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:
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.
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 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
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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
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
J Zhu et al.
Proceedings of the National Academy of Sciences of the United States of America, 96(9), 4832-4837 (1999-04-29)
TraR is an Agrobacterium transcriptional regulator whose activity requires the pheromone N-3-oxooctanoyl-L-homoserine lactone. TraR was purified as a complex with the pheromone and contained one pheromone molecule per protein monomer. TraR-pheromone complexes bound to a single DNA site and activated
Siqing Xia et al.
Journal of environmental sciences (China), 24(12), 2035-2040 (2012-01-01)
N-acyl-homoserines quenching, enzymatic quenching of bacterial quorum sensing, has recently applied to mitigate biofilm in membrane bioreactor. However, the effect of AHLs on the behavior of biofilm formation is still sparse. In this study, Pseudomonas aeruginosa biofilm was formed on
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