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Sigma-Aldrich

N-Dodecanoyl-L-homoserine lactone

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

Sinônimo(s):

N-Lauroyl-L-homoserine lactone, N-[(3S)-Tetrahydro-2-oxo-3-furanyl]dodecanamide, C12-HSL

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About This Item

Fórmula empírica (Notação de Hill):
C16H29NO3
Número CAS:
137173-46-7
Peso molecular:
283.41
Beilstein:
9281984
Número MDL:
MFCD11976890
Código UNSPSC:
12352211
ID de substância PubChem:
329760775
NACRES:
NA.28

Nome do produto

N-Dodecanoyl-L-homoserine lactone, ≥96% (HPLC)

Nível de qualidade

100

Ensaio

≥96% (HPLC)

Formulário

powder or crystals

atividade óptica

[α]/D -25±5°, c = 0.2 in methanol

técnica(s)

mass spectrometry (MS): suitable

cor

white to off-white

adequação

conforms to structure for Proton NMR spectrum

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

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

chave InChI

WILLZMOKUUPJSL-AWEZNQCLSA-N

Ações bioquímicas/fisiológicas

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

Frases de perigo

H413

Classificações de perigo

Aquatic Chronic 4

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Escolha uma das versões mais recentes:

Certificados de análise (COA)

Lot/Batch Number
BCCG3330
BCCF0845
BCCC0461
BCBZ7755
BCBW6571

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Visite a Biblioteca de Documentos

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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