25-Hydroxycholesterol

Cholest-5-ene-3β,25-diol · 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-3,25-diol

https://huagongshe.com/de/chemical/65094

Molekülstruktur von 25-Hydroxycholesterol

Identifikatoren & physikalische Daten

CAS No.	2140-46-7
Summenformel	C27H46O2
Durchschnittliche Molmasse	402,7 g/mol
Monoisotopische Masse	402,34978071 g/mol
SMILES	C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
InChIKey	INBGSXNNRGWLJU-ZHHJOTBYSA-N
PubChem CID	65094
ChEMBL	CHEMBL169046
ChEBI	CHEBI:42977
EC No.	635-752-4
DTXSID	DTXSID5044023

Chemische & physikalische Eigenschaften

XLogP	6,8
Polarare Oberfläche (TPSA)	40,5
H-Brücken-Donoren	2
H-Brücken-Akzeptoren	2
Frei drehbare Bindungen	5
Schwere Atome	29
Formalladung	0
Komplexität	636
Arzneimittel	Pharmaceuticals -> Listed in ZINC15
Lipide	Lipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Cholesterol and derivatives [ST0101]
Endocrine Disruptors	Potential endocrine disrupting compound
Collision Cross Section	202.81 Å² [M-H]- [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]
Schmelzpunkt	177-179 °C
Siedepunkt	513.1±23.0 °C(Predicted)
Dichte	1.03±0.1 g/cm3(Predicted)
Lagerbedingungen	-20°C
Löslichkeit	chloroform: 50 mg/mL, clear, colorless to slightly yellow
pKa (Säurekonstante)	15.03±0.70(Predicted)
Aggregatzustand	solid
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 & Vorschriften

GHS-Einstufung	WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Regulatorische Informationen	Cholest-5-ene-3,25-diol, (3.beta.)-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and Categories	Acute Tox. 4 (100%)
Wassergefährdungsklasse (WGK)	3
Zollcode	29062990
R-Sätze (R)	20/21/22-36/37/38-48
Gefahrensymbole	Xn
Sicherheitshinweise (S)	26-36-45
Lagerklasse	11 - Combustible Solids

Anwendungen & Verwendung

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.

Verwenden

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