A bacterial quorum sensing signal molecule
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N-phenylacetyl-L-Homoserine lactone

Item No. 9001737

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(3S)-tetrahydro-2-oxo-3-furanyl]-benzeneacetamide
CAS Number
55154-48-8
Synonyms
  • C8-HSL
  • N-phenylacetyl-L-HSL
Molecular Formula
C12H13NO3
Formula Weight
219.2
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): 0.1 mg/ml
SMILES
O=C1[C@@H](NC(CC2=CC=CC=C2)=O)CCO1
InChi Code
InChI=1S/C12H13NO3/c14-11(8-9-4-2-1-3-5-9)13-10-6-7-16-12(10)15/h1-5,10H,6-8H2,(H,13,14)/t10-/m0/s1
InChi Key
YJTHUPUWKQRCLF-JTQLQIEISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $69

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    5 mg

    $297

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    10 mg

    $525

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    25 mg

    $1,146

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    Product Description

    N-phenylacetyl-L-Homoserine lactone is a small diffusible signaling molecule involved in quorum sensing in the model symbiont V. fischeri and the pathogens A. tumefaciens and P. aeruginosa.1,2 It has been reported to antagonize TraR signaling in A. tumefaciens, LasR signaling in E. coli, and LuxR signaling in V. fischeri.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Geske, G.D., O'Neill, J.C., Miller, D.M., et al. Modulation of bacterial quorum sensing with synthetic ligands: Systematic evaluation of N-acylated homoserine lactones in multiple species and new insights into their mechanisms of action. J. Am. Chem. Soc. 129, 13613-13625 (2007).

    2. Geske, G.D., Wezeman, R.J., Siegel, A.P., et al. Small molecule inhibitors of bacterial quorum sensing and biofilm formation. J. Am. Chem. Soc. 127(37), 12762-12763 (2005).

    3. Geske, G.D., O'Neill, J.C., Miller, D.M., et al. Comparative analyses of N-acylated homoserine lactones reveal unique structural features that dictate their ability to activate or inhibit quorum sensing. Chembiochem 9(3), 389-400 (2008).