7-KETOCHOLESTEROL manufacturers
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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 | | biological source | synthetic (organic) | | InChIKey | YIKKMWSQVKJCOP-TWXHVRDXNA-N | | SMILES | C[C@]12CC[C@]3([H])[C@]4(CC[C@H](O)CC4=CC(=O)[C@@]3([H])[C@]1([H])CC[C@]2([H])[C@H](C)CCCC(C)C)C |&1:1,4,6,9,16,18,22,24,r| |
| WGK Germany | 3 | | RTECS | FZ8708000 | | Storage Class | 11 - Combustible Solids |
| | 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 | | References | [1] TZU PIN SHENTU. oxLDL-induced decrease in lipid order of membrane domains is inversely correlated with endothelial stiffness and network formation.[J]. American journal of physiology. Cell physiology, 2010, 299 2: C218-29. DOI: 10.1152/ajpcell.00383.2009
[2] A J BROWN. 7-Hydroperoxycholesterol and its products in oxidized low density lipoprotein and human atherosclerotic plaque.[J]. Journal of Lipid Research, 1997, 38 9: 1730-1745.
[3] IGNACIO R RODRIGUEZ S J F. Photodamage generates 7-keto- and 7-hydroxycholesterol in the rat retina via a free radical-mediated mechanism.[J]. Photochemistry and Photobiology, 2009, 85 5: 1116-1125. DOI: 10.1111/j.1751-1097.2009.00568.x
[4] RAKU SHINKYO. Conversion of 7-dehydrocholesterol to 7-ketocholesterol is catalyzed by human cytochrome P450 7A1 and occurs by direct oxidation without an epoxide intermediate.[J]. The Journal of Biological Chemistry, 2011, 286 38: 33021-33028. DOI: 10.1074/jbc.m111.282434
[5] TIJANA MITI . 11β-Hydroxysteroid dehydrogenase type 1 contributes to the balance between 7-keto- and 7-hydroxy-oxysterols in vivo[J]. Biochemical pharmacology, 2013, 86 1: Pages 146-153. DOI: 10.1016/j.bcp.2013.02.002
[6] MAANASA INDARAM. 7-Ketocholesterol increases retinal microglial migration, activation, and angiogenicity: a potential pathogenic mechanism underlying age-related macular degeneration.[J]. Scientific Reports, 2015: 9144. DOI: 10.1038/srep09144
[7] JUAN AMARAL. 7-Ketocholesterol induces inflammation and angiogenesis in vivo: a novel rat model.[J]. PLoS ONE, 2013: e56099. DOI: 10.1371/journal.pone.0056099 |
| | 7-KETOCHOLESTEROL Preparation Products And Raw materials |
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