863-57-0

Basic information

• Product Name: GLYCOCHOLIC ACID SODIUM SALT
• Synonyms: glycocholatesodium;glycocholatesodiumsalt;monosodiumglycocholicacid;n-choloyl-glycinmonosodiumsalt;sodium N-(3-alpha,7-alpha,12-alpha-trihydroxy-24-oxocholan-24-yl)glycinate;GLYCOCHOLIC ACID, SODIUM SALT HYDRATE, 9 7%;Glycine, N-(3.alpha.,5.beta.,7.alpha.,12.alpha.)-3,7,12-trihydroxy-24-oxocholan-24-yl-, monosodium salt;3α,7α,12α-trihydroxy-5β-cholan-24-oic acid n-(carboxymethyl)amide sodium salt
• CAS NO: 863-57-0
• Molecular Formula: C₂₆H₄₂NO₆*Na
• Molecular Weight: 487.6
• EINECS: 212-730-9
• Product Categories: Detergents;Bile Acids;Biochemistry;Steroids;Mutagenesis Research Chemicals
• Mol File: 863-57-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: 210-215 °C (subl.)(lit.)
• Boiling Point: 692oC at 760 mmHg
• Flash Point: 372.3oC
• Appearance: light green solid
• Vapor Pressure: 3.7E-22mmHg at 25°C
• Refractive Index: 30 ° (C=1, H2O)
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
• Stability: Hygroscopic
• Merck: 4494
• CAS DataBase Reference: GLYCOCHOLIC ACID SODIUM SALT(CAS DataBase Reference)
• NIST Chemistry Reference: GLYCOCHOLIC ACID SODIUM SALT(863-57-0)
• EPA Substance Registry System: GLYCOCHOLIC ACID SODIUM SALT(863-57-0)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: MB9265100
• F: 3-9
• Hazardous Substances Data: 863-57-0(Hazardous Substances Data)

Usage

Description

GLYCOCHOLIC ACID SODIUM SALT is a biochemical compound formed by the conjugation of cholic acid (C432600) with glycine (G615990). It is a bile acid that plays a crucial role in the digestion and absorption of dietary fats and fat-soluble vitamins in the human body.
Used in Pharmaceutical Industry:
GLYCOCHOLIC ACID SODIUM SALT is used as a pharmaceutical agent for the treatment of various liver and gallbladder disorders. It helps in dissolving gallstones and improving bile flow, thereby reducing the risk of gallstone formation.
Used in Cosmetic Industry:
GLYCOCHOLIC ACID SODIUM SALT is used as an ingredient in cosmetic products for its emulsifying, solubilizing, and cleansing properties. It helps in maintaining the skin's natural moisture balance and promoting a healthy skin barrier.
Used in Food Industry:
GLYCOCHOLIC ACID SODIUM SALT is used as a food additive to improve the taste, texture, and stability of various food products. It acts as an emulsifier, helping to mix oil and water-based ingredients, and enhances the absorption of fat-soluble nutrients.
Used in Research Applications:
GLYCOCHOLIC ACID SODIUM SALT is used as a research tool in the study of bile acid metabolism, liver function, and the development of new therapeutic agents for liver and gallbladder diseases. It helps researchers understand the role of bile acids in various physiological processes and their potential as therapeutic targets.

Purification Methods

Dissolve it in EtOH, filter it and concentrated to crystallisation, and recrystallise from a little EtOH. It also crystallises from 95% EtOH/Et2O. [Beilstein 3 IV 573.]

InChI:InChI=1/C26H43NO6.Na/c1-14(4-7-22(31)27-13-23(32)33)17-5-6-18-24-19(12-21(30)26(17,18)3)25(2)9-8-16(28)10-15(25)11-20(24)29;/h14-21,24,28-30H,4-13H2,1-3H3,(H,27,31)(H,32,33);/q;+1/p-1/t14-,15+,16-,17-,18+,19+,20-,21+,24+,25+,26-;/m1./s1

Synthetic route

cholic acid (81-25-4) + glycine (56-40-6) → sodium glycocholate (863-57-0)

Conditions	Yield
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; sodium hydroxide In water; dimethyl sulfoxide; acetonitrile; tert-butyl alcohol at 20 - 80℃;	95%

sodium glycocholate (863-57-0) → [(R)-4-((5R,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-Dihydroxy-10,13-dimethyl-3-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoylamino]-acetic acid (88725-38-6)

Conditions	Yield
With DL-dithiothreitol; NAD In water; ethyl acetate for 40h; Ambient temperature; 3α-hydroxysteroid dehydrogenase, puryvate/lactic dehydrogenase, serum albumin, potassium phosphate buffer pH=8.5; Yield given;

sodium glycocholate (863-57-0) → cholic acid (81-25-4) + glycine (56-40-6)

Conditions	Yield
With ethylenediaminetetraacetic acid; chloylglycine hydrolase; 2-hydroxyethanethiol In phosphate buffer at 20℃; for 0.333333h; pH=8;	A 100 % Chromat. B n/a

sodium glycocholate (863-57-0) → 7-ketodeoxycholic acid (911-40-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent Chromat. / chloylglycine hydrolase; β-mercaptoethanol; EDTA / aq. phosphate buffer / 0.33 h / 20 °C / pH 8 2: 8 percent / Sepharose-CL6B; 7β-hydroxysteroid dehydrogenase; TEA / NAD(+) / H2O / 120 h / 20 °C View Scheme

sodium glycocholate (863-57-0) → ursocholic acid (2955-27-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent Chromat. / chloylglycine hydrolase; β-mercaptoethanol; EDTA / aq. phosphate buffer / 0.33 h / 20 °C / pH 8 2: 80 percent / Sepharose-CL6B; 7β-hydroxysteroid dehydrogenase; TEA / NAD(+) / H2O / 120 h / 20 °C View Scheme

sodium glycocholate (863-57-0) → glycocholic acid (107589-98-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: NAD, DTT / ethyl acetate; H2O / 40 h / Ambient temperature; 3α-hydroxysteroid dehydrogenase, puryvate/lactic dehydrogenase, serum albumin, potassium phosphate buffer pH=8.5 2: NADH, DTT / ethanol; H2O / 30 h / 3β-hydroxysteroid dehydrogenase, formate/formate dehydrogenase, potassium phosphate buffer pH=7.2 View Scheme

sodium glycocholate (863-57-0) + β‐cyclodextrin (7585-39-9) → C26H42NO6(1-)*C42H70O35*Na(1+) (103419-27-8)

Conditions	Yield
In water at 25℃; pH=7; Thermodynamic data; Concentration; phosphate buffer;

Upstream product

• 81-25-4 cholic acid 
• 56-40-6 glycine 

Downstream Products

• 107589-98-0 glycocholic acid 
• 911-40-0 7-ketodeoxycholic acid 
• 81-25-4 cholic acid 
• 56-40-6 glycine 

Relevant articles and documents

Continuous flow synthesis and scale-up of glycine- and taurine-conjugated bile salts

A multi-gram scale protocol for the N-acyl amidation of bile acids with glycine and taurine has been successfully developed under continuous flow processing conditions. Selecting ursodeoxycholic acid (UDCA) as the model compound and N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (EEDQ) as the condensing agent, a modular mesoreactor assisted flow set-up was employed to significantly speed up the optimization of the reaction conditions and the flow scale-up synthesis. The results in terms of yield, in line purification, analysis, and implemented flow set-up for the reaction optimization and large scale production are reported and discussed.