| Identification | Back Directory | [Name]
5-CHOLESTEN-3-BETA, 7-ALPHA-DIOL | [CAS]
566-26-7 | [Synonyms]
7alpha-Cholesterol
7-ALPHA-HYDROXYCHOLESTEROL
7a-Hydroxycholest-5-en-3ol
7-alfa-Hydroxy-Cholesterol
3β,7α-Dihydroxycholest-5-ene
(3,7a)-Cholest-5-ene-3,7-diol
Cholest-5-ene-3,7-diol, (3b,7a)-
5-CHOLESTEN-3-BETA, 7-ALPHA-DIOL
cholest-5-en-3 beta,7 alpha-diol
Cholest-5-ene-3,7-diol, (3beta,7alpha)- | [Molecular Formula]
C27H46O2 | [MDL Number]
MFCD00201416 | [MOL File]
566-26-7.mol | [Molecular Weight]
402.65 |
| Chemical Properties | Back Directory | [Appearance]
White Solid | [Melting point ]
168-170°C | [Boiling point ]
515.3±38.0 °C(Predicted) | [density ]
1.03±0.1 g/cm3(Predicted) | [storage temp. ]
Refrigerator | [solubility ]
Soluble in DMSO or in Ethanol. | [form ]
solid | [pka]
14.11±0.70(Predicted) | [color ]
White or pale yellow | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months. | [InChIKey]
OYXZMSRRJOYLLO-RVOWOUOISA-N | [SMILES]
O[C@H]1[C@H]2[C@H]3[C@@]([C@H](CC3)[C@@H](CCCC(C)C)C)(CC[C@@H]2[C@]4(CC[C@@H](CC4=C1)O)C)C |
| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [Uses]
Secondary metabolite of Cholesterol | [Definition]
ChEBI: The 7alpha-hydroxy derivative of cholesterol. | [Description]
7α-Hydroxycholesterol (566-26-7) is a metabolite resulting from the action of cholesterol 7α-hydroxylase on cholesterol. 7α-Hydroxycholesterol is the first intermediate and a rate limiting step in the major pathway for bile acid synthesis in humans.??A pro-inflammatory mediator which upregulates production of CCL2 and MMP9 in macrophages and may promote progression of atherosclerosis.2,3?Possible biomarker for cellular lipid peroxidation.4 | [References]
1) Duane and Javitt (2002),?Conversion of 7 alpha-hydroxycholesterol to bile acid in human subjects: is there an alternate pathway favoring cholic acid synthesis?; J. Lab. Clin. Med.,?139?109
2) Kim?et al.?(2015)?7α-Hydroxycholesterol induces inflammation by enhancing production of chemokine (C-C motif) ligand 2; Biochem. Biophys. Res. Commun.,?467?879
3) Kim?et al.?(2014)?27-Hydroxycholesterol and 7alpha-hydroxycholesterol trigger a sequence of events leading to migration of CCR5-expressing Th1 lymphocytes; Toxicol. Appl. Pharmacol.,?274?462
4) Saito and Noguchi (2014)?7-Hydroxycholesterol as a possible biomarker of cellular lipid peroxidation: difference between cellular and plasma lipid peroxidation; Biochem. Biophys. Res. Commun.,?446?741 |
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