Cholestan-3-ol, (3beta,5alpha)-

Base Information

• Chemical Name: Cholestan-3-ol, (3beta,5alpha)-
• CAS No.: 80-97-7
• Molecular Formula: C27H48 O
• Molecular Weight: 388.678
• Hs Code.: 2906 13 10
• Mol file: 80-97-7.mol

Synonyms:5 alpha Cholestan 3 alpha ol;5 alpha Cholestan 3 beta ol;5 alpha-Cholestan-3 alpha-ol;5 alpha-Cholestan-3 beta-ol;5 beta Cholestan 3 beta ol;5 beta-Cholestan-3 alpha-ol;5 beta-Cholestan-3 beta-ol;beta Cholestanol;beta-Cholestan-3 beta-ol, 5;beta-Cholestanol;beta-ol, 5 beta-Cholestan-3;Cholestan 3 ol;Cholestan-3-ol;Cholestanol;Cholestanol, (3alpha, 5beta)-Isomer;Coprostanol;Coprosterol;Dihydrocholesterol

Chemical Property of Cholestan-3-ol, (3beta,5alpha)-

Chemical Property:

• Appearance/Colour: white powder.
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 138-142 °C
• Refractive Index: 1.504
• Boiling Point: 455.5 °C at 760 mmHg
• PKA: 15.14±0.70(Predicted)
• Flash Point: 190.7 °C
• PSA: 20.23000
• Density: 0.956 g/cm³
• LogP: 7.46860
• Storage Temp.: room temp
• Solubility.: chloroform: 0.1 g/mL, clear, colorless
• Water Solubility.: Insoluble in water.
• XLogP3: 9.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 388.370516150
• Heavy Atom Count: 28
• Complexity: 540

Purity/Quality:

99% ^*data from raw suppliers

5α-Cholestan-3β-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-38-40-48/20/22-67-36/38-20-63
• Safety Statements: 24/25-36/37-22-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)O)C)C
• Isomeric SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2CC[C@@H]4C3(CC[C@@H](C4)O)C)C
• Description: Cholestanol is a cholesterol metabolite formed by oxidation and an intermediate in the biosynthesis of chenodeoxycholic acid . Cholestanol (10 μg/ml) induces apoptosis in cornea and lens epithelial cells and increases the activity of IL-1β converting enzyme (ICE) and CPP32 proteases. Dietary administration of 1% cholestanol to mice increases serum and liver cholestanol levels and leads to corneal opacities and gallstones and in rats it leads to cholestanol deposition in the cerebellum. Cholestanol levels are increased in plasma of patients with cerebrotendinous xanthomatosis (CTX), a disease characterized by a deficiency in the mitochondrial enzyme sterol 27-hydrolylase (CYP27A1) that leads to progressive neurological symptoms.
• Uses: 5α-Cholestan-3β-ol is a carbon stanol formed from biohydrogenation of Cholesterol (C432501) in the gut. Studies have also examined the conversion of 5α-Cholestan-3β-ol catalyzed by 3-β-hydroxysteroid dehydrogenase of rat liver. 5alpha-Cholestan-3beta-ol is used as a standard in lipid analysis using HPLC. It acts as a derivitized steroid compound. It is used in agrochemical, pharmaceutical and dyestuff field .

Technology Process of Cholestan-3-ol, (3beta,5alpha)-

There total 248 articles about Cholestan-3-ol, (3beta,5alpha)- 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: 100.0%

2-[(3S,5R,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yloxy]-tetrahydro-furan (111222-20-9) → Coprostanol (80-97-7,360-68-9,516-92-7,516-95-0,566-84-7,14615-12-4,16720-60-8,17608-41-2,18769-46-5,27409-41-2,56193-35-2,57759-49-6,73465-18-6,103365-91-9,105119-51-5)

Guidance literature:

With toluene-4-sulfonic acid; In ethanol; for 1h; Ambient temperature;

DOI:10.1055/s-1987-27903

Reference yield: 97.0%

4-[(3S,5R,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yloxymethyl]-benzonitrile → Coprostanol (80-97-7,360-68-9,516-92-7,516-95-0,566-84-7,14615-12-4,16720-60-8,17608-41-2,18769-46-5,27409-41-2,56193-35-2,57759-49-6,73465-18-6,103365-91-9,105119-51-5)

Guidance literature:

With Triethylgermyl-natrium; In 1,4-dioxane; N,N,N,N,N,N-hexamethylphosphoric triamide; at 50 ℃; for 15h;

DOI:10.1246/cl.2002.1032

Reference yield: 84.0%

Trifluoro-methanesulfonic acid (3S,5R,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester → Coprostanol (80-97-7,360-68-9,516-92-7,516-95-0,566-84-7,14615-12-4,16720-60-8,17608-41-2,18769-46-5,27409-41-2,56193-35-2,57759-49-6,73465-18-6,103365-91-9,105119-51-5)

Guidance literature:

With 18-crown-6 ether; cesium acetate; In benzene; for 24h; Product distribution; Heating;

DOI:10.1016/0040-4039(96)01333-0

upstream raw materials:

ethanol

cholesterol

sodium ethanolate

hydrazone of 3-cholestanone

Downstream raw materials:

(3S,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl 4-methylbenzoate

phthalic acid mono-(5β-cholestan-3β-yl ester)

cholestane

(5α-cholestan-3β-yl)-methyl ether

Refernces

• 1、 -. "Method for synthesizing cholesterol by taking BA as raw material". . . Retrieved 2021/08/14.
• 2、 Cao, Yangmin,Hu, Ping,Huang, Cheng,Liu, Zhao,Lu, Qingquan,Ma, Wan,Peng, Pan,Qi, Xiaotian,Wang, Bingbing. "Electrochemical Borylation of Alkyl Halides: Fast, Scalable Access to Alkyl Boronic Esters". supporting information. p. 12985 - 12991. Retrieved 2021/09/03.