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09926

Sigma-Aldrich

N-Hexanoyl-DL-homoserine lactone

≥97.0% (HPLC)

Sinônimo(s):

N-Caproyl-DL-homoserine lactone

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About This Item

Fórmula empírica (Notação de Hill):
C10H17NO3
Número CAS:
106983-28-2
Peso molecular:
199.25
Beilstein:
1640340
Número MDL:
MFCD01862908
Código UNSPSC:
12352209
eCl@ss:
32160406
ID de substância PubChem:
329748862
NACRES:
NA.26

Nível de qualidade

100

Ensaio

≥97.0% (HPLC)

forma

powder or crystals

técnica(s)

LC/MS: suitable

cor

white to faint beige

pf

101-106 °C

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

CCCCCC(=O)NC1CCOC1=O

InChI

1S/C10H17NO3/c1-2-3-4-5-9(12)11-8-6-7-14-10(8)13/h8H,2-7H2,1H3,(H,11,12)

chave InChI

ZJFKKPDLNLCPNP-UHFFFAOYSA-N

Categorias relacionadas

Aplicação

Induces violacein expression in a Chromobacterium violaceum mutant usually not able to produce homoserine lactones.

Ações bioquímicas/fisiológicas

N-Hexanoyl-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 and are involved in quorum sensing, cell to cell communication among bacteria. Some AHLs are potent chemoattractants for human immune cells such as neutrophils.
Quorum-sensing signal generation

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)

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Albert Soler et al.
International journal of environmental research and public health, 15(5) (2018-05-23)
Quorum sensing (QS) is a mechanism dependent on bacterial density. This coordinated process is mediated by the synthesis and the secretion of signal molecules, called autoinducers (AIs). N-acyl-homoserine lactones (AHLs) are the most common AIs that are used by Gram-negative
Daniel Wynn et al.
The Analyst, 143(19), 4774-4782 (2018-09-15)
There are an estimated 48 million cases of foodborne illness in the United States every year. In general, these illnesses are the result of unintentional contamination and improper food handling. Because bacterial contamination plays a major role in food spoilage
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
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
Robert Czajkowski et al.
Acta biochimica Polonica, 56(1), 1-16 (2009-03-17)
Many Gram-positive and Gram-negative bacteria communicate using small diffusible signal molecules called autoinducers. This process, known as quorum sensing (QS), links cell density to the expression of genes as diverse as those associated with virulence factors production of plant and
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