Cholest-5-en-3β-ylhydrogensuccinat
Cholesteryl hemisuccinate
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Grundinformationen
- CAS
1510-21-0- Standard-SMILES
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](OC(=O)CCC(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C- InChIKey
WLNARFZDISHUGS-MIXBDBMTSA-N- Summenformel
- C31H50O4
- Durchschnittliche Molmasse
- 486,7 g/mol
- Monoisotopische Masse
- 486,37091008
Überblick
Cholesteryl hemisuccinate is a dicarboxylic acid monoester resulting from the formal condensation of the hydroxy group of cholesterol with one of the carboxy groups of succinic acid. A detergent that is often used to replace cholesterol in protein crystallography, biochemical studies of proteins, and pharmacology. It has a role as a detergent. It is a cholestane ester, a hemisuccinate and a dicarboxylic acid monoester. It is functionally related to a cholesterol.
Namen und Bezeichner
- Bevorzugter Name
- Cholesteryl hemisuccinate
- IUPAC
- 4-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4-oxobutanoic acid
- Lokaler Name
- Cholest-5-en-3β-ylhydrogensuccinat
- Englischer Name
- Cholesteryl hemisuccinate
- Summenformel
- C31H50O4
- Molmasse
- 486.73
Namen und Synonyme
Cholesteryl hemisuccinate1510-21-0Cholesteryl succinatemonocholesteryl succinateT3J4KS4201CHEBI:138742NSC-628321RefChem:576072216-148-6Cholesterol Hydrogen SuccinateCholesterol hemisuccinateCHEMS
Weitere Namen anzeigen
cholesterylsuccinateCholesterol SuccinateCholesteryl hemisucciteMONO-CHOLESTERYL-SUCCINATE5-CHOLESTEN-3β-OL HEMISUCCINATECholesterol Hydrogen Succinate >5-CHOLESTEN-3-BETA-OL HEMISUCCINATE
Cholesteryl hydrogen succinateMFCD000377054-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4-oxobutanoic acidCholest-5-en-3beta-yl hydrogen succinateSuccinic Acid Monocholesterol Ester3-cholesteryloxycarbonylpropanoic acidCholest-5-en-3-ol (3.beta.)-, hydrogen butanedioateCholest-5-en-3-ol (3beta)-, 3-(hydrogen butanedioate)
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 8,5
- Polarare Oberfläche (TPSA)
- 63,6 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 10
- Schwere Atome
- 35
- Formalladung
- 0
- Komplexität
- 815
Experimentelle und physikochemische Eigenschaften
Endocrine DisruptorsPotential endocrine disrupting compound
Physikochemische Eigenschaften
- Schmelzpunkt
- 178 °C · 178 °C
- Siedepunkt
- 586 · 586.0±43.0 °C(Predicted)
- Dichte
- 1.06 · 1.06±0.1 g/cm3(Predicted)
- Brechungsindex
- -34 ° · -34 ° (C=2, CHCl3)
- storage temp.
- -20 °C · -20°C
- Löslichkeit
- Chloroform (Slightly), Methanol (Slightly, Heated, Sonicated)
- Aggregatzustand
- Solid
- pka
- 4.4 · 4.40±0.17(Predicted)
- Farbe
- White to Off-White
- Kosmetik-Inhaltsstoffe Funktionen
- SKIN CONDITIONINGSKIN CONDITIONING - EMOLLIENT
- InChIKey
- WLNARFZDISHUGS-BLYFUZNHSA-N
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Warning
H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Gefahrenhinweise
Hazard Classes and CategoriesSkin Sens. 1 (100%)
Sicherheitsdaten
- wgk
- 3
- hs_code
- 29171900
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Anwendungen
BeschreibungCholesteryl hemisuccinate is a cholesterol ester with anticancer activity. It inhibits the growth of murine C1498 myeloid and L1210 lymphocytic leukemia cells when used at concentrations of 50 and 150 μM, respectively. Cholesteryl hemisuccinate acts as an ionizable anionic detergent and is commonly used to stabilize unilamellar vesicles and liposomes. It has also been used as an emulsifying agent in various vesicular drug delivery systems for anticancer drugs, antibiotics, and oligonucleotides and to solubilize various proteins including chemokine receptor 1 as well as erythrocyte ghosts.
VerwendenCholesteryl Hemisuccinate is an oxidation product of polyunsaturated fatty acid of cholesterol that alters lysosome structure and functions and induces proinflammatory cytokine production in macrophages.
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