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Merck

857521P

Avanti

N-Octanoyl-L-homoserine lactone

(S)-N-(2-Oxotetrahydrofuran-3-yl)octanamide, powder

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/REAXYS Number:
8148282
MDL number:
UNSPSC Code:
12352211
NACRES:
NA.25

assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 10 mg (857521P-10MG)
pkg of 1 × 50 mg (857521P-50MG)

manufacturer/tradename

Avanti Research - A Croda Brand

lipid type

bacterial lipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

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

InChI key

JKEJEOJPJVRHMQ-JTQLQIEISA-N

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General description

N-Octanoyl-L-homoserine lactone (C8-HSL) is a N-acyl homoserine lactone (N-acyl-HSL). It is highly nonpolar.

Biochem/physiol Actions

N-Octanoyl-L-homoserine lactone (C8-HSL) is produced by many gram-negative bacteria like Pseudomonas fluorescens, Ralstonia solanacearum, Vibrio fischeri, and Yersinia pseudotuberculosis. In Escherichia coli, C8-HSL is encoded by the gene Ytb1. Generally, these homoserine lactones (HSLs) are quorum sensing signaling molecules. HSLs play a key role in biofilm formation. They function as an autoinducer molecule and involved in cell to cell communication depending on cell density population.
Quorum-sensing signal generation

Packaging

5 mL Amber Glass Screw Cap Vial (857521P-10MG and 857521P-50MG)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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A hierarchical quorum-sensing system in Yersinia pseudotuberculosis is involved in the regulation of motility and clumping.
Atkinson S, et al.
Molecular Microbiology, 33(6), 1267-1277 (1999)
Characterization of N-acylhomoserine lactones produced by bacteria isolated from industrial cooling water systems.
Okutsu N, et al.
Sensors, 16(1), 44-44 (2016)
P D Shaw et al.
Proceedings of the National Academy of Sciences of the United States of America, 94(12), 6036-6041 (1997-06-10)
Many Gram-negative bacteria regulate gene expression in response to their population size by sensing the level of acyl-homoserine lactone signal molecules which they produce and liberate to the environment. We have developed an assay for these signals that couples separation

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