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44558

Sigma-Aldrich

N-Octanoyl-L-homoserine lactone

≥96% (HPLC)

Synonyma:

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

Přihlásitk zobrazení cen stanovených pro organizaci a smluvních cen
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About This Item

Empirický vzorec (Hillův zápis):
C12H21NO3
Číslo CAS:
147852-84-4
Molekulová hmotnost:
227.30
Beilstein/REAXYS Number:
8148282
MDL number:
MFCD11113139
UNSPSC Code:
12352211
PubChem Substance ID:
329756519
NACRES:
NA.85

product name

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

assay

≥96% (HPLC)

form

powder or crystals

optical activity

[α]/D -28±3°, c = 0.2 in methanol

color

white to off-white

suitability

conforms to structure for Proton NMR spectrum

application(s)

detection

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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Biochem/physiol Actions

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Osvědčení o analýze (COA)

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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
José Gomes et al.
Chemical communications (Cambridge, England), 49(2), 155-157 (2012-11-22)
We demonstrate the synthesis and immobilization of natural product hybrids featuring an acyl-homoserine lactone and a nitrodopamine onto biocompatible TiO(2) surfaces through an operationally simple dip-and-rinse procedure. The resulting immobilized hybrids were shown to be powerful quorum sensing (QS) activators
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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