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Merck

O1764

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

Key Documents

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Product Name

N-(3-Oxooctanoyl)-L-homoserine lactone, ≥97% (HPLC), white, powder

SMILES string

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

InChI key

FXCMGCFNLNFLSH-JTQLQIEISA-N

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

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

Quality Level

200

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.

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.

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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Certificates of Analysis (COA)

Lot/Batch Number
0000448128
0000448128
0000417048
0000417048
0000343677

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Developing Cyanobacterial Quorum Sensing Toolkits: Toward Interspecies Coordination in Mixed Autotroph/Heterotroph Communities
Kokarakis EJ, et al.
ACS Synthetic Biology, 12(1), 265-276 (2023)
J Zhu et al.
Journal of bacteriology, 180(20), 5398-5405 (1998-10-10)
The TraR and TraI proteins of Agrobacterium tumefaciens mediate cell-density-dependent expression of the Ti plasmid tra regulon. TraI synthesizes the autoinducer pheromone N-(3-oxooctanoyl)-L-homoserine lactone (3-oxo-C8-HSL), while TraR is an 3-oxo-C8-HSL-responsive transcriptional activator. We have compared the abilities of 3-oxo-C8-HSL and
Analogs of the autoinducer 3-oxooctanoyl-homoserine lactone strongly inhibit activity of the TraR protein of Agrobacterium tumefaciens
Zhu J, et al.
Journal of Bacteriology, 180(20), 5398-5405 (1998)
S Swift et al.
Molecular microbiology, 10(3), 511-520 (1993-11-01)
The pheromone N-(3-oxohexanoyl)-L-homoserine lactone (OHHL) regulates expression of bioluminescence in the marine bacterium Vibrio fischeri, the production of carbapenem antibiotic in Erwinia carotovora and exoenzymes in both E. carotovora and Pseudomonas aeruginosa. A characteristic feature of this regulatory mechanism in
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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