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25-hydroxycholesterol

25-hydroxycholesterol Struktur
2140-46-7
CAS-Nr.
2140-46-7
Englisch Name:
25-hydroxycholesterol
Synonyma:
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
Summenformel:
C27H46O2
Molgewicht:
402.65
MOL-Datei:
2140-46-7.mol

25-hydroxycholesterol Eigenschaften

Schmelzpunkt:
177-179 °C
Siedepunkt:
513.1±23.0 °C(Predicted)
Dichte
1.03±0.1 g/cm3(Predicted)
storage temp. 
-20°C
L?slichkeit
chloroform: 50 mg/mL, clear, colorless to slightly yellow
Aggregatzustand
solid
pka
15.03±0.70(Predicted)
Farbe
White or pale yellow
Merck 
13,4846
BRN 
3161259
Stabilit?t:
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|
Sicherheit
  • Risiko- und Sicherheitserkl?rung
  • Gefahreninformationscode (GHS)
Kennzeichnung gef?hrlicher Xn
R-S?tze: 20/21/22-36/37/38-48
S-S?tze: 26-36-45
WGK Germany  3
HS Code  29062990
Bildanzeige (GHS) GHS hazard pictogramsGHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H302 Gesundheitssch?dlich bei Verschlucken. Akute Toxizit?t oral Kategorie 4 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P270, P301+P312, P330, P501
H312 Gesundheitssch?dlich bei Hautkontakt. Akute Toxizit?t dermal Kategorie 4 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P280,P302+P352, P312, P322, P363,P501
H315 Verursacht Hautreizungen. Hautreizung Kategorie 2 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P280, P302+P352, P321,P332+P313, P362
H319 Verursacht schwere Augenreizung. Schwere Augenreizung Kategorie 2 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P280, P305+P351+P338,P337+P313P
H332 Gesundheitssch?dlich bei Einatmen. Akute Toxizit?t inhalativ Kategorie 4 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P261, P271, P304+P340, P312
H335 Kann die Atemwege reizen. Spezifische Zielorgan-Toxizit?t (einmalige Exposition) Kategorie 3 (Atemwegsreizung) Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" />
H373 Kann die Organe sch?digen bei l?ngerer oder wiederholter Exposition. Spezifische Zielorgan-Toxizit?t (wiederholte Exposition) Kategorie 2 Warnung P260, P314, P501
Sicherheit
P261 Einatmen von Staub vermeiden.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P305+P351+P338 BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach M?glichkeit entfernen. Weiter spülen.

25-hydroxycholesterol Chemische Eigenschaften,Einsatz,Produktion Methoden

R-S?tze Betriebsanweisung:

R20/21/22:Gesundheitssch?dlich beim Einatmen,Verschlucken und Berührung mit der Haut.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R48:Gefahr ernster Gesundheitssch?den bei l?ngerer Exposition.

S-S?tze Betriebsanweisung:

S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn m?glich, dieses Etikett vorzeigen).

Beschreibung

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.

Chemische Eigenschaften

Off-White Solid

Verwenden

25-Hydroxycholesterol was used to treat mouse neuroblastoma cells to activate the ABCA1 signaling and in studies related to fatty acid metabolism.

Biologische Funktion

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.

Allgemeine Beschreibung

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.

l?uterung methode

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.]

25-hydroxycholesterol Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


25-hydroxycholesterol Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

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2140-46-7()Verwandte Suche:


  • 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
  • 25-HYDROXYCHOLESTEROL
  • (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)-
  • 5-CHOLESTEN-3β, 25-DIOL
  • Perampanel Impurity 39
  • 2140-46-7
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