A bacterial quorum-sensing signaling molecule
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N-3-oxo-dodecanoyl-L-Homoserine lactone

Item No. 10007895

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-dodecanamide
CAS Number
168982-69-2
Synonyms
  • N-(3-oxododecanoyl) L-Homoserine lactone
  • 3-oxo-C12-HSL
Molecular Formula
C16H27NO4
Formula Weight
297.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/ml
λmax
250 nm
SMILES
CCCCCCCCCC(=O)CC(=O)N[C@H]1CCOC1=O
InChi Code
InChI=1S/C16H27NO4/c1-2-3-4-5-6-7-8-9-13(18)12-15(19)17-14-10-11-21-16(14)20/h14H,2-12H2,1H3,(H,17,19)/t14-/m0/s1
InChi Key
PHSRRHGYXQCRPU-AWEZNQCLSA-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

    N-3-oxo-dodecanoyl-L-Homoserine lactone (3-oxo-C12-HSL) is a bacterial quorum-sensing signaling molecule produced by P. aeruginosa and strains of the B. cepacia complex.1,2 It induces the production of IL-8 in 16HBE human bronchial epithelial cells when used at a concentration of 100 µM.3 Supernatants from 3-oxo-C12-HSL-stimulated 16HBE cells induce chemotaxis of isolated human neutrophils. 3-oxo-C12-HSL has been found in respiratory secretions from patients with cystic fibrosis infected with P. aeruginosa.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Pearson, J.P., Gray, K.M., Passador, L., et al. Structure of the autoinducer required for expression of Pseudomonas aeruginosa virulence genes. Proc. Natl. Acad. Sci. USA 91(1), 197-201 (1994).

    2. Chambers, C.E., Visser, M.B., Schwab, U., et al. Identification of N-acylhomoserine lactones in mucopurulent respiratory secretions from cystic fibrosis patients. FEMS Microbiol. Lett. 244(2), 297-304 (2005).

    3. Smith, R.S., Fedyk, E.R., Springer, T.A., et al. IL-8 production in human lung fibroblasts and epithelial cells activated by the Pseudomonas autoinducer N-3-oxododecanoyl homoserine lactone is transcriptionally regulated by NF-κB and activator protein-2. J. Immunol. 167(1), 366-374 (2001).