10937
N-Tetradecanoyl-DL-homoserin-lacton
≥97.0% (HPLC)
Synonym(e):
N-Myristoyl-DL-homoserin-lacton
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Alle Fotos(1)
About This Item
Empirische Formel (Hill-System):
C18H33NO3
CAS-Nummer:
Molekulargewicht:
311.46
Beilstein:
1649579
MDL-Nummer:
UNSPSC-Code:
12352209
eCl@ss:
32160406
PubChem Substanz-ID:
NACRES:
NA.26
Empfohlene Produkte
product name
N-Tetradecanoyl-DL-homoserin-lacton, ≥97.0% (HPLC)
Assay
≥97.0% (HPLC)
Form
powder
Farbe
white to slightly yellow
Anwendung(en)
cell analysis
Lagertemp.
2-8°C
SMILES String
CCCCCCCCCCCCCC(=O)NC1CCOC1=O
InChI
1S/C18H33NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(20)19-16-14-15-22-18(16)21/h16H,2-15H2,1H3,(H,19,20)
InChIKey
ZQAYHOXXVBVXPZ-UHFFFAOYSA-N
Anwendung
Induziert die Expression von Violacein in einer Chromobacterium violaceum-Mutante, die kein Homoserinlacton produziert (Lit. K.H. McClean et al. Microbiology 143, 3703 (1997)
Biochem./physiol. Wirkung
N-Tetradecanoyl-DL-homoserine lactone (C14-HSL) is among a group of homoserine lactones that includes; N-Heptanoyl-DL-homoserine lactone (C7HSL), N-octanoyl-homoserine lactone (N-C8-HSL), N-Decanoyl-DL-homoserine lactone (N-C10-HSL), N-Dodecanoyl-DL-homoserine lactone (C12-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-Tetradecanoyl-DL-homoserine lactone is a member of N-acyl-homoserine lactone family. N-acylhomoserine lactones (AHL) regulate gene expression in gram-negative bacteria, such as Echerichia 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.
Lagerklassenschlüssel
11 - Combustible Solids
WGK
WGK 3
Flammpunkt (°F)
Not applicable
Flammpunkt (°C)
Not applicable
Persönliche Schutzausrüstung
Eyeshields, Gloves, type N95 (US)
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Francisco Pérez-Montaño et al.
Research in microbiology, 162(7), 715-723 (2011-05-24)
Legume-nodulating rhizobia use N-acyl homoserine lactones (AHLs) to regulate several physiological traits related to the symbiotic plant-microbe interaction. In this work, we show that Sinorhizobium fredii SMH12, Rhizobium etli ISP42 and Rhizobium sullae IS123, three rhizobial strains with different nodulation
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
Tomohiro Morohoshi et al.
FEMS microbiology letters, 279(1), 124-130 (2008-01-08)
In tests, Chromobacterium violaceum ATCC 12472 produced several N-acyl-L-homoserine lactones (AHLs). Of these, N-(3-hydroxydecanoyl)-L-homoserine lactone was dominant, and controlled violacein production by quorum sensing. Strain VIR07, an AHL-deficient mutant, did not produce violacein. Violacein production in VIR07 was induced by
Selvaraj Poonguzhali et al.
Journal of microbiology and biotechnology, 17(2), 226-233 (2007-12-07)
Members of Methylobacterium, referred as pink-pigmented facultative methylotrophic bacteria, are frequently associated with terrestrial and aquatic plants, tending to form aggregates on the phyllosphere. We report here that the production of autoinducer molecules involved in the cell-to-cell signaling process, which
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