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C6512

Sigma-Aldrich

Cholesteryl hemisuccinate

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Synonym(s):
3β-Hydroxy-5-cholestene 3-hemisuccinate, 5-Cholesten-3β-ol 3-hemisuccinate, Cholesteryl hydrogen succinate
Empirical Formula (Hill Notation):
C31H50O4
CAS Number:
Molecular Weight:
486.73
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.23

form

liquid crystal

Quality Level

SMILES string

[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

InChI key

WLNARFZDISHUGS-MIXBDBMTSA-N

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1 of 4

This Item
C6013137672C8753
vibrant-m

C6512

Cholesteryl hemisuccinate

vibrant-m

C6013

Cholesteryl hemisuccinate tris salt

vibrant-m

137672

SyntheChol® Synthetic Cholesterol

vibrant-m

C8753

Cholesteryl arachidonate

Quality Level

200

Quality Level

200

Quality Level

500

Quality Level

200

General description

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Cholesteryl hemisuccinate exhibits pH sensitive polymorphic phase behavior.
Hafez IM and Cullis PR
Biochim. Biophys. Acta Gen. Subj., 1463(1), 107-114 (2000)
Y Yamamoto et al.
Plant physiology, 67(6), 1069-1072 (1981-06-01)
Cholesteryl hemisuccinate has been incorporated into pea chloroplast thylakoids to investigate the relationship between fluidity and functioning of this membrane system. Levels of sterol which increased the apparent viscosity of the membrane, estimated by fluorescence polarization measurements using the lipophilic
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
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

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