Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
2005-06-28
2005-06-28
Shippen, Michael L. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
Reexamination Certificate
active
06911564
ABSTRACT:
Disclosed are processes for conversion of (3R,3′R,6′R)-lutein to (3R,6′R)-α-cryptoxanthin, (3R)-β-cryptoxanthin, anhydroluteins I, II, and III (dehydration products of lutein), and a method for separating and purifying the individual carotenoids including the unreacted (3R,3′R)-zeaxanthin. The invention also includes two methods that transform (3R,3′R,6′R)-lutein into (3R,6′R)-α-cryptoxanthin in excellent yields.
REFERENCES:
patent: 4235820 (1980-11-01), Evans
patent: 1081104 (1967-08-01), None
patent: 1081104 (1967-09-01), None
patent: WO 99/20587 (1999-04-01), None
patent: WO 01/83414 (2001-11-01), None
Khachik, J. Chromatogr. B, vol. 670, pp. 219-233 (1995).
Zechmeistez, J. Am. Chem. Soc., vol. 65, pp. 1951-1965 (1943).
Aidhen, Indian J. Chem., vol. 328 , pp. 231-238 (1993).
Lau, J. Org. Chem., vol. 51, pp. 1038-3043 (1986).
Dehmol, Synth. Commun. vol. 26, pp. 1467-1172 (1996).
Wustrow, Tetrahedron Lett., vol. 35, pp. 61-64 (1994).
Buchecker, Helv. Chim. Acta, vol. 57, pp 631-656 (1974).
Aidhen, I.S., and Narasimhan, N.S., “A novel and versatile synthesis of 1-arylbenzocyclobutenols and 1-arylbenzocyclobutenes,”Ind. J. Chem. 32B:234-238, Council of Scientific & Industrial Research (1993).
Buchecker, R., et al., “Absolute Konfiguration von Xanthophyll (Lutein),”Helv. Chim. Acta 57:631-656, Schweizerische Chemische Gesellschaft (1974), (no translation).
da S. Costa, J. et al., “Deoxygenation of Furanmethanols with Znl2-NaCNBH3. An Efficient Protocol for the Preparation of 2- and 3-alkylfuran Compounds,”J. Braz. Chem. Soc. 5:113-116, Sociedade Brasileira de Química (1994).
Dehmlow, E.V., et al., “Mild and Fast Deoxygenation of Aromatic Carbonyl Compounds by Diethylamine Borane/Titanium Tetrachloride,”Synth. Commun. 26:1467-1472, Marcel Dekker, Inc. (1996).
Goodfellow, D., et al., “The Absolute Configuration of Lutein,” J. Chem. Soc. Chem. Commun. 13:1578, The Chemical Society (1978).
Isler, O., et al., “Synthesen in der Carotinoid-Reihe. Totalsynthese von Kryptoxanthin und eine weitere Synthese von Zeaxanthin,”Helv. Chim. Acta. 40:456-467 Schweizerische Chemische Gesellschaft (1957), (no translation).
Khachik, F., et al., “Isolation, structural elucidation, and partial synthesis of lutein dehydration products in extracts from human plasma,”J. Chrom. B. Biomed. Appl. 670:219-233, Elsevier Science B.V. (1995).
Lau, C.K. et al., “Reductive Deoxygenation of Aryl Aldehydes and Ketones and Benzylic, Allylic, and Tertiary Alcohols by Znl2-NaCNBH3,”J. Org. Chem. 51:3038-3043, American Chemical Society (1986).
Loeber, D.E., et al., “Carotenoids and Related Compounds. Part XXVIII. Synthesis of Zeaxanthin, β-Cryptoxanthin, and Zeinoxanthin (α-Cryptoxanthin),”J. Chem. Soc.(C)Part 1:404-408, The Chemical Society (1971).
Wustrow, D.J., et al., “Selective Deoxygenation of Allylic Alcohols and Acetates by Lithium Perchlorate Promoted Triethylsilane Reduction,”Tetrahedron Lett. 35:61-64, Pergamon Press Ltd. (1994).
Zechmeister, L., and Sease, J.W., “Conversion of Lutein in a Boric Acid-Naphthalene Melt. I,”J. Am. Chem. Soc. 65:1951-1955, American Chemical Society (1943).
International Search Report for International Application No. PCT/US01/23422, 3 pages, European Patent Office, Rijswijk, The Netherlands (mailed Mar. 19, 2002).
Shippen Michael L.
Sterne Kessler Goldstein & Fox P.L.L.C.
University of Maryland College Park
LandOfFree
Method for production of rare carotenoids from commercially... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Method for production of rare carotenoids from commercially..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method for production of rare carotenoids from commercially... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3520296