N-nonanoyl-L-Homoserine lactone
Item № 16868
CAS № 177158-21-3
Purity ≥98%
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5 mg $26.00 $0.00
10 mg $49.00 $0.00
25 mg $117.00 $0.00
50 mg $208.00 $0.00

Pricing updated 2015-11-25. Prices are subject to change without notice.

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  • C9-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 C9-HSL is a rare odd-numbered acyl carbon chain produced by wild-type Erwinia carotovora strain SCC 3193 grown in the nutrient-rich Luria-Bertani Broth (LB) medium.5

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Technical Information
Formal Name N-[(3S)-tetrahydro-2-oxo-3-furanyl]-nonanamide
CAS Number 177158-21-3
  • C9-HSL
Molecular Formula C13H23NO3
Formula Weight 241.3
Purity ≥98%
Formulation A crystalline solid
InChI Code 1S/C13H23NO3/c1-2-3-4-5-6-7-8-12(15)14-11-9-10-17-13(11)16/h11H,2-10H2,1H3,(H,14,15)/t11-/m0/s1

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

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Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
Stability 2 years
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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. Brader, G., Sjöblom, S., Hyytiäinen, H., et al. Altering substrate chain length specificity of an acylhomoserine lactone synthase in bacterial communication. J Biol Chem 280(11) 10403-10409 (2005).

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