Skip to Content
Merck
All Photos(1)

Documents

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

Sign Into View Organizational & Contract Pricing


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.

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
M I Moré et al.
Science (New York, N.Y.), 272(5268), 1655-1658 (1996-06-14)
Many bacteria, including several pathogens of plants and humans, use a pheromone called an autoinducer to regulate gene expression in a cell density-dependent manner. Agrobacterium autoinducer [AAI, N-(3-oxo-octanoyl)-L-homoserine lactone] of A. tumefaciens is synthesized by the Tral protein, which is
L Zhang et al.
Nature, 362(6419), 446-448 (1993-04-01)
Conjugal opines secreted by crown gall tumours induce strains of Agrobacterium tumefaciens that are donors of Ti plasmids to produce a diffusible conjugation factor. This enhances the conjugal transfer efficiency of the Ti plasmid in other strains of A. tumefaciens.
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)
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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service