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Merck
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09945

Sigma-Aldrich

N-Butyryl-DL-homoserine lactone

≥96.0% (HPLC)

Synonyme(s) :

N-(tetrahydro-2-oxo-3-furanyl)-Butanamide

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About This Item

Formule empirique (notation de Hill):
C8H13NO3
Numéro CAS:
98426-48-3
Poids moléculaire :
171.19
Numéro Beilstein :
6375
Numéro MDL:
MFCD01862909
Code UNSPSC :
12352209
eCl@ss :
32160406
ID de substance PubChem :
329748866
Nomenclature NACRES :
NA.26

Pureté

≥96.0% (HPLC)

Forme

powder or crystals

Couleur

white to faint beige

Chaîne SMILES 

CCCC(=O)NC1CCOC1=O

InChI

1S/C8H13NO3/c1-2-3-7(10)9-6-4-5-12-8(6)11/h6H,2-5H2,1H3,(H,9,10)

Clé InChI

VFFNZZXXTGXBOG-UHFFFAOYSA-N

Catégories apparentées

Application

Application test: Induces violacein expression in a Chromobacterium violaceum mutant usually not able to produce homoserine lactones.

Actions biochimiques/physiologiques

N-Butyryl-DL-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 are involved in quorum sensing, cell to cell communication among bacteria. Some AHLs are potent chemoattractants for human immune cells such as neutrophils.

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

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Longyi Lv et al.
Journal of hazardous materials, 354, 72-80 (2018-05-08)
Quorum sensing (QS) signalling has been extensively studied in single species populations, activated sludge, biofilm and aerobic granular sludge. However, ecological roles of QS in anaerobic granular sludge, particularly in the content of the relationship between QS signalling and microbial
Thommie Karlsson et al.
Journal of leukocyte biology, 91(1), 15-26 (2011-08-03)
In gram-negative bacteria, cell-cell communication based on HSL QS molecules is known to coordinate the production of virulence factors and biofilms. These bacterial signals can also modulate human immune cell behavior. Using a Transwell migration assay, we found that human
Tomohiro Morohoshi et al.
FEMS microbiology letters, 279(1), 124-130 (2008-01-08)
In tests, Chromobacterium violaceum ATCC 12472 produced several N-acyl-L-homoserine lactones (AHLs). Of these, N-(3-hydroxydecanoyl)-L-homoserine lactone was dominant, and controlled violacein production by quorum sensing. Strain VIR07, an AHL-deficient mutant, did not produce violacein. Violacein production in VIR07 was induced by
Robert Czajkowski et al.
Acta biochimica Polonica, 56(1), 1-16 (2009-03-17)
Many Gram-positive and Gram-negative bacteria communicate using small diffusible signal molecules called autoinducers. This process, known as quorum sensing (QS), links cell density to the expression of genes as diverse as those associated with virulence factors production of plant and
Joanne Hothersall et al.
Applied microbiology and biotechnology, 90(3), 1017-1026 (2011-02-15)
Transcription of the 74 kb Pseudomonas fluorescens mupirocin [pseudomonic acid (PA)] biosynthesis cluster depends on quorum sensing-dependent regulation via the LuxI/LuxR homologues MupI/MupR. To facilitate analysis of novel PAs from pathway mutants, we investigated factors that affect mup gene expression.
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