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

• ChemBase编号: 154310
• 分子式: C13H13NO4
• 平均质量: 247.24662
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 3-(4-hydroxyphenyl)-N-[(3S)-2-oxooxolan-3-yl]prop-2-enamide
• IUPAC传统名: 3-(4-hydroxyphenyl)-N-[(3S)-2-oxooxolan-3-yl]prop-2-enamide
• 别名: p-Coumaroyl (S)-(-)α-amino-γ-butyrolactone; pC-HSL; N-(p-Coumaroyl)-L-homoserine lactone

登记号

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

理论计算性质

• Acid pKa: 9.419579
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 0.9734568
• LogD (pH = 7.4): 0.9694156
• Log P: 0.97352284
• 摩尔折射率: 65.2551 cm^3
• 极化性: 24.931486 Å^3
• 极化表面积: 75.63 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 比旋光度: [α]/D -21.0±2.0°, c = 1% in ethanol

安全信息

• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

产品相关信息

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

详细说明

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.