N-octadecanoyl-L-Homoserine lactone, sometimes called C18-HSL, is an N-acylated homoserine lactone (AHL). AHLs vary in acyl group length (C4-C18), in the substitution of C3 (hydrogen, hydroxyl, or oxo group), and in the presence or absence of one or more carbon-carbon double bonds in the fatty acid chain. These differences confer signal specificity through the affinity of transcriptional regulators of the LuxR family. N-octadecanoyl-L-Homoserine lactone is one of four lipophilic, long acyl side-chain bearing AHLs produced by the LuxI AHL synthase homolog SinI involved in quorum-sensing signaling in strains of|Sinorhizobium meliloti|. This and other hydrophobic AHLs tend to localize in relatively lipophilic cellular environments of bacteria and cannot diffuse freely through the cell membrane. The long-chain N-acylhomoserine lactones may be exported from cells by efflux pumps or may be transported between communicating cells by way of extracellular outer membrane vesicles.