| Identification | Back Directory | [Name]
3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide | [CAS]
168982-69-2 | [Synonyms]
N-(3-OXODODECANOYL)-L-HOMOSERINE
3-oxo-N-[(3S)-2-oxooxolan-3-yl]dodecanamide
(S)-3-Oxo-N-(2-oxotetrahydrofuran-3-yl)dodecanamide
3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide
N-(3-oxododecanoyl)-L-homoserine lactone L-enantiomer
Dodecanamide, 3-oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]- | [Molecular Formula]
C16H27NO4 | [MDL Number]
MFCD08275140 | [MOL File]
168982-69-2.mol | [Molecular Weight]
297.39 |
| Chemical Properties | Back Directory | [Melting point ]
80-81 °C | [Boiling point ]
519.4±50.0 °C(Predicted) | [density ]
1.06 | [storage temp. ]
-20°C | [solubility ]
≤20mg/ml in DMSO;20mg/ml in dimethyl formamide | [form ]
crystalline solid | [pka]
11.22±0.46(Predicted) | [color ]
White to light yellow |
| Hazard Information | Back Directory | [Description]
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. | [Uses]
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. | [storage]
Store at -20°C | [References]
[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. |
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