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61698

Sigma-Aldrich

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

≥95% (sum of isomers, HPLC)

Sinónimos:

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

Fórmula empírica (notación de Hill):
C12H21NO4
Número de CAS:
853799-77-6
Peso molecular:
243.30
MDL number:
MFCD27952927
UNSPSC Code:
41116134
PubChem Substance ID:
329759646
NACRES:
NA.25

Quality Level

100

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

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. 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.

Storage Class

11 - Combustible Solids

wgk_germany

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
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
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
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
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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