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

Uses

Glycocholic Acid Sodium Salt is a biochemical formed by the conjugation of cholic acid (C432600) with glycine (G615990).

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.