C14 quorum-sensing lactone
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N-tetradecanoyl-L-Homoserine lactone

Item No. 10011200

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(3S)-tetrahydro-2-oxo-3-furanyl]-tetradecanamide
CAS Number
202284-87-5
Synonyms
  • C14-HSL
  • tDHL
Molecular Formula
C18H33NO3
Formula Weight
311.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlPBS (pH 7.2): 10 mg/ml
SMILES
CCCCCCCCCCCCCC(=O)N[C@H]1CCOC1=O
InChi Code
InChI=1S/C18H33NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(20)19-16-14-15-22-18(16)21/h16H,2-15H2,1H3,(H,19,20)/t16-/m0/s1
InChi Key
ZQAYHOXXVBVXPZ-INIZCTEOSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $49

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    10 mg

    $93

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    25 mg

    $213

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    50 mg

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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. Controlling bacterial infections by quenching their quorum sensing systems is a promising field of study. The expression of specific target genes, such as transcriptional regulators belonging to the LuxR family of proteins, is coordinated by the synthesis of diffusible acylhomoserine lactone (AHL) molecules. N-tetradecanoyl-L-Homoserine lactone (C14-HSL) is a small diffusible signaling molecule involved in quorum sensing, thereby controlling gene expression and affecting cellular metabolism in bacteria.1,2,3 It appears later than shorter acyl chain AHLs in developing biofilms4 and, like other long chain AHLs, stimulates bacterial growth.5 C14-HSL also alters the proteolytic activity and enhances the migration of some strains of Proteus mirabilis.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kuo, A., Blough, N.V., and Dunlap, P.V. Multiple N-acyl-ʟ-homoserine lactone autoinducers of luminescence in the marine symbiotic bacterium Vibrio fischeri. J. Bacteriol. 176(24), 7558-7565 (1994).

    2. Lithgow, J.K., Wilkinson, A., Hardman, A., et al. The regulatory locus cinRI in Rhizobium leguminosarum controls a network of quorum-sensing loci. Mol. Microbiol. 37(1), 81-97 (2000).

    3. McClean, K.H., Winson, M.K., Fish, L., et al. Quorum-sensing and Chromobacterium violaceum: Exploitation of violacein production and inhibition for the detection of N-acylhomoserine lactones. Microbiology 143(Pt 12), 3703-3711 (1997).

    4. Huang, Y.L., Ki, J.S., Lee, O.O., et al. Evidence for the dynamics of acyl homoserine lactone and AHL-producing bacteria during subtidal biofilm formation. ISME J. 3(3), 296-304 (2008).

    5. Huang, J.J., Han, J.I., Zhang, L.H., et al. Utilization of acyl-homoserine lactone quorum signals for growth by a soil pseudomonad and Pseudomonas aeruginosa PAO1. Appl. Environ. Microbiol. 69(10), 5941-5949 (2003).

    6. Stankowska, D., Kwinkowski, M., and Kaca, W. Quantification of Proteus mirabilis virulence factors and modulation by acylated homoserine lactones. J. Microbiol. Immunol. Infect. 41(3), 243-253 (2008).

    Product Citations

    Girard, L., Blanchet, É., Intertaglia, L., et al. Characterization of N-acyl homoserine lactones in Vibrio tasmaniensis LGP32 by a biosensor-based UHPLC-HRMS/MS method. Sensors (Basel) 17(4), 906 (2017).