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

Item No. 38195

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N,N,N-trimethyl-2,3-bis[[(9Z)-1-oxo-9-octadecen-1-yl]oxy]-1-propanaminium, monochloride
CAS Number
428506-51-8
Synonyms
  • (S)-DOTAP
  • (S)-N,N,N-Trimethyl-2,3-bis(oleoyloxy)propan-1-aminium
Molecular Formula
C42H80NO4 • Cl
Formula Weight
698.5
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: Slightly solubleDMSO: Slightly solubleEthanol: 20 mg/ml
SMILES
CCCCCCCC/C=C\CCCCCCCC(O[C@@H](C[N+](C)(C)C)COC(CCCCCCC/C=C\CCCCCCCC)=O)=O.[Cl-]
InChi Code
InChI=1S/C42H80NO4.ClH/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;1H/q+1;/p-1/b22-20-,23-21-;/t40-;/m0./s1
InChi Key
KSXTUUUQYQYKCR-KVINLOACSA-M
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(S)-trimethylammoniumpropane (S-DOTAP) is a cationic lipid and the less immunologically active isomer of DOTAP (Item No. 15110).1,2 Lipoplexes containing S-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 S-DOTAP-containing liposomes decrease tumor size but do not induce IFN-γ production by CD8+ T cells and tumor-infiltrating lymphocytes (TILs) in a murine cervical cancer model.2

    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).