3-(4-hydroxyphenyl)-N-[(3S)-2-oxooxolan-3-yl]prop-2-enamide

• ChemBase ID: 154310
• Molecular Formular: C13H13NO4
• Molecular Mass: 247.24662
• Monoisotopic Mass: 247.0844579
• SMILES: c1cc(ccc1/C=C/C(=O)N[C@H]1CCOC1=O)O
• Canonical SMILES: O=C(N[C@H]1CCOC1=O)/C=C/c1ccc(cc1)O
• InChI: InChI=1S/C13H13NO4/c15-10-4-1-9(2-5-10)3-6-12(16)14-11-7-8-18-13(11)17/h1-6,11,15H,7-8H2,(H,14,16)/t11-/m0/s1
• InChIKey: CCIXZFJYFQJTGK-NSHDSACASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(4-hydroxyphenyl)-N-[(3S)-2-oxooxolan-3-yl]prop-2-enamide
• IUPAC Traditional name: 3-(4-hydroxyphenyl)-N-[(3S)-2-oxooxolan-3-yl]prop-2-enamide
• Synonyms: p-Coumaroyl (S)-(-)α-amino-γ-butyrolactone; pC-HSL; N-(p-Coumaroyl)-L-homoserine lactone

Database IDs

• MDL Number: MFCD12912377
• PubChem SID: 162248449
• PubChem CID: 71311837

CALCULATED PROPERTIES

• Acid pKa: 9.419579
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.9734568
• LogD (pH = 7.4): 0.9694156
• Log P: 0.97352284
• Molar Refractivity: 65.2551 cm^3
• Polarizability: 24.931486 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]/D -21.0±2.0°, c = 1% in ethanol

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: ≥94% (HPLC)
• Empirical Formula (Hill Notation): C13H13NO4

DETAILS

Sigma Aldrich - 07077

Biochem/physiol Actions
New type of bacterial, quorum sensing signal compound1. Quorum sensing mechanism has been investigated in Rhodopseudomonas palustris, but the signal compound has been discovered in other bacteria such as Bradyrhizobium sp. or Silicibacter pomeroyi.
Application
N-(p-Coumaroyl)-L-homoserine lactone, or pC-HSL, can be used to study microbiology, quorum sensing and signaling compounds. pC-HSL has been used to study the activity of the Rhodopseudomonas palustris p-coumaroyl-homoserine lactone-responsive transcription factor RpaR.