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Safety Information

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:
108985-27-9
Molecular Weight:
259.34
MDL number:
MFCD07437949
UNSPSC Code:
12352005
PubChem Substance ID:
329770333
NACRES:
NA.25

Quality Level

100

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

H413

Hazard Classifications

Aquatic Chronic 4

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

94398-BULK:
94398-VAR:
94398-10MG:

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’.

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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
Stephen P Diggle et al.
Chemistry & biology, 14(1), 87-96 (2007-01-27)
Pseudomonas aeruginosa produces 2-heptyl-3-hydroxy-4(1H)-quinolone (PQS), a quorum-sensing (QS) signal that regulates numerous virulence genes including those involved in iron scavenging. Biophysical analysis revealed that 2-alkyl-3-hydroxy-4-quinolones form complexes with iron(III) at physiological pH. The overall stability constant of 2-methyl-3-hydroxy-4-quinolone iron(III) complex
E C Pesci et al.
Proceedings of the National Academy of Sciences of the United States of America, 96(20), 11229-11234 (1999-09-29)
Numerous species of bacteria use an elegant regulatory mechanism known as quorum sensing to control the expression of specific genes in a cell-density dependent manner. In Gram-negative bacteria, quorum sensing systems function through a cell-to-cell signal molecule (autoinducer) that consists
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
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
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