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Merck

17248

Sigma-Aldrich

N-Decanoyl-DL-homoserin-lacton

≥97.0% (HPLC)

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C14H25NO3
CAS-Nummer:
Molekulargewicht:
255.35
Beilstein:
1644700
MDL-Nummer:
UNSPSC-Code:
12352209
eCl@ss:
32160406
PubChem Substanz-ID:
NACRES:
NA.26

Produktbezeichnung

N-Decanoyl-DL-homoserin-lacton, ≥97.0% (HPLC)

Qualitätsniveau

Assay

≥97.0% (HPLC)

Form

powder

Farbe

white

mp (Schmelzpunkt)

111-114 °C

Anwendung(en)

cell analysis

Lagertemp.

2-8°C

SMILES String

CCCCCCCCCC(=O)NC1CCOC1=O

InChI

1S/C14H25NO3/c1-2-3-4-5-6-7-8-9-13(16)15-12-10-11-18-14(12)17/h12H,2-11H2,1H3,(H,15,16)

InChIKey

TZWZKDULKILUPV-UHFFFAOYSA-N

Anwendung

Induziert die Expression von Violacein in einer Chromobacterium violaceum-Mutante, die kein Homoserinlacton produziert (Lit. K.H. McClean et al. Microbiology 143, 3703 (1997)

Biochem./physiol. Wirkung

N-Decanoyl-DL-homoserine lactone (N-C10-HSL) is among a group of homoserine lactones that includes; N-octanoyl-homoserine lactone (N-C8-HSL), N-(3-oxodecanoyl) homoserine-L-lactone (3-oxo-C10 HSL), N-(3-oxododecanoyl)homoserine-L-lactone (3-oxo-C12-HSL), N-(3-Oxotetradecanoyl)-L-homoserine lactone (3-oxo-C14-HSL, N-(3-hydroxydecanoyl)-L-homoserine lactone, and N-(3-hydroxyoctanoyl)-L-homoserine lactone involved in the processes of bacterial quorum sensing. These N-acyl-homoserine lactones are used to study the processes and mechanisms of bacterial quorum sensing.
N-Decanoyl-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.

Verpackung

Bottomless glass bottle. Contents are inside inserted fused cone.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)


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Ali Tahrioui et al.
Life (Basel, Switzerland), 3(1), 260-275 (2013-01-01)
Cell-to-cell communication, or quorum-sensing (QS), systems are employed by bacteria for promoting collective behaviour within a population. An analysis to detect QS signal molecules in 43 species of the Halomonadaceae family revealed that they produced N-acyl homoserine lactones (AHLs), which
Catarina A Santos et al.
Frontiers in microbiology, 11, 990-990 (2020-06-13)
The emergence of bacterial strains resistant to different antibiotics has prompted the search for new sources of antimicrobial compounds. Studies have shown that jambolan [Syzygium cumini (L.) Skeels], a tropical fruit from the Mirtaceae family, contains a great variety of
Tingting Li et al.
Journal of food science and technology, 55(8), 3016-3025 (2018-08-02)
The spoilage of aquatic products is mainly caused by the bacterial growth, and the specific spoilage organism (SSO) plays an important role. Quorum sensing (QS) is a microbial cell-cell communication system which is coordinated with the population density, and is
A A Purohit et al.
Journal of applied microbiology, 115(3), 835-847 (2013-06-04)
The aim of this study was to use a sensitive method to screen and quantify 57 Vibrionaceae strains for the production of acyl-homoserine lactones (AHLs) and map the resulting AHL profiles onto a host phylogeny. We used a high-performance liquid
Ping Kong et al.
BMC microbiology, 10, 313-313 (2010-12-09)
Oomycetes attack a huge variety of economically and ecologically important plants. These pathogens release, detect and respond to signal molecules to coordinate their communal behaviors including the infection process. When signal molecules are present at or above threshold level, single

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