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7-Ketocholesterol (Standard)

CAT: 0804-HY-113342R-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-113342R-01Size:5 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
7-Ketocholesterol (Standard) is the analytical standard of 7-Ketocholesterol. This product is intended for research and analytical applications. 7-Ketocholesterol is an oxidation product of cholesterol, widely present in atherosclerotic plaques, and has a stronger atherogenic effect than cholesterol. 7-Ketocholesterol can inhibit the rate-limiting enzymes involved in bile acid and cholesterol synthesis, such as cholesterol 7α-hydroxylase and HMG-CoA reductase. 7-Ketocholesterol exhibits pro-inflammatory effects both in vivo and in vitro and can induce cell apoptosis (apoptosis) [1].
CAS Number
566-28-9
UNSPSC
12352100
Target
Endogenous Metabolite; p38 MAPK; Reference Standards
Related Pathways
MAPK/ERK Pathway; Metabolic Enzyme/Protease; Others
Field of Research
Metabolic Disease; Cardiovascular Disease
Smiles
C[C@]1(CC2)[C@](CC[C@]1([H])[C@H](C)CCCC(C)C)([H])[C@@](C(C=C3C[C@H]4O)=O)([H])[C@@]2([H])[C@]3(CC4)C
Molecular Formula
C27H44O2
Molecular Weight
400.64
References & Citations
[1]M A Lyons, et al. 7-Ketocholesterol. Int J Biochem Cell Biol. Mar-Apr 1999;31 (3-4) :369-75. |[2]Amelia Anderson, et al. 7-Ketocholesterol in disease and aging. Redox Biol. 2020 Jan;29:101380.|[3]Amaral J, et al. 7-Ketocholesterol induces inflammation and angiogenesis in vivo: a novel rat model. PLoS One. 2013;8 (2) :e56099.|[4]Tani M, et al. 7-Ketocholesterol enhances leukocyte adhesion to endothelial cells via p38MAPK pathway. PLoS One. 2018 Jul 31;13 (7) :e0200499.|[5]Luthra S, et al. 7-Ketocholesterol activates caspases-3/7, -8, and-12 in human microvascular endothelial cells in vitro[J]. Microvascular research, 2008, 75 (3) : 343-350.
Shipping Conditions
Room temperature
Scientific Category
Reference Standards

Chemical Information

7-Ketocholesterol

7-ketocholesterol is a cholestanoid that consists of cholesterol bearing an oxo substituent at position 7. It has a role as a neuroprotective agent. It is a 3beta-hydroxy-Delta(5)-steroid, a 3beta-sterol, a 7-oxo steroid and a cholestanoid. It is functionally related to a cholesterol.

CAS Number566-28-9
PubChem CID91474
IUPAC Name(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 FormulaC27H44O2
Molecular Weight400.6
XLogP7.5
Topological Polar Surface Area37.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count5
Heavy Atom Count29
Formal Charge0
Complexity663
SMILES
C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C(=O)C=C4[C@@]3(CC[C@@H](C4)O)C)C
InChI
InChI=1S/C27H44O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-23,25,28H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,25+,26+,27-/m1/s1
InChIKey
YIKKMWSQVKJCOP-ABXCMAEBSA-N
Chemical Structure
2D Structure
2D structure of 7-Ketocholesterol
CAS: 566-28-9
CID: 91474
Formula: C27H44O2
MW: 400.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight400.6
XLogP37.5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count5
Exact Mass400.334130642
Monoisotopic Mass400.334130642
Topological Polar Surface Area37.3 Ų
Heavy Atom Count29
Formal Charge0
Complexity663
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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