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CS-W001157 4
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N-(3-Hydroxyphenyl)cinnamamide

  • CAS No. 23478-25-3

  • Cat. No. CS-0149664
  • Purity≥97%
  • MDL No.None

*For research and further manufacturing use only, not for direct human use.

N-(3-Hydroxyphenyl)cinnamamide|CS-0149664

Structure of 23478-25-3

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General Information

  • CAS No. 23478-25-3
  • Cat. No. CS-0149664
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₁₃NO₂
  • Molecular Weight 239.27
  • Synonym(s) (2E)-N-(3-Hydroxyphenyl)-3-phenylacrylamide
  • SMILES OC1=CC=CC(NC(C=CC2=CC=CC=C2)=O)=C1

Description

N-(3-Hydroxyphenyl)cinnamamide features a phenolic hydroxyl group flanked by an electron-rich aromatic ring, paired with a conjugated cinnamamide linker. This combination enables strong hydrogen bonding and π-π stacking interactions, enhancing molecular recognition in supramolecular systems. The amide bond offers metabolic stability under physiological conditions, while the hydroxyl moiety imparts solubility and facilitates derivatization. This scaffold integrates well into bioactive molecules targeting enzyme inhibition and receptor modulation.

Application

N-(3-Hydroxyphenyl)cinnamamide serves as a versatile scaffold in medicinal chemistry, enabling the construction of bioactive heterocycles through its dual functionality: the phenolic hydroxyl supports hydrogen bonding and metabolic stability, while the cinnamide moiety facilitates amide bond formation and π–π stacking interactions. Its bench-stable nature and compatibility with standard coupling protocols make it suitable for modular synthesis of kinase inhibitors and anti-inflammatory agents.

Safety Information

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GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H332-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   49.33
  • LogP   3.0441
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   3

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