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Sigma-Aldrich

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:
929222-14-0
Molecular Weight:
271.35
MDL number:
MFCD28016586
UNSPSC Code:
41116134
PubChem Substance ID:
329761188
NACRES:
NA.25

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

Certificates of Analysis (COA)

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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.
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
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
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