124729-58-4

Basic information

• Product Name: 3,7-dihydroxy-7-n-propylcholanoic acid
• Synonyms: 3,7-dihydroxy-7-n-propylcholanoic acid
• CAS NO: 124729-58-4
• Molecular Formula: C27H46 O4
• Molecular Weight: 434.6517
• Mol File: 124729-58-4.mol

Chemical Properties

• Boiling Point: 569.8°Cat760mmHg
• Flash Point: 312.4°C
• Appearance: /
• Density: 1.085g/cm³
• Vapor Pressure: 2.36E-15mmHg at 25°C
• Refractive Index: 1.529
• CAS DataBase Reference: 3,7-dihydroxy-7-n-propylcholanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3,7-dihydroxy-7-n-propylcholanoic acid(124729-58-4)
• EPA Substance Registry System: 3,7-dihydroxy-7-n-propylcholanoic acid(124729-58-4)

Safety Data

• Hazardous Substances Data: 124729-58-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C27H46O4/c1-5-12-27(31)16-18-15-19(28)10-13-25(18,3)22-11-14-26(4)20(7-8-21(26)24(22)27)17(2)6-9-23(29)30/h17-22,24,28,31H,5-16H2,1-4H3,(H,29,30)/t17-,18?,19?,20+,21+,22+,24+,25+,26-,27?/m1/s1

Upstream product

• 10538-59-7 7-ketolithocholic methyl ester 
• 4651-67-6 7-Ketolithocholic acid 
• 2234-82-4 1-propylmagnesium chloride 

Relevant articles and documents

(E)-7-Ethylidene-lithocholic Acid (7-ELCA) Is a Potent Dual Farnesoid X Receptor (FXR) Antagonist and GPBAR1 Agonist Inhibiting FXR-Induced Gene Expression in Hepatocytes and Stimulating Glucagon-like Peptide-1 Secretion From Enteroendocrine Cells

Bile acids (BAs) are key signaling steroidal molecules that regulate glucose, lipid, and energy homeostasis via interactions with the farnesoid X receptor (FXR) and G-protein bile acid receptor 1 (GPBAR1). Extensive medicinal chemistry modifications of the BA scaffold led to the discovery of potent selective or dual FXR and GPBAR1 agonists. Herein, we discovered 7-ethylidene-lithocholic acid (7-ELCA) as a novel combined FXR antagonist/GPBAR1 agonist (IC50 = 15?μM/EC50 = 26?nM) with no off-target activation in a library of 7-alkyl substituted derivatives of BAs. 7-ELCA significantly suppressed the effect of the FXR agonist obeticholic acid in BSEP and SHP regulation in human hepatocytes. Importantly, 7-ELCA significantly stimulated the production of glucagon-like peptide-1 (GLP-1), an incretin with insulinotropic effect in postprandial glucose utilization, in intestinal enteroendocrine cells. We can suggest that 7-ELCA may be a prospective approach to the treatment of type II diabetes as the dual modulation of GPBAR1 and FXR has been supposed to be effective in the synergistic regulation of glucose homeostasis in the intestine.

Chemical synthesis

A process for the production of disubstituted bile acid analogs, including the disubstituted analogs of such bile acids as, lithocholic, hyodeoxycholic, cholic, chenodeoxycholic and ursodeoxycholic acids. This invention was made in the course of work performed under a grant from the U.S. National Heart Lung and Blood Institute.

Synthesis of bile acid analogs: 7-alkylated chenodesoxycholic acids

This paper describes a method for the preparation of 7-alkylated chenodesoxycholic acids from 3α-hydroxy-7-oxo-5β-cholanoic acid.The synthetic procedure is based upon Grignard reaction between the keto bile acid and an alkyl magnesium halide.Under the conditions employed, the introduction of alkyl groups is highly stereoselective.Only 7β-alkylated epimers are obtained.The overall yield is several-fold higher than that obtained by the previous method, which involved the preparation of an oxazoline intermediate.