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
- Molecular Weight:
- 402.65
- MDL Number:
- MFCD00057815
- MOL File:
- 2140-46-7.mol
- MSDS File:
- SDS
| 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 |
| 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| |
| FDA UNII | 767JTD2N31 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   GHS07,GHS08 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H302-H312-H315-H319-H332-H335-H373 | |||||||||
| Precautionary statements | P261-P280-P305+P351+P338 | |||||||||
| Hazard Codes | Xn | |||||||||
| Risk Statements | 20/21/22-36/37/38-48 | |||||||||
| Safety Statements | 26-36-45 | |||||||||
| WGK Germany | 3 | |||||||||
| HS Code | 29062990 | |||||||||
| NFPA 704 |
|
25-hydroxycholesterol price More Price(31)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | H1015 | 25-Hydroxycholesterol ≥98% | 2140-46-7 | 10mg | $131 | 2024-03-01 | Buy |
| Sigma-Aldrich | H1015 | 25-Hydroxycholesterol ≥98% | 2140-46-7 | 25mg | $208 | 2024-03-01 | Buy |
| Cayman Chemical | 11097 | 25-hydroxy Cholesterol ≥98% | 2140-46-7 | 5mg | $25 | 2024-03-01 | Buy |
| Cayman Chemical | 11097 | 25-hydroxy Cholesterol ≥98% | 2140-46-7 | 10mg | $48 | 2024-03-01 | Buy |
| Sigma-Aldrich | H1015 | 25-Hydroxycholesterol ≥98% | 2140-46-7 | 100mg | $634 | 2024-03-01 | Buy |
25-hydroxycholesterol Chemical Properties,Uses,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
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Changsha YuTeng New Materials Co., Ltd. | +86-13487087296 +86-13787794286 | rainbowz@cs-yuteng.com | China | 35 | 58 |
| Jinan Million Pharmaceutical Co., Ltd | 0531-68659554 +8613031714605 | info@millionpharm.com | China | 252 | 58 |
| Hebei Jingbo New Material Technology Co., Ltd | +8619931165850 | hbjbtech@163.com | China | 1000 | 58 |
| hebei hongtan Biotechnology Co., Ltd | +86-86-1913198-3935 +8617331935328 | sales03@chemcn.cn | China | 970 | 58 |
| Hebei Saisier Technology Co., LTD | +86-18400010335 +86-18034520335 | admin@hbsaisier.cn | China | 1015 | 58 |
| Hebei Longbang Technology Co., LTD | +86-18633929156 +86-18633929156 | admin@hblongbang.com | China | 941 | 58 |
| HebeiShuoshengImportandExportco.,Ltd | +86-18532138899 +86-18532138899 | L18532138899@163.com | China | 939 | 58 |
| Shanghai Daken Advanced Materials Co.,Ltd | +86-371-66670886 | info@dakenam.com | China | 18777 | 58 |
| Henan Tianfu Chemical Co.,Ltd. | +86-0371-55170693 +86-19937530512 | info@tianfuchem.com | China | 21634 | 55 |
| Hangzhou FandaChem Co.,Ltd. | +8615858145714 | FandaChem@Gmail.com | China | 9210 | 55 |
Related articles
- What is the Production and role of 25-hydroxycholesterol?
- 25-hydroxycholesterol can be generated by both enzymatic and nonenzymatic pathways. The enzyme responsible for 25-HC biogenesi....
- Sep 10，2024
View Lastest Price from 25-hydroxycholesterol manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2024-11-25 | 25-HYDROXYCHOLESTEROL
2140-46-7
|
US $1.00-0.50 / kg | 1kg | 99% | 200 | Jinan Million Pharmaceutical Co., Ltd | |
 |
2024-11-25 | 25-HYDROXYCHOLESTEROL
2140-46-7
|
US $6.00 / kg | 1kg | 99% | 2000KG/Month | HebeiShuoshengImportandExportco.,Ltd | |
 |
2024-11-25 | 25-HYDROXYCHOLESTEROL
2140-46-7
|
US $7.00 / KG | 1KG | 99% | 20TONS | Hebei Longbang Technology Co., Ltd |
-
- 25-HYDROXYCHOLESTEROL
2140-46-7
- US $1.00-0.50 / kg
- 99%
- Jinan Million Pharmaceutical Co., Ltd
-
- 25-HYDROXYCHOLESTEROL
2140-46-7
- US $6.00 / kg
- 99%
- HebeiShuoshengImportandExportco.,Ltd
-
- 25-HYDROXYCHOLESTEROL
2140-46-7
- US $7.00 / KG
- 99%
- Hebei Longbang Technology Co., Ltd