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
Quality Level
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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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.
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
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)
Quorum-sensing molecules: Sampling, identification and characterization of N-acyl-homoserine lactone in Vibrio sp
Laj N, et al.
Saudi Journal of Biological Sciences, 29(4), 2733-2737 (2022)
Z Q Luo et al.
The Journal of biological chemistry, 275(11), 7713-7722 (2000-03-14)
Conjugal transfer of Agrobacterium tumefaciens Ti plasmids is regulated by quorum sensing via the transcriptional activator TraR and the acyl-homoserine lactone Agrobacterium autoinducer (AAI). Unique to this system, the activity of TraR is negatively modulated by an antiactivator called TraM.
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