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

• ChemBase ID: 154106
• Molecular Formular: C18H31NO4
• Molecular Mass: 325.44304
• Monoisotopic Mass: 325.22530848
• SMILES: CCCCCCCCCCCC(=O)CC(=O)N[C@H]1CCOC1=O
• Canonical SMILES: CCCCCCCCCCCC(=O)CC(=O)N[C@H]1CCOC1=O
• InChI: InChI=1S/C18H31NO4/c1-2-3-4-5-6-7-8-9-10-11-15(20)14-17(21)19-16-12-13-23-18(16)22/h16H,2-14H2,1H3,(H,19,21)/t16-/m0/s1
• InChIKey: YQFJJDSGBAAUPW-INIZCTEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-oxo-N-[(3S)-2-oxooxolan-3-yl]tetradecanamide
• IUPAC Traditional name: 3-oxo-N-[(3S)-2-oxooxolan-3-yl]tetradecanamide
• Synonyms: N-(3-Oxotetradecanoyl)-L-homoserine lactone

Database IDs

• MDL Number: MFCD12912433
• PubChem SID: 162248245
• PubChem CID: 9883786

CALCULATED PROPERTIES

• Acid pKa: 10.296827
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.841157
• LogD (pH = 7.4): 3.8406146
• Log P: 3.8411639
• Molar Refractivity: 88.7891 cm^3
• Polarizability: 35.214638 Å^3
• Polar Surface Area: 72.47 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Shipped in: wet ice
• Empirical Formula (Hill Notation): C18H31NO4

DETAILS

Sigma Aldrich - O9264

Biochem/physiol Actions
Acyl homoserine lactone used as an autoinducer of quorum signaling by Sinorhizobium meliloti, Yersinia enterocolitica, and other Gram-negative bacteria.1
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.