N-3-oxo-dodecanoyl-L-homoserine lactone

Names

[ Name ]:
N-3-oxo-dodecanoyl-L-homoserine lactone

[Synonym ]:
Dodecanamide, 3-oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-
OHN
3-oxo-C12-HSL
3-oxo-C12-AHL
3-Oxo-N-[(3S)-2-oxotetrahydro-3-furanyl]dodecanamide

Biological Activity

[Description]:

N-3-oxo-dodecanoyl-L-Homoserine lactone (3-oxo-C12-HSL) is a bacterial quorum-sensing signaling molecule produced by P. aeruginosa and strains of the B. cepacia complex[1][2].Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density.N-3-oxo-dodecanoyl-L-Homoserine lactone induces the production of IL-8 in 16HBE human bronchial epithelial cells[3].

[Related Catalog]:

Research Areas >> Others

Signaling Pathways >> Anti-infection >> Bacterial

[References]

[1]. Pearson JP, Gray KM, Passador L, Tucker KD, Eberhard A, Iglewski BH, Greenberg EP. Structure of the autoinducer required for expression of Pseudomonas aeruginosa virulence genes. Proc Natl Acad Sci U S A. 1994 Jan 4;91(1):197-201.

[2]. Chambers CE, Visser MB, Schwab U, Sokol PA. Identification of N-acylhomoserine lactones in mucopurulent respiratory secretions from cystic fibrosis patients. FEMS Microbiol Lett. 2005 Mar 15;244(2):297-304.

[3]. Smith RS, Fedyk ER, Springer TA, Mukaida N, Iglewski BH, Phipps RP. IL-8 production in human lung fibroblasts and epithelial cells activated by the Pseudomonas autoinducer N-3-oxododecanoyl homoserine lactone is transcriptionally regulated by NF-kappa B a

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
519.4±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₆H₂₇NO₄

[ Molecular Weight ]:
297.390

[ Flash Point ]:
267.9±30.1 °C

[ Exact Mass ]:
297.194000

[ PSA ]:
72.47000

[ LogP ]:
2.02

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.484

[ Storage condition ]:
-20°C

Safety Information

[ Hazard Codes ]:
Xn

[ HS Code ]:
2932209090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932209090

[ Summary ]:
2932209090. other lactones. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%