7-KETOCHOLESTEROL
Synonym(s):3β-Hydroxy-5-cholesten-7-one;7-Ketocholesterol;7-oxocholesterol; 7-oxo-5-cholesten-3β-ol-7-one; 5-cholesten-3β-ol-7-one; 3β-hydroxycholest-5-en-7-one; 110806
- CAS NO.:566-28-9
- Empirical Formula: C27H44O2
- Molecular Weight: 400.65
- MDL number: MFCD00010474
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-05-18 11:31:16
What is 7-KETOCHOLESTEROL?
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
The Uses of 7-KETOCHOLESTEROL
A metabolite of Cholesterol
The Uses of 7-KETOCHOLESTEROL
5-Cholesten-3β-ol-7-one was used as a standard in the determination of cholesterol derivatives by GC-MS and HPLC.
What are the applications of Application
7-Ketocholesterol is 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
Properties of 7-KETOCHOLESTEROL
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 |
Safety information for 7-KETOCHOLESTEROL
Computed Descriptors for 7-KETOCHOLESTEROL
New Products
Tubulysin B 2,2-diethoxyethanethioamide Tubulysin F Tubulysin E 2,2-Difluoropropanol Methyl (R)-1-Boc-4,4-difluoropyrrolidine-2-carboxylate 3-Aminocyclobutanone hydrochloride tetrahydro-4-methyl-2H-pyran 1,2,3,6-TETRAHYDROPYRIDINE HYDROCHLORIDE 3-METHYLAZETIDIN-3-OL HYDROCHLORIDE 2-[2-[3(S)-3[2-(7-chloro-2-quinolinyl) ethenyl] phenyl-3- hydroxyl propyl] phenyl]-2-propanol 2-[[(3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol ethanedioate 2-(1-(Mercaptomethyl) cyclopropyl) acetonitrile Imeglimin Hydrochloride IH Calcium Sodium Phosphosilicate IH (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine Latanoprostene Bunod Lubiprostone Magnesium Trisilicate Flame Retardant Zinc Borate methyl 3-fluoro-4- thiomorpholino phenylcarbamate (R)-(3-(3-fluoro-4- thiomorpholinophenyl)-2- oxooxazolidin-4-yl) methyl methanesulfonate 7-Methoxyquinoline-4-carboxylic acid 1H-Imidazole-4-carbonitrileRelated products of tetrahydrofuran
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