24,25-Epoxy-cholesterol

Base Information Edit

Chemical Name:24,25-Epoxy-cholesterol
CAS No.:77058-74-3
Molecular Formula:C27H44 O2
Molecular Weight:400.645
Hs Code.:
DSSTox Substance ID:DTXSID30390608
Nikkaji Number:J86.435H
Wikidata:Q27071872
Pharos Ligand ID:SCUYRY9U5368
Metabolomics Workbench ID:34372
ChEMBL ID:CHEMBL434302
Mol file:77058-74-3.mol

Synonyms:24(S),25-epoxycholesterol;24,25-epoxycholesterol

Suppliers and Price of 24,25-Epoxy-cholesterol

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

Medical Isotopes, Inc.
24(S),25-Epoxycholesterol 98%
1 mg
$ 890.00

Cayman Chemical
24(S),25-epoxy Cholesterol
1mg
$ 82.00

American Custom Chemicals Corporation
(24S)-24,25-EPOXYCHOLESTEROL 95.00%
5MG
$ 502.54

Total 7 raw suppliers

Chemical Property of 24,25-Epoxy-cholesterol Edit

Chemical Property:

Vapor Pressure:6.18E-12mmHg at 25°C
Refractive Index:1.544
Boiling Point:496.4°C at 760 mmHg
Flash Point:201.2°C
PSA：32.76000
Density:1.05
LogP:6.52000
Storage Temp.:-20°C
Solubility.:Soluble in DMSO (up to 30 mg/ml).
XLogP3:6.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:4
Exact Mass:400.334130642
Heavy Atom Count:29
Complexity:680

Purity/Quality:

98%Min ^*data from raw suppliers

24(S),25-Epoxycholesterol 98% ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CC(CCC1C(O1)(C)C)C2CCC3C2(CCC4C3CC=C5C4(CCC(C5)O)C)C
Isomeric SMILES:C[C@H](CC[C@H]1C(O1)(C)C)[C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4(CC[C@@H](C5)O)C)C
Description 24(S),25-epoxy Cholesterol is an oxysterol and the most abundant oxysterol in mouse ventral midbrain. It activates liver X receptors (LXRs) in the developing ventral midbrain to induce stem cell differentiation into dopaminergic neurons. 24(S),25-epoxy Cholesterol inhibits IL-6 production and degranulation of bone marrow-derived murine mast cells that express LXRβ. It inhibits the conversion of desmosterol to cholesterol by 3β-hydroxysterol Δ24-reductase (DHCR24/Seladin-1) in CHO-7 and SRD-1 cells when used at a concentration of 2.5 μM.
Uses (24S)-24,25-Epoxycholesterol is a derivative of 4β-Hydroxy Cholesterol (H917980), a metabolite of Cholesterol. It is formed from Cholesterol by the drug-metabolizing enzyme cytochrome P 450 3A4. A potential ligand for the nuclear receptor LXR and also a new endogenous CYP3A marker.

Technology Process of 24,25-Epoxy-cholesterol

There total 32 articles about 24,25-Epoxy-cholesterol 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:

: Methanesulfonic acid (3S,8S,9S,10R,13R,14S,17R)-17-[(R)-3-((S)-3,3-dimethyl-oxiranyl)-1-methyl-propyl]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

: 77058-74-3,72542-49-5
(24S)-24,25-epoxycholesterol

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at -20 ℃; Yield given;
DOI:10.1016/S0040-4039(98)02181-9

Reference yield:

: 5255-17-4
3β-hydroxy-5-cholenoic acid

: 77058-74-3,72542-49-5
(24S)-24,25-epoxycholesterol

Guidance literature:: Multi-step reaction with 10 steps

1.1: 100 percent / diethyl ether; tetrahydrofuran / 0.67 h / 20 °C

2.1: 100 percent / conc. hydrochloric acid / 12 h / 20 °C

3.1: 98 percent / lithium aluminum hydride / 1 h / 20 °C

4.1: 86 percent / chromium(VI) oxide; pyridine / CHCl₃ / 12 h / 20 °C

5.1: butyllithium / tetrahydrofuran / 0.5 h / 0 °C

5.2: 77 percent / tetrahydrofuran / 2 h / 20 °C

6.1: conc. hydrochloric acid / tetrahydrofuran; methanol / 1 h / 20 °C

7.1: 1.4 g / pyridine; dimethylaminopyridine / 12 h / 20 °C

8.1: 87 percent / AD-mix-β; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 50 h / 20 °C

9.1: pyridine / CHCl₃ / 3 h / 20 °C

10.1: 1.8 g / K₂CO₃ / methanol; H₂O / 15 h / 20 - 40 °C

With pyridine; chromium(VI) oxide; hydrogenchloride; dmap; lithium aluminium tetrahydride; n-butyllithium; methanesulfonamide; AD-mix-β; potassium carbonate; In tetrahydrofuran; methanol; diethyl ether; chloroform; water; tert-butyl alcohol; 5.2: Wittig reaction / 8.1: Sharpless asymmetric hydroxylation;
DOI:10.1023/A:1015720707433

Reference yield:

: 20231-57-6
methyl 5-cholenoate

: 77058-74-3,72542-49-5
(24S)-24,25-epoxycholesterol

Guidance literature:: Multi-step reaction with 9 steps

1.1: 100 percent / conc. hydrochloric acid / 12 h / 20 °C

2.1: 98 percent / lithium aluminum hydride / 1 h / 20 °C

3.1: 86 percent / chromium(VI) oxide; pyridine / CHCl₃ / 12 h / 20 °C

4.1: butyllithium / tetrahydrofuran / 0.5 h / 0 °C

4.2: 77 percent / tetrahydrofuran / 2 h / 20 °C

5.1: conc. hydrochloric acid / tetrahydrofuran; methanol / 1 h / 20 °C

6.1: 1.4 g / pyridine; dimethylaminopyridine / 12 h / 20 °C

7.1: 87 percent / AD-mix-β; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 50 h / 20 °C

8.1: pyridine / CHCl₃ / 3 h / 20 °C

9.1: 1.8 g / K₂CO₃ / methanol; H₂O / 15 h / 20 - 40 °C

With pyridine; chromium(VI) oxide; hydrogenchloride; dmap; lithium aluminium tetrahydride; n-butyllithium; methanesulfonamide; AD-mix-β; potassium carbonate; In tetrahydrofuran; methanol; chloroform; water; tert-butyl alcohol; 4.2: Wittig reaction / 7.1: Sharpless asymmetric hydroxylation;
DOI:10.1023/A:1015720707433