Isoallolithocholic acid

Base Information

• Chemical Name: Isoallolithocholic acid
• CAS No.: 2276-93-9
• Molecular Formula: C24H40 O3
• Molecular Weight: 376.58
• NSC Number: 18169
• DSSTox Substance ID: DTXSID801309974
• Nikkaji Number: J82.425I
• Wikidata: Q63399713
• Metabolomics Workbench ID: 36248
• Mol file: 2276-93-9.mol

Synonyms:(4R)-4-((3S,5S,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta(a)phenanthren-17-yl)pentanoic acid;isoallolithocholic acid

Chemical Property of Isoallolithocholic acid

Chemical Property:

• Vapor Pressure: 1.4E-12mmHg at 25°C
• Melting Point: >170°C (dec.)
• Boiling Point: 511°Cat760mmHg
• Flash Point: 276.9°C
• PSA: 57.53000
• Density: 1.073g/cm³
• LogP: 5.50710
• Storage Temp.: -20°C, Inert atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• 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:

Isoallolithocholicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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: Isoallolithocholic Acid is used as a steroid compound as T regulatory lymphocyte modulators and uses for treatment of inflammatory or autoimmune disorders.

Technology Process of Isoallolithocholic acid

There total 28 articles about Isoallolithocholic 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: 97.0%

methyl 3β-acetyloxy-5β-cholan-24-oate (1255-51-2) → Isolithocholic acid (434-13-9,516-73-4,2276-93-9,2276-94-0,30627-77-1,30627-81-7,35498-67-0,106862-81-1,1534-35-6)

Guidance literature:

With ethanol; potassium hydroxide; for 3h; Reflux; Inert atmosphere;

DOI:10.1016/j.ejmech.2020.112083

Reference yield: 91.0%

4-[(3R,5S,8R,9S,10S,13R,14S,17R)-3-(2,2-Dimethyl-propionyloxy)-10,13-dimethyl-7,12-dioxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid methyl ester (91509-44-3) → lithocholic acid (434-13-9,516-73-4,1534-35-6,2276-93-9,2276-94-0,30627-77-1,30627-81-7,35498-67-0,106862-81-1)

Guidance literature:

DOI:10.1016/S0040-4039(01)90036-X

Reference yield: 90.0%

(3S,5R,8R,9S,10S,13R,14S,17R)-((R)-5-methoxy-5-oxopentan-2-yl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl 4-nitrobenzoate → Isolithocholic acid (434-13-9,516-73-4,2276-93-9,2276-94-0,30627-77-1,30627-81-7,35498-67-0,106862-81-1,1534-35-6)

Guidance literature:

With potassium hydroxide; In methanol; for 14h; Heating;

DOI:10.1248/bpb.30.1117

upstream raw materials:

4-[(3R,5S,8R,9S,10S,13R,14S,17R)-3-(2,2-Dimethyl-propionyloxy)-10,13-dimethyl-7,12-dioxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid methyl ester

3α,7α,12α-trihydroxy-5β-cholanic acid

methyl chlolate

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

Downstream raw materials:

methyl 3β-hydroxy-5β-cholan-24-oate

3α-Hydroxy-5β-cholansaeure-methylester

4-((R)-3-Hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester

N-(methoxycarbonylmethyl)-3-oxo-5β-cholan-24-oic acid amide