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

Boiling point:

569.7±50.0 °C(Predicted)

Density 

1.06±0.1 g/cm3(Predicted)

storage temp. 

Store at -20°C

solubility 

DMF: 20 mg/ml; DMSO: 20 mg/ml; DMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml

pka

14.22±0.20(Predicted)

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

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

Definition

ChEBI: N-(3-Hydroxy-7-cis-tetradecenoyl)homoserine lactone is a N-acyl-amino acid.

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 Sj?vall, 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).