N-pentadecanoyl-L-Homoserine lactone • C<sub>15</sub>-<wbr/>HSL (CAS 182359-66-6) (Inchi key QJWOQBGBEFNYKB-UHFFFAOYSA-N) || Cayman Chemical | Supplier
N-pentadecanoyl-L-Homoserine lactone
Item № 13094
CAS № 182359-66-6
Purity ≥98%
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5 mg $30.00 $0.00
10 mg $57.00 $0.00
25 mg $135.00 $0.00
50 mg $240.00 $0.00

Pricing updated 2015-08-28. Prices are subject to change without notice.

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Description
Synonyms
  • C15-HSL

Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density.1 This regulatory process manifests itself with a variety of phenotypes including biofilm formation and virulence factor production.2 Coordinated gene expression is achieved by the production, release, and detection of small diffusible signal molecules called autoinducers. The N-acylated homoserine lactones (AHLs) comprise one such class of autoinducers, each of which generally consists of a fatty acid coupled with homoserine lactone (HSL). Regulation of bacterial quorum sensing signaling systems to inhibit pathogenesis represents a new approach to antimicrobial therapy in the treatment of infectious diseases.3 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.4 C15-HSL is a product of Y. pseudituberculosis.5

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Technical Information
Formal Name N-​[(3S)-​tetrahydro-​2-​oxo-​3-​furanyl]-​pentadecanamide
CAS Number 182359-66-6
Synonyms
  • C15-HSL
Molecular Formula C19H35NO3
Formula Weight 325.5
Purity ≥98%
Formulation A crystalline solid
SMILES CCCCCCCCCCCCCCC(=O)​N[C@H]​1CCOC1=O
InChI Code ​1S/C14H19NO2/c1-11(15-9-3-4-10-15)​14(16)​12-5-7-13(17-2)​8-6-12/h5-8,11H,3-4,9-10H2,1-2H3
InChI Key QJWOQBGBEFNYKB-UHFFFAOYSA-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 2 years
Product Downloads & Resources
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Download Product Insert 104 Kb PDF

Download Safety Data Sheet (SDS) 23 Kb PDF

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Additional Information

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References & Background Reading
Product Description References

1. González, J.E., and Keshavan, N.D. Messing with bacterial quorum sensing. Microbiol Mol Biol Rev 70(4) 859-875 (2006).

2. Gould, T.A., Herman, J., Krank, J., et al. Specificity of acyl-homoserine lactone syntheses examined by mass spectrometry. J Bacteriol 188(2) 773-783 (2006).

3. Cegelski, L., Marshall, G.R., Eldridge, G.R., et al. The biology and future prospects of antivirulence therapies. Nat Rev Microbiol 6(1) 17-27 (2008).

4. Penalver, C.G.N., Morin, D., Cantet, F., et al. Methylobacterium extorquens AM1 produces a novel type of acyl-homoserine lactone with a double unsaturated side chain under methylotrophic growth conditions. FEBS Lett 580 561-567 (2006).

5. Ortori, C.A., Atkinson, S., Chhabra, S.R., et al. Comprehensive profiling of N-acylhomoserine lactones produced by Yersinia pseudotuberculosis using liquid chromatography coupled to hybrid quadrupole-linear ion trap mass spectrometry. Anal Bioanal Chem 387 497-511 (2007).

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