7beta-Hydroxysitosterol

Base Information

• Chemical Name: 7beta-Hydroxysitosterol
• CAS No.: 15140-59-7
• Molecular Formula: C₂₉H₅₀O₂
• Molecular Weight: 430.715
• UNII: 43TE8PG2TM
• ChEMBL ID: CHEMBL455367
• DSSTox Substance ID: DTXSID40934254
• Metabolomics Workbench ID: 135433
• Nikkaji Number: J707.549I
• Wikidata: Q27138862
• Mol file: 15140-59-7.mol

Synonyms:7beta-hydroxysitosterol;15140-59-7;43TE8PG2TM;Stigmast-5-ene-3beta,7-beta-diol;UNII-43TE8PG2TM;7beta-Hydroxy-beta-sitosterol;CHEMBL455367;Stigmast-5-ene-3,7-diol, (3beta,7beta)-;CHEBI:70531;Stigmast-5-ene-3,7-diol, (3.beta.,7.beta.)-;(3S,7R,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol;stigmast-5-ene-3,7-diol;5-stigmasten-3beta,7beta-diol;7.BETA.-HYDROXYSITOSTEROL;DTXSID40934254;7.BETA.-HYDROXYSITOSTEROL-;BDBM50242187;7.BETA.-HYDROXY-.BETA.-SITOSTEROL;5-STIGMASTEN-3.BETA.,7.BETA.-DIOL;STIGMAST-5-ENE-3.BETA.,7.BETA.-DIOL;Q27138862;(3.BETA.,7.BETA.)-STIGMAST-5-ENE-3,7-DIOL;(1R,3AS,3BS,4R,7S,9AR,9BS,11AR)-1-((2R,5R)-5-ETHYL-6-METHYLHEPTAN-2-YL)-9A,11A-DIMETHYL-1H,2H,3H,3AH,3BH,4H,6H,7H,8H,9H,9AH,9BH,10H,11H,11AH-CYCLOPENTA(A)PHENANTHRENE-4,7-DIOL;(3S,7R,8S,9S,10R,13R,14S,17R)-17-((1R,4R)-4-ETHYL-1,5-DIMETHYL-HEXYL)-10,13-DIMETHYL-2,3,4,7,8,9,11,12,14,15,16,17-DODECAHYDRO-1H-CYCLOPENTA(A)PHENANTHRENE-3,7-DIOL

Chemical Property of 7beta-Hydroxysitosterol

Chemical Property:

• 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:

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
• Isomeric SMILES: CC[C@H](CC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@H](C=C4[C@@]3(CC[C@@H](C4)O)C)O)C)C(C)C

Technology Process of 7beta-Hydroxysitosterol

There total 22 articles about 7beta-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: 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

Reference yield: 41.0%

3β-hydroxystigmast-5-en-7-one (2034-74-4,75521-66-3,88548-08-7,145163-97-9) → 7-α-hydroxy-β-sitosterol + 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; In methanol; at 20 ℃; for 3h;

DOI:10.1039/b505069c

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⁾