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(25R)-26-Hydroxycholesterol

HCID 123976
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Grundinformationen

CAS
20380-11-4
Standard-SMILES
C[C@@H](CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
InChIKey
FYHRJWMENCALJY-YSQMORBQSA-N
Summenformel
C27H46O2
Durchschnittliche Molmasse
402,663 g/mol
Monoisotopische Masse
402,34978071

Namen und Bezeichner

Bevorzugter Name
(25R)-26-Hydroxycholesterol
IUPAC
(25R)-Cholest-5-ene-3beta,26-diol
Englischer Name
27-Hydroxycholesterol
Summenformel
C27H46O2
Molmasse
402.65

Namen und Synonyme

27-OHC27-HYDROXYCHOLESTEROL5,25R-Cholesten-3betaCholesterol Impurity 3125(R)-27-hydroxy Cholesterolcholest-(25R)-5-ene-3,27-diol5,25R-Cholesten-3beta,26-diol5-, 25R-CHOLESTEN-3β, 26-DIOL(25R)-Cholest-5-en-3β,26β-diol(25R)-Cholest-5-ene-3β,26-diol

Datenbank-Bezeichner

CAS
20380-11-4
PubChem CID
123976
DTXSID
DTXSID40864941
ChEMBL
CHEMBL353882
ChEBI
CHEBI:76591
UNII
6T2NA6P5SQ
Nikkaji
J82.958G

Eigenschaften

Physikochemische Eigenschaften

Schmelzpunkt
172 · 172-174 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
Siedepunkt
517.1 · 517.1±23.0 °C(Predicted)
Dichte
1.03 · 1.03
storage temp.
-20 ° · -20°
Löslichkeit
Soluble in DMSO (up to 10 mg/ml) or in Ethanol (up to 10 mg/ml).
Aggregatzustand
White solid.
pka
15.03 · 15.03±0.70(Predicted)
Farbe
White
Stabilität
2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 2 months.
InChIKey
FYHRJWMENCALJY-LGIODXKMNA-N
SMILES
[C@@]12([H])CC[C@H]([C@H](C)CCC[C@@H](C)CO)[C@@]1(C)CC[C@]1([H])[C@@]3(C)CC[C@H](O)CC3=CC[C@@]21[H] |&1:0,4,5,10,14,18,20,24,30,r|

Sicherheit und Regulatorisches

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Sicherheitsdaten

wgk
WGK 3
Speicherklasse
11 - Combustible Solids

Chemie und Industrie

Anwendungen · 2 Einträge

Beschreibung27-Hydroxycholesterol (27-HC) is an endogenous oxysterol with multiple biological functions, including activity as a selective estrogen receptor modulator (SERM) (a mixed, tissue-specific agonist-antagonist of the estrogen receptor (ER)) and as an agonist of the liver X receptor (LXR). It is a metabolite of cholesterol that is produced by the enzyme CYP27A1. A link between high cholesterol and breast cancer has been identified, and it has been proposed that this is due to 27-HC production by CYP27A1. Because of its estrogenic action, 27-HC stimulates the growth of ER-positive breast cancer cells, and has been implicated in limiting the effectiveness of aromatase inhibitors in the treatment of breast cancer. As such, identified CYP27A1 inhibitors, including the marketed drugs anastrozole, fadrozole, bicalutamide, dexmedetomidine, ravuconazole, and posaconazole, have been proposed as potential adjuvant therapies in ER-positive breast cancer.www.abbexa.com/human-27-hydroxycholesterol-elisa-kit

VerwendenThe liver x receptors (LXRα and LXRβ) are nuclear hormone receptors whose native ligands, oxysterols, induce the expression of genes involved in cholesterol and fatty acid metabolism. 27-hydroxy Cholesterol, a sterol 27-hydroxylase-mediated cholesterol hydroxylation product, activates LXRα and LXRβ in vitro with EC50 values of 85 and 71 nM, respectively, and is a potent suppressor of cholesterol biosynthesis. 25(R)-27-hydroxy Cholesterol is the more predominant-occurring (~80%) stereoisomer of the endogenous oxysterol 27-hydroxy cholesterol.[Cayman Chemical]

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Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: 27-Hydroxycholesterol is a 26-hydroxycholesterol in which the 25-position has R-configuration. It has a role as an apoptosis inducer, a neuroprotective agent, a human metabolite and a mouse metabolite. It is functionally related to a cholesterol.