N-3-Oxo-octanoyl-L-homoserine lactone

Names

[ Name ]:
N-3-Oxo-octanoyl-L-homoserine lactone

[Synonym ]:
Aai-OOHL
LAE
HSL-OOA
OOHL
N-(3-Oxooctanoyl)-L-homoserine lactone
3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]octanamide
3-Oxo-N-[(3S)-2-oxotetrahydro-3-furanyl]octanamide
Octanamide, 3-oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-
3-OXO-OCTANOIC ACID (2-OXO-TETRAHYDRO-FURAN-3-YL)-AMIDE

Biological Activity

[Description]:

N-3-Oxo-octanoyl-L-homoserine lactone, a quorum-sensing signal, is an Agrobacterium autoinducer[1][2].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Others >> Others

[In Vitro]

N-3-Oxo-octanoyl-L-homoserine lactone (3OC8-HSL) pretreatment (10 μM; for 2 days) exerts strong inhibitory effect on pathogen proliferation in the leaves[1]. Plants treated with N-3-Oxo-octanoyl-L-homoserine lactone shows increased activities of defense-related enzymes including peroxidase, catalase, phenylalanine ammonialyase, and superoxide dismutase[1].

[References]

[1]. Fang Liu, et al. N-3-oxo-octanoyl-homoserine lactone-mediated priming of resistance to Pseudomonas syringae requires the salicylic acid signaling pathway in Arabidopsis thaliana. BMC Plant Biol. 2020 Jan 28;20(1):38.

[2]. Hai-Bao Zhang, et al. Genetic control of quorum-sensing signal turnover in Agrobacterium tumefaciens. Proc Natl Acad Sci U S A

Chemical & Physical Properties

[ Density]:
1.12g/cm3

[ Boiling Point ]:
490.1ºC at 760mmHg

[ Melting Point ]:
96-97 ºC (ethyl acetate )

[ Molecular Formula ]:
C₁₂H₁₉NO₄

[ Molecular Weight ]:
241.28

[ Flash Point ]:
250.2ºC

[ Exact Mass ]:
241.131409

[ PSA ]:
72.47000

[ LogP ]:
1.73860

[ Appearance of Characters ]:
White solid Chemodex

[ Vapour Pressure ]:
9.41E-10mmHg at 25°C

[ Index of Refraction ]:
1.484

[ Storage condition ]:
-20°C

[ Water Solubility ]:
Slightly soluble (7.2 g/L) (25 ºC)

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

Articles

Medicinal chemistry as a conduit for the modulation of quorum sensing.

J. Med. Chem. 53 , 7467-89, (2010)

Evaluation of a focused library of N-aryl L-homoserine lactones reveals a new set of potent quorum sensing modulators.

Bioorg. Med. Chem. Lett. 18 , 5978-81, (2008)

A focused library of N-aryl l-homoserine lactones was designed around known lactone leads and evaluated for antagonistic and agonistic activity against quorum-sensing receptors in Agrobacterium tumefa...

Synthetic ligands that activate and inhibit a quorum-sensing regulator in Pseudomonas aeruginosa.

Bioorg. Med. Chem. Lett. 18 , 3072-5, (2008)

The transcription factor QscR is a regulator of quorum sensing in Pseudomonas aeruginosa and plays a role in controlling virulence in this prevalent opportunistic pathogen. This study outlines the dis...

Related Compounds

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