Lithocholic acid

Base Information

• Chemical Name: Lithocholic acid
• CAS No.: 434-13-9
• Molecular Formula: C24H40 O3
• Molecular Weight: 376.58
• Hs Code.: 29181998
• European Community (EC) Number: 207-099-1
• NSC Number: 683770
• UNII: 5QU0I8393U
• DSSTox Substance ID: DTXSID6020779
• Nikkaji Number: J1.532F
• Wikipedia: Lithocholic_acid
• Wikidata: Q3323035
• Pharos Ligand ID: R7T63LWW3BWW
• Metabolomics Workbench ID: 36245
• ChEMBL ID: CHEMBL1478
• Mol file: 434-13-9.mol

Synonyms:Acid, Isolithocholic;Acid, Lithocholic;Isolithocholic Acid;Lithocholate;Lithocholic Acid

Chemical Property of Lithocholic acid

Chemical Property:

• Appearance/Colour: white to off-white powder
• Vapor Pressure: 1.4E-12mmHg at 25°C
• Melting Point: 183-188 °C(lit.)
• Refractive Index: 35.5 ° (C=1, EtOH)
• Boiling Point: 511°Cat760mmHg
• PKA: 4.76±0.10(Predicted)
• Flash Point: 276.9°C
• PSA: 57.53000
• Density: 1.073g/cm³
• LogP: 5.50710
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Dichloromethane (Slightly, Heated), DMSO (Slightly, Heate
• Water Solubility.: 18.83ug/L(25 oC)
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 376.29774513
• Heavy Atom Count: 27
• Complexity: 574

Purity/Quality:

98%, ^*data from raw suppliers

Lithocholic acid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC(=O)O)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)O)C)C
• Isomeric SMILES: C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)C
• Uses: A cholic acid derivative as TGR5 modulator. Found in ox bile, human bile, rabbit bile, and in ox and pig gallstones. LD50(mouse) 3900 mg/kg po Cholagogue;Anticholelithogenic Lithocholic acid has been used in a study to assess cholestasis and its action on several organs and tissues in rats. It has also been used in a study to investigate the regulation of hepatic phospholipid and bile acid homeostasis through SMAD3 activation by TGFβ.

Technology Process of Lithocholic acid

There total 117 articles about Lithocholic 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: 95.9%

ethyl 3α-hydroxy-5β-cholan-24-oate (6112-82-9) → Lithocholic acid (434-13-9)

Guidance literature:

With methanol; sodium hydroxide; Inert atmosphere;

Reference yield: 92.0%

methyl 3α-acetoxy-5β-cholan-24-oate (3253-69-8) → Lithocholic acid (434-13-9)

Guidance literature:

With methanol; potassium carbonate; In tetrahydrofuran; at 70 ℃; for 24h; Concentration; Inert atmosphere;

Reference yield: 92.0%

6-Ketolithocholic acid (10573-17-8,106439-47-8,106498-92-4,135503-49-0,2393-61-5) → Lithocholic acid (434-13-9)

Guidance literature:

6-Ketolithocholic acid; With hydrazine hydrate; In diethylene glycol; at 120 ℃; for 2h;

With potassium hydroxide; In diethylene glycol; at 70 - 200 ℃; for 6h;

upstream raw materials:

ethanol

3,7-diketocholanic acid

semicarbazide hydrochloride

sodium acetate

Downstream raw materials:

5β.14β.17βH.20ξH-cholen-(3)-oic acid-(24)

5-beta‐chol‐2‐en‐24‐oic acid

5β-chol-3-en-24-oic acid

glycolithocholic acid

Refernces

• 1、 Murata,Beppu,Takikawa,Otsuka,Kasama,Seyama. "Determination of sulfated and nonsulfated bile acids in serum by mass fragmentography". . p. 575 - 592. Retrieved 1983.
• 2、 -. "METHOD FOR HOMOGENIZING BILE ACID DERIVATIVES". . . Retrieved 2021/05/28.
• 3、 -. "Method for synthesizing lithocholic acid by taking BA as raw material". . . Retrieved 2020/09/01.