Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1999-05-12
2000-03-21
Kumar, Shailendra
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
560129, 560231, 568379, 568838, C07C 6702, C07C 49105, C07C 3506
Patent
active
060404752
ABSTRACT:
This invention is concerned with the synthesis of 3-(1-acetoxy-1-methylethyl)-6-oxo-heptanal; 3-(1-acetoxy-1-methylethyl)-2-formyl-1-methyl-cyclopentanol; 5-[2-hydroxy-5-(1-hydroxy-1-methylethyl)-2-methyl-2-cyclopentyl]-3-methyl- penta-2,4-dien-1-ol and 2,7,11-trimethyl-13-[2-hydroxy-5-(1-hydroxy-1-methylethyl)-2-methyl-cyclop entyl]-trideca-2,4,6,8,10,12-hexaenal which are useful as intermediates for the synthesis of lycopene metabolites.
REFERENCES:
patent: 3781314 (1973-12-01), Bollag
patent: 5166445 (1992-11-01), Meyer
Houben-Weyl, "Ketone II " , Methoden der org. Chem., vol. 7, Part 2B, pp. 1448-1487, 1980.
J. Bertram, "The chemoprevention of cancer by dietary carotenoids: studies in mouse and human cells," Pure & Appl. Chem., vol. 66, No. 5, pp. 1025-1032 (1994).
N. Krinsky, "Carotenoids and Cancer: Basic Research Studies," Nat. Antioxid. Health Dis., pp. 239-261 (1994).
J. Bertram, "The chemoprevention of cancer by dietary carotenoids: studies in mouse and human cells," Oxid. Stress and Aging, pp. 221-235 (1995).
Narisawa et al., "Inhibitory effects of natural carotenoids, .alpha.-carotene, .beta.-carotene, lycopene and lutein, on colonic aberrant crypt foci formation in rats," Cancer Letters, vol. 107, pp. 137-142 (1996).
Bendich, "Recent Advances in Clinical Research Involving Carotenoids," Pure & Appl. Chem., vol. 66, No. 5, pp. 1017-1024 (1994).
Levy et al., "Lycopene Is a More Potent Inhibitor of Human Cancer Cell Proliferation Than Either .alpha.-carotene, .beta.-carotene," Nutr. Cancer, vol. 24, pp. 257-266 (1995).
Giovannucci et al., "Intake of Carotenoids and Retinol in Relation to Risk of Prostate Cancer," J. of Natl. Cancer Inst., vol. 87, No. 23, pp. 1767-1776 (1995).
Khachik et al., "Lutein, Lycopene, and Their Oxidative Metabolites in Chemoprevention of Cancer," J. of Cell. Biochem., Suppl. 22, pp. 236-246 (1995).
Khachik et al., "Partial Synthesis of the Oxidative Metabolites of Lycopene Isolated from Human Serum," 11.sup.th International Symposium on Carotenoids, Leiden, The Netherlands, Aug. 18-23 1996.
Khachik et al., "Identification of Carotenoids and their Metabolites in Extracts from Human Plasma, Breastmilk, and Dissected Human Retina," 11.sup.th International Symposium on Carotenoids, Leiden, The Netherlands, Aug. 18-23, 1996.
Khachik et al., "Metabolism of Dietary Carotenoids and their Potential Role in Prevention of Cancer and Age-related Macular Degeneration," Book of Abstracts, 213.sup.th ACS Nat. Meeting, San Francisco, California, USA, Apr. 13-14, 1997.
Lu et al., "A New Carotenoid, Hydrogen Peroxide Oxidation Products from Lycopene," Biosci. Biotech. Biochem., vol. 59, (11), pp. 2153-2155 (1995).
Hirata et al., "The Stereospecific Hydroxylation of Endocyclic Ethylenic Linkage in the Biotransformation of .alpha.-Terpinyl Acetate with Cultured Suspension Cells of Nicotiana Tabacum," Chem. Letters, pp. 671-674 (1982).
