N-(2-oxooxolan-3-yl)tetradecanamide

• ChemBase ID: 155991
• Molecular Formular: C18H33NO3
• Molecular Mass: 311.45952
• Monoisotopic Mass: 311.24604392
• SMILES: CCCCCCCCCCCCCC(=O)NC1CCOC1=O
• Canonical SMILES: CCCCCCCCCCCCCC(=O)NC1CCOC1=O
• InChI: 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)
• InChIKey: ZQAYHOXXVBVXPZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(2-oxooxolan-3-yl)tetradecanamide
• IUPAC Traditional name: N-(2-oxooxolan-3-yl)tetradecanamide
• Synonyms: N-Myristoyl-DL-homoserine lactone; N-Tetradecanoyl-DL-homoserine lactone

Database IDs

• CAS Number: 98206-80-5
• MDL Number: MFCD01862913
• Beilstein Number: 1649579
• PubChem SID: 24846910; 162250129
• PubChem CID: 4534674

CALCULATED PROPERTIES

• Acid pKa: 12.613446
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.5084467
• LogD (pH = 7.4): 4.508445
• Log P: 4.508447
• Molar Refractivity: 88.0959 cm^3
• Polarizability: 35.125824 Å^3
• Polar Surface Area: 55.4 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (HPLC)
• Empirical Formula (Hill Notation): C18H33NO3

DETAILS

Sigma Aldrich - 10937

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.