25-hydroxycholesterol Struktur

25-hydroxycholesterol

Bezeichnung:25-hydroxycholesterol

CAS-Nr2140-46-7

Englisch Name:25-hydroxycholesterol

CBNumberCB7412673

SummenformelC27H46O2

Molgewicht402.65

MOL-Datei2140-46-7.mol

25-hydroxycholesterol physikalisch-chemischer Eigenschaften

Schmelzpunkt	177-179 °C
Siedepunkt	513.1±23.0 °C(Predicted)
Dichte	1.03±0.1 g/cm3(Predicted)
storage temp.	-20°C
Löslichkeit	chloroform: 50 mg/mL, clear, colorless to slightly yellow
Aggregatzustand	solid
pka	15.03±0.70(Predicted)
Farbe	White or pale yellow
Biologische Quelle	synthetic (organic)
Merck	13,4846
BRN	3161259
Stabilität	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

Kennzeichnung gefährlicher	Xn
R-Sätze:	20/21/22-36/37/38-48
S-Sätze:	26-36-45
WGK Germany	3
HS Code	29062990

Gefahreninformationscode (GHS)

25-hydroxycholesterol Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R48:Gefahr ernster Gesundheitsschäden bei längerer Exposition.
S-Sätze 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 möglich, 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.
Verwenden
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.
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.
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.
Lager
Store at -20°C
läuterung 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.]
Einzelnachweise
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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