N-dodecanoyl-L-Homoserine lactone

Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. Controlling bacterial infections by quenching their quorum sensing systems is a promising field of study. The expression of specific target genes, such as transcriptional regulators belonging to the LuxR family of proteins, is coordinated by the synthesis of diffusible acylhomoserine lactone (AHL) molecules. N-dodecanoyl-L-Homoserine lactone (C12-HSL) is a small diffusible signaling molecule involved in quorum sensing, thereby controlling gene expression and affecting cellular metabolism in bacteria. In addition to regulating bacterial functions, C12-HSL activates NF-kappaB in RAW 264.7 macrophages, increasing the expression of TNF-alpha, interleukin-1beta (IL-1beta), and IL-8, while other lactones do not. In addition, C12-HSL alters cell cycling and metabolism of human keratinocyte (HaCaT) cells. It is important to note that C12-HSL is distinct from N-3-oxo-dodecanoyl-L-homoserine lactone (Cay-10007895), which is produced at different times in biofilm development and has different cellular effects.Formal Name: N-[(3S)-tetrahydro-2-oxo-3-furanyl]-dodecanamide. CAS Number: 137173-46-7. Synonyms: C12-HSL, dDHL. Molecular Formula: C16H29NO3. Formula Weight: 283.4. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: Chloroform: 10 mg/ml, DMF: 1 mg/ml, DMSO: 1 mg/ml. SMILES: CCCCCCCCCCCC(=O)N[C@H]1CCOC1=O. InChi Code: InChI=1S/C16H29NO3/c1-2-3-4-5-6-7-8-9-10-11-15(18)17-14-12-13-20-16(14)19/h14H,2-13H2,1H3,(H,17,18)/t14-/m0/s1. InChi Key: WILLZMOKUUPJSL-AWEZNQCLSA-N.