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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:
Poids moléculaire :
227.30
Numéro Beilstein :
8148282
Numéro MDL:
Code UNSPSC :
12352211
ID de substance PubChem :
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


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Consulter la Bibliothèque de documents

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
Suman C, et al.
Cannabis sativa L.- Botany and Biotechnology (2017)
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
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
Meng Gui et al.
Frontiers in microbiology, 9, 1712-1712 (2018-08-16)
Sturgeon is an important fresh water-culture fish in China. A problem with sturgeon is its high susceptibility to spoilage. Food spoilage is reported to be regulated by quorum sensing (QS). To identify the QS signals acetylated homoserine lactones (AHLs) in

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