ARS | Publication request: Preparation and Characterization of 4-Methoxy Cinnamoyl Glycerol

Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: January 10, 2008
Publication Date: February 6, 2008
Citation: Holser, R.A., Harry O Kuru, R.E., Vaughn, S.F., Himmelsbach, D.S. 2008. Preparation and characterization of 4-methoxy cinnamoyl glycerol. Journal of the American Oil Chemists' Society. 85(4):347-351.

Interpretive Summary: A compound with the ability to absorb ultraviolet light was prepared from glycerol and cinnamic acid. These two agricultural materials were combined in a simple reaction to produce the ester glycerol cinnamate. This product is more water soluble than typical compounds used in sunscreens and therefore less likely to be transferred through skin. This is significant because there are reports of sunscreens that contain fatty compounds interacting with the human endocrine system following topical application and absorption by the body. The development of this glycerol-based sunscreen would provide an outlet for excess glycerol generated from biodiesel production and benefit U.S. agriculture and consumers. This topic would be of potential interest to biodiesel producers, cosmetic manufacturers and formulators, and the medical community.

Technical Abstract: Glycerol was combined with cinnamic acid to prepare the corresponding ester, glycerol cinnamate. Conversions of 81% were achieved after 16 hr in toluene at reflux conditions. The product was recovered by extraction with distilled water and diethyl ether. The isolated product displayed strong absorbance in the UVB range. It is expected to find applications as a UV filter in cosmetic and personal care formulations where a moderately hydrophilic compound would be advantageous.