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92243

Sigma-Aldrich

Cholesteryl N-(2-dimethylaminoethyl)carbamate

≥98% (TLC)

Synonym(s):

3β-{N-[2-(Dimethylamino)ethyl]carbamoyl}cholesterol, DC-Chol

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About This Item

Empirical Formula (Hill Notation):
C32H56N2O2
CAS Number:
Molecular Weight:
500.80
UNSPSC Code:
12352211
PubChem Substance ID:
NACRES:
NA.85

Quality Level

Assay

≥98% (TLC)

form

powder or crystals

functional group

ester

storage temp.

−20°C

SMILES string

CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(CC[C@]4(C)[C@H]3CC[C@]12C)OC(=O)NCCN(C)C

InChI

1S/C32H56N2O2/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)/t23-,25?,26+,27-,28+,29+,31+,32-/m1/s1

InChI key

HIHOWBSBBDRPDW-MTIZRNOUSA-N

Application


  • Role of interleukin-6 in antigen-specific mucosal immunoglobulin A induction by cationic liposomes.: This study investigates the use of cholesteryl N-(2-dimethylaminoethyl)carbamate in cationic liposomes for enhancing mucosal immunoglobulin A production, highlighting its potential in vaccine development (Tada et al., 2021).

  • Nasal vaccination with pneumococcal surface protein A in combination with cationic liposomes consisting of DOTAP and DC-chol confers antigen-mediated protective immunity against Streptococcus pneumoniae infections in mice.: This research demonstrates the efficacy of cholesteryl N-(2-dimethylaminoethyl)carbamate in nasal vaccines, providing a promising strategy for respiratory infection prevention (Tada et al., 2018).


Biochem/physiol Actions

Cationic liposome, investigated in cancer gene therapy, as vaccine delivery system/adjuvant.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Hazard Statements

Hazard Classifications

Aquatic Chronic 4

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Malou Henriksen-Lacey et al.
Molecular pharmaceutics, 8(1), 153-161 (2010-12-02)
The immunostimulatory capacities of cationic liposomes are well-documented and are attributed both to inherent immunogenicity of the cationic lipid and more physical capacities such as the formation of antigen depots and antigen delivery. Very few studies have however been conducted
Francesco Cardarelli et al.
Molecular pharmaceutics, 9(2), 334-340 (2011-12-27)
Here we investigate the cellular uptake mechanism and final intracellular fate of two cationic liposome formulations characterized by similar physicochemical properties but very different lipid composition and efficiency for intracellular delivery of DNA. The first formulation is made of cationic
Emmanuel A Ho et al.
Journal of pharmaceutical sciences, 99(6), 2839-2853 (2010-01-22)
Cationic liposomes exhibit a propensity to selectively target tumor-associated blood vessels demonstrating potential value as anti-cancer drug delivery vehicles. Their utility however, is hampered by their biological instability and rapid elimination following i.v. administration. Efforts to circumvent rapid plasma elimination
Jie Gao et al.
Biomaterials, 31(9), 2655-2664 (2009-12-29)
The development of a tumor-specific immunoliposome delivering small interfering RNA (siRNA) represents a practical way in cancer gene therapy. In this study, we developed PEGylated 3beta-[N-(N', N'-dimethylaminoethane) carbamoyl] cholesterol (DC-Chol)/dioleoylphosphatidyl ethanolamine (DOPE) immunoliposomes conjugated with the Fab' of recombinant humanized
Gene therapy using DC-Chol liposomes.
Goyal, K. and Huang, L.
Journal of liposome research, 5, 49-60 (1995)

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