Taurochenodeoxycholic acid

Base Information

• Chemical Name: Taurochenodeoxycholic acid
• CAS No.: 516-35-8
• Molecular Formula: C₂₆H₄₅NO₆S
• Molecular Weight: 499.712
• UNII: 651KU15938
• DSSTox Substance ID: DTXSID101020121
• Nikkaji Number: J13.987D
• Wikipedia: Taurochenodeoxycholic_acid
• Wikidata: Q7688892
• Metabolomics Workbench ID: 36989
• ChEMBL ID: CHEMBL185878
• Mol file: 516-35-8.mol

Synonyms:Acid, Taurochenodeoxycholic;Chenodeoxycholate, Taurine;Chenodeoxycholyltaurine;Taurine Chenodeoxycholate;Taurochenodeoxycholate;Taurochenodeoxycholic Acid

Chemical Property of Taurochenodeoxycholic acid

Chemical Property:

• Refractive Index: 1.552
• PKA: 1.42±0.50(Predicted)
• PSA: 132.31000
• Density: 1.216 g/cm³
• LogP: 4.86900
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform, Methanol
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 499.29675933
• Heavy Atom Count: 34
• Complexity: 858

Purity/Quality:

98%, ^*data from raw suppliers

Taurochenodesoxycholic acid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(=O)NCCS(=O)(=O)O)C1CCC2C1(CCC3C2C(CC4C3(CCC(C4)O)C)O)C
• Isomeric SMILES: C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
• Uses: Taurochenodeoxycholic Acid 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. Labelled analogue of Taurochenodeoxycholic Acid, 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.

Technology Process of Taurochenodeoxycholic acid

There total 12 articles about Taurochenodeoxycholic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.8%

C33H48O5 + taurine potassium 18-crown-6 complex → tauroursodeoxycholic acid (516-35-8,13164-17-5,14605-22-2,66255-08-1,81244-85-1,81244-86-2,90082-02-3,90082-03-4,130009-03-9,132076-82-5)

Guidance literature:

In dichloromethane; at 20 ℃; for 5h; Concentration; Temperature;

Reference yield: 85.2%

C30H44O4 (1260543-03-0) + taurine potassium 18-crown-6 complex → tauroursodeoxycholic acid (516-35-8,13164-17-5,14605-22-2,66255-08-1,81244-85-1,81244-86-2,90082-02-3,90082-03-4,130009-03-9,132076-82-5)

Guidance literature:

In dichloromethane; at 20 ℃; for 5h;

Reference yield: 85.0%

ursodeoxycholic acid (128-13-2) + N-chlorotaurine (51036-13-6) → tauroursodeoxycholic acid (516-35-8,13164-17-5,14605-22-2,66255-08-1,81244-85-1,81244-86-2,90082-02-3,90082-03-4,130009-03-9,132076-82-5)

Guidance literature:

With sodium hydroxide; In methanol; water; at 60 ℃; for 10h; Temperature; Solvent;

upstream raw materials:

chenodeoxycholic acid

Tau

ursodeoxycholic acid

tauroursodeoxycholic acid sodium salt

Downstream raw materials:

trisodium taurochenodeoxycholate 3,7-disulfate

3α-hydroxy-7-carbonylcholanoyl-N-taurine

trisodium tauroursodeoxycholate 3,7-disulfate

C₄₈H₈₀O₄₀*C₂₆H₄₅NO₆S

Refernces

• 1、 -. "Synthetic method of tauroursodeoxycholic acid". Page/Page column 7-11. . Retrieved 2019/03/17.
• 2、 -. "niu Huangxiong method for the preparation of sodium deoxycholate". Paragraph 0033-0041. . Retrieved 2017/05/06.