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N-(3-hydroxy-7-cis tetradecenoyl)-L-Homoserine lactone

Item No. 9002939

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-hydroxy-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-7Z-tetradecenamide
CAS Number
273734-65-9
Synonyms
  • N-(3-hydroxy-7-cis tetradecenoyl)-L-HSL
Molecular Formula
C18H31NO4
Formula Weight
325.4
Purity
≥95%
Formulation (Request formulation change)
A 5 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml
SMILES
O=C1[C@@H](NC(CC(O)CCC/C=C\CCCCCC)=O)CCO1
InChi Code
InChI=1S/C18H31NO4/c1-2-3-4-5-6-7-8-9-10-11-15(20)14-17(21)19-16-12-13-23-18(16)22/h7-8,15-16,20H,2-6,9-14H2,1H3,(H,19,21)/b8-7-/t15?,16-/m0/s1
InChi Key
GFSFGXWHLLUVRK-UPVLWJCGSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    N-(3-hydroxy-7-cis tetradecenoyl)-L-Homoserine lactone is a long-chain N-acyl-homoserine lactone (AHL) produced by some Gram-negative bacteria and is involved in quorum sensing.1 Quorum sensing enables bacteria to change gene expression based on cues from nearby bacteria and from eukaryotic hosts about nutrients, environmental conditions, or threats.2 Due to the benefit of quorum sensing for bacterial survival, quorum sensing molecules are potential targets for controlling bacterial infections.3 In mouse and human leukocyte immunoassays using LPS-stimulated macrophages, N-(3-hydroxy-7-cis tetradecenoyl)-L-homoserine lactone did not have an effect on cytokine or antibody production.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Laue, B.E., Jiang, Y., Chhabra, S.R., et al. The biocontrol strain Pseudomonas fluorescens F113 produces the Rhizobium small bacteriocin, N-(3-hydroxy-7-cis-tetradecenoyl)homoserine lactone, via HdtS, a putative novel N-acylhomoserine lactone synthase. Microbiology 146 (Pt. 10), 2469-2480 (2000).

    2. Williams, P. Quorum sensing, communication and cross-kingdom signalling in the bacterial world. Microbiology 153 (Pt 12), 3923-3938 (2007).

    3. Meng, L.J., and Sjövall, J. Method for combined analysis of profiles of conjugated progesterone metabolites and bile acids in serum and urine of pregnant women. J. Chromatogr. B Biomed. Sci. Appl. 688(1), 11-26 (1997).

    4. Telford, G., Wheeler, D., Williams, P., et al. The Pseudomonas aeruginosa quorum-sensing signal molecule N-(3-oxododecanoyl)-L-homoserine lactone has immunomodulatory activity. Infect. Immun. 66(1), 36-42 (1998).