ChemicalBook > CAS DataBase List > CHOLESTEROL-5ALPHA,6ALPHA-EPOXIDE

CHOLESTEROL-5ALPHA,6ALPHA-EPOXIDE

Product Name
CHOLESTEROL-5ALPHA,6ALPHA-EPOXIDE
CAS No.
1250-95-9
Chemical Name
CHOLESTEROL-5ALPHA,6ALPHA-EPOXIDE
Synonyms
cholesteroloxide;epoxycholesterol;Cholesterolepoxide;5β-Epoxycholesterol;5,6-epoxy Cholestanol;cholesterolalpha-oxide;ALPHA-EPOXYCHOLESTEROL;5a,6a-Epoxycholesterol;-9a,11b-dimethyl-9-((R);5α,6α-epoxy Cholestanol
CBNumber
CB5109966
Molecular Formula
C27H46O2
Formula Weight
402.65
MOL File
1250-95-9.mol
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CHOLESTEROL-5ALPHA,6ALPHA-EPOXIDE Property

Melting point:
147 °C
Boiling point:
464.74°C (rough estimate)
Density 
0.9932 (rough estimate)
refractive index 
1.4480 (estimate)
storage temp. 
-20°C
solubility 
Soluble in DMSO (up to 10 mg/ml) orin Ethanol (up to 10 mg/ml).
form 
solid
pka
15.20±0.70(Predicted)
color 
White
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 2 months.
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Safety

WGK Germany 
3
RTECS 
FZ6360000
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
C2773
Product name
Cholesterol 5α,6α-epoxide
Packaging
50mg
Price
$105
Updated
2024/03/01
Cayman Chemical
Product number
25539
Product name
5α,6α-epoxy Cholestanol
Purity
≥95%
Packaging
25mg
Price
$37
Updated
2024/03/01
Cayman Chemical
Product number
25539
Product name
5α,6α-epoxy Cholestanol
Purity
≥95%
Packaging
50mg
Price
$68
Updated
2024/03/01
Cayman Chemical
Product number
25539
Product name
5α,6α-epoxy Cholestanol
Purity
≥95%
Packaging
100mg
Price
$129
Updated
2024/03/01
Cayman Chemical
Product number
25539
Product name
5α,6α-epoxy Cholestanol
Purity
≥95%
Packaging
250mg
Price
$301
Updated
2024/03/01
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CHOLESTEROL-5ALPHA,6ALPHA-EPOXIDE Chemical Properties,Usage,Production

Description

5α,6α-Epoxycholesterol (1250-95-9) is a naturally occurring metabolite of cholesterol.? It is a major oxysterol found in processed food1?and has been implicated in atherosclerosis2,3. 5α,6α-Epoxycholesterol has been found to be an endogenous ligand for LXR (EC50?= 76 nM).4

Uses

Cholesterol 5alpha,6alpha-epoxide is used in the generation of oxysterols and in the studies of the biological significance of oxysterols.

Uses

Cholesterol 5α, 6α-epoxide was incorporated in culture medium of human arterial endothelial cells to study oxysterol-induced toxicity.

Uses

5α,6α-epoxycholestanol has been used as a sterol internal standard in ultra-performance liquid chromatography–high resolution mass spectrometry (UPLC-ESI-HRMS) analysis to quantify mice brain sterols. It may be used in calibration curve generation for the quantification of phytosterols in food samples and as an internal standard for oxysterol quantification in biological samples by gas chromatography-mass spectrometry (GC-MS)

Definition

ChEBI: 5,6alpha-epoxy-5alpha-cholestan-3beta-ol is a 3beta-hydroxy steroid, an oxysterol and an epoxy steroid. It derives from a hydride of a 5alpha-cholestane.

General Description

5α,6α-epoxycholestanol (5α,6α-EC) is generated by cholesterol epoxidation and is a diastereoisomer of 5β,6β-epoxycholestanol (5β,6β-EC).

Biochem/physiol Actions

Cholesterol 5α, 6α-epoxide is an oxysterol, a cholesterol derivative by auto-oxidation. Oxysterols are non-genomic regulators of cholesterol homeostasis. The biological effects include protein prenylation, apoptosis, modulation of sphingolipid metabolism and platelet aggregation. Oxysterols bind to liver X receptors, modulate cholesterol efflux and decrease the uptake of cholesterol by the cells.

References

1) Leonarduzzi?et al.?(2002),?Oxidized products of cholesterol: dietary and metabolic origin, and proatherosclerotic effect (review);?J.?Nutr. Biochem.,?13?700 2) Bj?rkhem?et al. (1988),?Assay of unesterified cholesterol-5,6-epoxide in human serum by isotope dilution mass spectrometry. Levels in the healthy state and in hyperlipoproteinemia; J. Lipid Res.,?29?1031 3) Staprans?et al.?(2005),?The role of dietary oxidized cholesterol and oxidized fatty acids in the development of atherosclerosis; Mol. Nutr. Food Res.,?49?1075 4) Berrodin?et al. (2010),?Identification of 5α,6α-Epoxycholesterol as a novel modulator of Liver X Receptor; Mol. Pharmacol.,?78?1046

CHOLESTEROL-5ALPHA,6ALPHA-EPOXIDE Preparation Products And Raw materials

Raw materials

Preparation Products

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CHOLESTEROL-5ALPHA,6ALPHA-EPOXIDE Suppliers

