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C6512

Sigma-Aldrich

Cholesteryl hemisuccinate

Synonyme(s) :

3β-Hydroxy-5-cholestene 3-hemisuccinate, 5-Cholesten-3β-ol 3-hemisuccinate, Cholesteryl hydrogen succinate

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About This Item

Formule empirique (notation de Hill):
C31H50O4
Numéro CAS:
1510-21-0
Poids moléculaire :
486.73
Numéro CE :
216-148-6
Numéro MDL:
MFCD00037705
Code UNSPSC :
12352103
ID de substance PubChem :
24892873
Nomenclature NACRES :
NA.23

Forme

liquid crystal

Niveau de qualité

200

Chaîne SMILES 

[H][C@@]([C@H](C)CCCC(C)C)([C@@]1(C)CC[C@@]23[H])CC[C@]1([C@](CC=C4C[C@H](CC[C@]34C)OC(CCC(O)=O)=O)2[H])[H]

InChI

1S/C31H50O4/c1-20(2)7-6-8-21(3)25-11-12-26-24-10-9-22-19-23(35-29(34)14-13-28(32)33)15-17-30(22,4)27(24)16-18-31(25,26)5/h9,20-21,23-27H,6-8,10-19H2,1-5H3,(H,32,33)/t21-,23+,24+,25-,26+,27+,30+,31-/m1/s1

Clé InChI

WLNARFZDISHUGS-MIXBDBMTSA-N

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Catégories apparentées

Description générale

Cholesteryl hemisuccinate (CHEMS) is an acidic cholesterol ester. It self assembles into bilayers in alkaline and neutral aqueous media. CHEMS exhibits pH sensitive polymorphism. It consists of succinic acid esterified to the beta-hydroxyl group of cholesterol. This chemical modification results in the ability of CHEMS to adopt a lamellar assembly in suitable aqueous media, whereas cholesterol forms monohydrate crystals in an aqueous environment.

Application

  • Experimental determination and computational interpretation of biophysical properties of lipid bilayers enriched by Cholesteryl Hemisuccinate: Provides insights into the effects of Cholesteryl Hemisuccinate on phospholipid bilayers, contributing to a deeper understanding of its biophysical properties (W Kulig et al., 2015).

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Denitsa Momekova et al.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 32(4-5), 308-317 (2007-10-12)
A major hurdle towards in vivo utilization of pH-sensitive liposomes is their prompt sequestration by reticuloendothelial system and hence short circulation time. Prolonged circulation of liposomes is usually achieved by incorporation of pegylated lipids, which have been frequently reported to
Cholesteryl hemisuccinate exhibits pH sensitive polymorphic phase behavior.
Hafez IM and Cullis PR
Biochim. Biophys. Acta Gen. Subj., 1463(1), 107-114 (2000)
Julia Lehtinen et al.
Journal of controlled release : official journal of the Controlled Release Society, 131(2), 145-149 (2008-08-12)
Cationic polymers are efficient gene delivery vectors in in vitro conditions, but these carriers can fail in vivo due to interactions with extracellular polyanions, i.e. glycosaminoglycans (GAG). The aim of this study was to develop a stable gene delivery vector
Zhe Zhang et al.
eLife, 7 (2018-05-11)
Transient receptor potential melastatin 2 (TRPM2) is a Ca2+-permeable cation channel required for immune cell activation, insulin secretion, and body heat control. TRPM2 is activated by cytosolic Ca2+, phosphatidyl-inositol-4,5-bisphosphate and ADP ribose. Here, we present the ~3 Å resolution electron
Michael Zocher et al.
Proceedings of the National Academy of Sciences of the United States of America, 109(50), E3463-E3472 (2012-11-16)
The steroid cholesterol is an essential component of eukaryotic membranes, and it functionally modulates membrane proteins, including G protein-coupled receptors. To reveal insight into how cholesterol modulates G protein-coupled receptors, we have used dynamic single-molecule force spectroscopy to quantify the
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