N-cis-octadec-9Z-enoyl-L-Homoserine lactone

For research use only. Not for therapeutic Use.

  • CAT Number: R041815
  • CAS Number: 1400974-23-3
  • Molecular Formula: C22H39NO3
  • Molecular Weight: 365.6
  • Purity: ≥95%
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Quorum sensing is a regulatory process used by bacteria for controlling gene expression in response to increasing cell density. This regulatory process manifests itself with a variety of phenotypes including biofilm formation and virulence factor production. Coordinated gene expression is achieved by the production, release, and detection of small diffusible signal molecules called autoinducers. The N-<wbr></wbr>acylated homoserine lactones (AHLs) comprise one such class of autoinducers, each of which generally consists of a fatty acid coupled with homoserine lactone (HSL). AHLs vary in acyl group length (C<sub>4</sub>-<wbr></wbr>C<sub>18</sub>), in the substitution of C3 (hydrogen, hydroxyl, or oxo group) and in the presence or absence of one or more carbon-<wbr></wbr>carbon double bonds in the fatty acid chain. These differences confer signal specificity through the affinity of transcriptional regulators of the LuxR family. C18:1-<wbr></wbr>Δ and thus, might be used to inhibit pathogenesis by regulating bacerial quorum sensing signaling.


Catalog Number R041815
CAS Number 1400974-23-3
Synonyms

C18:1-Δ9 cis-(L)-HSL;N-(2-oxotetrahydrofuran-3S-yl) Oleyl Amide

Molecular Formula C22H39NO3
Purity ≥95%
Target Bacterial
Storage -20°C
InChI InChI=1S/C22H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)23-20-18-19-26-22(20)25/h9-10,20H,2-8,11-19H2,1H3,(H,23,24)/b10-9-/t20-/m0/s1
InChIKey PYEKBLYUYSJMKS-QJRAZLAKSA-N
SMILES CCCCCCCC/C=CCCCCCCCC(=O)N[C@H]1CCOC1=O
Reference

1.González, J.E., and Keshavan, N.D. Messing with bacterial quorum sensing. Microbiology and Molecular Biology Reviews 70(4), 859-875 (2006).

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