145-42-6

Basic information

• Product Name: Sodium taurocholate
• Synonyms: ethanesulfonicacid,2-[[(3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxy-24;monosodiumtaurocholicacid;n-choloyl-taurinsodiumsalt;taurocholatesodium;taurocholatesodiumsalt;5BETA-CHOLANIC ACID-3ALPHA,7ALPHA,12ALPHA-TRIOL 24-N-(2-SULFOETHYL) AMIDE SODIUM;5-BETA-CHOLANIC ACID-3-ALPHA, 7-ALPHA, 12-ALPHA-TRIOL N-(2-SULPHOETHYL)-AMIDE SODIUM SALT;5BETA-CHOLAN-24-OIC ACID N-[2-SULFOETHYL]AMIDE-3ALPHA,7ALPHA,12ALPHA-TRIOL SODIUM SALT
• CAS NO: 145-42-6
• Molecular Formula: C₂₆H₄₄NO₇S*Na
• Molecular Weight: 537.68
• EINECS: 205-653-7
• Product Categories: Bile Acids;Biochemistry;Steroids
• Mol File: 145-42-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 230 °C
• Flash Point: 9℃
• Appearance: /
• Density: 1.177 g/cm3(Temp: 22.5 °C)
• Refractive Index: 23 ° (C=3, H2O)
• Storage Temp.: 0-6°C
• Solubility: H2O: 0.5 M at 20 °C, clear, colorless to f
• Water Solubility: > 250 g/L (20 ºC)
• Merck: 14,9075
• BRN: 3901620
• CAS DataBase Reference: Sodium taurocholate(CAS DataBase Reference)
• NIST Chemistry Reference: Sodium taurocholate(145-42-6)
• EPA Substance Registry System: Sodium taurocholate(145-42-6)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39-24/25
• RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution
• WGK Germany: 3
• RTECS: WX0400000
• F: 3-10
• Hazardous Substances Data: 145-42-6(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

Uses

Different sources of media describe the Uses of 145-42-6 differently. You can refer to the following data:
1. selectively activates retinoid X receptors (RXRs)
2. Sodium taurocholate is a detergent useful for the solubilization of lipids and membrane-bound proteins.

Purification Methods

Purify it by recrystallisation and gel chromatography using Sephadex LH-20. [Beilstein 10 III 1655, 10 IV 2078.]

InChI:InChI=1/C26H45NO7S.Na/c1-15(4-7-23(31)27-10-11-35(32,33)34)18-5-6-19-24-20(14-22(30)26(18,19)3)25(2)9-8-17(28)12-16(25)13-21(24)29;/h15-22,24,28-30H,4-14H2,1-3H3,(H,27,31)(H,32,33,34);/q;+1/p-1/t15-,16+,17-,18-,19+,20+,21-,22+,24+,25+,26-;/m1./s1

Synthetic route

Tau (107-35-7) + cholic acid (81-25-4) → sodium taurocholate (145-42-6)

Conditions	Yield
Stage #1: Tau; cholic acid With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine In N,N-dimethyl-formamide at 90℃; for 2h; Stage #2: With sodium hydroxide In methanol at 20℃; for 1h;	95%
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; sodium hydroxide In water; dimethyl sulfoxide; acetonitrile; tert-butyl alcohol at 20 - 80℃;	88%

2-[carbamimidoyl(methyl)amino]acetic acid hydrochloride (17050-09-8) + sodium taurocholate (145-42-6) → amino((carboxymethyl)(methyl)amino)methaniminium 2-((R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanamido)ethane-1-sulfonate

Conditions	Yield
In ethanol at 50℃; for 4h;	97%

ethyl 2-(3-methylguanidino)acetate hydrochloride (15366-32-2) + sodium taurocholate (145-42-6) → amino((2-ethoxy-2-oxoethyl)(methyl)amino)methaniminium 2-((R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanamido)ethane-1-sulfonate

Conditions	Yield
In ethanol at 50℃; for 4h;	95%

sodium taurocholate (145-42-6) → N-nitrosotaurochoic acid (82660-96-6)

Conditions	Yield
With sodium acetate; nitrosylchloride In acetic acid at 10 - 15℃; for 1h;	72%

metformin hydrochloride (1115-70-4) + sodium taurocholate (145-42-6) → tauro-CA-metformin complex

Conditions	Yield
In methanol at 20℃;	72%

sodium taurocholate (145-42-6) → Tau (107-35-7) + cholic acid (81-25-4)

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

sodium taurocholate (145-42-6) → 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 taurocholate (145-42-6) → 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

N,N’-ethylenebismethacrylamide (6117-25-5) + sodium taurocholate (145-42-6) + 2-aminoethylmethacrylate hydrochloride → poly(2-aminoethyl methacrylate hydrochloride-co-ethylene bis methacrylamide-co-sodium taurocholate)

Conditions	Yield
With potassium persulfate In water at 65℃; for 18.5h; Product distribution / selectivity;

sodium taurocholate (145-42-6) + β‐cyclodextrin (7585-39-9) → C26H44NO7S(1-)*C42H70O35*Na(1+) (103419-28-9)

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

sodium taurocholate (145-42-6) → tert-butyl alcohol (75-65-0)

Conditions	Yield
In water

sodium taurocholate (145-42-6) + novantrone (70476-82-3) → 2C26H45NO7S*C22H28N4O6

Conditions	Yield
In aq. phosphate buffer at 49.99℃; pH=7.4;

Upstream product

• 81-25-4 cholic acid 
• 7347-25-3 sodium taurinate 
• 107-35-7 Tau 

Downstream Products

• 75-65-0 tert-butyl alcohol 
• 107-35-7 Tau 
• 81-25-4 cholic acid 
• 82660-96-6 N-nitrosotaurochoic acid 
• 911-40-0 7-ketodeoxycholic acid 

Relevant articles and documents

Synthetic method and medicinal preparation of sodium taurocholate

The method comprises the following steps: S10, dissolving taurine and a base in water for salt formation reaction, drying the generated salt after the reaction is ended, and obtaining taurine sodium. S20, the taurine sodium and cholic acid are subjected to condensation reaction under 2 - ethoxy -1 - ethoxycarbonyl -1 and 2 - 80 - 120 °C dihydroquinoline, and a product solution containing sodium taurocholate is obtained. S30, sodium taurocholate in the product solution is separated and purified to obtain the sodium taurocholate product. To the method, taurine and a base are subjected to salt formation reaction to obtain sodium taurocholate, and condensation reaction is carried out, so that an existing 'one-pot' is changed into a two-step method. In addition, the synthetic method provided by the invention is simple to operate and low in cost.

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.