A C8 quorum-sensing lactone
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N-3-hydroxyoctanoyl-L-Homoserine lactone

Item No. 9001150

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-hydroxy-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-octanamide
CAS Number
192883-14-0
Synonyms
  • OH-C8-HSL
Molecular Formula
C12H21NO4
Formula Weight
243.3
Purity
≥98%
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(O)CCCCC)=O)CCO1
InChi Code
InChI=1S/C12H21NO4/c1-2-3-4-5-9(14)8-11(15)13-10-6-7-17-12(10)16/h9-10,14H,2-8H2,1H3,(H,13,15)/t9?,10-/m0/s1
InChi Key
XCZVBYOXRSFQBH-AXDSSHIGSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $72

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    5 mg

    $258

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    10 mg

    $418

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    25 mg

    $783

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    Product Description

    Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. Different quorum sensing molecules are produced at different times in bacterial population growth and have distinct cellular effects mediated through changes in gene expression.1,2 N-3-hydroxyoctanoyl-L-Homoserine lactone is a small diffusible signaling molecule secreted by various bacteria.3,4 This lactone can have activating or suppressing effects on gene expression and biofilm formation, respectively.5,6 N-3-hydroxyoctanoyl-L-Homoserine lactone is produced via lactonolysis from 3-oxooctanoyl-homoserine lactone, altering quorum sensing or contributing to quorum quenching.7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kristiansen, S., Bjarnsholt, T., Adeltoft, D., et al. The Pseudomonas aeruginosa autoinducer dodecanoyl-homoserine lactone inhibits the putrescine synthesis in human cells. APMIS 116(5), 361-371 (2008).

    2. Huang, Y.L., Ki, J.S., Lee, O.O., et al. Evidence for the dynamics of acyl homoserine lactone and AHL-producing bacteria during subtidal biofilm formation. ISME J. 3(3), 296-304 (2008).

    3. Flodgaard, L.R., Dalgaard, P., Andersen, J.B., et al. Nonbioluminescent strains of Photobacterium phosphoreum produce the cell-to-cell communication signal N-(3-hydroxyoctanoyl)homoserine lactone. Appl. Environ. Microbiol. 71(4), 2113-2120 (2005).

    4. Lumjiaktase, P., Diggle, S.P., Loprasert, S., et al. Quorum sensing regulates dpsA and the oxidative stress response in Burkholderia pseudomallei. Microbiology (Reading) 152(Pt 12), 3651-3659 (2006).

    5. Duerkop, B.A., Herman, J.P., Ulrich, R.L., et al. The Burkholderia mallei BmaR3-BmaI3 quorum-sensing system produces and responds to N-3-hydroxy-octanoyl homoserine lactone. J. Bacteriol. 190(14), 5137-5141 (2008).

    6. Gamage, A.M., Shui, G., Wenk, M.R., et al. N-Octanoylhomoserine lactone signalling mediated by the BpsI-BpsR quorum sensing system plays a major role in biofilm formation of Burkholderia pseudomallei. Microbiology (Reading) 157(Pt 4), 1176-1186 (2011).

    7. Chan, K.G., Atkinson, S., Mathee, K., et al. Characterization of N-acylhomoserine lactone-degrading bacteria associated with the Zingiber officinale (ginger) rhizosphere: Co-existence of quorum quenching and quorum sensing in Acinetobacter and Burkholderia. BMC Microbiol. 11(51), 1-13 (2011).

    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).