An internal standard for the quantification of N-butyryl-L-homoserine lactone
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Unlabeled Version(s)
10007898N-butyryl-L-Homoserine lactone
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N-butyryl-L-Homoserine lactone-d5

Item No. 10007899

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(3S)-tetrahydro-2-oxo-3-furanyl]-butanamide-3,3,4,4,4-d5
CAS Number
2701379-46-4
Synonyms
  • BHL-d5
  • C4-HSL-d5
  • PAI-2-d5
Molecular Formula
C8H8D5NO3
Formula Weight
176.2
Purity
≥99% deuterated forms (d1-d5)
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlPBS (pH 7.2): 10 mg/ml
SMILES
CCCC(=O)N[C@H]1CCOC1=O
InChi Code
InChI=1S/C8H13NO3/c1-2-3-7(10)9-6-4-5-12-8(6)11/h6H,2-5H2,1H3,(H,9,10)/t6-/m0/s1/i1D3,2D2
InChi Key
VFFNZZXXTGXBOG-PLFILOGFSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

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    Cayman Chemical
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    Product Description

    N-butyryl-L-Homoserine lactone-d5 is intended for use as an internal standard for the quantification of N-butyryl-L-homoserine lactone (Item No. 10007898) by GC- or LC-MS. N-butyryl-L-Homoserine lactone is a quorum-sensing signaling molecule produced by P. aeruginosa.1 It induces expression of the virulence genes lasB and rhlA in P. aeruginosa when used at a concentration of 10 µM.2 N-butyryl-L-Homoserine lactone (50 µM) induces rhamnolipid accumulation in P. aeruginosa growth media.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Pearson, J.P., Passador, L., Igleweski, B.H., et al. A second N-acylhomoserine lactone signal produced by Pseudomonas aeruginosa. Proc. Natl. Acad. Sci. USA 92(5), 1490-1494 (1995).

    2. Ikeda, T., Kajiyama, K., Kita, T., et al. The synthesis of optically pure enantiomers of N-acyl-homoserine lactone autoinducers and their analogues. Chem. Lett. 30(4), 314-315 (2001).

    3. Schooling, S.R., Charaf, U.K., Allison, D.G., et al. A role for rhamnolipid in biofilm dispersion. Biofilm 1(2), 91-99 (2004).