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Merck

68224

Sigma-Aldrich

N-Dodecanoyl-L-homoserin-lacton

≥96% (HPLC), suitable for mass spectrometry (MS)

Synonym(e):

N-Lauroyl-L-homoserin-lacton, N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-dodecanamid

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About This Item

Empirische Formel (Hill-System):
C16H29NO3
CAS-Nummer:
Molekulargewicht:
283.41
Beilstein:
9281984
MDL-Nummer:
UNSPSC-Code:
12352211
PubChem Substanz-ID:
NACRES:
NA.28

product name

N-Dodecanoyl-L-homoserin-lacton, ≥96% (HPLC)

Qualitätsniveau

Assay

≥96% (HPLC)

Form

powder or crystals

Optische Aktivität

[α]/D -25±5°, c = 0.2 in methanol

Methode(n)

mass spectrometry (MS): suitable

Farbe

white to off-white

Eignung

conforms to structure for Proton NMR spectrum

Lagertemp.

−20°C

SMILES String

O=C1OCC[C@@H]1NC(CCCCCCCCCCC)=O

InChI

1S/C16H29NO3/c1-2-3-4-5-6-7-8-9-10-11-15(18)17-14-12-13-20-16(14)19/h14H,2-13H2,1H3,(H,17,18)/t14-/m0/s1

InChIKey

WILLZMOKUUPJSL-AWEZNQCLSA-N

Biochem./physiol. Wirkung

N-Dodecanoyl-L-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; for reviews see. Bacterial intercellular communication has become a target for the development of new anti-virulence drugs, and a research focus for the prevention of biofilm formation.
Quorum-sensing signal generation

H-Sätze

Gefahreneinstufungen

Aquatic Chronic 4

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable


Analysenzertifikate (COA)

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Die Dokumentenbibliothek aufrufen

Cytotoxicity of N-dodecanoyl-Lhomoserine lactone and 5-N-dodecyl resorcinol to human granulocytes and monocytes: a comparative study.
Sviridova, T. et al.
Central European Journal of Immunology, 38, 310-316 (2013)
G Brelles-Mariño et al.
Journal of biotechnology, 91(2-3), 197-209 (2001-09-22)
Quorum sensing (also called autoinduction) is a term that describes an environmental sensing system that allows bacteria to monitor their own population density. Autoinduction relies upon the interaction of a small diffusible signal molecule (the autoinducer) with a transcriptional activator
Sun-Yang Park et al.
Applied and environmental microbiology, 71(5), 2632-2641 (2005-05-05)
N-acylhomoserine lactones (AHLs) play an important role in regulating virulence factors in pathogenic bacteria. Recently, the enzymatic inactivation of AHLs, which can be used as antibacterial targets, has been identified in several soil bacteria. In this study, strain M664, identified
Nishaben M Patel et al.
PloS one, 11(10), e0163469-e0163469 (2016-10-06)
N-acyl L-homoserine lactones (AHLs) constitute a predominant class of quorum-sensing signaling molecules used by Gram-negative bacteria. Here, we report a sensitive and non-targeted HPLC-MS/MS method based on parallel reaction monitoring (PRM) to identify and quantitate known, unanticipated, and novel AHLs
Xiaoxiang Liu et al.
International journal of food microbiology, 270, 31-38 (2018-02-23)
Microorganism activities are considered the main cause of most food spoilage, leading to great economic losses. Pseudomonas fluorescens is a Gram-negative bacterium that is widely found in food and has high spoilage activity. RpoS is considered an important global regulator

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