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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

product name

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

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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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
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

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