ChemicalBook > CAS DataBase List > 7-KETOCHOLESTEROL

7-KETOCHOLESTEROL

Product Name
7-KETOCHOLESTEROL
CAS No.
566-28-9
Chemical Name
7-KETOCHOLESTEROL
Synonyms
7-oxocholesterol;Ketocholesterol;5-cholesten-3B-ol-7-one;5-cholesten-3β-ol-7-one;5-Cholesten-3β-ol-7-one;sc4722;7-KetoC;7-oxo-cholestero;7-KETOCHOLESTEROL;7-Ketocholesterolk
CBNumber
CB7158120
Molecular Formula
C27H44O2
Formula Weight
400.65
MOL File
566-28-9.mol
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7-KETOCHOLESTEROL Property

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
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Safety

WGK Germany 
3
RTECS 
FZ8708000
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
C2394
Product name
5-Cholesten-3β-ol-7-one
Purity
≥90%
Packaging
100mg
Price
$89.9
Updated
2024/03/01
Sigma-Aldrich
Product number
C2394
Product name
5-Cholesten-3β-ol-7-one
Purity
≥90%
Packaging
1g
Price
$511
Updated
2024/03/01
Cayman Chemical
Product number
16339
Product name
7-keto Cholesterol
Purity
≥98%
Packaging
5mg
Price
$57
Updated
2024/03/01
Cayman Chemical
Product number
16339
Product name
7-keto Cholesterol
Purity
≥98%
Packaging
10mg
Price
$107
Updated
2024/03/01
Sigma-Aldrich
Product number
C2394
Product name
5-Cholesten-3β-ol-7-one
Purity
≥90%
Packaging
250mg
Price
$172
Updated
2024/03/01
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7-KETOCHOLESTEROL Chemical Properties,Usage,Production

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 Preparation Products And Raw materials

Raw materials

Preparation Products

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566-28-9, 7-KETOCHOLESTEROLRelated Search:

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

  • 7-KETOCHOLESTEROL
  • 5-CHOLESTEN-3BETA-OL-7-ONE
  • 3BETA-HYDROXY-5-CHOLESTEN-7-ONE
  • Cholest-5-en-3beta-ol-7-one
  • 3-hydroxy-5-cholestene-7-one
  • (3-beta)-cholest-5-en-7-on
  • 3-beta-hydroxy-cholest-5-en-7-on
  • 3-HYDROXY-5-CHOLESTENE-7-ONE;7-KETOCHOLESTEROL
  • 3-beta-hydroxycholest-5-en-7-one
  • 7-oxo-cholestero
  • 7-oxocholesterol
  • sc4722
  • 5-cholesten-3B-ol-7-one
  • Cholest-5-en-7-one, 3-hydroxy-, (3.beta.)-
  • 3β-hydroxy-5-cholesten-7-one
  • 5-cholesten-3β-ol-7-one
  • 5A-CHOLESTAN-3B-OL-7-ONE
  • 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
  • (3)-3-Hydroxycholest-5-en-7-one
  • 3-Hydroxycholest-5-en-7-one
  • Cholest-5-en-3-ol-7-one
  • 3β-Hydroxy-5-cholesten-7-one, 7-Ketocholesterol
  • 7-KetoC
  • (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
  • Cholest-5-en-7-one, 3-hydroxy-, (3b)-
  • 7-Ketocholesterolk
  • 7-Keto Cholesterol (~98%)
  • 7-Ketocholesterol (Solution)
  • Ketocholesterol
  • Cholesterol 7-Keto
  • Cholest-5-en-7-one, 3-hydroxy-, (3β)-
  • Cholesterol Impurity 23
  • 5-Cholesten-3β-ol-7-one
  • HMG-CoA reductase,inhibit,7 Ketocholesterol,Endogenous Metabolite,Inhibitor,coronary artery disease,7-Ketocholesterol,7Ketocholesterol,cholesterol biosynthesis,orphan disease
  • Cholester-3-hydroxy-5-en-7-one
  • 566-28-9
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