O9139
N-(3-Oxododecanoyl)-L-homoserine lactone
≥98% (TLC)
Synonym(s):
3-Oxo-C12-HSL
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All Photos(3)
About This Item
Empirical Formula (Hill Notation):
C16H27NO4
CAS Number:
Molecular Weight:
297.39
MDL number:
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.26
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product name
N-(3-Oxododecanoyl)-L-homoserine lactone, quorum sensing signaling molecule
Quality Level
Assay
≥98% (TLC)
form
powder
color
white
application(s)
cell analysis
shipped in
wet ice
storage temp.
−20°C
SMILES string
CCCCCCCCCC(=O)CC(=O)N[C@H]1CCOC1=O
InChI
1S/C16H27NO4/c1-2-3-4-5-6-7-8-9-13(18)12-15(19)17-14-10-11-21-16(14)20/h14H,2-12H2,1H3,(H,17,19)/t14-/m0/s1
InChI key
PHSRRHGYXQCRPU-AWEZNQCLSA-N
Application
N-(3-Oxododecanoyl)-L-homoserine lactone (3-Oxo-C12-HSL), a member of a family of acyl homoserine lactones, may be used to determine its mechanisms and specificity of action as a signaling molecule involved in the regulation of bacterial quorum sensing.
Biochem/physiol Actions
N-(3-oxododecanoyl)homoserine-L-lactone (3-oxo-C12-HSL) is among a group of homoserine lactones that includes: N-octanoyl-homoserine lactone (N-C8-HSL), N-(3-oxodecanoyl) homoserine-L-lactone (3-oxo-C10 HSL), N-(3-Oxotetradecanoyl)-L-homoserine lactone (3-oxo-C14-HSL, N-(3-hydroxydecanoyl)-L-homoserine lactone, and N-(3-hydroxyoctanoyl)-L-homoserine lactone involved in the processes of bacterial quorum sensing. These N-acyl-homoserine lactones are used to study the processes and mechanisms of bacterial quorum sensing.
Acyl homoserine lactone that is an autoinducer of quorum sensing by Pseudomonas aeruginosa. Degraded by paraoxonase (PON) family members.
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Product No.
Description
Pricing
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral
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
Certificates of Analysis (COA)
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Lundgren BR, et al.
Journal of Bacteriology, 195(9), 2087-2100 (2013)
Yang Yang et al.
Frontiers in microbiology, 9, 1924-1924 (2018-09-05)
Quorum sensing (QS) is a central mechanism for regulating bacterial social networks in biofilm via the production of diffusible signal molecules (autoinducers). In this work, we assess the contribution of QS autoinducers to microbial extracellular electron transfer (EET) by Pseudomonas
Stephanie J Cole et al.
Nature communications, 9(1), 4436-4436 (2018-10-27)
Chronic bacterial infections on medical devices, including catheter-associated urinary tract infections (CAUTI), are associated with bacterial biofilm communities that are refractory to antibiotic therapy and resistant to host immunity. Previously, we have shown that Pseudomonas aeruginosa can cause CAUTI by
Nathaniel C Cady et al.
PloS one, 7(6), e38492-e38492 (2012-06-21)
Using a microplate-based screening assay, the effects on Pseudomonas aeruginosa PAO1 biofilm formation of several S-substituted cysteine sulfoxides and their corresponding disulfide derivatives were evaluated. From our library of compounds, S-phenyl-L-cysteine sulfoxide and its breakdown product, diphenyl disulfide, significantly reduced
Lisheng Liao et al.
Proceedings of the National Academy of Sciences of the United States of America, 115(29), 7587-7592 (2018-07-04)
Many species of Proteobacteria produce acyl-homoserine lactone (AHL) compounds as quorum-sensing (QS) signals for cell density-dependent gene regulation. Most known AHL synthases, LuxI-type enzymes, produce fatty AHLs, and the fatty acid moiety is derived from an acyl-acyl carrier protein (ACP)
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