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Sigma-Aldrich

cis-2-Decenoic acid

≥95.0% (HPLC)

Synonym(s):

2-Decenoic acid, (2Z)-

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About This Item

Empirical Formula (Hill Notation):
C10H18O2
CAS Number:
Molecular Weight:
170.25
Beilstein:
1721990
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
NACRES:
NA.25

Quality Level

Assay

≥95.0% (HPLC)
95.0-105.0% (T)

form

liquid

functional group

carboxylic acid

lipid type

unsaturated FAs

storage temp.

−20°C

SMILES string

CCCCCCC\C=C/C(O)=O

InChI

1S/C10H18O2/c1-2-3-4-5-6-7-8-9-10(11)12/h8-9H,2-7H2,1H3,(H,11,12)/b9-8-

InChI key

WXBXVVIUZANZAU-HJWRWDBZSA-N

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Application

cis-2-Decenoic acid may be used to study its cytotoxic effect on the human HepG2 cell line. It has also been used to study its synergistic anti-spirochetal effect.

Biochem/physiol Actions

cis-2-Decenoic acid is a fatty acid messenger (signaling molecule) produced by Pseudomonas aeruginosa. It possesses anti-biofilm property and converts most of the cells to planktonic (free-swimming) phenotype. cis-2-Decenoic acid retains the susceptibility of the bacteria towards antimicrobial agents. It does not exhibit any toxicity towards human cells and thus, might be used for treating biofilm-associated infections. cis-2-Decenoic acid is considered active even in nano-molar ranges. It mediates the transition of dormant P. aeruginosa and Escherichia coli to their biologically active state without affecting the number of cells. cis-2-Decenoic acid is effective against E. coli and Klebsiella pneumoniae mixed-species biofilms when used along with antimicrobial agents.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Aquatic Chronic 3 - Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 1


Certificates of Analysis (COA)

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Majed Alrobaian et al.
Molecules (Basel, Switzerland), 24(10) (2019-05-28)
Two series of novel 5-arylazo-3-cyano-2-(2″,3″,4″,6″-tetra-O-acetyl-β-d-galacto pyranosyloxy) pyridines and 3-cyano-2-(2″,3″,4″,6″-tetra-O-acetyl-β-d-galactopyranosyloxy) pyridines were synthesized in high yields utilizing a microwave-assisted synthesis tool guided by the principles of green chemistry. The chemical structures of the new substances were confirmed on the basis of
Martha María Juárez-Rodríguez et al.
Frontiers in cellular and infection microbiology, 10, 597517-597517 (2021-02-16)
Blocking virulence is a promising alternative to counteract Pseudomonas aeruginosa infections. In this regard, the phenomenon of cell-cell communication by quorum sensing (QS) is an important anti-virulence target. In this field, fatty acids (FA) have gained notoriety for their role
Han-Shin Kim et al.
Biotechnology and bioengineering, 118(1), 82-93 (2020-09-04)
Bacterial biofilm formation causes serious problems in various fields of medical, clinical, and industrial settings. Antibiotics and biocide treatments are typical methods used to remove bacterial biofilms, but biofilms are difficult to remove effectively from surfaces due to their increased
A Goc et al.
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Thomas Tørring et al.
Chembiochem : a European journal of chemical biology, 18(7), 638-646 (2017-01-25)
Legionella pneumophila, the causative agent of Legionnaires' disease, is a Gram-negative gammaproteobacterial pathogen that infects and intracellularly replicates in human macrophages and a variety of protozoa. L. pneumophila encodes an orphan biosynthetic gene cluster (BGC) that contains isocyanide-associated biosynthetic genes and

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