3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide
- Product Name
- 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
- Formula Weight
- 297.39
- MOL File
- 168982-69-2.mol
3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide Property
- 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)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- O9139
- Product name
- N-(3-Oxododecanoyl)-L-homoserine lactone
- Purity
- quorum sensing signaling molecule
- Packaging
- 10MG
- Price
- $83
- Updated
- 2023/06/20
- Product number
- O9139
- Product name
- N-(3-Oxododecanoyl)-L-homoserine lactone
- Purity
- quorum sensing signaling molecule
- Packaging
- 100MG
- Price
- $378
- Updated
- 2023/06/20
- Product number
- 10007895
- Product name
- N-3-oxo-dodecanoyl-L-Homoserine lactone
- Purity
- ≥98%
- Packaging
- 1mg
- Price
- $33
- Updated
- 2024/03/01
- Product number
- 10007895
- Product name
- N-3-oxo-dodecanoyl-L-Homoserine lactone
- Purity
- ≥98%
- Packaging
- 5mg
- Price
- $107
- Updated
- 2024/03/01
- Product number
- 10007895
- Product name
- N-3-oxo-dodecanoyl-L-Homoserine lactone
- Purity
- ≥98%
- Packaging
- 10mg
- Price
- $196
- Updated
- 2024/03/01
3-Oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]dodecanamide Chemical Properties,Usage,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
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