N-(3-Oxotetradecanoyl)-L-homoserine lactone
- Product Name
- N-(3-Oxotetradecanoyl)-L-homoserine lactone
- CAS No.
- 177158-19-9
- Chemical Name
- N-(3-Oxotetradecanoyl)-L-homoserine lactone
- Synonyms
- 3OC14-HSL;3-oxo-C14-HSL;N-3-oxo-Myristoyl-L-Homoserine lactone;N-(3-Oxotetradecanoyl)-L-homoserine lactone;3-oxo-N-[(3S)-2-oxooxolan-3-yl]tetradecanamide;(S)-3-Oxo-N-(2-oxotetrahydrofuran-3-yl)tetradecanamide;N-3-oxo-tetradecanoyl-L-Homoserine lactone Exclusive;Tetradecanamide, 3-oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-
- CBNumber
- CB12094820
- Molecular Formula
- C18H31NO4
- Formula Weight
- 325.44
- MOL File
- 177158-19-9.mol
N-(3-Oxotetradecanoyl)-L-homoserine lactone Property
- Melting point:
- 96-97 °C(Solv: ethyl acetate (141-78-6))
- Boiling point:
- 537.3±50.0 °C(Predicted)
- Density
- 1.04±0.1 g/cm3(Predicted)
- storage temp.
- −20°C
- solubility
- DMF: 20 mg/ml; DMSO: 20 mg/ml
- form
- A crystalline solid
- pka
- 11.21±0.46(Predicted)
- color
- White to off-white
Safety
- WGK Germany
- 3
N-Bromosuccinimide Price
- Product number
- O9264
- Product name
- <I>N</I>-(3-Oxotetradecanoyl)-<SC>L</SC>-homoserine lactone
- Packaging
- 10 mg
- Price
- $46.2
- Updated
- 2025/07/31
- Product number
- O9264
- Product name
- <I>N</I>-(3-Oxotetradecanoyl)-<SC>L</SC>-homoserine lactone
- Packaging
- 100 mg
- Price
- $389
- Updated
- 2025/07/31
- Product number
- O9264
- Product name
- N-(3-Oxotetradecanoyl)-L-homoserine lactone
- Packaging
- 10mg
- Price
- $86.3
- Updated
- 2024/03/01
- Product number
- O9264
- Product name
- N-(3-Oxotetradecanoyl)-L-homoserine lactone
- Packaging
- 100mg
- Price
- $365
- Updated
- 2024/03/01
- Product number
- 13063
- Product name
- N-3-oxo-tetradecanoyl-L-Homoserine lactone
- Purity
- ≥98%
- Packaging
- 1mg
- Price
- $31
- Updated
- 2024/03/01
N-(3-Oxotetradecanoyl)-L-homoserine lactone Chemical Properties,Usage,Production
Uses
Quorum sensing is a regulatory system used by bacteria for controlling gene expression in response to increasing cell density. Controlling bacterial infections by quenching their quorum sensing systems is a promising field of study. The expression of specific target genes, such as transcriptional regulators belonging to the LuxIR family of proteins, is coordinated by the synthesis of diffusible acylhomoserine lactone (AHL) molecules. N-3-oxo-tetradecanoyl-L-homoserine lactone (3-oxo-C14-HSL) is a small diffusible signaling molecule involved in quorum sensing, thereby controlling gene expression and affecting cellular metabolism in bacteria. It appears later than shorter acyl chain AHLs in developing biofilms and, like other long chain 3-oxo-AHLs, stimulates the production of putisolvin, which in turn, inhibits biofilm formation.
Uses
N-(3-Oxotetradecanoyl)-L-homoserine lactone (3-Oxo-C14-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.
Definition
ChEBI: 3-oxo-N-[(3S)-2-oxotetrahydrofuran-3-yl]tetradecanamide is a monocarboxylic acid amide that is tetradecanamide substituted by an oxo group at position 3 and a (3S)-2-oxotetrahydrofuran-3-yl group at the N atom. It is a gamma-lactone, a member of furans and a monocarboxylic acid amide.
Biochem/physiol Actions
N-(3-Oxotetradecanoyl)-L-homoserine lactone (3-oxo-C14-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-oxododecanoyl)homoserine-L-lactone (3-oxo-C12-HSL), N-(3-hydroxydecanoyl)-L-homoserine lactone, and N-(3-hydroxyoctanoyl)-L-homoserine lactone involved in the processes of bacterial quorum sensing. These homoserine lactones are used to study the processes and mechanisms of bacterial quorum sensing.
N-(3-Oxotetradecanoyl)-L-homoserine lactone Preparation Products And Raw materials
Raw materials
Preparation Products
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