3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide Struktur

3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide

Bezeichnung:3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide

CAS-Nr168982-69-2

Englisch Name:3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide

CBNumberCB82489993

SummenformelC16H27NO4

Molgewicht297.39

MOL-Datei168982-69-2.mol

3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide physikalisch-chemischer Eigenschaften

Schmelzpunkt	80-81 °C
Siedepunkt	519.4±50.0 °C(Predicted)
Dichte	1.06
storage temp.	-20°C
Löslichkeit	≤20mg/ml in DMSO;20mg/ml in dimethyl formamide
Aggregatzustand	crystalline solid
pka	11.22±0.46(Predicted)
Farbe	White to light yellow

Gefahreninformationscode (GHS)

3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
N-3-oxo-dodecanoyl-L-Homoserine lactone (3-oxo-C12-HSL) is a bacterial quorum-sensing signaling molecule produced by P. aeruginosa and strains of the B. cepacia complex. It induces the production of IL-8 in 16HBE human bronchial epithelial cells when used at a concentration of 100 μM. Supernatants from 3-oxo-C12-HSL-stimulated 16HBE cells induce chemotaxis of isolated human neutrophils. 3-oxo-C12-HSL has been found in respiratory secretions from patients with cystic fibrosis infected with P. aeruginosa.
Verwenden
N-(3-Oxododecanoyl)-L-homoserine Lactone is a bacterial quorum sensing signal molecule. Inhibits lymphocyte proliferation and TNF-α and IL-12 production by LPS-stimulated macrophages. Inhibits or promotes antibody production at high and low concentrations, respectively, in keyhole limpet hemocyanin (KLH)-stimulated spleen cells.
Definition
ChEBI: N-(3-oxododecanoyl)-L-homoserine lactone is an N-acyl-L-homoserine lactone having 3-oxododecanoyl as the acyl substituent. It has a role as a bacterial metabolite. It is a N-(3-oxododecanoyl)homoserine lactone and a N-acyl-L-homoserine lactone. It is an enantiomer of a N-(3-oxododecanoyl)-D-homoserine lactone.
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.
Lager
Store at -20°C
Einzelnachweise
[1]. henke jm, bassler bl. bacterial social engagements. trends cell biol. 2004 nov;14(11):648-56.
[2]. chambers ce, visser mb, schwab u, et al. identification of n-acylhomoserine lactones in mucopurulent respiratory secretions from cystic fibrosis patients. fems microbiol lett. 2005 mar 15;244(2):297-304.
[3]. smith rs, fedyk er, springer ta, et al. il-8 production in human lung fibroblasts and epithelial cells activated by the pseudomonas autoinducer n-3-oxododecanoyl homoserine lactone is transcriptionally regulated by nf-kappa b and activator protein-2. j immunol. 2001 jul 1;167(1):366-74.

3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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