Hengartner et al., "Synthesis, Isolation, and NMR-Spectroscopic Characterization of Fourteen (Z)-Isomers of Lycopene and of Some Acetylenic Didehydro- and Tetradehydrolycopenes," Helv. Chim. Acta, vol. 75, pp. 1848-1865 (1992).
Weber et al., "An Improved Procedure for the KMnO.sub.4 Oxidation of Olefins to Cis-1,2-Glycols by use of Phase Transfer Catalysis," Tetr. Letters, No. 48, pp. 4907-4908 (1972).
Milas et al., "The Hydroxylation of the Double Bond," J.A.C.S., vol. 58, pp. 1302-1304 (1936).
Koyama et al., "Synthesis of (-) Ambrox from L-Abietic Acid," Tetr. Letters, vol. 28, No. 25, pp. 2863-2866 (1987).
Newhall, "Derivatives of (+)-Limonene.I. Esters of trans-p-Methane-1,2-diol," J. Org. Chem, vol. 23, pp. 1274-1276 (1958).
Viski et al., "A Novel Procedure for the Cleavage of Olefin Derivatives to Aldehydes Using Potassium Permanganate," J. Org. Chem., vol. 51, pp. 3213-3214 (1986).
Meinwald et al., "Synthesis and Sterochemistry of Chrysomelidial and Plagiolactone," J.A.C.S., vol. 100, pp. 1883-1886 (Mar. 15, 1978).
Sakai et al., "Revisions of the Absolute Configurations of C-8 Methyl Groups in Dehydroiridodiol, Neonepetalactone, and Matatabiether from Actinidia Polygama MIQ," Tetrahedron Letters, vol. 36, pp. 3115-3119 (1980).
Wolf et al., "n-Butyl Glyoxylate," Organic Synthesis, vol. IV, pp. 124-125 (1963).
Merrer et al., "Total Synthesis of Leukotriene (+)-LTB.sub.4 from D-Mannitol," Tetr. Letters, vol. 27, No. 35, pp. 4161-4164 (1986).
Wolinsky et al., "Synthesis of 4-(2-Methyl-5-isopropenyl-1-cyclopenten-1-yl)butan-2-one," J. Org. Chem., vol. 29, pp. 3740-3742 (1964).
Greene et al., Protective Groups in Organic Synthesis, 2.sup.nd Edition, John Wiley & Sons, Inc., New York, pp. 68-83, 1981.
Traber et al., "Synthesis of (all-E,2R,2'R)-Oscillol," Helv. Chim. Acta, vol. 79, pp. 499-506 (1996).
Kienzle et al., "Die Synthese von Actinioerthrol, Violerythrin und anderen 2,2'-Dinorcarotenoiden," Helv. Chim. Acta, vol. 61, Nr. 18, pp. 242-249 (1978).
Haag et al., "Isozeaxanthins: Chiralitat und enantioselektive Synthese von 4R,4'R)-Isozeaxanthin ((-)-(4R,4'R)-.beta.,.beta.-Carotin-4,4'-diol)," Helv. Chim. Acta, vol. 65, Nr. 177, pp. 1795-1803 (1982).
Buschor et al., "Synthese der (3S,4R,3'S,4'R)-und (3S,4S,3'S, 4'S)-Crustaxanthine sowie weiterer verbindungen mit 3,4-Dihydroxy-.beta.-Endgruppen," Helv. Chim. Acta, vol. 73, pp. 1002-1021 (1990).
Organikum, Organisch-chemisches Grundpraktikum, 17.sup.th Edition (VEB Deutscher Verlag der Wissenschaften, Berlin), p. 261 (1988).
Pfander Hanspeter
Traber Bruno
Cave LLP Bryan
Haracz Stephen M.
Kumar Shailendra
Padmanabhan Sreeni
Roche Vitamins Inc.
LandOfFree
Intermediate compounds for making metabolites of lycopene does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Intermediate compounds for making metabolites of lycopene, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Intermediate compounds for making metabolites of lycopene will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-731759