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C2832

Sigma-Aldrich

Cholesteryl 3β-N-(di­methyl­amino­ethyl)­carbamate hydrochloride

≥95%

Synonym(s):

3β-[N-(Dimethylaminoethane)­carbamoyl]­cholesterol, DC-Chol

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About This Item

Empirical Formula (Hill Notation):
C32H57ClN2O2
CAS Number:
166023-21-8
Molecular Weight:
537.26
MDL number:
MFCD00467173
UNSPSC Code:
12352200
PubChem Substance ID:
24892536
NACRES:
NA.77

Assay

≥95%

form

powder

storage temp.

−20°C

SMILES string

Cl[H].[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC(=O)NCCN(C)C)[C@H](C)CCCC(C)C

InChI

1S/C32H56N2O2.ClH/c1-22(2)9-8-10-23(3)27-13-14-28-26-12-11-24-21-25(36-30(35)33-19-20-34(6)7)15-17-31(24,4)29(26)16-18-32(27,28)5;/h11,22-23,25-29H,8-10,12-21H2,1-7H3,(H,33,35);1H/t23-,25+,26+,27-,28+,29+,31+,32-;/m1./s1

InChI key

ISXSJGHXHUZXNF-LXZPIJOJSA-N

Application

Cholesteryl 3β-N-(di­methyl­amino­ethyl)­carbamate hydrochloride has been used as a bilayer-membrane stabiliser and for nucleic acid transfer.
This cationic cholesterol derivative forms liposomes with L-α-phosphatidylethanolamine, dioleoyl, that efficiently transfect mammalian cell lines.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Gene Targeting Protocols (2000)
S Szala et al.
Gene therapy, 3(11), 1026-1031 (1996-11-01)
An attempt was made to use simple cationic liposomes DC-Chol/DOPE and DDAB/DOPE (DC-Chol is 3 beta (N(N',N-dimethylaminoethane) carbamoyl) cholesterol, DDAB is dimethyldioctadecyl ammonium bromide and DOPE is dioleoylphosphatidylethanolamine) for transfer of Escherichia coli cytosine deaminase 'suicide' gene under the control
X Gao et al.
Biochemical and biophysical research communications, 179(1), 280-285 (1991-08-30)
A novel cationic derivative of cholesterol, 3 beta [N-(N',N'-dimethylaminoethane)-carbamoyl] cholesterol (DC-Chol), has been synthesized and used to prepare sonicated liposomes with dioleoylphosphatidylethanolamine. This novel cationic liposome reagent facilitates efficient DNA mediated transfection in A431 human epidermoid carcinoma cells, A549 human
P S Ajmani et al.
Neurochemical research, 24(5), 699-703 (1999-05-27)
Cationic lipid formulations consisting of 3beta [N-(N', N'-dimethylaminoethane)-carbamoyl] cholesterol (DC-Chol) and the helper lipid dioleoylphosphatidylethanolamine (DOPE) (1.5: 1 molar ratio) were prepared by solvent evaporation and sized by high pressure extrusion. Liposomes made of 1:1 molar ratio 1 ,2-dioleoyl-3-trimethyl-ammonium-propane (DOTAP)/DOPE
N J Caplen et al.
Gene therapy, 2(9), 603-613 (1995-11-01)
Clinical trials using cationic liposome-mediated DNA transfer have now been initiated for several disorders including cystic fibrosis. Previous studies have shown that the level of gene expression achieved may be dependent on the formulation of the DNA-liposome complex and the
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