3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide
- CAS No.
- 168982-69-2
- Chemical Name:
- 3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide
- Synonyms
- N-(3-OXODODECANOYL)-L-HOMOSERINE;3-oxo-N-[(3S)-2-oxooxolan-3-yl]dodecanamide;(S)-3-Oxo-N-(2-oxotetrahydrofuran-3-yl)dodecanamide;N-(3-oxododecanoyl)-L-homoserine lactone L-enantiomer;3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide;Dodecanamide, 3-oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-
- CBNumber:
- CB82489993
- Molecular Formula:
- C16H27NO4
- Molecular Weight:
- 297.39
- MDL Number:
- MFCD08275140
- MOL File:
- 168982-69-2.mol
- MSDS File:
- SDS
SAFETY
Risk and Safety Statements
Symbol(GHS) | GHS07 |
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Signal word | Warning | |||||||||
Hazard statements | H302-H315-H319-H335 | |||||||||
Precautionary statements | P261-P305+P351+P338 | |||||||||
NFPA 704 |
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3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide price More Price(21)
Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
---|---|---|---|---|---|---|---|
Sigma-Aldrich | O9139 | N-(3-Oxododecanoyl)-L-homoserine lactone quorum sensing signaling molecule | 168982-69-2 | 10MG | $83 | 2023-06-20 | Buy |
Sigma-Aldrich | O9139 | N-(3-Oxododecanoyl)-L-homoserine lactone quorum sensing signaling molecule | 168982-69-2 | 100MG | $378 | 2023-06-20 | Buy |
Cayman Chemical | 10007895 | N-3-oxo-dodecanoyl-L-Homoserine lactone ≥98% | 168982-69-2 | 1mg | $33 | 2024-03-01 | Buy |
Cayman Chemical | 10007895 | N-3-oxo-dodecanoyl-L-Homoserine lactone ≥98% | 168982-69-2 | 5mg | $107 | 2024-03-01 | Buy |
Cayman Chemical | 10007895 | N-3-oxo-dodecanoyl-L-Homoserine lactone ≥98% | 168982-69-2 | 10mg | $196 | 2024-03-01 | Buy |
3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide Chemical Properties,Uses,Production
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.
3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide Preparation Products And Raw materials
Raw materials
Preparation Products
3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide Suppliers
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