl 3β-hydroxy-5-cholenate (6) is described.