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Merck
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09926

Sigma-Aldrich

N-Hexanoyl-DL-homoserine lactone

≥97.0% (HPLC)

Synonyme(s) :

N-Caproyl-DL-homoserine lactone

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About This Item

Formule empirique (notation de Hill):
C10H17NO3
Numéro CAS:
106983-28-2
Poids moléculaire :
199.25
Numéro Beilstein :
1640340
Numéro MDL:
MFCD01862908
Code UNSPSC :
12352209
eCl@ss :
32160406
ID de substance PubChem :
329748862
Nomenclature NACRES :
NA.26

Niveau de qualité

100

Pureté

≥97.0% (HPLC)

Forme

powder or crystals

Technique(s)

LC/MS: suitable

Couleur

white to faint beige

Pf

101-106 °C

Température de stockage

2-8°C

Chaîne SMILES 

CCCCCC(=O)NC1CCOC1=O

InChI

1S/C10H17NO3/c1-2-3-4-5-9(12)11-8-6-7-14-10(8)13/h8H,2-7H2,1H3,(H,11,12)

Clé InChI

ZJFKKPDLNLCPNP-UHFFFAOYSA-N

Catégories apparentées

Application

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

Actions biochimiques/physiologiques

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

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Albert Soler et al.
International journal of environmental research and public health, 15(5) (2018-05-23)
Quorum sensing (QS) is a mechanism dependent on bacterial density. This coordinated process is mediated by the synthesis and the secretion of signal molecules, called autoinducers (AIs). N-acyl-homoserine lactones (AHLs) are the most common AIs that are used by Gram-negative
Daniel Wynn et al.
The Analyst, 143(19), 4774-4782 (2018-09-15)
There are an estimated 48 million cases of foodborne illness in the United States every year. In general, these illnesses are the result of unintentional contamination and improper food handling. Because bacterial contamination plays a major role in food spoilage
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
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.
L Eberl
Systematic and applied microbiology, 22(4), 493-506 (2000-05-04)
The view of bacteria as unicellular organisms has strong roots in the tradition of culturing bacteria in liquid media. However, in nature microbial activity is mainly associated with surfaces where bacteria form highly structured and cooperative consortia which are commonly
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