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N-Tetradecanoyl-DL-homoserin-lacton

≥97.0% (HPLC)

Synonym(e):

N-Myristoyl-DL-homoserin-lacton

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PackungsgrößeSKUVerfügbarkeitPreis
25 mg
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€ 211,00
€ 158,25

Über diesen Artikel

Empirische Formel (Hill-System):
C18H33NO3
CAS-Nummer:
Molekulargewicht:
311.46
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.26
Beilstein/REAXYS Number:
1649579
MDL number:

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Produktname

N-Tetradecanoyl-DL-homoserin-lacton, ≥97.0% (HPLC)

Quality Level

assay

≥97.0% (HPLC)

form

powder

color

white to slightly yellow

application(s)

cell analysis

storage temp.

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)

InChI key

ZQAYHOXXVBVXPZ-UHFFFAOYSA-N

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Dieser Artikel
17247K3007K3255
form

powder

form

powder

form

powder

form

-

assay

≥97.0% (HPLC)

assay

≥97.0% (HPLC)

assay

≥98%

assay

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

−20°C

Quality Level

100

Quality Level

100

Quality Level

200

Quality Level

400

color

white to slightly yellow

color

white to faint beige

color

white

color

-

application(s)

cell analysis

application(s)

-

application(s)

detection
peptide synthesis

application(s)

forensics and toxicology
pharmaceutical (small molecule)
veterinary

Application

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 Actions

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.

Lagerklasse

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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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
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
Thommie Karlsson et al.
Journal of leukocyte biology, 91(1), 15-26 (2011-08-03)
In gram-negative bacteria, cell-cell communication based on HSL QS molecules is known to coordinate the production of virulence factors and biofilms. These bacterial signals can also modulate human immune cell behavior. Using a Transwell migration assay, we found that human
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.

Global Trade Item Number

SKUGTIN
216135-125G04061835561674
216135-25G04061835561681
216135-5G04061838774231
497274-25G04061832417776
497274-5G04061832417783
10937-25MG04061838688330

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