3-oxo-C14 quorum-sensing lactone
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N-3-oxo-tetradecanoyl-L-Homoserine lactone

Item No. 13063

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-tetradecanamide
CAS Number
177158-19-9
Synonyms
  • 3-oxo-C14-HSL
  • N-3-oxo-myristoyl-L-Homoserine lactone
Molecular Formula
C18H31NO4
Formula Weight
325.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/ml
λmax
204, 248 nm
SMILES
CCCCCCCCCCCC(=O)CC(=O)N[C@H]1CCOC1=O
InChi Code
InChI=1S/C18H31NO4/c1-2-3-4-5-6-7-8-9-10-11-15(20)14-17(21)19-16-12-13-23-18(16)22/h16H,2-14H2,1H3,(H,19,21)/t16-/m0/s1
InChi Key
YQFJJDSGBAAUPW-INIZCTEOSA-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. 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 LuxIR family of proteins, is coordinated by the synthesis of diffusible acylhomoserine lactone (AHL) molecules. N-3-oxo-tetradecanoyl-L-homoserine lactone (3-oxo-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 biofilms and, like other long chain 3-oxo-AHLs, stimulates the production of putisolvin, which in turn, inhibits biofilm formation.4,5

    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. Dubern, J.F., Lugtenberg, B.J.J., and Bloemberg, G.V. The ppuI-rsaL-ppuR quorum-sensing system regulates biofilm formation of Pseudomonas putida PCL1445 by controlling biosynthesis of the Cyclic Lipopeptides Putisolvins I and II. J. Bacteriol. 188(8), 2898-2906 (2006).