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Merck

44558

Sigma-Aldrich

N-Octanoyl-L-homoserine lactone

≥96% (HPLC)

Sinónimos:

N-[(3S)-Tetrahydro-2-oxo-3-furanyl]octanamide, C8-HSL

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About This Item

Fórmula empírica (notación de Hill):
C12H21NO3
Número de CAS:
Peso molecular:
227.30
Beilstein:
8148282
Número MDL:
Código UNSPSC:
12352211
ID de la sustancia en PubChem:
NACRES:
NA.85

Nombre del producto

N-Octanoyl-L-homoserine lactone, ≥96% (HPLC)

Nivel de calidad

Ensayo

≥96% (HPLC)

Formulario

powder or crystals

actividad óptica

[α]/D -28±3°, c = 0.2 in methanol

color

white to off-white

idoneidad

conforms to structure for Proton NMR spectrum

aplicaciones

detection

temp. de almacenamiento

−20°C

cadena SMILES

O=C1OCC[C@@H]1NC(CCCCCCC)=O

InChI

1S/C12H21NO3/c1-2-3-4-5-6-7-11(14)13-10-8-9-16-12(10)15/h10H,2-9H2,1H3,(H,13,14)/t10-/m0/s1

Clave InChI

JKEJEOJPJVRHMQ-JTQLQIEISA-N

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Acciones bioquímicas o fisiológicas

N-Octanoyl-L-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, colonization, chemical defense and cell to cell communication among bacteria; for reviews see. AHLs are released as oligopeptides in Gram positive bacteria and as quorum signal in Gram negative bacteria. Bacterial intercellular communication has become a target for the development of new anti-virulence drugs, and a research focus for the prevention of biofilm formation.
Quorum-sensing signal generation

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable


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A Kuo et al.
Journal of bacteriology, 178(4), 971-976 (1996-02-01)
Population density-dependent expression of luminescence in Vibrio fischeri is controlled by the autoinducer N-3-oxohexanoyl-L-homoserine lactone (autoinducer 1 [AI-1]), which via LuxR activates transcription of the lux operon (luxICDABEG, encoding the putative autoinducer synthase [LuxI] and the luminescence enzymes). We recently
Suman C, et al.
Cannabis sativa L.- Botany and Biotechnology (2017)
J B Andersen et al.
Applied and environmental microbiology, 67(2), 575-585 (2001-02-07)
In order to perform single-cell analysis and online studies of N-acyl homoserine lactone (AHL)-mediated communication among bacteria, components of the Vibrio fischeri quorum sensor encoded by luxR-P(luxI) have been fused to modified versions of gfpmut3* genes encoding unstable green fluorescent
Mattia Marenda et al.
Scientific reports, 6, 39142-39142 (2016-12-15)
Bacterial communities undergo collective behavioural switches upon producing and sensing diffusible signal molecules; a mechanism referred to as Quorum Sensing (QS). Exemplarily, biofilm organic matrices are built concertedly by bacteria in several environments. QS scope in bacterial ecology has been
Xiaoxiang Liu et al.
International journal of food microbiology, 270, 31-38 (2018-02-23)
Microorganism activities are considered the main cause of most food spoilage, leading to great economic losses. Pseudomonas fluorescens is a Gram-negative bacterium that is widely found in food and has high spoilage activity. RpoS is considered an important global regulator

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