Invention Grant
- Patent Title: Process for the preparation of β- and α-cryptoxanthin
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Application No.: US12834460Application Date: 2010-07-12
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Publication No.: US08097762B2Publication Date: 2012-01-17
- Inventor: Frederick Khachik , Yufa Liu , Holly Showalter
- Applicant: Frederick Khachik , Yufa Liu , Holly Showalter
- Applicant Address: US MD College Park
- Assignee: University of Maryland, College Park
- Current Assignee: University of Maryland, College Park
- Current Assignee Address: US MD College Park
- Agency: Sterne, Kessler, Goldstein & Fox P.L.L.C.
- Main IPC: C07C35/18
- IPC: C07C35/18 ; C07C35/21

Abstract:
The present invention relates to a process for converting lutein and/or lutein esters to (3R)-β-cryptoxanthin and (3R,6′R)-α-cryptoxanthin, suitable for human consumption as dietary supplements, by employing safe and environmentally friendly reagents. (3R)-β-Cryptoxanthin and (3R,6′R)-α-cryptoxanthin are two rare food carotenoids that are not commercially available and the former exhibits vitamin A activity. In the first synthetic step, commercially available lutein and/or lutein esters are transformed into a mixture of dehydration products of lutein (anhydroluteins) in the presence of a catalytic amount of an acid. The resulting anhydroluteins are then converted to (3R)-β-cryptoxanthin (major product) and (3R,6′R)-α-cryptoxanthin (minor product) by heterogeneous catalytic hydrogenation employing transition elements of group VIII (Pt, Pd, Rh supported on alumina or carbon) in a variety of organic solvents under atmospheric pressure of hydrogen and at temperatures ranging from −15° C. to 40° C. Among these catalysts, Pt supported on alumina at 40° C. in ethyl acetate provides the best yield of (3R)-β-cryptoxanthin and (3R,6′R)-α-cryptoxanthin. Several homogeneous catalysts can also promote the regioselective hydrogenation of anhydroluteins to a mixture of (3R)-β-cryptoxanthin and (3R,6′R)-α-cryptoxanthin in low to moderate yields. The catalysts may be transition metal complexes such as palladium acetylacetonate, Rh(Ph3P)3Cl (Wilkinson's catalyst), [(C6H11)3P[C8H12][C5H5N]Ir+PF6− (Crabtree catalyst), or [C8H12][(MePh2P)2]Ir+PF6−. Among these, Wilkinson catalyst converts anhydroluteins to (3R)-β-cryptoxanthin and (3R,6′R)-α-cryptoxanthin in nearly quantitative yield. A novel feature of this invention is the regioselective hydrogenation of anhydroluteins while the highly conjugated polyene chain of these carotenoids remains intact.
Public/Granted literature
- US20100280286A1 Process For The Preparation of Beta and Alpha Cryptoxanthin Public/Granted day:2010-11-04
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