A cationic lipid
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1,2-Dioleoyl-3(R)-trimethylammoniumpropane (chloride)

Item No. 38194

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N,N,N-trimethyl-2R,3-bis[[(9Z)-1-oxo-9-octadecen-1-yl]oxy]-1-propanaminium, monochloride
CAS Number
328250-28-8
Synonyms
  • R-DOTAP
Molecular Formula
C42H80NO4 • Cl
Formula Weight
698.5
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 3 mg/mlEthanol: 16 mg/ml
SMILES
CCCCCCCC/C=C\CCCCCCCC(O[C@H](C[N+](C)(C)C)COC(CCCCCCC/C=C\CCCCCCCC)=O)=O
InChi Code
InChI=1S/C42H80NO4/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-41(44)46-39-40(38-43(3,4)5)47-42(45)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h20-23,40H,6-19,24-39H2,1-5H3/q+1/b22-20-,23-21-/t40-/m1/s1
InChi Key
KWVJHCQQUFDPLU-KNEFWTSXSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    1,2-Dioleoyl-3(R)-trimethylammoniumpropane (R-DOTAP) is a cationic lipid and the more immunologically active isomer of DOTAP (Item No. 15110).1,2 Lipoplexes containing R-DOTAP and encapsulating siRNA targeting the gene encoding aromatase, CYP19A1, decrease aromatase activity in MCF-7 breast cancer cells.1 Vaccination with a peptide epitope from human papillomavirus (HPV) 16 protein E7 in R-DOTAP-containing liposomes induces IFN-γ production by CD8+ T cells and tumor-infiltrating lymphocytes (TILs) and decreases tumor size in a murine cervical cancer model.2 Subcutaneous immunization with recombinant influenza B hemagglutinin using R-DOTAP as an adjuvant increases IL-2 and IFN-γ production in CD4+ T cells isolated from mouse draining lymph nodes and spleen.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Terp, M.C., Bauer, F., Sugimoto, Y., et al. Differential efficacy of DOTAP enantiomers for siRNA delivery in vitro. Int. J. Pharm. 430(1-2), 328-334 (2012).

    2. Vasievich, E.A., Chen, W., and Huang, L. Enantiospecific adjuvant activity of cationic lipid DOTAP in cancer vaccine. Cancer Immunol. Immunother. 60(5), 629-638 (2011).

    3. Henson, T.R., Richards, K.A., Gandhapudi, S.K., et al. R-DOTAP cationic lipid nanoparticles outperform squalene-based adjuvant systems in elicitation of CD4 T cells after recombinant influenza hemagglutinin vaccination. Viruses 15(2), 538 (2023).