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CHOLESTEROL-5ALPHA,6ALPHA-EPOXIDE

CAS No.
1250-95-9
Chemical Name:
CHOLESTEROL-5ALPHA,6ALPHA-EPOXIDE
Synonyms
epoxycholesterol;cholesteroloxide;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
Molecular Weight:
402.65
MDL Number:
MFCD00046980
MOL File:
1250-95-9.mol
MSDS File:
SDS
Last updated:2023-09-04 15:50:00

CHOLESTEROL-5ALPHA,6ALPHA-EPOXIDE Properties

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.
FDA UNII 3UQ9PF5XBD

SAFETY

Risk and Safety Statements

WGK Germany  3
RTECS  FZ6360000

CHOLESTEROL-5ALPHA,6ALPHA-EPOXIDE price More Price(10)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich C2773 Cholesterol 5α,6α-epoxide 1250-95-9 50mg $105 2024-03-01 Buy
Cayman Chemical 25539 5α,6α-epoxy Cholestanol ≥95% 1250-95-9 25mg $37 2024-03-01 Buy
Cayman Chemical 25539 5α,6α-epoxy Cholestanol ≥95% 1250-95-9 50mg $68 2024-03-01 Buy
Cayman Chemical 25539 5α,6α-epoxy Cholestanol ≥95% 1250-95-9 100mg $129 2024-03-01 Buy
Cayman Chemical 25539 5α,6α-epoxy Cholestanol ≥95% 1250-95-9 250mg $301 2024-03-01 Buy
Product number Packaging Price Buy
C2773 50mg $105 Buy
25539 25mg $37 Buy
25539 50mg $68 Buy
25539 100mg $129 Buy
25539 250mg $301 Buy

CHOLESTEROL-5ALPHA,6ALPHA-EPOXIDE Chemical Properties,Uses,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

604-35-3
1250-95-9
Synthesis of CHOLESTEROL-5ALPHA,6ALPHA-EPOXIDE from Cholesteryl acetate

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

CHOLESTEROL-5ALPHA,6ALPHA-EPOXIDE Suppliers

Global( 54)Suppliers
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LEAP CHEM CO., LTD.
+86-852-30606658 market18@leapchem.com China 24738 58
Amadis Chemical Company Limited
571-89925085 sales@amadischem.com China 132020 58
J & K SCIENTIFIC LTD. 010-82848833 400-666-7788 jkinfo@jkchemical.com China 96815 76
Meryer (Shanghai) Chemical Technology Co., Ltd. 4006608290; 18621169109 market03@meryer.com China 40241 62
TCI (Shanghai) Development Co., Ltd. 021-67121386 Sales-CN@TCIchemicals.com China 24539 81
Energy Chemical 021-021-58432009 400-005-6266 sales8178@energy-chemical.com China 44751 61
TOKYO CHEMICAL INDUSTRY CO., LTD. 03-36680489 Sales-JP@TCIchemicals.com Japan 28398 80
TCI Europe 320-37350700 sales@tcieurope.eu Europe 23680 75
9ding chemical ( Shanghai) Limited 4009209199 sales@9dingchem.com China 22519 55
Shanghai CanSpecsci Instrument Co., Ltd. 400-6087598 15021221957 order@canspecsci.com China 2079 56
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 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 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 > 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)- 1250-95-9 Biochemicals and Reagents BioChemical Cholesterol and Derivatives Lipids Sterols