Submitted to: Lipids Journal
Publication Type: Peer reviewed journal
Publication Acceptance Date: 6/10/2004
Publication Date: 11/28/2005
Citation: Harry-O'kuru, R.E. 2005. 4-Hydroxy-3-methoxycinnamate esters of milkweed oil: Synthesis and characterization. Lipids. 40:1179-1183. Interpretive Summary: Milkweed is a new industrial crop whose fiber (floss) is in the market as a component of hypoallergenic pillows and comforters. In order to improve the economical success of this new crop, a continuing effort has been underway to develop a variety of co-products to milkweed fiber. This manuscript reports a novel compound usable as a skin-protectant against ultra-violet radiation. The compound has been designed and sythesized from modified milkweed oil.
Technical Abstract: The common milkweed (Asclepias syriaca) is a new industrial crop. Its seed oil (triglycerides) is polyunsaturated with olefinic groups. In the search for novel applications for milkweed seed oil, the olefinic groups in the triglycerides were oxidized to polyhydroxy triglycerides via epoxidation and subsequent epoxy ring opening reactions. These polyhydroxy triglycerides exhibit unique industrially desirable emulsoid properties in water. Esterification of the secondary polyhydroxy functionalities of the triglycerides of the oil with trans-4-hydroxy-3-methoxycinnamic acid (ferulic acid) has resulted in the development of novel cinnamate esters of milkweed oil. These cinnamates are also accessible via direct ring opening of the epoxy triglyceride intermediate with ferulic acid. Among the interesting characteristics of the ester derivatives is their ultraviolet radiation absorbing property.