22-Hydroxycholesterol

Base Information Edit

Chemical Name:22-Hydroxycholesterol
CAS No.:17711-16-9
Molecular Formula:C₂₇H₄₆O₂
Molecular Weight:402.661
Hs Code.:
UNII:TJ9HV8VPD2
DSSTox Substance ID:DTXSID30904340
Nikkaji Number:J549.409E
Wikipedia:22R-Hydroxycholesterol
Metabolomics Workbench ID:34383
ChEMBL ID:CHEMBL3218924
Mol file:17711-16-9.mol

Synonyms:(22R)-22-hydroxycholesterol;22(R)-hydroxycholesterol;22(R)OH cholesterol;22-hydroxycholesterol;22-hydroxycholesterol, (3beta,20R,22R)-isomer;22-hydroxycholesterol, (3beta,20R,22S)-isomer;22-hydroxycholesterol, (3beta,22R)-isomer;22-hydroxycholesterol, (3beta,22S)-isomer;22R-hydroxycholesterol;22S-hydroxycholesterol;cholest-5-ene-3beta,22-diol

Suppliers and Price of 22-Hydroxycholesterol

Supply Marketing:Edit

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

TRC
22-HydroxyCholesterol(MixtureofDiastereomers)
250mg
$ 1320.00

Total 3 raw suppliers

Chemical Property of 22-Hydroxycholesterol Edit

Chemical Property:

Vapor Pressure:1.13E-12mmHg at 25°C
Boiling Point:513.1°Cat760mmHg
Flash Point:213.5°C
PSA：40.46000
Density:1.03g/cm³
LogP:6.35950
XLogP3:7
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:

97% ^*data from raw suppliers

22-HydroxyCholesterol(MixtureofDiastereomers) ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CC(C)CCC(C(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)O
Isomeric SMILES:C[C@@H]([C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)C(CCC(C)C)O
Uses A metabolite of Cholesterol (C432501). 22-Hydroxycholesterol inhibits chemokine receptor activity.

Technology Process of 22-Hydroxycholesterol

There total 55 articles about 22-Hydroxycholesterol 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: 21.9%

: 57-88-5
cholesterol

: 566-28-9
7-Oxocholesterol

: 566-27-8
cholest-5-en-3β,7β-diol

: 17711-16-9,17954-98-2,22348-64-7,59532-44-4,59532-45-5
22-(S)-hydroxycholesterol

: 1250-95-9
5α,6α-epoxycholestan-3β-ol

Guidance literature:: at 150 ℃; Further byproducts given;
DOI:10.1271/bbb.60.1362

Reference yield:

: (22S)-3β-((tert-butyldimethylsilyl)oxy)-cholest-5-en-22-ol

: 17711-16-9,17954-98-2,22348-64-7,59532-44-4,59532-45-5
22-(S)-hydroxycholesterol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 3h;
DOI:10.1016/j.steroids.2016.12.003

Reference yield:

: 109004-00-4
[(1aR,3aR,3bS,5aS,7R,8aS,8bR,10R,10aR)-6-Eth-(E)-ylidene-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-7-yloxy]-acetic acid

: 17711-16-9,17954-98-2,22348-64-7,59532-44-4,59532-45-5
22-(S)-hydroxycholesterol

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) LDA / 1.) THF, -78 deg C, 2 h, 2.) H₂O

2: 97 percent / H₂ / PtO₂ / ethyl acetate / 10 h

4: 2.) p-TsOH / 1.) CuI / 1.) THF, 0 deg C, 1 h, 2.) DME, H₂O, reflux, 2 h

With hydrogen; toluene-4-sulfonic acid; lithium diisopropyl amide; platinum(IV) oxide; copper(l) iodide; In ethyl acetate;
DOI:10.1021/jo00371a042