Hydroxysitosterol

Base Information

• Chemical Name: Hydroxysitosterol
• CAS No.: 34427-61-7
• Molecular Formula: C₂₉H₅₀O₂
• Molecular Weight: 430.715
• Wikidata: Q105263164
• Metabolomics Workbench ID: 75635
• Mol file: 34427-61-7.mol

Synonyms:7-hydroxysitosterol;hydroxysitosterol

Chemical Property of Hydroxysitosterol

Chemical Property:

• Vapor Pressure: 1.12E-13mmHg at 25°C
• Boiling Point: 535°Cat760mmHg
• Flash Point: 218.2°C
• PSA: 40.46000
• Density: 1.02g/cm³
• LogP: 6.99560
• XLogP3: 8.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 430.381080833
• Heavy Atom Count: 31
• Complexity: 668

Purity/Quality:

98%Min ^*data from raw suppliers

Ikshusterol 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(CCC(C)C1CCC2C1(CCC3C2C(C=C4C3(CCC(C4)O)C)O)C)C(C)C

Technology Process of Hydroxysitosterol

There total 30 articles about Hydroxysitosterol 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: 92.0%

7β-hydroxysitost-5-en-3β-yl acetate (881413-59-8) → 5-stigmasten-3β,7β-diol (4863-54-1,15140-59-7,34427-61-7,75521-67-4,145163-98-0,145985-29-1)

Guidance literature:

With sodium methylate; In methanol; chloroform; at 20 ℃; for 2h;

DOI:10.1021/jm1007769

Reference yield: 65.0%

3β-acetoxysitost-5-ene-7α-ol (73336-57-9) → 7α-hydroxysitosterol (34427-61-7)

Guidance literature:

With sodium carbonate; In methanol; water; at 25 ℃;

DOI:10.1016/j.steroids.2005.06.003

Reference yield: 57.0%

3β-hydroxystigmast-5-en-7-one (2034-74-4,75521-66-3,88548-08-7,145163-97-9) → 5-stigmasten-3β,7β-diol (4863-54-1,15140-59-7,34427-61-7,75521-67-4,145163-98-0,145985-29-1)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride heptahydrate; In methanol; at 0 - 20 ℃; for 18h; Inert atmosphere;

DOI:10.1021/jf506361r

upstream raw materials:

Acetic acid (3S,7R,8S,9S,10R,13R,14S,17R)-3-acetoxy-17-((1R,4R)-4-ethyl-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-7-yl ester

(3S,8S,9S,10R,13R,14S,17R)-17-((1R,4R)-4-Ethyl-1,5-dimethyl-hexyl)-7-hydroperoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

aluminum isopropoxide

(24R)-3β-acetoxystigmast-5-en-7-one

Downstream raw materials:

7-Dehydrositosterol benzoate

stigmastadien-(5.7)-yl-(3β)-acetate

stigmastadien-(5.7)-ol-(3β)

(3S)-9.10-seco-stigmastatriene-(5seqcis.7seqtrans.10⁽¹⁹⁾)-ol-⁽³⁾

Refernces

• 1、 Carvalho, Jo?o F. S.,Silva, M. Manuel Cruz,Moreira, Jo?o N.,Sim?es, Sérgio,Sá E Melo, M. Luisa. "Sterols as anticancer agents: Synthesis of ring-B oxygenated steroids, cytotoxic profile, and comprehensive SAR analysis". supporting information; experimental part. p. 7632 - 7638. Retrieved 2011/02/21.
• 2、 Zhang, Xin,Geoffroy, Philippe,Miesch, Michel,Julien-David, Diane,Raul, Francis,Aoude-Werner, Dalal,Marchioni, Eric. "Gram-scale chromatographic purification of β-sitosterol: Synthesis and characterization of β-sitosterol oxides". . p. 886 - 895. Retrieved 2007/10/03.