Synthesis of beta-cryptoxanthin via unusual regioselective catalytic hydrogenation

ORGN 685

Yufa Liu, Yufa.Liu@Kemin.com1, Holly Showalter, Holly.Showalter@Kemin.com1, and Frederick Khachik, khachik@umd.edu2. (1) R&D, Kemin Health, 2100 Maury Street, Des Moines, IA 50317, (2) Chemistry and Biochemistry, Joint Institute for Food Safety & Applied Nutrition, University of Maryland, Building 091, College Park, MD 20742
Beta-Cryptoxanthin (1) is one of the major carotenoids found in the human serum and tissues. Compared to other carotenoids such as (3R,3'R,6'R)-lutein (2) and (3R,3'R)-zeaxanthin, 1 has unique beneficial effects to the support of cardiovascular and bone health. For example, the serum level of 1 in humans has been inversely associated with blood pressure as well as fibrinogen level while no such association has been observed with other carotenoids. In a human clinical trial, 1 was also shown to have a beneficial effect on bone biomarkers related to calcium absorption and bone resorption. 1 is among the rare carotenoids in nature and consequently its isolation from natural products is not economically viable. We have developed an efficient and patented process that converts (3R)-3',4'-anhydrolutein (3), a dehydration product of 2, to 1 by regioselective catalytic hydrogenation employing 5% Pt on alumina.
 

Biologically-Related Molecules and Processes
8:00 AM-12:00 PM, Wednesday, August 22, 2007 BCEC -- 258B, Oral

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007