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|

Safety Information

WGK Germany 

3

RTECS 

FZ8708000

MSDS

• Language:English Provider:SigmaAldrich

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(566-28-9)Related Product Information

• 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