IUPAC Name
3-(dimethylamino)propane-1,2-diyl (9Z,9'Z,12Z,12'Z)-bis(octadeca-9,12-dienoate)
Chemical Formula
C₄₁H₇₅NO₄
Molecular Weight
646
Form
Solid
SMILES
O=C(OCC(CN(C)C)OC(CCCCCCC/C=C\C/C=C\CCCCC)=O)CCCCCCC/C=C\C/C=C\CCCCC
Synonyms
DLinDMA (2,3-dilinoleoyloxy-N,N-dimethylpropylamine)
3-(Dimethylamino)propane-1,2-diyl (9Z,9′Z,12Z,12′Z)-bis(octadeca-9,12-dienoate) is a cationic lipid that contains two polyunsaturated linoleoyl chains (C18:2) esterified to a glycerol backbone with a tertiary dimethylamino headgroup. This structure makes it amphiphilic, biocompatible, and membrane-active, and it is commonly found in the design of lipid-based gene delivery systems, liposomes, and nanoparticles. This compound is closely related to DLinDMA (dilinoleyl dimethylamino propane), a well-known cationic lipid used in mRNA and siRNA delivery systems such as lipid nanoparticles (LNPs). It is a core cationic lipid component for mRNA and siRNA delivery (forms ionizable cationic lipids that complex with nucleic acids), it's protonated amine binds to negatively charged phosphate groups in nucleic acids, facilitating endosomal escape and cellular uptake, it contributes to membrane fusion and high transfection efficiency and is used to investigate the role of unsaturated lipid tails and cationic headgroups in bilayer fluidity and permeability.
