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Preparation and Characterization of 4‐Methoxy Cinnamoyl Glycerol
Author(s) -
Holser R. A.,
Mitchell T. R.,
HarryO’kuru R. E.,
Vaughn S. F.,
Walter E.,
Himmelsbach D.
Publication year - 2008
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/s11746-008-1197-y
Subject(s) - glycerol , chemistry , cinnamic acid , yield (engineering) , mass spectrometry , catalysis , toluene , organic chemistry , absorbance , proton nmr , carboxylic acid , fourier transform infrared spectroscopy , nuclear chemistry , chromatography , materials science , physics , quantum mechanics , metallurgy
Glycerol was reacted with 4‐methoxy cinnamic acid to prepare the corresponding 4‐methoxy cinnamoyl glycerol. The reaction proceeded in toluene under reflux conditions with p ‐toluenesulfonic acid catalyst. Reaction of equimolar amounts of reactants produced the monoester in 20% yield after 2 h. The product was isolated and characterized by FTIR, mass spectrometry, and NMR techniques. Results of mass spectrometry and NMR experiments showed that the ester linkage formed between the carboxylic acid and the primary hydroxyl of glycerol. The ester displayed strong absorbance between 250 and 350 nm and shows potential as a UV filter in formulations where hydrophilic compounds are advantageous.