Cholesterol-5α,6α-epoxide

Names

[ Name ]:
Cholesterol-5α,6α-epoxide

[Synonym ]:
Cholesterol epoxide
5,6alpha-epoxy-5alpha-cholestan-3beta-ol
Cholesterol-5α,6α-epoxide
MFCD00046980
Epoxycholesterol
cholestanol
EINECS 215-007-6
Cholesterol-5alpha,6alpha-epoxide

Biological Activity

[Description]:

Cholesterol-5α,6α-epoxide is a biochemical reagent that can be used as a biological material or organic compound for life science related research.

[Related Catalog]:

Research Areas >> Others

Chemical & Physical Properties

[ Density]:
1.04g/cm3

[ Boiling Point ]:
497.7ºC at 760mmHg

[ Molecular Formula ]:
C₂₇H₄₆O₂

[ Molecular Weight ]:
402.65300

[ Flash Point ]:
200.9ºC

[ Exact Mass ]:
402.35000

[ PSA ]:
32.76000

[ LogP ]:
6.59990

[ Vapour Pressure ]:
5.43E-12mmHg at 25°C

[ Index of Refraction ]:
1.533

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: FZ6360000

CHEMICAL NAME :: 5-alpha-Cholestan-3-beta-ol, 5,6-alpha-epoxy-

CAS REGISTRY NUMBER :: 1250-95-9

BEILSTEIN REFERENCE NO. :: 0089511

LAST UPDATED :: 199612

DATA ITEMS CITED :: 8

MOLECULAR FORMULA :: C27-H46-O2

MOLECULAR WEIGHT :: 402.73

WISWESSER LINE NOTATION :: T3 F5 E666 1A R AXO CH&TTTTJ IY1&3Y1&1 J1 QQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 750 mg/kg/9W-I

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Tumorigenic - tumors at site of application

MUTATION DATA

TYPE OF TEST :: Mutation in mammalian somatic cells

TEST SYSTEM :: Rodent - hamster Lung

DOSE/DURATION :: 25 umol/L

REFERENCE :: FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 24,1103,1986

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
FZ6360000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Oxysterols: modulators of cholesterol metabolism and other processes.

Physiol. Rev. 80 , 361-554, (2000)

Oxygenated derivatives of cholesterol (oxysterols) present a remarkably diverse profile of biological activities, including effects on sphingolipid metabolism, platelet aggregation, apoptosis, and pro...

Oxysterols as non-genomic regulators of cholesterol homeostasis.

Trends Endocrinol. Metab. 23 , 99-106, (2012)

Tight regulation of cellular and plasma cholesterol is crucial to proper cellular functioning because excess free cholesterol is toxic to cells and is associated with atherosclerosis and heart disease...

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...