6009-98-9

Basic information

• Product Name: TAUROCHENODEOXYCHOLIC ACID SODIUM SALT
• Synonyms: Sodium taurochenodeoxycholate,2-([3α,7α-Dihydroxy-24-oxo-5β-cholan-24-yl]amino)ethanesulfonic acid sodium salt, 3α,7α-Dihydroxy-5β-cholan-24-oic acid N-(2-sulfoethyl)amide sodium salt, Taurochenodeoxy;taurochenodeoxycholic acid soduim salt;3α,7α-Dihydroxy-5β-cholan-24-oic acid N-(2-sulfoethyl)amide sodium salt;Taurochenodeoxycholic Acid D4 Sodium Salt;2-([3-ALPHA,7-ALPHA-DIHYDROXY-24-OXO-5-BETA-CHOLAN-24-YL]AMINO)ETHANESULFONIC ACID;2-[(3ALPHA,7ALPHA-DIHYDROXY-24-OXO-5BETA-CHOLAN-24-YL)AMINO]ETHANESULFONIC ACID SODIUM SALT;5-BETA-CHOLANIC ACID-3-ALPHA, 7-ALPHA-DIOL N-(2-SULPHOETHYL)-AMIDE SODIUM SALT;5BETA-CHOLANIC ACID-3ALPHA,7ALPHA-DIOL-24-N-(2-SULFOETHYL)-AMIDE SODIUM
• CAS NO: 6009-98-9
• Molecular Formula: C₂₆H₄₄NO₆S*Na
• Molecular Weight: 521.69
• Mol File: 6009-98-9.mol
• Article Data: 1

Chemical Properties

• Melting Point: 165-175 °C
• Appearance: /
• Storage Temp.: room temp
• Solubility: Methanol (Slightly), Water (Slightly)
• Stability: Hygroscopic
• BRN: 3901205
• CAS DataBase Reference: TAUROCHENODEOXYCHOLIC ACID SODIUM SALT(CAS DataBase Reference)
• NIST Chemistry Reference: TAUROCHENODEOXYCHOLIC ACID SODIUM SALT(6009-98-9)
• EPA Substance Registry System: TAUROCHENODEOXYCHOLIC ACID SODIUM SALT(6009-98-9)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 6009-98-9(Hazardous Substances Data)

Usage

Description

Taurochenodeoxycholic acid (TCDCA) is a taurine-conjugated form of the primary bile acid chenodeoxycholic acid (CDCA; ). Serum levels of TCDCA increase approximately 5-fold in within two hours and begin to decrease within four hours during an oral lipid tolerance test in humans. Serum levels of TCDCA are increased in patients with liver cirrhosis and may serve as a marker of disease progression.

Chemical Properties

Solid

Uses

Different sources of media describe the Uses of 6009-98-9 differently. You can refer to the following data:
1. Taurochenodeoxycholic acid sodium salt is a bile acid conjugate and metabolite Taurolithocholic Acid (T009100) with antiinflammatory activity. It has been shown to inhibit hepatocyte apopt osis through suppression of Bid translocation to mitochondria.
2. Labeled Taurochenodeoxycholic Acid, intended for use as an internal standard for the quantification of Taurochenodeoxycholic Acid by GC- or LC-mass spectrometry.
3. Taurochenodeoxycholic Acid Sodium Salt is a bile acid conjugate and metabolite Taurolithocholic Acid (T009100) with antiinflammatory activity. Taurochenodeoxycholic Acid has been shown to inhibit hepatocyte apoptosis through suppression of Bid translocation to mitochondria.

General Description

An ionic detergent used for solubilizing lipids and proteins.

InChI:InChI=1/C26H45NO6S.Na/c1-16(4-7-23(30)27-12-13-34(31,32)33)19-5-6-20-24-21(9-11-26(19,20)3)25(2)10-8-18(28)14-17(25)15-22(24)29;/h16-22,24,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33);/t16-,17+,18-,19-,20+,21+,22-,24+,25+,26-;/m1./s1

Synthetic route

Tau (107-35-7) + chenodeoxycholic acid (474-25-9) → sodium taurochenodeoxycholate (6009-98-9)

Conditions	Yield
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; sodium hydroxide In water; acetonitrile; tert-butyl alcohol at 20 - 80℃;	93%

sodium taurochenodeoxycholate (6009-98-9) → tauroursodeoxycholic acid sodium salt (35807-85-3)

Conditions	Yield
With 7α-hydroxysteroid dehydrogenases co-immobilised on modified chitosan microspheres; NADPH In aq. buffer at 25℃; for 5h; pH=8.5; Catalytic behavior; Reagent/catalyst; Enzymatic reaction;	70%

sodium taurochenodeoxycholate (6009-98-9) → Tau (107-35-7) + chenodeoxycholic acid (474-25-9)

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 taurochenodeoxycholate (6009-98-9) → ursodeoxycholic acid (128-13-2)

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: 75 percent / Sepharose-CL6B; 7β-hydroxysteroid dehydrogenase; TEA / NAD(+) / H2O / 120 h / 20 °C View Scheme

sodium taurochenodeoxycholate (6009-98-9) + β‐cyclodextrin (7585-39-9) → C26H44NO6S(1-)*C42H70O35*Na(1+)

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

Upstream product

• 107-35-7 Tau 
• 474-25-9 chenodeoxycholic acid 

Downstream Products

• 107-35-7 Tau 
• 474-25-9 chenodeoxycholic acid 
• 35807-85-3 tauroursodeoxycholic acid sodium salt 
• 128-13-2 ursodeoxycholic acid 

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.