N-Dodecanoyl-L-homoserine lactone

N-Dodecanoyl-L-homoserine lactone (C12-HSL) is a small diffusible signalling 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, which is produced at different times in biofilm development and has different cellular effects.

Catalog Number CDX-D0335-M005
Alternative Name(s) N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-dodecanamide; dDHL; C12-HSL
Research Area Biochemicals, Immunology, Inflammation
Molecular Formula C16H29NO3
CAS# 137173-46-7
Purity >98%
Inchi 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
SMILES CCCCCCCCCCCC(=O)N[C@H]1CCOC1=O
Size 5 mg
Supplier Page http://www.adipogen.com/cdx-d0335/n-dodecanoyl-l-homoserine-lactone.html