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O1764

N-(3-Oxooctanoyl)-L-homoserine lactone

Name: N-(3-Oxooctanoyl)-L-homoserine lactone
Brand: SIGMA

≥97% (HPLC), white, powder

Synonym(s):

3-oxo-C8-HSL, 3OC8-HSL, N-(β-Ketooctanoyl)-L-homoserine

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About This Item

Empirical Formula (Hill Notation):

C₁₂H₁₉NO₄

CAS Number:

147795-39-9

Molecular Weight:

241.28

UNSPSC Code:

12352202

eCl@ss:

32160406

PubChem Substance ID:

24897950

NACRES:

NA.32

MDL number:

MFCD08277025

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Properties

Quality Level

200

assay

≥97% (HPLC)

form

powder

mol wt

241.28

technique(s)

protein expression: suitable

color

white

solubility

chloroform: 50 mg/mL, clear, colorless

shipped in

wet ice

storage temp.

−20°C

SMILES string

CCCCCC(=O)CC(=O)N[C@H]1CCOC1=O

InChI

1S/C12H19NO4/c1-2-3-4-5-9(14)8-11(15)13-10-6-7-17-12(10)16/h10H,2-8H2,1H3,(H,13,15)/t10-/m0/s1

InChI key

FXCMGCFNLNFLSH-JTQLQIEISA-N

Description

General description

N-(3-Oxooctanoyl)-L-homoserine lactone is a common quorum sensing (QS) signal.
It is a signaling molecule that is produced by Gram negative bacteria.

Application

N-(3-Oxooctanoyl)-L-homoserine lactone has been used:

to study the effects of pH, temperature, and salinity on extracellular polymeric substances (EPS) of Pseudomonas aeruginosa biofilm.
as an AHL inducer to activate the quorum sensing pathways in Synechococcus elongatus.

Biochem/physiol Actions

N-(3-Oxooctanoyl)-L-homoserine lactone stimulates the tra gene expression. It is an autoinducer and potent antagonist.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Effects of pH, Temperature and Salinity on Extracellular Polymeric
Substances of Pseudomonasaeruginosa Biofilm with
N-(3-Oxooxtanoyl)-L-Homoserine Lactone Addition

Lijie Zhou

J. Water Res. (2014)

The crystal structure of the quorum sensing protein TraR bound to its autoinducer and target DNA.

Alessandro Vannini et al.

The EMBO journal, 21(17), 4393-4401 (2002-08-29)

The quorum sensing system allows bacteria to sense their cell density and initiate an altered pattern of gene expression after a sufficient quorum of cells has accumulated. In Agrobacterium tumefaciens, quorum sensing controls conjugal transfer of the tumour- inducing plasmid

Crystallization and preliminary X-ray diffraction studies of the transcriptional regulator TraR bound to its cofactor and to a specific DNA sequence.