61698
N-(3-Hydroxyoctanoyl)-DL-homoserine lactone
≥95% (sum of isomers, HPLC)
Synonym(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
Empirical Formula (Hill Notation):
C12H21NO4
CAS Number:
Molecular Weight:
243.30
MDL number:
UNSPSC Code:
41116134
PubChem Substance ID:
NACRES:
NA.25
Pricing and availability is not currently available.
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Quality Level
assay
≥95% (sum of isomers, HPLC)
storage temp.
−20°C
SMILES string
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)
InChI key
XCZVBYOXRSFQBH-UHFFFAOYSA-N
Related Categories
Biochem/physiol Actions
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[1][2][3][4][5]. Bacterial intercellular communication has become a target for the development of new anti-virulence drugs[3], and a research focus for the prevention of biofilm formation[6][7][8].
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Bonnie L Bassler
Cell, 109(4), 421-424 (2002-06-28)
In a process called quorum sensing, groups of bacteria communicate with one another to coordinate their behavior and function like a multicellular organism. A diverse array of secreted chemical signal molecules and signal detection apparatuses facilitate highly productive intra- and
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
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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
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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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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
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