C12 quorum-sensing lactone
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N-dodecanoyl-L-Homoserine lactone

Item No. 10011203

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(3S)-tetrahydro-2-oxo-3-furanyl]-dodecanamide
CAS Number
137173-46-7
Synonyms
  • C12-HSL
  • dDHL
Molecular Formula
C16H29NO3
Formula Weight
283.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Chloroform: 10 mg/mlDMF: 1 mg/mlDMSO: 1 mg/ml
SMILES
CCCCCCCCCCCC(=O)N[C@H]1CCOC1=O
InChi Code
InChI=1S/C16H29NO3/c1-2-3-4-5-6-7-8-9-10-11-15(18)17-14-12-13-20-16(14)19/h14H,2-13H2,1H3,(H,17,18)/t14-/m0/s1
InChi Key
WILLZMOKUUPJSL-AWEZNQCLSA-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

    $354

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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-dodecanoyl-L-Homoserine lactone (C12-HSL) is a small diffusible signaling molecule involved in quorum sensing, thereby controlling gene expression and affecting cellular metabolism in bacteria.1,2,3 In addition to regulating bacterial functions, C12-HSL activates NF-κB in RAW 264.7 macrophages, increasing the expression of TNF-α, interleukin-1β (IL-1β), and IL-8, while other lactones do not.4 In addition, C12-HSL alters cell cycling and metabolism of human keratinocyte (HaCaT) cells.5 It is important to note that C12-HSL is distinct from N-3-oxo-dodecanoyl-L-homoserine lactone (Item No. 10007895), which is produced at different times in biofilm development and has different cellular effects.5,6

    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. Gomi, K., Kikuchi, T., Tokue, Y., et al. Mouse and human cell activation by N-dodecanoyl-ᴅʟ-homoserine lactone, a Chromobacterium violaceum autoinducer. Infect. Immun. 74(12), 7029-7031 (2006).

    5. Kristiansen, S., Bjarnsholt, T., Adeltoft, D., et al. The Pseudomonas aeruginosa autoinducer dodecanoyl-homoserine lactone inhibits the putrescine synthesis in human cells. APMIS 116(5), 361-371 (2008).

    6. 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).

    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).