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;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

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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

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Safety

WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word: Warning
Hazard statements: H319Causes serious eye irritation
Precautionary statements: P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: O9264
Product name: N-(3-Oxotetradecanoyl)-L-homoserine lactone
Packaging: 10mg
Price: $86.3
Updated: 2024/03/01

Sigma-Aldrich

Product number: O9264
Product name: N-(3-Oxotetradecanoyl)-L-homoserine lactone
Packaging: 100mg
Price: $365
Updated: 2024/03/01

Cayman Chemical

Product number: 13063
Product name: N-3-oxo-tetradecanoyl-L-Homoserine lactone
Purity: ≥98%
Packaging: 1mg
Price: $31
Updated: 2024/03/01

Cayman Chemical

Product number: 13063
Product name: N-3-oxo-tetradecanoyl-L-Homoserine lactone
Purity: ≥98%
Packaging: 5mg
Price: $133
Updated: 2024/03/01

Cayman Chemical

Product number: 13063
Product name: N-3-oxo-tetradecanoyl-L-Homoserine lactone
Purity: ≥98%
Packaging: 10mg
Price: $234
Updated: 2024/03/01

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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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177158-19-9, N-(3-Oxotetradecanoyl)-L-homoserine lactoneRelated Search:

N-(3-Oxotetradecanoyl)-L-homoserine lactone

3-oxo-N-[(3S)-2-oxooxolan-3-yl]tetradecanamide

3OC14-HSL

3-oxo-C14-HSL

N-3-oxo-Myristoyl-L-Homoserine lactone

N-3-oxo-tetradecanoyl-L-Homoserine lactone Exclusive

Tetradecanamide, 3-oxo-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-

177158-19-9

Amino Acids

Modified Amino Acids

Quorum Sensing / Signaling Compounds

Homoserine LactonesMicrobiology