68873
N-(3-Hydroxydecanoyl)-DL-homoserine lactone
Synonym(s):
3-Hydroxy-N-(tetrahydro-2-oxo-3-furanyl)decanamide, N-[(RS)-3-Hydroxydecanoyl]-DL-homoserine lactone
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About This Item
Empirical Formula (Hill Notation):
C14H25NO4
CAS Number:
Molecular Weight:
271.35
MDL number:
UNSPSC Code:
41116134
PubChem Substance ID:
NACRES:
NA.25
Recommended Products
form
powder
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 Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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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
Regulation of gene expression by cell-to-cell communication: acyl-homoserine lactone quorum sensing.
C Fuqua et al.
Annual review of genetics, 35, 439-468 (2001-11-09)
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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
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
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
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