Date published: 2026-2-6

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N-octadecanoyl-L-Homoserine lactone (CAS 479050-96-9)

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Application:
N-octadecanoyl-L-Homoserine lactone is an AHL involved in cell signaling and bacterial quorum sensing
CAS Number:
479050-96-9
Molecular Weight:
367.6
Molecular Formula:
C22H41NO3
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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N-octadecanoyl-L-Homoserine lactone, sometimes called C18-HSL, is an N-acylated homoserine lactone (AHL). AHLs vary in acyl group length (C4-C18), in the substitution of C3 (hydrogen, hydroxyl, or oxo group), and in the presence or absence of one or more carbon-carbon double bonds in the fatty acid chain. These differences confer signal specificity through the affinity of transcriptional regulators of the LuxR family. N-octadecanoyl-L-Homoserine lactone is one of four lipophilic, long acyl side-chain bearing AHLs produced by the LuxI AHL synthase homolog SinI involved in quorum-sensing signaling in strains of Sinorhizobium meliloti. This and other hydrophobic AHLs tend to localize in relatively lipophilic cellular environments of bacteria and cannot diffuse freely through the cell membrane. The long-chain N-acylhomoserine lactones may be exported from cells by efflux pumps or may be transported between communicating cells by way of extracellular outer membrane vesicles.


N-octadecanoyl-L-Homoserine lactone (CAS 479050-96-9) References

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  2. Quorum sensing controls exopolysaccharide production in Sinorhizobium meliloti.  |  Marketon, MM., et al. 2003. J Bacteriol. 185: 325-31. PMID: 12486070
  3. Use of Sinorhizobium meliloti as an indicator for specific detection of long-chain N-acyl homoserine lactones.  |  Llamas, I., et al. 2004. Appl Environ Microbiol. 70: 3715-23. PMID: 15184178
  4. Methylobacterium extorquens AM1 produces a novel type of acyl-homoserine lactone with a double unsaturated side chain under methylotrophic growth conditions.  |  Nieto Penalver, CG., et al. 2006. FEBS Lett. 580: 561-7. PMID: 16412429
  5. Special delivery: vesicle trafficking in prokaryotes.  |  Mashburn-Warren, LM. and Whiteley, M. 2006. Mol Microbiol. 61: 839-46. PMID: 16879642
  6. Effector-stimulated single molecule protein-DNA interactions of a quorum-sensing system in Sinorhizobium meliloti.  |  Bartels, FW., et al. 2007. Biophys J. 92: 4391-400. PMID: 17384071
  7. The biology and future prospects of antivirulence therapies.  |  Cegelski, L., et al. 2008. Nat Rev Microbiol. 6: 17-27. PMID: 18079741
  8. Characterization of diverse homoserine lactone synthases in Escherichia coli.  |  Daer, R., et al. 2018. PLoS One. 13: e0202294. PMID: 30138364
  9. Short-Chain N-Acylhomoserine Lactone Quorum-Sensing Molecules Promote Periodontal Pathogens in In Vitro Oral Biofilms.  |  Muras, A., et al. 2020. Appl Environ Microbiol. 86: PMID: 31757829
  10. Detection of gut microbiota and pathogen produced N-acyl homoserine in host circulation and tissues.  |  Xue, J., et al. 2021. NPJ Biofilms Microbiomes. 7: 53. PMID: 34183673
  11. Clostridium butyricum alleviates LPS-induced acute immune stress in goats by regulating bacterial communities and blood metabolites.  |  Zhang, C., et al. 2023. Front Immunol. 14: 1099186. PMID: 36756118
  12. Gram-negative quorum sensing signalling enhances biofilm formation and virulence traits in gram-positive pathogen Enterococcus faecalis.  |  Parga, A., et al. 2023. J Oral Microbiol. 15: 2208901. PMID: 37187675
  13. Active efflux and diffusion are involved in transport of Pseudomonas aeruginosa cell-to-cell signals.  |  Pearson, JP., et al. 1999. J Bacteriol. 181: 1203-10. PMID: 9973347

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

N-octadecanoyl-L-Homoserine lactone, 5 mg

sc-224146
5 mg
$46.00

N-octadecanoyl-L-Homoserine lactone, 10 mg

sc-224146A
10 mg
$88.00