25-hydroxycholesterol
- Product Name
- 25-hydroxycholesterol
- CAS No.
- 2140-46-7
- Chemical Name
- 25-hydroxycholesterol
- Synonyms
- 25-HYDROXYCHOLESTEROL;5-Cholesten-3β,25-diol;Cholesterol 25-Hydroxy;Perampanel Impurity 39;5-cholestene-3β,25-diol;5-CHOLESTEN-3β, 25-DIOL;Cholest-5-ene-3β,25-diol;5-CHOLESTENE-3BETA,25-DIOL;5-CHOLESTEN-3-BETA, 25-DIOL;26-Hydroxy-Cholesterol - d5
- CBNumber
- CB7412673
- Molecular Formula
- C27H46O2
- Formula Weight
- 402.65
- MOL File
- 2140-46-7.mol
25-hydroxycholesterol Property
- 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
- 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|
Safety
- Hazard Codes
- Xn
- Risk Statements
- 20/21/22-36/37/38-48
- Safety Statements
- 26-36-45
- WGK Germany
- 3
- HS Code
- 29062990
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H312Harmful in contact with skin
H315Causes skin irritation
H319Causes serious eye irritation
H332Harmful if inhaled
H335May cause respiratory irritation
H373May cause damage to organs through prolonged or repeated exposure
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- H1015
- Product name
- 25-Hydroxycholesterol
- Purity
- ≥98%
- Packaging
- 10mg
- Price
- $131
- Updated
- 2024/03/01
- Product number
- H1015
- Product name
- 25-Hydroxycholesterol
- Purity
- ≥98%
- Packaging
- 25mg
- Price
- $208
- Updated
- 2024/03/01
- Product number
- 11097
- Product name
- 25-hydroxy Cholesterol
- Purity
- ≥98%
- Packaging
- 5mg
- Price
- $25
- Updated
- 2024/03/01
- Product number
- 11097
- Product name
- 25-hydroxy Cholesterol
- Purity
- ≥98%
- Packaging
- 10mg
- Price
- $48
- Updated
- 2024/03/01
- Product number
- H1015
- Product name
- 25-Hydroxycholesterol
- Purity
- ≥98%
- Packaging
- 100mg
- Price
- $634
- Updated
- 2024/03/01
25-hydroxycholesterol Chemical Properties,Usage,Production
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.
Biological Functions
25-Hydroxycholesterol (25-HC) is an oxysterol, an early intermediate in the metabolism of cholesterol to bile acids. Studies have shown that 25-HC is closely linked to intracellular cholesterol synthesis and metabolism, and that increased 25-HC synthesis leads to decreased cholesterol synthesis and uptake. 25-HC is also an important component in the control of intracellular cholesterol metabolism, interacting with inflammatory states. In immune function, 25-HC inhibits a wide range of viral infections by regulating the synthesis and distribution of sterols in cells, and is the first line of defence for the lungs. It has a protective effect against tumour growth and metastasis development. In addition, 25-HC and its metabolite 7α, 25-DHC also show beneficial properties by modulating immune cell migration or endothelial/epithelial barrier properties, thus making them involved in atherosclerosis and CNS diseases.
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
25-hydroxycholesterol Preparation Products And Raw materials
Raw materials
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View Lastest Price from 25-hydroxycholesterol manufacturers
- Product
- 25-hydroxycholesterol 2140-46-7
- Price
- US $0.00/g
- Min. Order
- 500g
- Purity
- 99%
- Supply Ability
- 100kg
- Release date
- 2024-08-30
- Product
- 25-HYDROXYCHOLESTEROL 2140-46-7
- Price
- US $1.00-0.50/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 200
- Release date
- 2024-01-12
- Product
- 25-HYDROXYCHOLESTEROL 2140-46-7
- Price
- US $6.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 2000KG/Month
- Release date
- 2024-08-05