7-KETOCHOLESTEROL Chemical Properties

Melting point:

158-160°C

Boiling point:

463.26°C (rough estimate)

Density 

1.0044 (rough estimate)

refractive index 

1.4480 (estimate)

storage temp. 

room temp

solubility 

Acetonitrile (Slightly), Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

14.68±0.70(Predicted)

color 

Crystals from CHCl3/Et2O

biological source

synthetic (organic)

Safety Information

WGK Germany 

3

RTECS 

FZ8708000

MSDS

• Language:English Provider:SigmaAldrich

7-KETOCHOLESTEROL Usage And Synthesis

Description

7-keto Cholesterol is a bioactive sterol and a major oxysterol component of oxidized LDL. It is produced by oxidation of cholesterol via ethanol-mediated lipid peroxidation or photodamage as well as oxidation of 7-dehydro cholesterol by the cytochrome P450 (CYP) isoform CYP7A1. 7-keto Cholesterol inhibits CYP7A1 (IC₅₀ = ~1 μM). It induces activation and chemotaxis of retinal microglia as well as polarization to a pro-inflammatory state via NLRP3 inflammasome activation in vitro. Intraocular implantation of 7-keto cholesterol coated wafers increases ocular levels of VEGF, IL-1β, and GRO/KC, macrophage infiltration, and neovascularization in rat eye. Levels of 7-keto cholesterol in lipid deposits are increased in a variety of chronic diseases, including atherosclerosis, Alzheimer''s disease, and age-related macular degeneration.

Chemical Properties

Off-White Solid

Uses

5-Cholesten-3β-ol-7-one was used as a standard in the determination of cholesterol derivatives by GC-MS and HPLC.

Uses

A metabolite of Cholesterol

Definition

ChEBI: A cholestanoid that consists of cholesterol bearing an oxo substituent at position 7.

General Description

7-ketocholesterol is a major oxidation product of cholesterol.

Biochem/physiol Actions

7-ketocholesterol is a strong inhibitor of cytochrome P450 7A1. It modulates cholesterol homeostasis, cytotoxicity and apoptosis. 7-ketocholesterol stimulates inflammation, growth inhibition and vascular endothelial growth factor. Cellular accumulation of 7-ketocholesterol enhances oxidative stress, endoplasmic reticulum stress and apoptosis in macrophages.

Safety Profile

Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits acrid smoke and irritating fumes

7-KETOCHOLESTEROL(566-28-9)Related Product Information

• 5-CHOLESTEN-3-BETA, 7-ALPHA-DIOL
• 25-HYDROXYCHOLESTEROL
• 7BETA-HYDROXYCHOLESTEROL
• Cholesterol
• 7-KETOCHOLESTEROL ACETATE
• 22-KETOCHOLESTEROL
• 22-KETOCHOLESTEROL ACETATE
• 5-CHOLESTEN-3-BETA-OL-7-ONE BENZOATE
• 7-oxocholest-5-en-3-beta-yl acetate
• 25-HYDROXYCHOLESTEROL, 7-KETONE
• 7-KETO CHOLESTEROL, [1,2-3H]
• 5-CHOLESTEN-3-BETA, 25-DIOL-7-ONE ACETATE
• 7-KETOCHOLESTEROL
• 7-KETOCHOLESTEROL-D7,7-KETOCHOLESTEROL-25,26,26,26,27,27,27-D7
• 5,25R-SPIROSTEN-3BETA-OL-7-ONE