3360-89-2

Basic information

• Product Name: (5β,6α)-6-Hydroxy-3-oxo-cholan-24-oic Acid Methyl Ester
• Synonyms: (5β,6α)-6-Hydroxy-3-oxo-cholan-24-oic Acid Methyl Ester
• CAS NO: 3360-89-2
• Molecular Formula: C₂₅H₄₀O₄
• Molecular Weight: 404.5827
• Product Categories: Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals, Steroids
• Mol File: 3360-89-2.mol

Chemical Properties

• Melting Point: 99-100 °C
• Boiling Point: 505.7±25.0 °C(Predicted)
• Appearance: /
• Density: 1.085±0.06 g/cm3(Predicted)
• Solubility: Dichloromethane, Ethyl Acetate, Hexane
• PKA: 14.68±0.70(Predicted)
• CAS DataBase Reference: (5β,6α)-6-Hydroxy-3-oxo-cholan-24-oic Acid Methyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: (5β,6α)-6-Hydroxy-3-oxo-cholan-24-oic Acid Methyl Ester(3360-89-2)
• EPA Substance Registry System: (5β,6α)-6-Hydroxy-3-oxo-cholan-24-oic Acid Methyl Ester(3360-89-2)

Safety Data

• Hazardous Substances Data: 3360-89-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(5β,6α)-6-Hydroxy-3-oxo-cholan-24-oic Acid Methyl Ester is used as an intermediate compound in the synthesis of important pharmaceutical products, such as progesterone (P755900) and α-Hyodeoxycholic Acid (H998100). These compounds have significant applications in the treatment of various medical conditions and hormonal imbalances.
Used in Chemical Industry:
(5β,6α)-6-Hydroxy-3-oxo-cholan-24-oic Acid Methyl Ester is also utilized as a key building block in the chemical industry for the development of novel steroidal compounds with potential applications in various fields, including pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 128-08-5 N-Bromosuccinimide 
• 2868-48-6 methyl hyodeoxycholate 
• 15086-27-8 aluminium(III) phenoxide 
• 67-64-1 acetone 
• 83-49-8 Hyodeoxycholic Acid 
• 186581-53-3 diazomethane 
• 67733-54-4 6α-hydroxy-3-oxo-5β-cholan-24-oic acid 
• 108-94-1 cyclohexanone 

Downstream Products

• 1516887-33-4 (E)-3α-hydroxy-6-ethylidene-7-keto-5β-cholan-24-oic acid 
• 1312468-58-8 methyl 3-oxo-6α-benzoyloxycholanate 
• 1452-33-1 methyl 3-oxo-4-cholenolate 

Relevant articles and documents

Analysis of conjugated bile acids in human biological fluids. Synthesis of hyodeoxycholic acid 3- and 6-glycosides and related compounds

The glucuronide, glucoside and N-acetylglucosaminide conjugates of hyodeoxycholic acid were synthesized. In addition, murideoxycholic acid 3- glycosides and some of their C-5 epimeric analogs were also prepared. The principal reactions used are 1) the Koenigs-Knorr condensation reaction of 3- oxo-6α-hydroxy and 6-oxo-3α-hydroxy esters with an appropriate α- acetohalosugar catalyzed by cadmium carbonate in benzene under reflux, 2) reduction of the resulting bile acid glycoside methyl ester-acetates with tert-butylamine-borane complex, and 3) subsequent hydrolysis with aqueous lithium hydroxide.

Efficient synthesis of cholic acid derivates through stereoselective C–H functionalization from hyodeoxycholic acid

Five cholic acid derivatives (including allo-ω-muricholic acid and CDCA) were synthesized from hyodeoxycholic acid via selective oxidation of C3- or C6-hydroxyl groups by IBX and NBS oxidants and stereocontrolled conversion. The hydroxyl group could be introduced through hydrolyzing α-Br keto with K2CO3 aqueous solution or through oxidizing the double bond by monoperoxyphthalic acid. The reduction of C6-O6 carbonyl to methylene could undergo with PTSH, NaBH3CN and ZnCl2 only at 5β configuration. A feasible synthetic route of CDCA from HDCA has been established to avoid the epimerization with the yield of 45% (8 steps). These strategies provided good yields, stereoselectivity and reproducibility for the preparation of cholic acid derivates and CDCA.

METHOD FOR PREPARING A FARNESOID X RECEPTOR AGONIST

The invention relates to a process for preparing a compound of formula (I) in particular obeticholic acid and intermediates suitable for its synthesis.

A Facile Route to Ursodeoxycholic Acid Based on Stereocontrolled Conversion and Aggregation Behavior Research

A facile route to ursodeoxycholic acid (UDCA) and its aggregation behavior in aqueous phase solution, which is rarely known, are reported. The starting material, hyodeoxycholic acid (HDCA), is a relatively less expensive material and more easily obtained compared with chenodeoxycholic acid (CDCA). A facile route was developed to synthesize UDCA from HDCA with a Shapiro reaction as the key step and in 26% overall yield. A new strategy using organosilane reagent considering its stability, nontoxicity, and abundance in nature was carried out for a more rapid route and higher yield. It was found that the critical micelle concentration value, which is a critical value for surfactants of bile salts, was influenced by the number of hydroxyl groups.

NEW STEROID INHIBITORS OF PGP FOR USE FOR INHIBITING MULTIDRUG RESISTANCE

The present invention relates to a compound of formula (I) for its use for reversing or inhibiting multidrug resistance.

Selective dimethyldioxirane oxidation of bile acid methyl esters

DMDO oxidation of the hydroxy groups of bile acid methyl esters establishes the positional order of reactivity as 3-7 > 6 > 12 and supports a mechanism involving C-H oxygen insertion through a planar intramolecularly hydrogen bonded transition state.