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CAS 147795-40-2

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N-(3-Oxodecanoyl)-L-homoserine lactone

Description:
N-(3-Oxodecanoyl)-L-homoserine lactone, commonly referred to as 3-oxo-C10-HSL, is a signaling molecule belonging to the class of acyl-homoserine lactones (AHLs). It plays a crucial role in bacterial quorum sensing, a process that enables bacteria to communicate and coordinate their behavior based on population density. This compound features a homoserine lactone ring, which is essential for its biological activity, and an acyl chain that contributes to its hydrophobic properties. The presence of a keto group at the third position of the decanoyl chain enhances its stability and reactivity. 3-oxo-C10-HSL is primarily produced by certain Gram-negative bacteria and is involved in regulating various physiological processes, including biofilm formation, virulence factor production, and bioluminescence. Its ability to influence gene expression makes it a significant molecule in microbial ecology and pathogenesis. Additionally, due to its role in intercellular communication, it has potential applications in biotechnology and medicine, particularly in the development of antimicrobial strategies targeting quorum sensing pathways.
Formula:C14H23NO4
InChI:InChI=1S/C14H23NO4/c1-2-3-4-5-6-7-11(16)10-13(17)15-12-8-9-19-14(12)18/h12H,2-10H2,1H3,(H,15,17)/t12-/m0/s1
InChI key:InChIKey=KYGIKEQVUKTKRR-LBPRGKRZSA-N
SMILES:N(C(CC(CCCCCCC)=O)=O)[C@@H]1C(=O)OCC1
Synonyms:
  • 3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]decanamide
  • Decanamide, 3-oxo-N-(tetrahydro-2-oxo-3-furanyl)-, (S)-
  • (S)-3-Oxo-N-(2-oxotetrahydrofuran-3-yl)decanamide
  • Decanamide, 3-oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-
  • N-(3-Oxodecanoyl)-L-homoserine lactone
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