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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

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.

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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Robust multicellular computing using genetically encoded NOR gates and chemical `wires?
Tamsir A, et al.
Nature, 469(7329), 212-215 (2011)
Kaihao Tang et al.
Scientific reports, 3, 2935-2935 (2013-10-15)
Quorum sensing (QS) is a population-dependent mechanism for bacteria to synchronize social behaviors such as secretion of virulence factors. The enzymatic interruption of QS, termed quorum quenching (QQ), has been suggested as a promising alternative anti-virulence approach. In order to
Yunhui Zhang et al.
BMC genomics, 16, 38-38 (2015-02-06)
Intestinal microbes play significant roles in fish and can be possibly used as probiotics in aquaculture. In our previous study, Flaviramulus ichthyoenteri Th78(T), a novel species in the family Flavobacteriaceae, was isolated from fish intestine and showed strong quorum quenching
Chihiro Ueda et al.
Antimicrobial agents and chemotherapy, 54(2), 683-688 (2009-11-18)
We have examined the potential bactericidal activities of several tetramic acids derived from Pseudomonas autoinducers against Clostridium difficile, a cause of antibiotic-associated pseudomembranous colitis. Clinical isolates of C. difficile (n=4) were incubated in broth with a chemically synthesized Pseudomonas autoinducer
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)
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