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C6013

Sigma-Aldrich

Cholesteryl hemisuccinate tris salt

anionic detergent

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C31H50O4 · C4H11NO3
Numéro CAS:
102601-49-0
Poids moléculaire :
607.86
Numéro MDL:
MFCD00058298
Code UNSPSC :
12352211
eCl@ss :
39023139
ID de substance PubChem :
329775108
Nomenclature NACRES :
NA.77

Source biologique

synthetic (organic)

Niveau de qualité

200

Essai

≥98% (TLC)

Forme

powder

Groupe fonctionnel

ester

Conditions d'expédition

ambient

Température de stockage

−20°C

Chaîne SMILES 

NC(CO)(CO)CO.CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)OC(=O)CCC(O)=O

InChI

1S/C31H50O4.C4H11NO3/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;5-4(1-6,2-7)3-8/h9,20-21,23-27H,6-8,10-19H2,1-5H3,(H,32,33);6-8H,1-3,5H2/t21-,23+,24+,25-,26+,27+,30+,31-;/m1./s1

Clé InChI

SLDYONDUXRBLLR-XTCKSVDZSA-N

Application

Cholesteryl hemisuccinate tris salt has been used:
  • to prepare solubilization buffer for glucan synthase assay
  • to prepare immunoprecipitation buffer for immobilization of opioid receptors on paramagnetic beads.
  • as a membrane stabilizer for liposomes and protein synaptogyrin-1
  • as a component of a folate-modified self-microemulsifying drug delivery system.
  • with N-dodecyl β-D-maltoside (DDM) to solubilize erythrocyte ghosts and chemokine receptor CCR1
  • for protein solubilization

Actions biochimiques/physiologiques

Cholesteryl hemisuccinate is an ionizable anionic detergent that stabilizes large unilamellar vesicles. These liposome vesicles act as delivery agents for anticancer drugs, oligonucleotides and antibiotics. Cholesteryl succinate also reportedly exhibits antiproliferative activity and may be clinically useful as antitumor agent.

Notes préparatoires

Cholesteryl hemisuccinate tris salt yields clear, colorless solution in methanol at 10 mg/ml.

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

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Certificats d'analyse (COA)

Lot/Batch Number
0000393632
0000367168
0000367098
0000360468
0000338040

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Consulter la Bibliothèque de documents

P Mazur et al.
The Journal of biological chemistry, 271(24), 14604-14609 (1996-06-14)
In the yeast Saccharomyces cerevisiae, the family of RHO genes are implicated in the control of morphogenetic events although the molecular targets of these GTP-binding proteins remain largely unknown. The activity of 1,3-beta-D-glucan synthase, the product of which is essential
Samantha J Allen et al.
Protein expression and purification, 66(1), 73-81 (2009-03-12)
Chemokine receptors are a specific class of G-protein-coupled receptors (GPCRs) that control cell migration associated with routine immune surveillance, inflammation and development. In addition to their roles in normal physiology, these receptors and their ligands are involved in a large
David Ott et al.
Protein engineering, design & selection : PEDS, 18(3), 153-160 (2005-03-26)
Opioid receptors, like many G protein-coupled receptors (GPCRs), are notoriously unstable in detergents. We have now developed a more stable variant of the mu-opioid receptor (MOR) and also a method for the immobilization of solubilized, functional opioid receptors on a
I M Hafez et al.
Biophysical journal, 79(3), 1438-1446 (2000-09-02)
The pH-dependent fusion properties of large unilamellar vesicles (LUVs) composed of binary mixtures of anionic and cationic lipids have been investigated. It is shown that stable LUVs can be prepared from the ionizable anionic lipid cholesteryl hemisuccinate (CHEMS) and the
Cholesteryl hemisuccinate as a membrane stabilizer in dipalmitoylphosphatidylcholine liposomes containing saikosaponin-d.
Ding, W.X., et al.
International Journal of Pharmaceutics, 300, 37-47 (2005)
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