A bacterial quorum-sensing signaling molecule
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N-3-oxo-hexadec-11(Z)-enoyl-L-Homoserine lactone

Item No. 10011238

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-(11Z)-hexadecenamide
CAS Number
1269663-80-0
Synonyms
  • 3-oxo-C16:1-Δ11cis-(L)-HSL
Molecular Formula
C20H33NO4
Formula Weight
351.5
Purity
≥98%
Formulation (Request formulation change)
A 10 mg/ml solution in acetonitrile
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/ml
λmax
246 nm
SMILES
O=C1[C@@H](NC(CC(CCCCCCC/C=C\CCCC)=O)=O)CCO1
InChi Code
InChI=1S/C20H33NO4/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(22)16-19(23)21-18-14-15-25-20(18)24/h5-6,18H,2-4,7-16H2,1H3,(H,21,23)/b6-5-/t18-/m0/s1
InChi Key
UKVJHGAETBFGBY-XFHJGTJQSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    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 An unspecified positional and geometric isomer of 3-oxo-C16:1-(L)-HSL is produced by the F2/5 strain of A. vitis, the bacterium responsible for grape crown gall and its resulting loss of agricultural productivity.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    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(2), 561-567 (2006).

    5. Hao, G., and Burr, T.J. Regulation of long-chain N-acyl-homoserine lactones in agrobacterium vitis. J. Bacteriol. 188(6), 2173-2183 (2006).