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44558

Sigma-Aldrich

N-Octanoyl-L-homoserine lactone

≥96% (HPLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C12H21NO3
Numéro CAS:
147852-84-4
Poids moléculaire :
227.30
Numéro Beilstein :
8148282
Numéro MDL:
MFCD11113139
Code UNSPSC :
12352211
ID de substance PubChem :
329756519
Nomenclature NACRES :
NA.85

product name

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

Pureté

≥96% (HPLC)

Forme

powder or crystals

Activité optique

[α]/D -28±3°, c = 0.2 in methanol

Couleur

white to off-white

Adéquation

conforms to structure for Proton NMR spectrum

Application(s)

detection

Température de stockage

−20°C

Chaîne 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

Clé InChI

JKEJEOJPJVRHMQ-JTQLQIEISA-N

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Actions biochimiques/physiologiques

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Suman C, et al.
Cannabis sativa L.- Botany and Biotechnology (2017)
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
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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