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CAS 137173-46-7

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N-Dodecanoyl-L-homoserine lactone

Description:
N-Dodecanoyl-L-homoserine lactone (C12-H23-N-O3) 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 long hydrophobic dodecanoyl chain, which contributes to its lipid solubility, and a homoserine lactone moiety that plays a crucial role in cell-to-cell communication among bacteria. The presence of the dodecanoyl group enhances its ability to diffuse across cell membranes, facilitating its role in regulating gene expression in response to population density. N-Dodecanoyl-L-homoserine lactone is known to influence various physiological processes, including biofilm formation, virulence factor production, and bioluminescence in certain bacterial species. Its structural characteristics allow it to interact with specific receptors in target cells, triggering a cascade of biological responses. This compound is of significant interest in microbiology and biotechnology, particularly for its potential applications in controlling bacterial behavior and developing antimicrobial strategies.
Formula:C16H29NO3
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:InChIKey=WILLZMOKUUPJSL-AWEZNQCLSA-N
SMILES:N(C(CCCCCCCCCCC)=O)[C@@H]1C(=O)OCC1
Synonyms:
  • (S)-N-(2-Oxotetrahydrofuran-3-yl)dodecanamide
  • C12-HSL (autoinducer)
  • Dodecanamide, N-(tetrahydro-2-oxo-3-furanyl)-, (S)-
  • N-Dodecanoyl-<span class="text-smallcaps">L</span>-homoserine lactone
  • N-[(3S)-Tetrahydro-2-oxo-3-furanyl]dodecanamide
  • dodecanamide, N-[(3S)-tetrahydro-2-oxo-3-furanyl]-
  • N-Dodecanoyl-L-homoserine lactone
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