| Identification | Back 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 Properties | Back 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) | [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| |
| Hazard Information | Back Directory | [Description]
7-keto Cholesterol is a bioactive sterol and a major oxysterol component of oxidized LDL.1,2 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 CYP7A1.3,4,5 7-keto Cholesterol inhibits CYP7A1 (IC50 = ~1 μM).4 It induces activation and chemotaxis of retinal microglia as well as polarization to a pro-inflammatory state via NLRP3 inflammasome activation in vitro.6 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.7 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 | [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 |
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