O9014
N-(3-Oxodecanoyl)-L-homoserine lactone
≥98% (TLC)
Synonym(s):
3-Oxo-N-[(3s)-2-Oxotetrahydrofuran-3-Yl]decanamide
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About This Item
Empirical Formula (Hill Notation):
C14H23NO4
Molecular Weight:
269.34
MDL number:
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.26
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Product Name
N-(3-Oxodecanoyl)-L-homoserine lactone,
Assay
≥98% (TLC)
Quality Level
form
powder
color
white
application(s)
cell analysis
shipped in
wet ice
storage temp.
−20°C
SMILES string
CCCCCCCC(=O)CC(=O)N[C@H]1CCOC1=O
InChI
1S/C14H23NO4/c1-2-3-4-5-6-7-11(16)10-13(17)15-12-8-9-19-14(12)18/h12H,2-10H2,1H3,(H,15,17)/t12-/m0/s1
InChI key
KYGIKEQVUKTKRR-LBPRGKRZSA-N
General description
N-(3-oxodecanoyl) homoserine-L-lactone (3-oxo-C10 HSL) is among belongs to the group of homoserine lactones that includes N-octanoyl-homoserine lactone (N-C8-HSL), N-(3-oxododecanoyl)homoserine-L-lactone (3-oxo-C12-HSL), N-(3-Oxotetradecanoyl)-L-homoserine lactone (3-oxo-C14-HSL, N-(3-hydroxydecanoyl)-L-homoserine lactone, and N-(3-hydroxyoctanoyl)-L-homoserine lactone.
Application
N-(3-Oxodecanoyl)-L-homoserine lactone (3-Oxo-C10-HSL) may be used to study the signaling involved in the regulation of bacterial quorum sensing.
Biochem/physiol Actions
Acyl homoserine lactone used as an autoinducer of quorum signaling by Pseudomonas putida, Yersinia enterocolitica, and other Gram-negative bacteria.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Rumana Rashid et al.
Microbes and environments, 26(2), 144-148 (2011-04-20)
N-Acylhomoserine lactones (AHLs) are used as quorum-sensing signaling molecules by many Gram-negative bacteria. Here, 413 bacterial strains were obtained from the roots of potato plants and screened for AHL-degrading bacteria using Chromobacterium violaceum reporter strains. Sixty one isolates degraded N-hexanoyl-L-homoserine
Bijay K Khajanchi et al.
Infection and immunity, 79(7), 2646-2657 (2011-05-04)
Aeromonas hydrophila leads to both intestinal and extraintestinal infections in animals and humans, and the underlying mechanisms leading to mortality are largely unknown. By using a septicemic mouse model of infection, we showed that animals challenged with A. hydrophila die
John F Teiber et al.
Methods in molecular biology (Clifton, N.J.), 692, 291-298 (2010-10-30)
Mammalian paraoxonases (PONs) are a unique, highly conserved family of calcium-dependent esterases consisting of PON1, PON2, and PON3. The PONs can hydrolyze the lactone ring of a range of N-acyl-L: -homoserine lactone (AHL) quorum sensing signaling molecules, rendering them inactive.
Manabu Horikawa et al.
Bioorganic & medicinal chemistry letters, 16(8), 2130-2133 (2006-02-08)
The synthesis of the analogs of N-3-oxododecanoyl-L-homoserine lactone (1) and their structure-activity relationship for the apoptotic induction in macrophages, P388D1 cells, are described. It was revealed that the position of the oxo group in the acyl side chain in addition
Mair E A Churchill et al.
Methods in molecular biology (Clifton, N.J.), 692, 159-171 (2010-10-30)
Quorum sensing plays a central role in regulating many community-derived symbiotic and pathogenic relationships of bacteria, and as such has attracted much attention in recent years. Acyl-homoserine lactones (AHLs) are important signaling molecules in the quorum sensing gene-regulatory processes found
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