1352328-64-3

Basic information

• Product Name: Cholan-24-oic acid,3-hydroxy-7-oxo-, phenylmethyl ester,(3α,5β)-
• Synonyms: Cholan-24-oic acid,3-hydroxy-7-oxo-, phenylmethyl ester,(3α,5β)-;(3alpha,5beta)-3-Hydroxy-7-oxocholan-24-oic acid phenylmethyl ester;BENZYL 3-HYDROXY-7-KETO-5-CHOLAN-24-OATE
• CAS NO: 1352328-64-3
• Molecular Formula: C₃₁H₄₄O₄
• Molecular Weight: 480.67866
• Mol File: 1352328-64-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 588.4±30.0 °C(Predicted)
• Appearance: /
• Density: 1.109±0.06 g/cm3(Predicted)
• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• PKA: 15.02±0.70(Predicted)
• CAS DataBase Reference: Cholan-24-oic acid,3-hydroxy-7-oxo-, phenylmethyl ester,(3α,5β)-(CAS DataBase Reference)
• NIST Chemistry Reference: Cholan-24-oic acid,3-hydroxy-7-oxo-, phenylmethyl ester,(3α,5β)-(1352328-64-3)
• EPA Substance Registry System: Cholan-24-oic acid,3-hydroxy-7-oxo-, phenylmethyl ester,(3α,5β)-(1352328-64-3)

Safety Data

• Hazardous Substances Data: 1352328-64-3(Hazardous Substances Data)

Usage

Uses

Phenylmethyl (3α,5β)-3-Hydroxy-7-oxo-cholan-24-oic Acid Ester is an intermediate used in the synthesis of 6-Ethylchenodeoxycholic-d5 Acid (E899812), which is an isotope labelled compound of 6-Ethylchenodeoxycholic Acid (E899810), which is used in the investigative treatment of primary biliary cholangitis. Primary biliary cholangitis is an autoimmune disease of the liver that slowly progresses to cirrhosis.

Upstream product

• 474-25-9 chenodeoxycholic acid 
• 4651-67-6 7-Ketolithocholic acid 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 

Downstream Products

• 1352328-65-4 benzyl 3α,7-trimethylsilyloxy-5β-cholan-6-en-24-oate 

Relevant articles and documents

SYNTHESIS OF OBETICHOLIC ACID AND SYNTHESIS INTERMEDIATE

The present invention relates to a new intermediate for the synthesis of obeticholic acid, the compound of formula (I) or a geometric isomer thereof, a process for obtaining the same, as well as the use of said intermediate in the synthesis of obeticholic acid.

Method for preparing obeticholic acid from new derivative of 3alpha-hydroxy-7-oxo-5beta-cholanic acid

The invention discloses a method for preparing obeticholic acid from a new derivative of 3alpha-hydroxy-7-oxo-5beta-cholanic acid. The synthesis method comprises the following steps: firstly, carrying out hydroxyl and carboxyl protection on the 3alpha-hydroxy-7-oxo-5beta-cholanic acid to prepare the corresponding new derivative; secondly, obtaining the obeticholic acid respectively according to two synthesis routes. According to the method disclosed by the invention, a safer protecting group reagent is utilized, and the problem that ultraviolet absorption of an intermediate is not strong is solved; the intermediate is easier to purify, the yield is improved, and the cost is reduced, so that the method is more suitable for industrialized amplification, and has remarkable creativity and actual application value.

Conicasterol E, a small heterodimer partner sparing farnesoid X receptor modulator endowed with a pregnane X receptor agonistic activity, from the marine sponge Theonella swinhoei

We report the isolation and pharmacological characterization of conicasterol E isolated from the marine sponge Theonella swinhoei. Pharmacological characterization of this steroid in comparison to CDCA, a natural FXR ligand, and 6-ECDCA, a synthetic FXR agonist generated by an improved synthetic strategy, and rifaximin, a potent PXR agonist, demonstrated that conicasterol E is an FXR modulator endowed with PXR agonistic activity. Conicasterol E induces the expression of genes involved in bile acids detoxification without effect on the expression of small heterodimer partner (SHP), thus sparing the expression of genes involved in bile acids biosynthesis. The relative positioning in the ligand binding domain of FXR, explored through docking calculations, demonstrated a different spatial arrangement for conicasterol E and pointed to the presence of simultaneous and efficient interactions with the receptor. In summary, conicasterol E represents a FXR modulator and PXR agonist that might hold utility in treatment of liver disorders.