25-HYDROXYCHOLESTEROL
25-HYDROXYCHOLESTEROL Basic information
- Product Name:
- 25-HYDROXYCHOLESTEROL
- Synonyms:
-
- 25-HYDROXYCHOLESTEROL
- 3BETA,25-DIHYDROXY-5-CHOLESTENE
- 5-CHOLESTEN-3-BETA, 25-DIOL
- 5-CHOLESTENE-3BETA,25-DIOL
- 25-Hydroxycholesterol (not deuterated)
- Cholest-5-ene-3,25-diol, (3.beta.)-
- 5-cholestene-3β,25-diol
- (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
- CAS:
- 2140-46-7
- MF:
- C27H46O2
- MW:
- 402.65
- Product Categories:
-
- Hydroxycholesterol
- Apoptosis
- Inhibitors
- Intermediates & Fine Chemicals
- Metabolites & IMpurities
- Pharmaceuticals
- Steroids
- Mol File:
- 2140-46-7.mol
25-HYDROXYCHOLESTEROL Chemical Properties
- Melting point:
- 177-179 °C
- Boiling point:
- 513.1±23.0 °C(Predicted)
- Density
- 1.03±0.1 g/cm3(Predicted)
- storage temp.
- -20°C
- solubility
- chloroform: 50 mg/mL, clear, colorless to slightly yellow
- pka
- 15.03±0.70(Predicted)
- form
- solid
- 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
Safety Information
- Hazard Codes
- Xn
- Risk Statements
- 20/21/22-36/37/38-48
- Safety Statements
- 26-36-45
- WGK Germany
- 3
- HS Code
- 29062990
MSDS
- Language:English Provider:SigmaAldrich
25-HYDROXYCHOLESTEROL Usage And Synthesis
Description
25-hydroxy Cholesterol is an oxysterol. It is formed from cholesterol by cholesterol-25-hydroxylase, and its production can be induced by inflammation or infection. 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). 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. 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
25-Hydroxycholesterol was used to treat mouse neuroblastoma cells to activate the ABCA1 signaling and in studies related to fatty acid metabolism.
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 inducing 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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