A bacterial quorum-sensing signaling molecule
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N-undecanoyl-L-Homoserine lactone

Item No. 16827

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(3S)-tetrahydro-2-oxo-3-furanyl]-undecanamide
CAS Number
216596-71-3
Synonyms
  • N-undecanoyl-L-HSL
  • C11-HSL
Molecular Formula
C15H27NO3
Formula Weight
269.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 25 mg/ml
SMILES
CCCCCCCCCCC(=O)N[C@H]1CCOC1=O
InChi Code
InChI=1S/C15H27NO3/c1-2-3-4-5-6-7-8-9-10-14(17)16-13-11-12-19-15(13)18/h13H,2-12H2,1H3,(H,16,17)/t13-/m0/s1
InChi Key
YAWJNUREPGJHSG-ZDUSSCGKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    25 mg

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    50 mg

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    Cayman Chemical
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    Product Description

    N-undecanoyl-L-Homoserine lactone is a bacterial quorum-sensing signaling molecule.1 It induces GFP production in an E. coli reporter strain expressing the V. fischeri LuxR-PluxI quorum-sensing operon when used at concentrations ranging from 100 to 1,000 nM. N-undecanoyl-L-Homoserine lactone also inhibits the proliferation of isolated mouse splenocytes induced by concanavalin A (Item No. 14951; IC50 = 90 µM).2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Syrpas, M., Ruysbergh, E., Stevens, C.V., et al. Synthesis and biological evaluation of novel N-α-haloacylated homoserine lactones as quorum sensing modulators. Beilstein J. Org. Chem. 10, 2539-2549 (2014).

    2. Chhabra, S.R., Harty, C., Hooi, D.S.W., et al. Synthetic analogues of the bacterial signal (quorum seensing) molecule N-(3-oxododecanoyl)-L-homoserine lactone as immune modulators. J. Med. Chem. 46(1), 97-104 (2003).

    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).