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O1764

Sigma-Aldrich

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

≥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
MDL number:
MFCD08277025
UNSPSC Code:
12352202
eCl@ss:
32160406
PubChem Substance ID:
24897950
NACRES:
NA.32

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

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.

also commonly purchased with this product

Product No.
Description
Pricing

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Alessandro Vannini et al.
Acta crystallographica. Section D, Biological crystallography, 58(Pt 8), 1362-1364 (2002-07-24)
TraR is an Agrobacterium tumefaciens transcriptional regulator which binds the pheromone N-3-oxooctanoyl-L-homoserine lactone (AAI) in response to the bacterial population density. The TraR-AAI complex dimerizes and interacts with a specific 18-base-pair DNA sequence (TraBox), activating promoters containing this site. TraR
Z Q Luo et al.
Journal of bacteriology, 183(13), 3919-3930 (2001-06-08)
Conjugal transfer of Agrobacterium tumefaciens Ti plasmids is regulated by quorum sensing via TraR and its cognate autoinducer, N-(3-oxo-octanoyl)-L-homoserine lactone. We isolated four Tn5-induced mutants of A. tumefaciens C58 deficient in TraR-mediated activation of tra genes on pTiC58DeltaaccR. These mutations
Kayode K Ojo et al.
The Journal of antimicrobial chemotherapy, 57(6), 1065-1069 (2006-03-23)
To determine whether mef(A)-msr(D) and tet(M) genes are linked in representative Gram-negative isolates and/or transferred together during conjugation. To molecularly characterize the Acinetobacter junii element and compare the structure and sequence with the non-conjugative Streptococcus pneumoniae Tn2009 element. PCR assays
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
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)
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