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Caffeic acid phenethyl ester (CAPE): synthesis and X-ray crystallographic analysis
S Son1, E B Lobkowsky, B A Lewis
1Department of Food Science, Cornell University, Ithaca, NY 14853, USA.
Chemical & Pharmaceutical Bulletin
|February 24, 2001
Summary
The crystal structure of caffeic acid phenethyl ester was determined using X-ray diffraction. This analysis confirmed its molecular arrangement and identified stabilizing intermolecular hydrogen bonds within the crystal lattice.
Area of Science:
- Crystallography
- Organic Chemistry
- Molecular Structure Analysis
Background:
- Caffeic acid phenethyl ester (CAPE) is a compound with known biological activities.
- Understanding the precise molecular structure is crucial for structure-activity relationship studies.
Purpose of the Study:
- To elucidate the crystal structure of caffeic acid phenethyl ester.
- To confirm the molecular structure and investigate intermolecular interactions.
Main Methods:
- Synthesis of caffeic acid phenethyl ester via base-catalyzed alkylation.
- Recrystallization from benzene.
- Single crystal X-ray diffraction analysis.
Main Results:
- The crystal structure was determined to be triclinic, space group P1, with specific unit cell dimensions.
- The molecular formula and packing were confirmed.
- Intermolecular hydrogen bonds (O1H...O4 and O1...HO2) were identified as stabilizing forces.
Conclusions:
- The crystal structure of caffeic acid phenethyl ester was successfully determined.
- The X-ray diffraction data provides definitive structural confirmation.
- Hydrogen bonding plays a significant role in the crystal packing of this compound.