10939
N-Heptanoyl-DL-homoserine lactone
≥97.0% (HPLC)
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About This Item
Empirical Formula (Hill Notation):
C11H19NO3
CAS Number:
Molecular Weight:
213.27
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.26
MDL number:
Product Name
N-Heptanoyl-DL-homoserine lactone, ≥97.0% (HPLC)
SMILES string
CCCCCCC(=O)NC1CCOC1=O
InChI
1S/C11H19NO3/c1-2-3-4-5-6-10(13)12-9-7-8-15-11(9)14/h9H,2-8H2,1H3,(H,12,13)
InChI key
FTMZLSDESAOPSZ-UHFFFAOYSA-N
assay
≥97.0% (HPLC)
form
powder with small lumps
color
white to faintly brown
storage temp.
−20°C
Related Categories
Application
Application test: Induces violacein expression in a Chromobacterium violaceum mutant usually not able to produce homoserine lactones.
Biochem/physiol Actions
N-Heptanoyl-DL-homoserine lactone (C7HSL) is among a group of homoserine lactones that includes; N-octanoyl-homoserine lactone (N-C8-HSL), N-Decanoyl-DL-homoserine lactone (N-C10-HSL), N-(3-oxodecanoyl) homoserine-L-lactone (3-oxo-C10 HSL), N-(3-oxododecanoyl)homoserine-L-lactone (3-oxo-C12-HSL), N-(3-Oxotetradecanoyl)-L-homoserine lactone (3-oxo-C14-HSL, N-(3-hydroxydecanoyl)-L-homoserine lactone, and N-(3-hydroxyoctanoyl)-L-homoserine lactone involved in the processes of bacterial quorum sensing. These N-acyl-homoserine lactones are used to study the processes and mechanisms of bacterial quorum sensing.
N-Heptanoyl-DL-homoserine lactone is a member of N-acyl-homoserine lactone family. N-acylhomoserine lactones (AHL) regulate gene expression in gram-negative bacteria, such asEcherichia and Salmonella are involved in quorum sensing, cell to cell communication among bacteria. Some AHLs are potent chemoattractants for human immune cells such as neutrophils.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Armando M Pomini et al.
Journal of natural products, 71(6), 1032-1036 (2008-05-10)
(S)-N-Heptanoylhomoserine lactone is an uncommon acyl odd-chain natural product employed by many Gram-negative bacteria as a signaling substance in chemical communication mechanisms known as quorum sensing. The absolute configuration determination of the metabolite produced by the phytopathogen Pantoea ananatis Serrano
Detection of acyl-homoserine lactones by Escherichia and Salmonella.
Soares JA, Ahmer BM.
Current Opinion in Microbiology, 12, 188-193 (2011)
Frank Wilco Bartels et al.
Biophysical journal, 92(12), 4391-4400 (2007-03-27)
Intercellular communication by means of small signal molecules coordinates gene expression among bacteria. This population density-dependent regulation is known as quorum sensing. The symbiotic nitrogen-fixing bacterium Sinorhizobium meliloti Rm1021 possesses the Sin quorum sensing system based on N-acyl homoserine lactones
Ali E McClean et al.
Phytopathology, 102(2), 195-203 (2012-01-13)
Several members of the bacterial genus Brenneria are pathogenic on different tree species. Cell-free extracts from the bacterial phytopathogens Brenneria rubrifaciens, B. salicis, and B. nigrifluens induced production of the red pigment rubrifacine in the B. rubrifaciens bruI insertional mutant
Joanne Hothersall et al.
Applied microbiology and biotechnology, 90(3), 1017-1026 (2011-02-15)
Transcription of the 74 kb Pseudomonas fluorescens mupirocin [pseudomonic acid (PA)] biosynthesis cluster depends on quorum sensing-dependent regulation via the LuxI/LuxR homologues MupI/MupR. To facilitate analysis of novel PAs from pathway mutants, we investigated factors that affect mup gene expression.
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