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Title: SYNTHESIS OF NOVEL ULTRAVIOLET FILTERS FROM NEW CROP (JOJOBA) OIL

Author
item Harry O Kuru, Rogers
item Mohamed, Abdellatif
item ABBOTT, THOMAS - RETIRED ARS

Submitted to: Association for the Advancement of Industrial Crops Conference
Publication Type: Abstract Only
Publication Acceptance Date: 9/8/2004
Publication Date: 9/23/2004
Citation: Harry O Kuru, R.E., Mohamed, A., Abbott, T.P. 2004. Synthesis of novel ultraviolet filter s from new crop (jojoba) oil [abstract]. Association for the Advancement of Industrial Crops Conference. p.16.

Interpretive Summary:

Technical Abstract: Jojoba (Simmondsia chinensis) is a semi-arid perennial shrub native to the Sonoran desert. The seed contains a liquid wax ester comprising 50 to 60% of the seed weight. This oil is unique being made up primarily of C38:2, C40:2, C42:2, C44:2 and C46:2 species with one double bond in the carboxyl moiety and the other in the alcohol portion of the molecule. This structural feature gives the oil skin-softening characteristics similar to that of sperm whale oil. As a result jojoba oil is already in the market in many cosmetic formulations. In order to further diversify and expand utilization of the oil, which is presently the only marketable component of the crop, we have chemically modified the carbon-carbon double bonds of the oil to generate new derivatives. Facile epoxidation of the olefinic groups followed by ring-opening in dilute mineral acid gave the tetrahydroxyjojoba intermediate. Esterification of the hydroxyl groups of the intermediate with trans-4-hydroxy-3-methoxycinnamic acid (ferulic acid) in the presence of anhydrous ZnCl2 as catalyst gave jojobacinnamoyl esters. These ferulates strongly absorb both long and short wavelength ultraviolet radiation at very low concentrations. Their strong UV absorbance makes these materials excellent UV-filter candidates in an assortment of applications. The natural emollience of the native oil amplifies the utilitarian efficiency of the ferulates as sunscreen base materials. Finally, the impact of this material would be increased demand for jojoba oil and consequently increased acreage of planted jojoba crop.