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ChemicalBook--->CAS DataBase List--->566-28-9

566-28-9

566-28-9 Structure

566-28-9 Structure
IdentificationBack Directory
[Name]

7-KETOCHOLESTEROL
[CAS]

566-28-9
[Synonyms]

sc4722
7-KetoC
Ketocholesterol
7-oxo-cholestero
7-oxocholesterol
7-KETOCHOLESTEROL
Cholesterol 7-Keto
7-Ketocholesterolk
Cholest-5-en-3-ol-7-one
5-cholesten-3B-ol-7-one
5-cholesten-3β-ol-7-one
5A-CHOLESTAN-3B-OL-7-ONE
7-Keto Cholesterol (~98%)
5-CHOLESTEN-3BETA-OL-7-ONE
(3-beta)-cholest-5-en-7-on
Cholest-5-en-3beta-ol-7-one
3-Hydroxycholest-5-en-7-one
3β-hydroxy-5-cholesten-7-one
3-hydroxy-5-cholestene-7-one
7-Ketocholesterol (Solution)
3BETA-HYDROXY-5-CHOLESTEN-7-ONE
(3)-3-Hydroxycholest-5-en-7-one
3-beta-hydroxycholest-5-en-7-one
3-beta-hydroxy-cholest-5-en-7-on
Cholest-5-en-7-one, 3-hydroxy-, (3β)-
Cholest-5-en-7-one, 3-hydroxy-, (3b)-
Cholest-5-en-7-one, 3-hydroxy-, (3.beta.)-
3-HYDROXY-5-CHOLESTENE-7-ONE;7-KETOCHOLESTEROL
3β-Hydroxy-5-cholesten-7-one, 7-Ketocholesterol
3-hydroxy-10,13-dimethyl-17-(6-methylheptan-2-yl)-1,2,3,4,8,9,11,12,14,15,1 6,17-dodecahydrocyclopenta[a]phenanthren-7-one
(3S,8S,9S,10R,13R,14S,17R)-17-[(1R)-1,5-dimethylhexyl]-3-hydroxy-10,13-dimethyl-1,2,3,4,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-7-one
(3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-7-one
[Molecular Formula]

C27H44O2
[MDL Number]

MFCD00010474
[MOL File]

566-28-9.mol
[Molecular Weight]

400.64
Chemical PropertiesBack Directory
[Melting point ]

158-160°C
[Boiling point ]

463.26°C (rough estimate)
[density ]

1.0044 (rough estimate)
[refractive index ]

1.4480 (estimate)
[storage temp. ]

Refrigerator
[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 DataBack Directory
[WGK Germany ]

3
[RTECS ]

FZ8708000
Hazard InformationBack Directory
[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 (Item No. 14612) 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]

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
Spectrum DetailBack Directory
[Spectrum Detail]

7-KETOCHOLESTEROL(566-28-9)MS
7-KETOCHOLESTEROL(566-28-9)1HNMR
7-KETOCHOLESTEROL(566-28-9)IR1
7-KETOCHOLESTEROL(566-28-9)IR2
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