N-3-oxo-dodecanoyl-L-Homoserine lactone • 3-<wbr/>oxo-<wbr/>C12-<wbr/>HSL (CAS 168982-69-2) (Inchi key PHSRRHGYXQCRPU-AWEZNQCLSA-N) || Cayman Chemical | Supplier
N-3-oxo-dodecanoyl-L-Homoserine lactone
Item № 10007895
CAS № 168982-69-2
Purity ≥98%
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1 mg $23.00 $0.00
5 mg $104.00 $0.00
10 mg $184.00 $0.00
50 mg $805.00 $0.00

Pricing updated 2015-08-30. Prices are subject to change without notice.

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Description
Synonyms
  • 3-oxo-C12-HSL

Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density.1 A promising field of study involves controlling bacterial infections by quenching their quorum sensing systems. The expression of specific target genes, such as transcriptional regulators belonging to the LuxIR family of proteins, is coordinated by synthesis of diffusible acylhomoserine lactone (AHL) molecules.1 N-3-oxo-dodecanoyl-L-homoserine lactone (3-oxo-C12-HSL) is one of the AHLs frequently identified in extracts of respiratory secretions from cystic fibrosis patients infected with P. aeruginosa and/or strains of the B. cepacia complex.2 3-oxo-C12-HSL activates the transcription factors NF-κB and AP-2 to induce interleukin-8 production in human lung fibroblasts and epithelial cells, possibly contributing to the neutrophil infiltration and inflammation found in P. aeruginosa infections.3

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Technical Information
Formal Name 3-​oxo-​N-​[(3S)-​tetrahydro-​2-​oxo-​3-​furanyl]-​dodecanamide
CAS Number 168982-69-2
Synonyms
  • 3-oxo-C12-HSL
Molecular Formula C16H27NO4
Formula Weight 297.4
Purity ≥98%
Formulation A crystalline solid
λmax 202, 250 nm
SMILES CCCCCCCCCC(=O)​CC(=O)​N[C@H]​1CCOC1=O
InChI Code ​1S/C16H27NO4/c1-2-3-4-5-6-7-8-9-13(18)​12-15(19)​17-14-10-11-21-16(14)​20/h14H,2-12H2,1H3,(H,17,19)​/t14-/m0/s1
InChI Key PHSRRHGYXQCRPU-AWEZNQCLSA-N

WARNING - This product is not for human or veterinary use.

Shipping & Storage
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
Stability 1 year
Product Downloads & Resources
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Additional Information

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References & Background Reading
Product Description References

1. Henke, J.M., and Bassler, B.L. Bacterial social engagements. Trends Cell Biol 14(11) 648-656 (2004).

2. Chambers, C.E., Visser, M.B., Schwab, U., et al. Identification of N-acylhomoserine lactones in mucopurulent respiratory secretions from cystic fibrosis patients. FEMS Microbiol Lett 244 297-304 (2005).

3. Smith, R.S., Fedyk, E.R., Springer, T.A., et al. IL-8 production in human lung fibroblasts and epithelial cells activated by the Pseudomonas autoinducer N-3-oxododecanoyl homoserine lactone is transcriptionally regulated by NF-κB and activator protein-2. J Immunol 167 366-374 (2001).

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