| Identification | Back Directory | [Name]
25-HYDROXYCHOLESTEROL | [CAS]
2140-46-7 | [Synonyms]
25-HYDROXYCHOLESTEROL
5-Cholesten-3β,25-diol
Cholesterol 25-Hydroxy
5-cholestene-3β,25-diol
Cholest-5-ene-3β,25-diol
5-CHOLESTENE-3BETA,25-DIOL
5-CHOLESTEN-3-BETA, 25-DIOL
26-Hydroxy-Cholesterol - d5
(3β)-Cholest-5-ene-3,25-diol
3β,25-Dihydroxycholest-5-ene
25-Hydroxy-5-cholestene-3β-ol
Cholest-5-ene-3,25-diol, (3β)-
3BETA,25-DIHYDROXY-5-CHOLESTENE
Cholest-5-ene-3,25-diol, (3.beta.)-
25-Hydroxycholesterol (not deuterated)
(3beta,9beta,14beta)-cholest-5-ene-3,25-diol
(3S,8S,9S,10R,13R,14S,17R)-17-[(1R)-5-hydroxy-1,5-dimethyl-hexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
(3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-6-hydroxy-6-methyl-heptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
(8S,9S,10R,13R,14S,17R)-17-((R)-6-Hydroxy-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
(3S,8S,9S,10R,13R,14S,17R)-17-[(R)-6-Hydroxy-6-methyl-2-heptyl]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
(3S,8S,9S,10R,13R,14S,17R)-17-((R)-6-hydroxy-6-Methylheptan-2-yl)-10,13-diMethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol | [Molecular Formula]
C27H46O2 | [MDL Number]
MFCD00057815 | [MOL File]
2140-46-7.mol | [Molecular Weight]
402.65 |
| Chemical Properties | Back Directory | [Melting point ]
177-179 °C | [Boiling point ]
513.1±23.0 °C(Predicted) | [density ]
1.03±0.1 g/cm3(Predicted) | [storage temp. ]
room temp | [solubility ]
chloroform: 50 mg/mL, clear, colorless to slightly yellow
| [form ]
solid | [pka]
15.03±0.70(Predicted) | [color ]
White or pale yellow | [Merck ]
13,4846 | [BRN ]
3161259 | [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]
INBGSXNNRGWLJU-ZHHJOTBYSA-N | [SMILES]
[C@@]12([H])CC[C@H]([C@H](C)CCCC(O)(C)C)[C@@]1(C)CC[C@]1([H])[C@@]3(C)CC[C@H](O)CC3=CC[C@@]21[H] |&1:0,4,5,14,18,20,24,30,r| |
| Hazard Information | Back Directory | [Description]
25-hydroxy Cholesterol is an oxysterol.1 It is formed from cholesterol by cholesterol-25-hydroxylase, and its production can be induced by inflammation or infection.2 25-hydroxy Cholesterol suppresses endogenous cholesterol synthesis by binding to insulin-induced gene (INSIG) proteins and preventing sterol regulatory element binding proteins (SREBPs) from being transported to the Golgi. It inhibits IgA class switching induced by LPS and various cytokines in B cells (IC50 = ~50 nM).3 25-hydroxy Cholesterol inhibits replication of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) in Vero cells (EC50 = 3.675 μM) and reduces increases in viral protein production in infected Vero cells when used prior to infection.4 It reduces viral RNA loads in the lung and trachea in a mouse model of SARS-CoV-2 infection when administered at a dose of 100 mg/kg per day. Serum levels of 25-hydroxy cholesterol are increased in mice expressing human angiotensin-converting enzyme 2 (hACE2), the functional receptor for SARS-CoV-2, in a model of SARS-CoV-2 infection and in a patient with COVID-19, the primarily respiratory disease caused by SARS-CoV-2. | [Chemical Properties]
Off-White Solid | [Uses]
An oxygenated derivative of Cholesterol (C432501); an oxysterol. An inhibitor of human immunodeficiency virus replication in vitro. It induces apoptosis in human monocytic cell lines as well as induc
ing apoptosis in CEM cells associated with negative regulation of c-Myc. | [Definition]
ChEBI: 25-hydroxycholesterol is an oxysterol and a 25-hydroxy steroid. It has a role as a human metabolite. It is functionally related to a cholesterol. | [General Description]
25-hydroxy-cholesterol is a side chain substituted oxysterol. Avanti′s unique sterol reverses cataracts in mice. Gestwicki′s team ...... settled on compound 29, a steroid found naturally in the bloodstream but not in the lens, which has no blood supply. Mice with age-related and hereditary cataracts received drops in the right eye, whereas the left eye went untreated. After just a few weeks, the treated eye was visibly clearer, says Gestwicki, who conducted the work while at the University of Michigan. Cataract severity is measured on a scale of zero to four, with four being the worst case. On average, mice in the study had about a one-grade improvement in cataract severity after 4 weeks of treatment. Science DOI: 10.1126/science.aad7400 It has been recently shown that activation of a macrophage toll-like receptor (TLR) by microbial antigens induces synthesis of 25-hydroxycholesterol, and that this oxysterol potently suppresses IgA production. | [Biochem/physiol Actions]
25-Hydroxycholesterol is a side-chain oxysterol that reportedly triggers activation of a number of cholesterol molecules. This triggers their movement from cell membrane to the endoplasmic reticulum (ER). 25-Hydroxycholesterol affects the immune system and has a key role in the pathogenesis of atherosclerosis. | [storage]
Store at -20°C | [Purification Methods]
25-Hydroxycholesterol forms colourless needles from MeOH [Schwartz Tetrahedron Lett 22 4655 1981]. The 3acetoxy derivative has m 142-142.8o (from Me2CO) and [] D -40.4o (c 2, CHCl3). The 3,25-diacetoxy derivative has m 119-120.5o (from MeOH) and [] 25D -35.5o (CHCl3). [Dauben & Bradlow J Am Chem Soc 72 4248 1950, Ryer et al. J Am Chem Soc 72 4247 1950, Beilstein 6 IV 6437.] | [References]
1) Diczialusy (2013),?On the formation and possible biological role of 25-hydroxcholesterol; Biochimie,?95?455
2) McDonald and Russell (2010),?25-hydroxycholesterol: a new life in immunology: J. Leuko. Biol.?88?1071 |
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