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Merck
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Documentos

68873

Sigma-Aldrich

N-(3-Hydroxydecanoyl)-DL-homoserine lactone

Sinónimos:

3-Hydroxy-N-(tetrahydro-2-oxo-3-furanyl)decanamide, N-[(RS)-3-Hydroxydecanoyl]-DL-homoserine lactone

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About This Item

Fórmula empírica (notación de Hill):
C14H25NO4
Número de CAS:
929222-14-0
Peso molecular:
271.35
MDL number:
MFCD28016586
UNSPSC Code:
41116134
PubChem Substance ID:
329761188
NACRES:
NA.25

form

powder

Quality Level

100

storage temp.

−20°C

SMILES string

O=C(CC(O)CCCCCCC)NC1C(OCC1)=O

InChI

1S/C14H25NO4/c1-2-3-4-5-6-7-11(16)10-13(17)15-12-8-9-19-14(12)18/h11-12,16H,2-10H2,1H3,(H,15,17)

InChI key

DOICJCCMIBBSOO-UHFFFAOYSA-N

Biochem/physiol Actions

N-(3-Hydroxydecanoyl)-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, 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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Dilani Senadheera et al.
Advances in experimental medicine and biology, 631, 178-188 (2008-09-17)
Streptococcus mutans is the primary causative agent involved in dental caries in humans. Among important virulence factors of this pathogen, its ability to form and sustain a polysaccharide-encased biofilm (commonly called dental plaque) is vital not only to its survival
Margrith E Mattmann et al.
The Journal of organic chemistry, 75(20), 6737-6746 (2010-08-03)
Bacteria use small molecule signals to access their local population densities in a process called quorum sensing (QS). Once a threshold signal concentration is reached, and therefore a certain number of bacteria have assembled, bacteria use QS to change gene
C Fuqua et al.
Annual review of genetics, 35, 439-468 (2001-11-09)
Quorum sensing is an example of community behavior prevalent among diverse bacterial species. The term "quorum sensing" describes the ability of a microorganism to perceive and respond to microbial population density, usually relying on the production and subsequent response to
M R Parsek et al.
Proceedings of the National Academy of Sciences of the United States of America, 96(8), 4360-4365 (1999-04-14)
Acyl homoserine lactones (acyl-HSLs) are important intercellular signaling molecules used by many bacteria to monitor their population density in quorum-sensing control of gene expression. These signals are synthesized by members of the LuxI family of proteins. To understand the mechanism
Barbara Thallinger et al.
Biotechnology journal, 8(1), 97-109 (2013-01-03)
With the increasing prevalence of antibiotic resistance, antimicrobial enzymes aimed at the disruption of bacterial cellular machinery and biofilm formation are under intense investigation. Several enzyme-based products have already been commercialized for application in the healthcare, food and biomedical industries.
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