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| | 7-KETOCHOLESTEROL Basic information |
| | 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 |
| WGK Germany | 3 | | RTECS | FZ8708000 |
| | 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 | A metabolite of Cholesterol | | Uses | 5-Cholesten-3β-ol-7-one was used as a standard in the determination of cholesterol derivatives by GC-MS and HPLC. | | 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 |
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