7-KETOCHOLESTEROL

Modify Date: 2025-08-21 09:43:46

7-KETOCHOLESTEROL Structure
7-KETOCHOLESTEROL structure
Common Name 7-KETOCHOLESTEROL
CAS Number 566-28-9 Molecular Weight 400.637
Density 1.0±0.1 g/cm3 Boiling Point 516.7±29.0 °C at 760 mmHg
Molecular Formula C27H44O2 Melting Point 158-160ºC
MSDS Chinese USA Flash Point 218.5±16.9 °C

 Use of 7-KETOCHOLESTEROL


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].

 Names

Name 7-ketocholesterol
Synonym More Synonyms

 7-KETOCHOLESTEROL 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
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
InChIKey YIKKMWSQVKJCOP-ABXCMAEBSA-N
SMILES CC(C)CCCC(C)C1CCC2C3C(=O)C=C4CC(O)CCC4(C)C3CCC12C
Storage condition -20°C

 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

 Articles47

More 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...

 Synonyms

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
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