title: Caffeic acid phenethyl ester (CAPE): synthesis and X-ray crystallographic analysis.
abstract: The structure of caffeic acid phenethyl ester [2-propenoic acid, 3-(3,4-dihydroxyphenyl)-, 2-phenethyl ester] (I), C17H16O4 x 1/2C6H6, synthesized by base-catalyzed alkylation of caffeic acid salt with beta-bromoethylbenzene in HMPA (hexamethylphosphoramide) and recrystallized from benzene, was confirmed by single crystal X-ray diffraction. The crystals are triclinic, space group P1, Z=2, unit cell dimension a=5.8129 (9) A, b=11.122 (2) A, c=13.226 (2) A, alpha=97.080 (3) degrees, beta=101.467 (3) degrees, gamma=95.405 (3) degrees , V=825.4 (2) A3, Dcalc=1.301 g/cm3, F(000)=342. The packing of the molecule is stabilized by intermolecular O1H...O4 (2.69 A) and O1...HO2 (2.82 A) hydrogen bonds.
authors.affiliation: Department of Food Science, Cornell University, Ithaca, NY 14853, USA.
authors.forename: S
authors.initials: S
authors.lastname: Son
authors.forename: E B
authors.initials: EB
authors.lastname: Lobkowsky
authors.forename: B A
authors.initials: BA
authors.lastname: Lewis
mesh_terms: D002109:Caffeic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010626:Phenylethyl Alcohol / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry*; D013055:Spectrophotometry, Infrared
chemical_list: D002109:Caffeic Acids; C055494:caffeic acid phenethyl ester; D010626:Phenylethyl Alcohol