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Key Documents

17248

Sigma-Aldrich

N-Decanoyl-DL-homoserine lactone

≥97.0% (HPLC)

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C14H25NO3
Numero CAS:
Peso molecolare:
255.35
Beilstein:
1644700
Numero MDL:
Codice UNSPSC:
12352209
eCl@ss:
32160406
ID PubChem:
NACRES:
NA.26

product name

N-Decanoyl-DL-homoserine lactone, ≥97.0% (HPLC)

Livello qualitativo

Saggio

≥97.0% (HPLC)

Forma fisica

powder

Colore

white

Punto di fusione

111-114 °C

applicazioni

cell analysis

Temperatura di conservazione

2-8°C

Stringa SMILE

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)
TZWZKDULKILUPV-UHFFFAOYSA-N

Applicazioni

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

Azioni biochim/fisiol

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.

Confezionamento

Bottomless glass bottle. Contents are inside inserted fused cone.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)


Certificati d'analisi (COA)

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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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