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O9139

Sigma-Aldrich

N-(3-Oxododecanoyl)-L-homoserine lactone

≥98% (TLC)

Synonyme(s) :

3-Oxo-C12-HSL

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About This Item

Formule empirique (notation de Hill):
C16H27NO4
Numéro CAS:
168982-69-2
Poids moléculaire :
297.39
Numéro MDL:
MFCD08275140
Code UNSPSC :
12352209
eCl@ss :
32160406
ID de substance PubChem :
329818935
Nomenclature NACRES :
NA.26

product name

N-(3-Oxododecanoyl)-L-homoserine lactone, quorum sensing signaling molecule

Niveau de qualité

200

Pureté

≥98% (TLC)

Forme

powder

Couleur

white

Application(s)

cell analysis

Conditions d'expédition

wet ice

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

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.

Actions biochimiques/physiologiques

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.

Souvent commandé avec ce produit

Réf. du produit
Description
Tarif

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Gene PA2449 Is Essential for Glycine Metabolism and Pyocyanin
Biosynthesis in Pseudomonas aeruginosa PAO1
Lundgren BR, et al.
Journal of Bacteriology, 195(9), 2087-2100 (2013)
Robust multicellular computing using genetically encoded NOR gates and chemical `wires?
Tamsir A, et al.
Nature, 469(7329), 212-215 (2011)
Megha Shah et al.
Molecular cell, 81(3), 571-583 (2021-01-08)
The arms race between bacteria and phages has led to the evolution of diverse anti-phage defenses, several of which are controlled by quorum-sensing pathways. In this work, we characterize a quorum-sensing anti-activator protein, Aqs1, found in Pseudomonas phage DMS3. We
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
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
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