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94398

Sigma-Aldrich

2-Heptyl-3-hydroxy-4(1H)-quinolone

≥96.0% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C16H21NO2
CAS Number:
Molecular Weight:
259.34
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.25

Assay

≥96.0% (HPLC)

form

powder

storage temp.

−20°C

SMILES string

CCCCCCCC1=C(O)C(=O)c2ccccc2N1

InChI

1S/C16H21NO2/c1-2-3-4-5-6-11-14-16(19)15(18)12-9-7-8-10-13(12)17-14/h7-10,19H,2-6,11H2,1H3,(H,17,18)

InChI key

CEIUIHOQDSVZJQ-UHFFFAOYSA-N

General description

2-heptyl-3-hydroxy-4-quinolone can function as an intercellular signal.

Application

Quorum sensing is a signaling system used by bacteria to coordinate activity based upon their population density. The system involves the exchange of signaling molecules among bacteria via cell receptors. Heptyl-3-hydroxy-4(1H)-quinolone (PQS) is a quorum sensing-regulated virulence factor used to induce and study the regulation of virulence genes such as those involved in iron scavenging.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Hazard Statements

Hazard Classifications

Aquatic Chronic 4

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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Jintae Lee et al.
Microbial biotechnology, 2(1), 75-90 (2009-01-01)
Indole is an extracellular biofilm signal for Escherichia coli, and many bacterial oxygenases readily convert indole to various oxidized compounds including 7-hydroxyindole (7HI). Here we investigate the impact of indole and 7HI on Pseudomonas aeruginosa PAO1 virulence and quorum sensing
Doreen S W Hooi et al.
Infection and immunity, 72(11), 6463-6470 (2004-10-27)
Pseudomonas aeruginosa releases a spectrum of well-regulated virulence factors, controlled by intercellular communication (quorum sensing) and mediated through the production of small diffusible quorum-sensing signal molecules (QSSM). We hypothesize that QSSM may in fact serve a dual purpose, also allowing
Jin-Hyung Lee et al.
Environmental microbiology, 13(1), 62-73 (2010-07-24)
Intercellular signal indole and its derivative hydroxyindoles inhibit Escherichia coli biofilm and diminish Pseudomonas aeruginosa virulence. However, indole and bacterial indole derivatives are unstable in the microbial community because they are quickly degraded by diverse bacterial oxygenases. Hence, this work
Jin-Hyung Lee et al.
FEMS microbiology letters, 329(1), 36-44 (2012-01-19)
The emergence of antibiotic resistance has necessitated new therapeutic approaches for combating persistent bacterial infection. An alternative approach is regulation of bacterial virulence instead of growth suppression, which can readily lead to drug resistance. The virulence of the opportunistic human
Monique Donnert et al.
PLoS pathogens, 16(12), e1009126-e1009126 (2020-12-23)
Embedded in an extracellular matrix, biofilm-residing bacteria are protected from diverse physicochemical insults. In accordance, in the human host the general recalcitrance of biofilm-grown bacteria hinders successful eradication of chronic, biofilm-associated infections. In this study, we demonstrate that upon addition

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