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7α-Hydroxycholesterol

CAT: 0804-HY-N7264-02Size: 10 mM - 1 mLDry Ice: NoHazardous: No
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CAT#:0804-HY-N7264-02Size:10 mM - 1 mL
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Description
7α-Hydroxycholesterol is a cholesterol oxide and can serve as a biomarker for oxidative stress and lipid peroxidation. 7α-Hydroxycholesterol has cytotoxic and pro-inflammatory activities. 7α-Hydroxycholesterol can also inhibit sterol synthesis and reduce the activity of HMG-CoA reductase. 7α-Hydroxycholesterol can be used in the research of diseases such as diabetes and atherosclerosis[1][2][3][4][5].
CAS Number
566-26-7
UNSPSC
12352211
Target
Akt; ERK; HMG-CoA Reductase (HMGCR) ; MDM-2/p53; Src; Toll-like Receptor (TLR)
Type
Natural Products
Related Pathways
Apoptosis; Immunology/Inflammation; MAPK/ERK Pathway; Metabolic Enzyme/Protease; PI3K/Akt/mTOR; Protein Tyrosine Kinase/RTK; Stem Cell/Wnt
Applications
Metabolism-sugar/lipid metabolism
Field of Research
Metabolic Disease; Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/7-alpha-hydroxycholesterol.html
Purity
99.99
Solubility
DMSO : 50 mg/mL (ultrasonic)
Smiles
CC(C)CCC[C@@H](C)[C@H]1CC[C@@]2([H])[C@]3([H])[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C
Molecular Formula
C27H46O2
Molecular Weight
402.65
References & Citations
[1] Ferderbar S, et al. Cholesterol oxides as biomarkers of oxidative stress in type 1 and type 2 diabetes mellitus. Diabetes Metab Res Rev. 2007 Jan;23 (1) :35-42.|[2]Kitano S, et al. Oxidative status of human low density lipoprotein isolated by anion-exchange high-performance liquid chromatography--assessment by total hydroxyoctadecadienoic acid, 7-hydroxycholesterol, and 8-iso-prostaglandin F (2alpha) . Anal Chim Acta. 2007 Feb 28;585 (1) :86-93.|[3]Nury T, et al. Improved synthesis and in vitro evaluation of the cytotoxic profile of oxysterols oxidized at C4 (4α- and 4β-hydroxycholesterol) and C7 (7-ketocholesterol, 7α- and 7β-hydroxycholesterol) on cells of the central nervous system. Eur J Med Chem. 2013;70:558-67.|[4]Kandutsch AA, et al. Inhibition of sterol synthesis in cultured mouse cells by 7alpha-hydroxycholesterol, 7beta-hydroxycholesterol, and 7-ketocholesterol. J Biol Chem. 1973 Dec 25;248 (24) :8408-17.|[5]Son Y, et al. Glucocorticoids Impair the 7α-Hydroxycholesterol-Enhanced Innate Immune Response. Immune Netw. 2023 Oct 19;23 (5) :e40.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

7Alpha-Hydroxycholesterol

7alpha-hydroxycholesterol is the 7alpha-hydroxy derivative of cholesterol. It has a role as a mouse metabolite. It is a 3beta-hydroxy-Delta(5)-steroid, a 7alpha-hydroxy steroid and an oxysterol. It is functionally related to a cholesterol.

CAS Number566-26-7
PubChem CID107722
IUPAC Name(3S,7S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol
Molecular FormulaC27H46O2
Molecular Weight402.7
XLogP7.4
Topological Polar Surface Area40.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count5
Heavy Atom Count29
Formal Charge0
Complexity624
SMILES
C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@@H](C=C4[C@@]3(CC[C@@H](C4)O)C)O)C
InChI
InChI=1S/C27H46O2/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/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,24-,25+,26+,27-/m1/s1
InChIKey
OYXZMSRRJOYLLO-RVOWOUOISA-N
Chemical Structure
2D Structure
2D structure of 7Alpha-Hydroxycholesterol
CAS: 566-26-7
CID: 107722
Formula: C27H46O2
MW: 402.7
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight402.7
XLogP37.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count5
Exact Mass402.349780706
Monoisotopic Mass402.349780706
Topological Polar Surface Area40.5 Ų
Heavy Atom Count29
Formal Charge0
Complexity624
Isotope Atom Count0
Defined Atom Stereocenter Count9
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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