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N-dodecanoyl-L-Homoserine lactone Exclusive
Cayman Chemical Item Number 10011203
Description 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.1↗,2↗,3↗ In addition to regulating bacterial functions, C12-HSL activates NF-κB in RAW 264.7 macrophages, increasing the expression of TNF-α, interleukin-1β (IL-1β), and IL-8, while other lactones do not.4↗ In addition, C12-HSL alters cell cycling and metabolism of human keratinocyte (HaCaT) cells.5↗ It is important to note that C12-HSL is distinct from N-3-oxo-dodecanoyl-L-Homoserine lactone (Catalog No. 10007895), which is produced at different times in biofilm development6↗ and has different cellular effects.5↗
Synonyms dDHL C12-HSL
Formal Name N-[(3S)-tetrahydro-2-oxo-3-furanyl]-dodecanamide
CAS Number 137173-46-7
Molecular Formula C16H29NO3
Formula Weight 283.4
Formulation A crystalline solid
Purity ≥98%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES CCCCCCCCCCCC(=O)N[C@H]1CCOC1=O
InCHI Code 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 |