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| | 5-Cholesten-3-beta, 7-alpha-diol Basic information |
| Product Name: | 5-Cholesten-3-beta, 7-alpha-diol | | Synonyms: | 7-ALPHA-HYDROXYCHOLESTEROL;cholest-5-en-3 beta,7 alpha-diol;(3,7a)-Cholest-5-ene-3,7-diol;7a-Hydroxycholest-5-en-3ol;3β,7α-Dihydroxycholest-5-ene;7alpha-Cholesterol;Cholest-5-ene-3,7-diol, (3beta,7alpha)-;Cholest-5-ene-3,7-diol, (3b,7a)- | | CAS: | 566-26-7 | | MF: | C27H46O2 | | MW: | 402.66 | | EINECS: | | | Product Categories: | Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Steroids | | Mol File: | 566-26-7.mol |  |
| | 5-Cholesten-3-beta, 7-alpha-diol Chemical Properties |
| 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. | | pka | 14.11±0.70(Predicted) | | form | solid | | 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 |
| WGK Germany | WGK 3 | | Storage Class | 11 - Combustible Solids |
| | 5-Cholesten-3-beta, 7-alpha-diol Usage And Synthesis |
| 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.2,3Possible biomarker for cellular lipid peroxidation.4 | | Chemical Properties | White Solid | | Uses | Secondary metabolite of Cholesterol. | | Definition | ChEBI: The 7alpha-hydroxy derivative of cholesterol. | | References | [1] WILLIAM C. DUANE Norman B J. Conversion of 7α-hydroxycholesterol to bile acid in human subjects: Is there an alternate pathway favoring cholic acid synthesis[J]. Journal of Laboratory and Clinical Medicine, 2002, 139 2: Pages 109-115. DOI:10.1067/mlc.2002.121023
[2] SUN-MI KIM . 7α-Hydroxycholesterol induces inflammation by enhancing production of chemokine (C–C motif) ligand 2[J]. Biochemical and biophysical research communications, 2015, 467 4: Pages 879-884. DOI:10.1016/j.bbrc.2015.10.050
[3] SUN-MI KIM . 27-Hydroxycholesterol and 7alpha-hydroxycholesterol trigger a sequence of events leading to migration of CCR5-expressing Th1 lymphocytes[J]. Toxicology and applied pharmacology, 2014, 274 3: Pages 462-470. DOI:10.1016/j.taap.2013.12.007
[4] YOSHIRO SAITO Noriko N. 7-Hydroxycholestrol as a possible biomarker of cellular lipid peroxidation: Difference between cellular and plasma lipid peroxidation[J]. Biochemical and biophysical research communications, 2014, 446 3: Pages 741-744. DOI:10.1016/j.bbrc.2013.12.083 |
| | 5-Cholesten-3-beta, 7-alpha-diol Preparation Products And Raw materials |
| Preparation Products | (7R,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one-->7-Ketocholesterol |
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