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CAS 147852-84-4

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N-Octanoyl-L-homoserine lactone

Description:
N-Octanoyl-L-homoserine lactone (C10H19NO3S) is a signaling molecule belonging to the class of acyl-homoserine lactones (AHLs), which are primarily involved in bacterial quorum sensing. This compound features a lactone ring, which is a cyclic ester formed from the reaction of a hydroxy acid and an alcohol, and it contains an octanoyl acyl chain that contributes to its hydrophobic properties. The presence of the homoserine moiety allows for interactions with specific receptors in bacterial cells, facilitating communication and coordination of group behaviors such as biofilm formation and virulence factor production. N-Octanoyl-L-homoserine lactone is typically synthesized through enzymatic or chemical methods and can be found in various environmental settings, particularly in association with Gram-negative bacteria. Its role in microbial ecology and potential applications in biotechnology and medicine, such as in the development of antimicrobial agents or biofilm inhibitors, make it a compound of interest in both research and industrial contexts.
Formula:C12H21NO3
InChI:InChI=1S/C12H21NO3/c1-2-3-4-5-6-7-11(14)13-10-8-9-16-12(10)15/h10H,2-9H2,1H3,(H,13,14)/t10-/m0/s1
InChI key:InChIKey=JKEJEOJPJVRHMQ-JTQLQIEISA-N
SMILES:N(C(CCCCCCC)=O)[C@@H]1C(=O)OCC1
Synonyms:
  • N-[(3S)-Tetrahydro-2-oxo-3-furanyl]octanamide
  • (S)-N-(2-Oxotetrahydrofuran-3-yl)octanamide
  • N-Octanoyl-L-homoserine lactone
  • Octanamide, N-[(3S)-tetrahydro-2-oxo-3-furanyl]-
  • Octanamide, N-(tetrahydro-2-oxo-3-furanyl)-, (S)-
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