A bacterial quorum-sensing signaling molecule
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N-cis-tetradec-9Z-enoyl-L-Homoserine lactone

Item No. 10012672

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(S,Z)-N-(2-oxotetrahydrofuran-3-yl)tetradec-9-enamide
CAS Number
1675245-06-3
Synonyms
  • C14:1-Δ9-cis-(L)-HSL
  • N-(2-oxotetrahydrofuran-3S-yl) Myristoleyl Amide
Molecular Formula
C18H31NO3
Formula Weight
309.4
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlDMSO:PBS(pH7.2) 1:1: 0.5 mg/ml
SMILES
CCCC/C=C\CCCCCCCC(=O)N[C@H]1CCOC1=O
InChi Code
InChI=1S/C18H31NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(20)19-16-14-15-22-18(16)21/h5-6,16H,2-4,7-15H2,1H3,(H,19,20)/b6-5-/t16-/m0/s1
InChi Key
CNVCBUGVTPVVJB-KJPDOMRESA-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 process 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). 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.3 C14:1-Δ9-cis-(L)-HSL is a long-chain AHL that functions as a signaling molecule in the quorum sensing of A. vitis.4 Regulating bacterial quorum sensing signaling can be used to inhibit pathogenesis and thus, represents a new approach to antimicrobial therpy in the treatment of infectious diseases.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. 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).

    4. Li, Y., Gronquist, M.R., Hao, G., et al. Chromosome and plasmid-encoded N-acyl homoserine lactones produced by Agrobacterium vitis wildtype and mutants that differ in their interactions with grape and tobacco. Physiol. Mol. Plant Pathol. 67, 284-290 (2006).

    5. 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).