Nutriacholate

Base Information

• Chemical Name: Nutriacholate
• CAS No.: 4651-67-6
• Molecular Formula: C24H38O4
• Molecular Weight: 390.563
• Hs Code.: 2918990090
• Mol file: 4651-67-6.mol

Synonyms:7-Ketochenodeoxycholic acid;Nutriacholate;7-Ketochenodeoxycholate;5b-Cholanic acid-3a-ol-7-one;3a-hydroxy-7-oxo-5b-cholanoate;7-Oxo-3a-hydroxycholan-24-oate;3a-hydroxy-7-oxo-5b-cholanoic acid;7-Oxo-3a-hydroxycholan-24-oic acid

Chemical Property of Nutriacholate

Chemical Property:

• Vapor Pressure: 3.42E-14mmHg at 25°C
• Melting Point: 205oC
• Boiling Point: 545.9°C at 760 mmHg
• PKA: 4.76±0.10(Predicted)
• Flash Point: 298°C
• PSA: 74.60000
• Density: 1.124g/cm³
• LogP: 4.68610
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Dioxane (Slightly), DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: 2.062mg/L at 25℃
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 390.27700969
• Heavy Atom Count: 28
• Complexity: 645

Purity/Quality:

99%, ^*data from raw suppliers

NutriacholicAcid ^*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(CCC3C2C(=O)CC4C3(CCC(C4)O)C)C
• Isomeric SMILES: C[C@@H](CCC(=O)O)C1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C(=O)C[C@H]4[C@@]3(CC[C@H](C4)O)C)C
• Uses: Nutriacholic Acid (Ursodeoxycholic Acid EP Impurity F) is derivative of Lithocholic Acid (L469180), a cholic acid derivative as TGR5 modulator.

Technology Process of Nutriacholate

There total 87 articles about Nutriacholate 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: 99.0%

3α-hydroxy-7-keto-5β-chol-11-en-24-oic acid → 7-Ketolithocholic acid (4651-67-6)

Guidance literature:

With palladium on activated charcoal; hydrogen; In methanol; at 70 ℃; for 12h; under 30003 Torr;

Reference yield: 98.6%

chenodeoxycholic acid (474-25-9) → 7-Ketolithocholic acid (4651-67-6)

Guidance literature:

With dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In dichloromethane; at -30 ℃; for 1.5h; Temperature;

Reference yield: 97.0%

sodium chenodeoxycholate (2646-38-0) → 7-Ketolithocholic acid (4651-67-6)

Guidance literature:

With ethylenediaminetetraacetic acid; Acinetobacter calcoaceticus lwoffii 7α-hydroxysteroid dehydrogenase; sodium pyruvate; NAD; 2-hydroxyethanethiol; lactate dehydrogenase; In aq. phosphate buffer; at 22 ℃; pH=8.5; Enzymatic reaction;

DOI:10.1016/j.steroids.2008.06.013

upstream raw materials:

3,7-diketocholanic acid

chenodeoxycholic acid

ursodeoxycholic acid

Dodecanoic acid (3R,5S,8R,9S,10S,13R,14S,17R)-17-((R)-3-methoxycarbonyl-1-methyl-propyl)-10,13-dimethyl-7-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester

Downstream raw materials:

chenodeoxycholic acid

ursodeoxycholic acid

7-ketolithocholic methyl ester

3α-formyloxy-7-keto-5β-cholan-24-oic acid

Refernces

• 1、 Yu, Donna,Mattern, Daniell L.,Forman, Barry M.. "An improved synthesis of 6α-ethylchenodeoxycholic acid (6ECDCA), a potent and selective agonist for the Farnesoid X Receptor (FXR)". . p. 1335 - 1338. Retrieved 2012.
• 2、 Grobe, Sascha,Badenhorst, Christoffel P. S.,Bayer, Thomas,Hamnevik, Emil,Wu, Shuke,Grathwol, Christoph W.,Link, Andreas,Koban, Sven,Brundiek, Henrike,Gro?johann, Beatrice,Bornscheuer, Uwe T.. "Engineering Regioselectivity of a P450 Monooxygenase Enables the Synthesis of Ursodeoxycholic Acid via 7β-Hydroxylation of Lithocholic Acid". supporting information. p. 753 - 757. Retrieved 2020/12/01.
• 3、 -. "Preparation method of low-cost, high-yield and high-purity 7-ketolithocholic acid". Paragraph 0048-0055. . Retrieved 2020/07/24.