10937

N-Tetradecanoyl-DL-homoserine lactone

≥97.0% (HPLC)

• Synonym(s): N-Myristoyl-DL-homoserine lactone
• Empirical Formula (Hill Notation): C₁₈H₃₃NO₃
• CAS Number: 98206-80-5
• Molecular Weight: 311.46
• Beilstein/REAXYS Number: 1649579
• MDL number: MFCD01862913
• UNSPSC Code: 12352209
• eCl@ss: 32160406
• PubChem Substance ID: 57646860
• NACRES: NA.26

Properties

• Product Name: N-Tetradecanoyl-DL-homoserine lactone, ≥97.0% (HPLC)
• assay: ≥97.0% (HPLC)
• form: powder
• color: white to slightly yellow
• application(s): cell analysis
• storage temp.: 2-8°C
• SMILES string: CCCCCCCCCCCCCC(=O)NC1CCOC1=O
• InChI: 1S/C18H33NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(20)19-16-14-15-22-18(16)21/h16H,2-15H2,1H3,(H,19,20)
• InChI key: ZQAYHOXXVBVXPZ-UHFFFAOYSA-N

Description

Application

Induces violacein expression in a Chromobacterium violaceum mutant usually not able to produce homoserine lactones.[1]

Biochem/physiol Actions

N-Tetradecanoyl-DL-homoserine lactone (C14-HSL) is among a group of homoserine lactones that includes; N-Heptanoyl-DL-homoserine lactone (C7HSL), N-octanoyl-homoserine lactone (N-C8-HSL), N-Decanoyl-DL-homoserine lactone (N-C10-HSL), N-Dodecanoyl-DL-homoserine lactone (C12-HSL), N-(3-oxodecanoyl) homoserine-L-lactone (3-oxo-C10 HSL), N-(3-oxododecanoyl)homoserine-L-lactone (3-oxo-C12-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.

N-Tetradecanoyl-DL-homoserine lactone is a member of N-acyl-homoserine lactone family. N-acylhomoserine lactones (AHL) regulate gene expression in gram-negative bacteria, such as Echerichia and Salmonella are involved in quorum sensing, cell to cell communication among bacteria. Some AHLs are potent chemoattractants for human immune cells such as neutrophils.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)