An unusual, substituted, long-chain N-acyl-homoserine lactone
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N-3-oxo-hexadecanoyl-L-Homoserine lactone

Item No. 13062

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-hexadecanamide
CAS Number
925448-37-9
Synonyms
  • 3-oxo-C16-HSL
  • N-3-oxo-palmitoyl-L-Homoserine lactone
Molecular Formula
C20H35NO4
Formula Weight
353.5
Purity
≥97%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/ml
SMILES
O=C1[C@@H](NC(CC(CCCCCCCCCCCCC)=O)=O)CCO1
InChi Code
InChI=1S/C20H35NO4/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(22)16-19(23)21-18-14-15-25-20(18)24/h18H,2-16H2,1H3,(H,21,23)/t18-/m0/s1
InChi Key
YZBAMTUXUHIYCQ-SFHVURJKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $42

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    10 mg

    $79

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    25 mg

    $183

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    50 mg

    $303

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    Cayman Chemical
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    Product Description

    N-3-oxo-hexadecanoyl-L-Homoserine lactone is an unusual, substituted, long-chain N-acyl-homoserine lactone (AHL) produced by some bacteria, including strains of Agrobacterium vitis and Pseudomonas.1,2 Like other AHLs, this C16-containing form is thought to be involved in quorum sensing. Substituted, long-chain AHLs, including N-3-oxo-tetradecanoyl-L-homoserine lactone (Item No. 13063), prime for systemic acquired resistance to pathogen attack in plants.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chang, C.-Y., Koh, C.-L., Sam, C.-K., et al. Unusual long-chain N-acyl homoserine lactone production by and presence of quorum quenching activity in bacterial isolates from diseased tilapia fish. PLoS One 7(8), e44034 (2012).

    2. Savka, M.A., Le, P.T., and Burr, T.J. LasR receptor for detection of long-chain quorum-sensing signals: identification of N-acyl-homoserine lactones encoded by the avsI locus of Agrobacterium vitis. Curr. Microbiol. 62(1), 101-110 (2011).

    3. Schenk, S.T., and Schikora, A. AHL-priming functions via oxylipin and salicylic acid. Front. Plant Sci. 14(5), 784 (2015).