C6013

Cholesteryl hemisuccinate tris salt

anionic detergent

• Synonym(s): 3β-Hydroxy-5-cholestene 3-hemisuccinate, 5-Cholesten-3β-ol 3-hemisuccinate, CHEMS, CHS, Cholesteryl hydrogen succinate
• Empirical Formula (Hill Notation): C₃₁H₅₀O₄ · C₄H₁₁NO₃
• CAS Number: 102601-49-0
• Molecular Weight: 607.86
• UNSPSC Code: 12352211
• eCl@ss: 39023139
• PubChem Substance ID: 329775108
• NACRES: NA.77
• MDL number: MFCD00058298

Properties

• biological source: synthetic (organic)
• Quality Segment: 200
• assay: ≥98% (TLC)
• form: powder
• functional group: ester
• shipped in: ambient
• storage temp.: −20°C
• SMILES string: 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
• InChI key: SLDYONDUXRBLLR-XTCKSVDZSA-N

Description

Application

Cholesteryl hemisuccinate tris salt has been used:

• to prepare solubilization buffer for glucan synthase assay[1]
• to prepare immunoprecipitation buffer for immobilization of opioid receptors on paramagnetic beads.[2]
• as a membrane stabilizer for liposomes and protein synaptogyrin-1[3]
• as a component of a folate-modified self-microemulsifying drug delivery system.[4]
• with N-dodecyl β-D-maltoside (DDM) to solubilize erythrocyte ghosts[5] and chemokine receptor CCR1[6]
• for protein solubilization

Biochem/physiol Actions

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.[7][8] Cholesteryl succinate also reportedly exhibits antiproliferative activity and may be clinically useful as antitumor agent.[9]

Preparation Note

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

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable