7-KETOCHOLESTEROL

Names

[ CAS No. ]:
566-28-9

[ Name ]:
7-KETOCHOLESTEROL

[Synonym ]:
cholest-3,5-dien-7-one
Cholest-5-en-7-one, 3-hydroxy-, (3β)-
3b-Hydroxycholest-5-en-7-one
Cholesta-3,5-dien-7-on
7-KETOCHOLESTEROL
7-Ketocholesta-3,5-diene
(3β)-3-Hydroxycholest-5-en-7-one
3,5-cholestadien-7-one
Cholesta-3,5-diene-7-one-d7
7-oxo-3,5-cholestadiene
cholesta-3,5-dien-7-one
7-oxocholesta-3,5-diene
cholest-3,5-diene-7-one
7-Oxocholesterol
7-Keto Cholesterol

Biological Activity

[Description]:

7-Ketocholesterol, toxic oxysterol, inhibits the rate-limiting step in bile acid biosynthesis cholesterol 7 alpha-hydroxylase, as well as strongly inhibiting HMG-CoA reductase (the rate-limiting enzyme in cholesterol biosynthesis). 7-Ketocholesterol induces cell apoptosis[1].

[Related Catalog]:

Research Areas >> Metabolic Disease

[Target]

Human Endogenous Metabolite

[References]

[1]. M A Lyons, et al. 7-Ketocholesterol. Int J Biochem Cell Biol. Mar-Apr 1999;31(3-4):369-75.

[2]. Amelia Anderson, et al. 7-Ketocholesterol in disease and aging. Redox Biol. 2020 Jan;29:101380.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
516.7±29.0 °C at 760 mmHg

[ Melting Point ]:
158-160ºC

[ Molecular Formula ]:
C₂₇H₄₄O₂

[ Molecular Weight ]:
400.637

[ Flash Point ]:
218.5±16.9 °C

[ Exact Mass ]:
400.334137

[ PSA ]:
37.30000

[ LogP ]:
7.57

[ Vapour Pressure ]:
0.0±3.0 mmHg at 25°C

[ Index of Refraction ]:
1.531

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: FZ8708000

CHEMICAL NAME :: Cholesterol, 7-oxo-

CAS REGISTRY NUMBER :: 566-28-9

BEILSTEIN REFERENCE NO. :: 2169084

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C27-H44-O2

MOLECULAR WEIGHT :: 400.71

WISWESSER LINE NOTATION :: L E5 B666 KV LUTJ A1 E1 FY1&3Y1&1 OQ

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 :: DNA inhibition

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

Articles

Genistein as a potential inducer of the anti-atherogenic enzyme paraoxonase-1: studies in cultured hepatocytes in vitro and in rat liver in vivo.

J. Cell. Mol. Med. 16(10) , 2331-41, (2012)

A number of cardioprotective effects, including the reduced oxidation of the low-density lipoprotein (LDL) particles, have been attributed to dietary soy isoflavones. Paraoxonase 1 (PON1), an enzyme m...

On-line liquid chromatography-gas chromatography: A novel approach for the analysis of phytosterol oxidation products in enriched foods.

J. Chromatogr. A. 1396 , 98-108, (2015)

A novel methodology for the automated qualitative and quantitative determination of phytosterol oxidation products in enriched foods via on-line liquid chromatography-gas chromatography (LC-GC) was es...

Analysis of oxysterols and vitamin D metabolites in mouse brain and cell line samples by ultra-high-performance liquid chromatography-atmospheric pressure photoionization-mass spectrometry.

J. Chromatogr. A. 1364 , 214-22, (2014)

We have developed an ultra-high-performance liquid chromatography-atmospheric pressure photoionization-tandem mass spectrometric (UHPLC-APPI-MS/MS) method for the simultaneous quantitative analyses of...

Related Compounds

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