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

• ChemBase ID: 155904
• Molecular Formular: C16H29NO3
• Molecular Mass: 283.40636
• Monoisotopic Mass: 283.21474379
• SMILES: CCCCCCCCCCCC(=O)NC1CCOC1=O
• Canonical SMILES: CCCCCCCCCCCC(=O)NC1CCOC1=O
• InChI: InChI=1S/C16H29NO3/c1-2-3-4-5-6-7-8-9-10-11-15(18)17-14-12-13-20-16(14)19/h14H,2-13H2,1H3,(H,17,18)
• InChIKey: WILLZMOKUUPJSL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(2-oxooxolan-3-yl)dodecanamide
• IUPAC Traditional name: N-(2-oxooxolan-3-yl)dodecanamide
• Synonyms: N-Lauroyl-DL-homoserine lactone; N-Dodecanoyl-DL-homoserine lactone

Database IDs

• CAS Number: 18627-38-8
• MDL Number: MFCD03100412
• PubChem SID: 162250042; 24850402
• PubChem CID: 11565426

CALCULATED PROPERTIES

• Acid pKa: 12.613446
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.6193094
• LogD (pH = 7.4): 3.6193078
• Log P: 3.61931
• Molar Refractivity: 78.8939 cm^3
• Polarizability: 31.446163 Å^3
• Polar Surface Area: 55.4 Å^2
• Rotatable Bonds: 11
• 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): C16H29NO3

DETAILS

Sigma Aldrich - 17247

Application
Application test: Induces violacein expression in a Chromobacterium violaceum mutant usually not able to produce homoserine lactones1.
Biochem/physiol Actions
Quorum-sensing signal generation.2
N-Dodecanoyl-DL-homoserine lactone (C12-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-(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-Lauroyl- 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.