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61698

Sigma-Aldrich

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

≥95% (sum of isomers, HPLC)

Synonyme(s) :

3-Hydroxy-N-(tetrahydro-2-oxo-3-furanyl)octanamide, 3-Hydroxy-C8-HSL, N-[(RS)-3-Hydroxyoctanoyl]-DL-homoserine lactone

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About This Item

Formule empirique (notation de Hill):
C12H21NO4
Numéro CAS:
853799-77-6
Poids moléculaire :
243.30
Numéro MDL:
MFCD27952927
Code UNSPSC :
41116134
ID de substance PubChem :
329759646
Nomenclature NACRES :
NA.25

Niveau de qualité

100

Pureté

≥95% (sum of isomers, HPLC)

Température de stockage

−20°C

Chaîne SMILES 

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

InChI

1S/C12H21NO4/c1-2-3-4-5-9(14)8-11(15)13-10-6-7-17-12(10)16/h9-10,14H,2-8H2,1H3,(H,13,15)

Clé InChI

XCZVBYOXRSFQBH-UHFFFAOYSA-N

Actions biochimiques/physiologiques

N-(3-Hydroxyoctanoyl)-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.

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

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Consulter la Bibliothèque de documents

M B Miller et al.
Annual review of microbiology, 55, 165-199 (2001-09-07)
Quorum sensing is the regulation of gene expression in response to fluctuations in cell-population density. Quorum sensing bacteria produce and release chemical signal molecules called autoinducers that increase in concentration as a function of cell density. The detection of a
Jie Zhu et al.
Current opinion in pharmacology, 13(5), 688-698 (2013-07-24)
With the emergence of microbial pathogens increasingly resistant against commonly used antibiotics, new treatment strategies are desperately needed. Bacterial quorum sensing has attracted a lot of attention over the last decade as a potential new target for antimicrobial therapy. Interference
David G Davies et al.
Journal of bacteriology, 191(5), 1393-1403 (2008-12-17)
It is well established that in nature, bacteria are found primarily as residents of surface-associated communities called biofilms. These structures form in a sequential process initiated by attachment of cells to a surface, followed by the formation of matrix-enmeshed microcolonies
Clay Fuqua et al.
Nature reviews. Molecular cell biology, 3(9), 685-695 (2002-09-05)
Bacterial cell-to-cell signalling has emerged as a new area in microbiology. Individual bacterial cells communicate with each other and co-ordinate group activities. Although a lot of detail is known about the mechanisms of a few well-characterized bacterial communication systems, other
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
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