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

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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|

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Safety

Hazard Codes: Xn
Risk Statements: 20/21/22-36/37/38-48
Safety Statements: 26-36-45
WGK Germany: 3
HS Code: 29062990

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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.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: H1015
Product name: 25-Hydroxycholesterol
Purity: ≥98%
Packaging: 10mg
Price: $131
Updated: 2024/03/01

Sigma-Aldrich

Product number: H1015
Product name: 25-Hydroxycholesterol
Purity: ≥98%
Packaging: 25mg
Price: $208
Updated: 2024/03/01

Cayman Chemical

Product number: 11097
Product name: 25-hydroxy Cholesterol
Purity: ≥98%
Packaging: 5mg
Price: $25
Updated: 2024/03/01

Cayman Chemical

Product number: 11097
Product name: 25-hydroxy Cholesterol
Purity: ≥98%
Packaging: 10mg
Price: $48
Updated: 2024/03/01

Sigma-Aldrich

Product number: H1015
Product name: 25-Hydroxycholesterol
Purity: ≥98%
Packaging: 100mg
Price: $634
Updated: 2024/03/01

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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

Preparation Products

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25-hydroxycholesterol Suppliers

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View Lastest Price from 25-hydroxycholesterol manufacturers

hebei hongtan Biotechnology Co., Ltd

Product: 25-hYdroxycholesterol 2140-46-7
Price: US $50.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 2000kg
Release date: 2024-05-17

hebei hongtan Biotechnology Co., Ltd

Product: 1,3-Dimethylbarbituric acid 2140-46-7
Price: US $50.00-30.00/kg
Min. Order: 1kg
Purity: 99.9%
Supply Ability: 500
Release date: 2024-05-17

HebeiShuoshengImportandExportco.,Ltd

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

2140-46-7, 25-hydroxycholesterolRelated Search:

7BETA-HYDROXYCHOLESTEROL Lovastatin ML335 FILIPIN III Fluvastatin sodium salt 7-KETOCHOLESTEROL 5-CHOLESTEN-3-BETA, 7-ALPHA-DIOL CHOLESTENONE(RG) JC 40 25-HYDROXYCHOLESTEROL 5-CHOLESTENE (20S)-25-Hydroxycholesterol 25-hydroxycholesterol 7alpha-hydroxylase 25-HYDROXYCHOLESTEROL-(26,27-3H) 7-KETO, 25-HYDROXYCHOLESTEROL, ACETATE 25-HYDROXYCHOLESTEROL 3-HEMISUCCINATE 25-HYDROXYCHOLESTEROL 3-OLEATE 5-CHOLESTEN-3-BETA, 25-DIOL 3-ACETATE

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

3β,25-Dihydroxycholest-5-ene

Cholest-5-ene-3β,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

(3β)-Cholest-5-ene-3,25-diol

25-Hydroxy-5-cholestene-3β-ol

5-Cholesten-3β,25-diol

(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

26-Hydroxy-Cholesterol - d5

(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

(3beta,9beta,14beta)-cholest-5-ene-3,25-diol

Cholesterol 25-Hydroxy

Cholest-5-ene-3,25-diol, (3β)-

25-hydroxycholesterol(2140-46-7)

Bicyclo[4.1.0]heptane-3,4-diol,3,7,7-trimethyl-, (1S,3S,4S,6R)-

Perampanel Impurity 39

5-CHOLESTEN-3β, 25-DIOL

2140-46-7

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