IUPAC Name
Sodium hydrogen (2,3-bis(((Z)-hexadec-9-enoyl)oxy)propyl)phosphonate
Chemical Formula
C₃₅H₆₆NaO₈P
Molecular Weight
685
Form
Solid
SMILES
CCCCCC/C=C\CCCCCCCC(OC(CP(O)(O[Na])=O)COC(CCCCCCC/C=C\CCCCCC)=O)=O
AAPharmaSyn Stock ID
00035
Sodium hydrogen (2,3-bis(((Z)-hexadec-9-enoyl)oxy)propyl)phosphonate is a synthetic phospholipid analog belonging to the class of phosphonate lipids, designed to mimic the structure and self-assembly behavior of natural glycerophospholipids while offering greater chemical and enzymatic stability due to its phosphonate (P–C) linkage instead of a phosphate (P–O–C) bond. This compound is amphiphilic, with a hydrophilic, negatively charged phosphonate headgroup and two hydrophobic monounsaturated C16 (palmitoleoyl-like) fatty acid chains, giving it strong bilayer-forming ability similar to natural phosphatidic acid derivatives. It is used in biophysical studies of anionic lipid bilayers, mimicking phosphatidic acid or phosphatidylglycerol analogs, forms stable, negatively charged bilayers, useful in liposome-based delivery systems or nanocarriers, is a stable anionic phosphonate head prevents enzymatic breakdown, ideal for long-circulating liposomes and is useful in forming robust phosphonate monolayers on metal oxides or nanomaterials.