J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
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76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
021-61259108 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40228
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62
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24529
Advantage
81
Energy Chemical
Tel
021-021-58432009 400-005-6266
Fax
021-58436166
Email
sales8178@energy-chemical.com
Country
China
ProdList
44688
Advantage
61
TOKYO CHEMICAL INDUSTRY CO., LTD.
Tel
03-36680489
Fax
03-3668-0520
Email
Sales-JP@TCIchemicals.com
Country
Japan
ProdList
28387
Advantage
80
TCI Europe
Tel
320-37350700
Fax
+32 (0)37350701
Email
sales@tcieurope.eu
Country
Europe
ProdList
23671
Advantage
75
9ding chemical ( Shanghai) Limited
Tel
4009209199
Fax
86-021-52271987
Email
sales@9dingchem.com
Country
China
ProdList
22514
Advantage
55
Shanghai CanSpecsci Instrument Co., Ltd.
Tel
400-6087598 15021221957
Fax
4006087598-8012
Email
order@canspecsci.com
Country
China
ProdList
2045
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56
Sigma-Aldrich
Tel
021-61415566 800-8193336
Email
orderCN@merckgroup.com
Country
China
ProdList
51456
Advantage
80
Codow Chemical Co.,Ltd.
Tel
18620099427
Fax
+86-20-62619665
Email
amy@howeipharm.com
Country
China
ProdList
17687
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55
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View Lastest Price from CHOLESTEROL-5ALPHA,6ALPHA-EPOXIDE manufacturers

Shaanxi Dideu Medichem Co. Ltd
Product
Cholesterol-5alpha,6alpha-epoxide 1250-95-9
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99.0%
Supply Ability
10000KG
Release date
2024-08-09

1250-95-9, CHOLESTEROL-5ALPHA,6ALPHA-EPOXIDERelated Search:


  • CHOLESTERYL -ALPHA-EPOXIDE
  • CHOLESTAN-5-ALPHA, 6-ALPHA-EPOXY-3-BETA-OL
  • CHOLESTEROL-5A,6A-EPOXIDE
  • CHOLESTEROL-5ALPHA,6ALPHA-EPOXIDE
  • 5,6-alpha-epoxy-5-alpha-cholestan-3-beta-o
  • 5,6-epoxy-,(3-beta,5-alpha,6-alpha)-cholestan-3-o
  • 5-alpha,6-alpha-epoxycholestanol
  • 3BETA-HYDROXY-5ALPHA,6ALPHA-EPOXYCHOLESTANE
  • 5-ALPHA-EPOXYCHOLESTEROL
  • 5ALPHA,6ALPHA-EPOXYCHOLESTAN-3BETA-OL
  • cholestanol, 5α,6α-epoxy
  • cholesterol-alpha-epoxide
  • cholesterolalpha-oxide
  • cholesteroloxide
  • epoxycholesterol
  • 5,6-alpha-epoxy-5-alpha-cholestan-3-beta-ol
  • Cholesterolepoxide
  • Cholestan-3-ol, 5,6-epoxy-, (3.beta.,5.alpha.,6.alpha.)-
  • 5α,6α-epoxycholestan-3β-ol
  • cholesterol 5α,6α-epoxide
  • ALPHA-EPOXIDECHOLESTEROL
  • ALPHA-EPOXYCHOLESTEROL
  • 5-ALPHA-CHOLESTAN-3-BETA-OL,5,6-ALPHA-EPOXY-
  • 5β,6β-Epoxy-5β-cholestan-3β-ol
  • 5β-Epoxycholesterol
  • 5,6-Dihydro-5α,6α-epoxycholesterol
  • (4aR,5aS,6aS,6bS,9R,9aR,11aS,11bR)
  • -9a,11b-dimethyl-9-((R)
  • hexadecahydrocyclopenta[1,2]phenanthro[8a,9-b]oxiren-3-ol
  • 5,6-epoxy Cholestanol
  • (4aR,5aS,6aS,6bS,9R,9aR,11aS,11bR)-9a,11b-dimethyl-9-((R)-6-methylheptan-2-yl)hexadecahydrocyclopenta[1,2]phenanthro[8a,9-b]oxiren-3-ol
  • Cholesterol-5α,6α-epoxide &gt
  • Cholesterol 5α,6α-Εpoxide
  • 5 alfa, 6 alfa-Epoxy-Cholestanol
  • CHOLESTEROL 5-ALFA,6-ALFA-EPOXIDE
  • 5α,6α-epoxy Cholestanol
  • Cholesterol-5α,6α-epoxide
  • 5alpha,6alpha-Epoxycholesterol
  • Cholesterol 5α,6α-Εpoxide
  • 5,6α-epoxy-5α-cholestan-3β-ol
  • 5α,6αepoxy Cholestanol,5α,6α epoxy Cholestanol
  • 5a,6a-Epoxycholesterol
  • Cholestan-3-ol, 5,6-epoxy-, (3β,5α,6α)-
  • Epoxycholesterol|||5α,6α-epoxy Cholestanol|||NSC 18176
  • 1250-95-9
  • Biochemicals and Reagents
  • BioChemical
  • Cholesterol and Derivatives
  • Lipids
  • Sterols