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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:
Molecular Weight:
241.28
MDL number:
UNSPSC Code:
12352202
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.32

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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
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)
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

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