N-cis-hexadec-9Z-enoyl-L-Homoserine lactone

Quorum sensing is a regulatory process used by bacteria for controlling gene expression in response to increasing cell density. This regulatory process manifests itself with a variety of phenotypes including biofilm formation and virulence factor production. Coordinated gene expression is achieved by the production, release, and detection of small diffusible signal molecules called autoinducers. The N-acylated homoserine lactones (AHLs) comprise one such class of autoinducers, each of which generally consists of a fatty acid coupled with homoserine lactone (HSL). 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-cis-hexadec-9Z-enoyl-L-Homoserine lactone is a long-chain AHL that functions as a quorum sensing signaling molecule in strains of S. meliloti. Regulating bacterial quorum sensing signaling can be used to inhibit pathogenesis and thus, represents a new approach to antimicrobial therapy in the treatment of infectious diseases.Formal Name: N-[(2S,9Z)-tetrahydro-2-oxo-3-furanyl]-9-hexadecenamide. CAS Number: 479050-94-7. Synonyms: C16:1-Delta9-(L)-HSL, N-(2-oxotetrahydrofuran-3S-yl) Palmitoleyl Amide. Molecular Formula: C20H35NO3. Formula Weight: 337.5. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 20 mg/ml, DMSO: 20 mg/ml, DMSO:PBS(pH7.2) 1:1: 0.5 mg/ml. SMILES: CCCCCC/C=C\CCCCCCCC(=O)N[C@H]1CCOC1=O. InChi Code: InChI=1S/C20H35NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(22)21-18-16-17-24-20(18)23/h7-8,18H,2-6,9-17H2,1H3,(H,21,22)/b8-7-/t18-/m0/s1. InChi Key: BDQHAQLGRDSHKW-ZEVQVBBLSA-N.