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Key Documents

17248

Sigma-Aldrich

N-Decanoyl-DL-homoserine lactone

≥97.0% (HPLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C14H25NO3
Numéro CAS:
Poids moléculaire :
255.35
Numéro Beilstein :
1644700
Numéro MDL:
Code UNSPSC :
12352209
eCl@ss :
32160406
ID de substance PubChem :
Nomenclature NACRES :
NA.26

product name

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

Pureté

≥97.0% (HPLC)

Forme

powder

Couleur

white

Pf

111-114 °C

Application(s)

cell analysis

Température de stockage

2-8°C

Chaîne SMILES 

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)

Clé InChI

TZWZKDULKILUPV-UHFFFAOYSA-N

Application

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

Actions biochimiques/physiologiques

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.

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

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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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
Xinqi Huang et al.
Current microbiology, 74(1), 68-76 (2016-11-04)
Marine algae provide a unique niche termed the phycosphere for microorganism inhabitation. The phycosphere environment is an important niche for mutualistic and competitive interactions between algae and bacteria. Quorum sensing (QS) serves as a gene regulatory system in the microbial
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
S J Jo et al.
Journal of applied microbiology, 128(3), 907-918 (2019-11-12)
Quorum quenching (QQ) is an attractive strategy for mitigating biofouling in membrane bioreactors (MBRs). However, the effects of QQ on the activated sludge (AS) process have not been adequately evaluated. This study investigated the long-term effects of QQ on a
Selvaraj Poonguzhali et al.
Journal of microbiology and biotechnology, 17(2), 226-233 (2007-12-07)
Members of Methylobacterium, referred as pink-pigmented facultative methylotrophic bacteria, are frequently associated with terrestrial and aquatic plants, tending to form aggregates on the phyllosphere. We report here that the production of autoinducer molecules involved in the cell-to-cell signaling process, which

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