IUPAC Name
Hexadec-15-ynoic acid
Chemical Formula
C₁₆H₂₈O₂
Molecular Weight
252.39
Form
Solid
SMILES
C#CCCCCCCCCCCCCCC(O)=O
AAPharmaSyn Stock ID
00039
Synonyms
15-Hexadecynoic acid; 15-PA (Palmitic acid analog with alkyne); ω-Alkynyl hexadecanoic acid
Hexadec-15-ynoic acid is a long-chain fatty acid containing 16 carbon atoms with a terminal alkyne functional group (a carbon–carbon triple bond) near the end of the chain. It is a synthetic analog of palmitic acid (hexadecanoic acid) in which the terminal methyl group is replaced by an ethynyl group (–C≡CH), giving the molecule distinct chemical reactivity while maintaining similar hydrophobic and amphiphilic properties. The terminal alkyne enables covalent attachment to azide-functionalized probes via Cu(I)-catalyzed azide–alkyne cycloaddition (CuAAC) — a key reaction in chemical biology for labeling biomolecules. It is used as a metabolic probe to track lipid incorporation, fatty acid transport, and enzyme activity in cells. It qcts as a chemical reporter lipid—the alkyne allows visualization or enrichment of labeled lipid species using azide-linked fluorescent or affinity tags. The compouns can be metabolically incorporated into proteins at sites of palmitoylation, enabling click-based detection of lipid-modified proteins.
