Cholest-5-ene-1alpha,3beta-diol

Base Information

• Chemical Name: Cholest-5-ene-1alpha,3beta-diol
• CAS No.: 26358-75-8
• Molecular Formula: C27H46 O2
• Molecular Weight: 414.672
• European Community (EC) Number: 247-630-4
• DSSTox Substance ID: DTXSID70949215
• Nikkaji Number: J21.473F
• Wikidata: Q82927080
• Mol file: 26358-75-8.mol

Synonyms:Cholest-5-ene-1alpha,3beta-diol;26358-75-8;EINECS 247-630-4;1alpha-Hydroxycholesterol;Cholest-5-ene-1,3-diol;SCHEMBL5343868;DTXSID70949215;UXFVRWPSABSGRQ-AFWJMSMISA-N;1alpha,3beta-dihydroxycholest-5-ene;(1S,3R,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-1,3-diol

Chemical Property of Cholest-5-ene-1alpha,3beta-diol

Chemical Property:

• Boiling Point: 514°Cat760mmHg
• Flash Point: 214°C
• PSA: 40.46000
• Density: 1.03g/cm³
• LogP: 6.35950
• XLogP3: 7.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 402.349780706
• Heavy Atom Count: 29
• Complexity: 624

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2CC=C4C3(C(CC(C4)O)O)C)C
• Isomeric SMILES: C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3([C@H](C[C@@H](C4)O)O)C)C

Technology Process of Cholest-5-ene-1alpha,3beta-diol

There total 38 articles about Cholest-5-ene-1alpha,3beta-diol 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: 78.0%

1α,2α-epoxycholesta-1,4,6-trien-3-one (28893-44-9) → 1α,3β-dihydroxycholest-5-ene (26358-75-8)

Guidance literature:

With ammonium chloride; In tetrahydrofuran; ammonia; water; acetone; benzene;

Reference yield: 28.3%

1α-Hydroxy-5-cholesten-3-on (80239-44-7) → 5-Cholesten-1α,3α-diol (50392-20-6) + 1α,3β-dihydroxycholest-5-ene (26358-75-8)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at -20 ℃; for 0.5h;

DOI:10.1002/hlca.19810640621

Reference yield:

1α-Hydroxy-5-cholesten-3-on (80239-44-7) → cholesterol (57-88-5) + 5-Cholesten-1α,3α-diol (50392-20-6) + 1α,3β-dihydroxycholest-5-ene (26358-75-8)

Guidance literature:

With lithium; ammonium chloride; In diethyl ether; ammonia; at -33 ℃; for 0.5h; Yield given. Yields of byproduct given;

DOI:10.1002/hlca.19810640621

upstream raw materials:

1α-Hydroxy-5-cholesten-3-on

1α,3β,25-Tris<(tetrahydropyran-2-yl)oxy>-5-cholesten

cholest-5-ene-1α,3β-diol 3-acetate

3β-acetoxy-cholesta-1,5-diene

Downstream raw materials:

1α,3β-dibenzoyloxycholest-5-ene

(5-Cholesten-1α,3β-diol)-diacetat

cholest-5-ene-1α,3β-diol 3-acetate

cholest-5-ene-1α,3β-diol 3β-acetate

Refernces

• 1、 Morisaki,Bannai,Ikekawa. "Synthesis of active forms of vitamin D. II. Synthesis of 1α hydroxycholesterol". . p. 1853 - 1854. Retrieved 1973.
• 2、 Morisaki,Bannai,Ikekawa. "Studies on steroids. XXXVIII. A new preparation of 1α hydroxycholesterol". . p. 1948 - 1949. Retrieved 1976.
• 3、 Mihailovic,Lorenc,Popov,Kalvoda. "Synthesis, structure and reactions of secosteroids with a central ring. V. Photochemical cyclization of cis- and trans-3 -acetoxy-5-oxo- 1(10)-5,10-secocholestaen". . p. 2281 - 2287. Retrieved 1971.
• 4、 -. "Process for production of 1-α, 3-β, 24-trihydroxy Δ-5". . . Retrieved 2008/06/13.