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

Item No. 13026

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-decanamide
CAS Number
147795-40-2
Synonyms
  • N-3-oxo-decanoyl-L-HSL
Molecular Formula
C14H23NO4
Formula Weight
269.3
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/ml
SMILES
O=C1[C@@H](NC(CC(CCCCCCC)=O)=O)CCO1
InChi Code
InChI=1S/C14H23NO4/c1-2-3-4-5-6-7-11(16)10-13(17)15-12-8-9-19-14(12)18/h12H,2-10H2,1H3,(H,15,17)/t12-/m0/s1
InChi Key
KYGIKEQVUKTKRR-LBPRGKRZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    5 mg

    $42

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    50 mg

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    Cayman Chemical
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    Product Description

    N-3-oxo-decanoyl-L-Homoserine lactone is a quorum-sensing signaling molecule that is produced by bacteria in response to increasing cell density.1 It increases expression of the bacterial conjugation gene tra in A. tumefaciens in a reporter cell assay. N-3-oxo-decanoyl-L-Homoserine lactone (100 nM) induces adventitious root formation and increases expression of the auxin-response genes AUX22c and AUX22d and the cell division genes CDC2, ARC, and CDPK in mung bean seedlings.2 It decreases expression of glucanase genes in A. thaliana when used at a concentration of 6 µM.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Zhang, L., Murphy, P.J., Kerr, A., et al. Agrobacterium conjugation and gene regulation by N-acyl-L-homoserine lactones. Nature 362(6419), 446-448 (1993).

    2. Bai, X., Todd, C.D., Desikan, R., et al. N-3-oxo-decanoyl-L-homoserine-lactone activates auxin-induced adventitious root formation via hydrogen peroxide- and nitric oxide-dependent cyclic GMP signaling in mung bean. Plant Physiol. 158(2), 725-736 (2012).

    3. Schenk, S.T., Hernández-Reyes, C., Samans, B., et al. N-acyl-homoserine lactone primes plants for cell wall reinforcement and induces resistance to bacterial pathogens via the salicylic acid/oxylipin pathway. Plant Cell 26(6), 2708-2723 (2014).