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

Item No. 13201

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-pentanamide
CAS Number
148433-21-0
Synonyms
  • 3-oxo-C5-HSL
Molecular Formula
C9H13NO4
Formula Weight
199.2
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/ml
SMILES
O=C(CC(CC)=O)N[C@H]1CCOC1=O
InChi Code
InChI=1S/C9H13NO4/c1-2-6(11)5-8(12)10-7-3-4-14-9(7)13/h7H,2-5H2,1H3,(H,10,12)/t7-/m0/s1
InChi Key
SCRBQXWVQAXYJP-ZETCQYMHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $36

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    5 mg

    $128

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    10 mg

    $203

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    25 mg

    $378

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    Cayman Chemical
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    Product Description

    N-3-oxo-pentanoyl-L-Homoserine lactone is a chain-shortened derivative of the bacterial quorum sensing signaling molecule N-3-oxo-octanoyl-L-homoserine lactone (Item No. 10011206).1 It inhibits binding of the autoinducer N-3-oxo-hexanoyl homoserine lactone to E. coli containing the transcription factor LuxR when used at a concentration of 230 nM.2 It acts as an autoinducer to activate the V. fischeri luminescence system in E. coli when used at concentrations ranging from 20 to 200 nM.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chhabra, S.R., Stead, P., Bainton, N.J., et al. Autoregulation of carbapenem biosynthesis in Erwinia carotovora by analogues of N-(3-oxohexanoyl)-L-homoserine lactone. J. Antibiot. (Tokyo) 46(3), 441-454 (1993).

    2. Schaefer, A.L., Hanzelka, B.L., Eberhard, A., et al. Quorum sensing in Vibrio fischeri: Probing autoinducer-LuxR interactions with autoinducer analogs. J. Bacteriol. 178(10), 2897-2901 (1996).