CAS 4025-59-6|(3-beta,5-beta,6-beta)-5,6-Epoxycholestan-3-ol

Introduction:Basic information about CAS 4025-59-6|(3-beta,5-beta,6-beta)-5,6-Epoxycholestan-3-ol, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Common Name(3-beta,5-beta,6-beta)-5,6-Epoxycholestan-3-ol
CAS Number4025-59-6Molecular Weight402.65300
Density1.04g/cm3Boiling Point497.7ºC at 760 mmHg
Molecular FormulaC27H46O2Melting Point/
MSDSUSAFlash Point200.9ºC

Names

Name5,6β-epoxy-5β-cholestan-3β-ol
SynonymMore Synonyms

BiologicalActivity

DescriptionCholesterol 5beta,6beta-epoxide is an oxidative metabolite of cholesterol formed by free-radical and non-radical oxidation of cholesterol at the 5,6 double bond. [1] [2] Induces lactate dehydrogenase (LDH) release and apoptosis in macrophage-differentiated U937 cells. [3] 5β,6β-epoxycholestanol has been found in human fatty streaks and advanced atherosclerotic lesions, but not in normal aortic tissue. [4] References: [1]. Pulfer, MK, and Murphy, RC Formation of bioactive oxygen sterols during ozonolysis of cholesterol present in lung surfactants. Journal of Biochemistry 279(25), 26331-26338 (2004). [2]. Aringer, L. and Eneroth, P. In vitro formation and metabolism of cholesterol and β-sitosterol 5,6-epoxides. J. Lipid Research. 15(4), 389-398 (1974).[3]. Lordan, S., O'Brien, NM, and Mackrill, JJ Calcium in 7β-hydroxycholesterol and cholesterol-5β,6β-epoxide-induced apoptosis. J. Biochemistry. Moore. poison. 23(5), 324-332 (2009).[4]. Garcia-Cruset, S., Carpenter, KL, Guardiola, F. et al. Oxysterol profiles of normal human arteries, fatty streaks, and advanced lesions. free radicals. reservoir. 35(1), 31-41 (2001).
Related CatalogResearch Areas >>Others

Chemical & Physical Properties

Density1.04g/cm3
Boiling Point497.7ºC at 760 mmHg
Molecular FormulaC27H46O2
Molecular Weight402.65300
Flash Point200.9ºC
Exact Mass402.35000
PSA32.76000
LogP6.59990
Vapour Pressure5.43E-12mmHg at 25°C
Index of Refraction1.533
InChIKeyPRYIJAGAEJZDBO-DTLXENBRSA-N
SMILESCC(C)CCCC(C)C1CCC2C3CC4OC45CC(O)CCC5(C)C3CCC12C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
FZ6380000
CHEMICAL NAME :
5-beta-Cholestan-3-beta-ol, 5,6-beta-epoxy-
CAS REGISTRY NUMBER :
4025-59-6
LAST UPDATED :
199410
DATA ITEMS CITED :
3
MOLECULAR FORMULA :
C27-H46-O2
MOLECULAR WEIGHT :
402.73

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :
Mutation in mammalian somatic cells
TEST SYSTEM :
Rodent - hamster Lung
DOSE/DURATION :
10 umol/L
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 203,355,1988

Safety Information

Personal Protective Equipmentdust mask type N95 (US);Eyeshields;Faceshields;Gloves
Hazard CodesXn
Risk Phrases20/21/22-48/20/21/22
Safety Phrases7-36/37
RIDADRNONH for all modes of transport

Articles27

More Articles
Surprising unreactivity of cholesterol-5,6-epoxides towards nucleophiles.

J. Lipid Res. 53(4) , 718-25, (2012)

We recently established that drugs used for the treatment and the prophylaxis of breast cancers, such as tamoxifen, were potent inhibitors of cholesterol-5,6-epoxide hydrolase (ChEH), which led to the...

Formation of biologically active oxysterols during ozonolysis of cholesterol present in lung surfactant.

J. Biol. Chem. 279(25) , 26331-8, (2004)

Exposure of the lung to concentrations of ozone found in ambient air is known to cause toxicity to the epithelial cells of the lung. Because of the chemical reactivity of ozone, it likely reacts with ...

Comparative study of the cytotoxicity and apoptosis-inducing potential of commonly occurring oxysterols.

Cell Biol. Toxicol. 17(2) , 127-37, (2001)

The cytotoxicity of the oxysterols 25-hydroxycholesterol, 7beta-hydroxycholesterol, cholesterol-5alpha,6alphaepoxide, cholesterol-5beta,6beta-epoxide, 19-hydroxycholesterol and 7-ketocholesterol was e...

Synonyms

5beta,6beta-Epoxycholestanol
CHOLESTEROL-5BETA,6BETA-EPOXIDE
5,6beta-epoxy-5beta-cholestan-3beta-ol
5BETA,6BETA-EPOXYCHOLESTAN-3BETA-OL
cholestanol,5ß,6ß-epo
cholesterol-5B,6B-epoxide
cholesterolbeta-epoxide
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