1249-75-8

Basic information

• Product Name: 3-ALPHA-HYDROXY-5-BETA-CHOLAN-24-OIC ACID METHYL ESTER
• Synonyms: 3-ALPHA-HYDROXY-5-BETA-CHOLAN-24-OIC ACID METHYL ESTER;5-BETA-CHOLANIC ACID-3-ALPHA-OL METHYL ESTER;5-BETA-CHOLAN-24-OIC ACID 3-ALPHA-OL METHYL ESTER;METHYL LITHOCHOLATE;LITHOCHOLIC ACID METHYL ESTER;5.beta.-Cholan-24-oic acid, 3.alpha.-hydroxy-, methyl ester;3α-Hydroxy-5β-cholan-24-oic acid methyl ester;3α-Ol-5β-24-cholanoic acid methyl ester
• CAS NO: 1249-75-8
• Molecular Formula: C₂₅H₄₂O₃
• Molecular Weight: 390.6
• EINECS: 215-002-9
• Product Categories: Pharmaceuticals, Intermediates & Fine Chemicals, Steroids
• Mol File: 1249-75-8.mol
• Article Data: 86

Chemical Properties

• Melting Point: 125-126 °C
• Boiling Point: 474.1°Cat760mmHg
• Flash Point: 177.5°C
• Appearance: /
• Density: 1.038g/cm³
• Vapor Pressure: 5.56E-11mmHg at 25°C
• Refractive Index: 1.512
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 15.14±0.70(Predicted)
• CAS DataBase Reference: 3-ALPHA-HYDROXY-5-BETA-CHOLAN-24-OIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ALPHA-HYDROXY-5-BETA-CHOLAN-24-OIC ACID METHYL ESTER(1249-75-8)
• EPA Substance Registry System: 3-ALPHA-HYDROXY-5-BETA-CHOLAN-24-OIC ACID METHYL ESTER(1249-75-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1249-75-8(Hazardous Substances Data)

Usage

Uses

Methyl Lithocholate is an derivative of Lithocholic Acid (L469180),a cholic acid derivative as TGR5 modulator. Found in ox bile, human bile, rabbit bile, and in ox and pig gallstones.

InChI:InChI=1/C25H42O3/c1-16(5-10-23(27)28-4)20-8-9-21-19-7-6-17-15-18(26)11-13-24(17,2)22(19)12-14-25(20,21)3/h16-22,26H,5-15H2,1-4H3/t16-,17-,18-,19-,20-,21-,22-,24-,25+/m0/s1

Upstream product

• 67-56-1 methanol 
• 2276-94-0 3α-hydroxy-5α-cholanic acid 
• 434-13-9 Lithocholic acid 
• 75-36-5 acetyl chloride 
• 1634-04-4 tert-butyl methyl ether 
• 2276-93-9 3β-hydroxy-5α-cholan-24-oic acid 
• 434-13-9 Isolithocholic acid 
• 434-13-9 4-((R)-3-Hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid 
• 108655-60-3 1-(3α-hydroxy-24-oxo-5β-cholan-24-yl)-1H-v-triazolo<4,5-b>pyridine 
• 474-25-9 chenodeoxycholic acid 
• 40736-33-2 (20S)-20-hydroxymethylpregn-4-en-3-one 
• 3986-89-8 (20S)-3-oxopregn-4-ene-20-carboxaldehyde 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 3057-04-3 chenodeoxycholic acid methyl ester 

Downstream Products

• 42151-48-4 24,24-diphenyl-5α-cholanediol-(3α,24) 
• 42151-48-4 24,24-diphenyl-5α-cholanediol-(3β,24) 
• 15074-03-0 (R)-methyl 4-((5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate 
• 4144-29-0 3α-acetoxy-24,24-diphenyl-5β-chol-23-ene 
• 3664-90-2 (3α,5β)-3-hydroxycholan-24-hydrazide 
• 1173-32-6 methyl 3-oxo-5β-cholan-24-oate 
• 1261-92-3 3α-tosyloxy-5β-cholan-24-oic acid methyl ester 
• 107180-35-8 3α-(toluene-4-sulfonyloxy)-5β-cholan-24-oic acid ethyl ester 
• 134878-46-9 Methyl-3α-benzyloxy-5percentb-cholan-24-oate 
• 84061-62-1 methyl 3β-tosyloxy-5α-cholan-24-oate 
• 1249-75-8 methyl 3α-hydroxy-5α-cholan-24-oate 
• 3253-69-8 methyl 3α-acetoxy-5β-cholan-24-oate 

Relevant articles and documents

Membrane transport inspired hydrolysis of non-activated esters at near physiological pH

A positively charged micelle loaded with substrates was transported selectively to the reaction site (cathode) to promote the proximity and localization of the reactants (ester and hydroxide). The guided vehicular delivery coupled with electrolysis allows the hydrolysis of non-activated esters at near physiological pH with significant yields along with recyclability.

Preparation method of lithocholic acid and intermediates thereof

The invention discloses a synthesis method of lithocholic acid and an intermediates thereof. According to the preparation method of the lithocholic acid intermediate, a compound I reacts with hydrogento generate a compound II in a mixed solvent by taking palladium on carbon as a catalyst and adding specific alkali; a low-price botanical bulk fermentation product BA is used as a raw material, andlithocholic acid is synthesized through side chain construction, hydrogenation, reduction, hydrolysis and other reactions; and the selectivity of 5beta hydrogen in the hydrogenation reaction is improved, high-toxicity reagents such as hydrazine hydrate are prevented from being used for hydroxyl due to removal of other animal-derived cholic acids, and the method is environmentally friendly, high insafety, simple in route, mild in reaction condition and suitable for industrial mass production.

Green Esterification of Carboxylic Acids Promoted by tert-Butyl Nitrite

In this work, the green esterification of carboxylic acids promoted by tert-butyl nitrite has been well developed. This transformation is compatible with a broad range of substrates and exhibits excellent functional group tolerance. Various drugs and substituted amino acids are applicable to this reaction under near neutral conditions, with good to excellent yields.