1352328-66-5

Basic information

• Product Name: Cholan-24-oic acid,6-ethylidene-3-hydroxy-7-oxo-,phenylmethyl ester, (3α,5β)-
• Synonyms: Cholan-24-oic acid,6-ethylidene-3-hydroxy-7-oxo-,phenylmethyl ester, (3α,5β)-;OCA-E1;(R)-Benzyl 4-((3R,5R,8S,9S,10R,13R,14S,17R,E)-6-ethylidene-3-hydroxy-10,13-dimethyl-7-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate;benzyl 3α-hydroxy-6-ethylidene-7-keto-5β-cholan-24-oate; (3alpha,5beta)-6-Ethylidene-3-hydroxy-7-oxo-cholan-24-oic acid phenylmethyl ester
• CAS NO: 1352328-66-5
• Molecular Formula: C₃₃H₄₆O₄
• Molecular Weight: 506.71594
• Mol File: 1352328-66-5.mol

Chemical Properties

• Boiling Point: 614.2±48.0 °C(Predicted)
• Appearance: /
• Density: 1.124±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.94±0.70(Predicted)
• CAS DataBase Reference: Cholan-24-oic acid,6-ethylidene-3-hydroxy-7-oxo-,phenylmethyl ester, (3α,5β)-(CAS DataBase Reference)
• NIST Chemistry Reference: Cholan-24-oic acid,6-ethylidene-3-hydroxy-7-oxo-,phenylmethyl ester, (3α,5β)-(1352328-66-5)
• EPA Substance Registry System: Cholan-24-oic acid,6-ethylidene-3-hydroxy-7-oxo-,phenylmethyl ester, (3α,5β)-(1352328-66-5)

Safety Data

• Hazardous Substances Data: 1352328-66-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ursodiol is used as a therapeutic agent for the treatment of gallstones and certain liver conditions. Its cholesterol-lowering and bile-dissolving properties help prevent the formation of gallstones, while its anti-inflammatory and immunomodulatory effects contribute to the management of liver conditions.
Used in Gallstone Treatment:
Ursodiol is employed as a gallstone treatment, working by reducing the amount of cholesterol produced by the liver and dissolving cholesterol in bile. This dual action helps to prevent the formation of gallstones and provides relief to patients suffering from this condition.
Used in Liver Condition Management:
Ursodiol is utilized in the management of certain liver conditions due to its potential anti-inflammatory and immunomodulatory properties. These properties contribute to the alleviation of symptoms and improvement of liver function in patients with specific liver disorders.
Formulations:
Ursodiol is available in various forms, including capsules and tablets, for oral administration. It is considered a relatively safe and well-tolerated medication, with common side effects such as diarrhea and stomach discomfort.

Upstream product

• 75-07-0 acetaldehyde 
• 1352328-65-4 benzyl 3α,7-trimethylsilyloxy-5β-cholan-6-en-24-oate 

Downstream Products

• 1352328-67-6 benzyl 3α,7α-dihydroxy-6-ethyliden-5β-cholan-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.

AN IMPROVED PROCESS FOR PREPARATION OF OBETICHOLIC ACID

The invention relates to an improved process for the preparation of compound of formula (A), which is an intermediate in the preparation of Obeticholic acid or its analogous compounds thereof.

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.

Preparation method for obeticholic acid and intermediate thereof

The invention relates to a preparation method for obeticholic acid and an intermediate thereof. The intermediate 3alpha-hydroxy-6alpha-ethyl-7-keto-5beta-cholanic acid is obtained by subjecting 3alpha-hydroxy-6-ethylidene-7-keto-5beta-cholanic acid benzyl ester compounds to a reaction under the action of a catalyst and a hydrogen donor. The catalyst is selected from Pd/C or PtO2 or Raney Ni. The hydrogen donor is selected from cyclohexene or cyclohexadiene or tetrahydronaphthalene. According to the method, the yield is high, the stereoselectivity is high, safety is good, the reaction condition is mild, and the method is applicable to industrial production.

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.