14772-98-6

Basic information

• Product Name: 3α,7α-Dihydroxy-5α-cholan-24-oic acid methyl ester
• Synonyms: Methyl allochenodeoxycholate
• CAS NO: 14772-98-6
• Molecular Formula: C₂₅H₄₂O₄
• Molecular Weight: 406.59858
• Mol File: 14772-98-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 125-126 °C
• Boiling Point: 507.6±25.0 °C(Predicted)
• Appearance: /
• Density: 1.089±0.06 g/cm3(Predicted)
• PKA: 14.79±0.70(Predicted)
• CAS DataBase Reference: 3α,7α-Dihydroxy-5α-cholan-24-oic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3α,7α-Dihydroxy-5α-cholan-24-oic acid methyl ester(14772-98-6)
• EPA Substance Registry System: 3α,7α-Dihydroxy-5α-cholan-24-oic acid methyl ester(14772-98-6)

Safety Data

• Hazardous Substances Data: 14772-98-6(Hazardous Substances Data)

Upstream product

• 14772-96-4 methyl 3-oxo-7α-hydroxy-5α-cholan-24-oate 
• 67-56-1 methanol 
• 15357-34-3 (3α,5α,7α)-3,7-dihydroxy-cholan-24-oic acid 
• 6038-71-7 3β-acetoxy-5α-cholestan-7-one 
• 40823-41-4 acetic acid-(7α-hydroxy-5α-cholestanyl-(3β)-ester) 
• 14772-97-5 methyl 3β,7α-dihydroxy-5α-cholan-24-oate 
• 106351-13-7 4β-bromo-7α-formyloxy-3-oxo-5β-cholanic acid 
• 106351-14-8 7α-formyloxy-3-oxo-4-cholenic acid 
• 106351-12-6 7α-formyloxy-3-oxo-5α-cholanic acid 
• 14772-95-3 7α-hydroxy-3-oxochol-4-en-24-oic acid 
• 16265-22-8 3-oxo-5α-7α-hydroxy-cholan-24-al 
• 125626-79-1 methyl 7α-formyloxy-3-oxo-1,4-choladienoate 
• 125626-76-8 7α-hydroxy-3-oxo-1,4-choladienoic acid 
• 71781-42-5 methyl 7α-formyloxy-3α-hydroxy-5β-cholanoate 

Downstream Products

• 474-25-9 chenodeoxycholic acid 

Relevant articles and documents

Chenodeoxycholic acid and preparation method thereof

The invention relates to the field of medicine synthesis, and in particular to chenodeoxycholic acid and a preparation method thereof. The preparation method of the chenodeoxycholic acid provided by the invention comprises the following steps of: using 3 alpha,7 alpha-dihydroxy-5 alpha-ursodeoxycholic acid as raw materials to form an intermediate compound E through chemical reaction; then, performing chemical reaction on the intermediate compound E to form the chenodeoxycholic acid. The structure formula of the intermediate compound E is shown in the description, wherein R1 is alkyl, alkenylor aromatic group; R2 is acyl. The preparation method has the advantages that extracted byproducts can be used as raw materials for fast synthesizing the chenodeoxycholic acid; each step in the process is mild in condition; the yield is high; the method is suitable for mass preparation.

Potential bile acid metabolites. XXI. A new synthesis of allochenodeoxycholic and allocholic acids

A new method for the preparation of allochenodeoxycholic and allocholic acids is described. The key steps in the synthesis are 1) simultaneous oxidation-dehydrogenation reaction of 3α-hydroxy 5β-bile acid formyl esters with iodoxybenzene catalyzed by benzeneseleninic anhydride, 2) reductive allomerization at C-5 of the 1,4-dien-3-oxo bydroxy acids with lithium/liq. ammonia, and 3) subsequent reduction of the resulting 3-oxo 5α-compounds with K-Selectride.

BILE ACIDS LXIX. SELECTIVE K-SELECTRIDE REDUCTION OF 3,7-DIKETO STEROIDS

The K-Selectride reduction at low temperature (-45 C) of 7-oxo-5α-cholestan-3β-yl acetate and methyl 7-oxo-3α-hydroxy-5β-cholanoate resulted in almost quantitative yield of the 7α-alcohol in the 5α-compound but only moderate yield of the 5β-analog.The simultaneous reduction of two carbonyl in the 3 and 7 positions afforded good to excellent yields of the diaxial diol in planar steroids (methyl 3,7-dioxo-5α-cholanoate, 3,7-dioxo-5α-cholestane and methyl 3,7-dioxo-5α-cholestan-27-oate) and only 14percent of 3α,7α-(OH)2 from methyl 3,7-dioxo-5β-cholanoate.