
CAS Name: D-Glucuronic acid g-lactone
Additional Names: D-glucofuranurono-6,3-lactone; glucurolactone; glucurone
Trademarks: Dicurone; Glucoxy; Guronsan
Percent Composition: C 40.92%, H 4...
Literature References: Found in many plant gums in polymeric combination with other carbohydrates. Important structural constituent of practically all fibrous and connective tissues in the animal organism, cf. D-glucuronic acid. Prepd synthetically from many polysaccharides or suitable glucosides where the hydroxyl at carbon 6 may be oxidized while the other sensitive groups are protected. Prepn: Stacey, J. Chem. Soc. 1939, 1529; Hardegger, Spitz, Helv. Chim. Acta 33, 337 (1950); Marsh, Proc. Biochem. Soc. [Biochem. J.], 50, XI (1951); Mehltretter et al., J. Am. Chem. Soc. 73, 2424 (1951); Phillips, Moody, J. Chem. Soc. 1960, 762. Structure: J. Stanek et al., The Monosaccharides (Academic Press, New York, 1963) p 259. For isoln procedures see the ref under glucuronic acid.
CAS Name: 5,6,7,7a-Tetrahydro-4,4,7a-trimethyl-2(4H)-benzofuranone
Additional Names: 2-oxo-4,4,7a-trimethyl-2,4,5,6,6,7a-hexahydrobenzofuran; (2,6,6-trimethyl-2-hydroxycyclohexylidene)acetic ac...
Literature References: Found in many plant sources including tea and tobacco. (-)-Form is naturally occurring. Produced by photo-oxidation of carotenoid flavor compounds. Pheromone component for queen recognition in red fire ants. Isoln from black tea aroma: J. Bricout et al., Helv. Chim. Acta 50, 1517 (1967); from Actinidia polygama Miq. and structure determn: T. Sakan et al., Tetrahedron Lett. 8, 1623 (1967); from tobacco and synthesis: W. C. Bailey, Jr. et al., J. Org. Chem. 33, 2819 (1968). Synthesis: S. Isoe et al., Tetrahedron Lett. 9, 5561 (1968); by photo-oxidation of b-carotene: eidem, ibid. 10, 279 (1969). Abs config study: eidem, ibid. 13, 2517 (1972). Prepn of enantiomers: K. Mori, Y. Nakazono, Tetrahedron 42, 283 (1986). Improved prepns: G. V. Subbaraju et al., Tetrahedron Lett. 32, 4871 (1991); A. Bosser et al., Biotechnol. Prog. 11, 689 (1995). Prepn of (R)-form: S. Yao et al., J. Org. Chem. 63, 118 (1998). Germination inhibition in wheat grains: T. Kato et al., J. Agric. Food Chem. 51, 2161 (2003).
CAS Name: 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one
Additional Names: 3',4',5,7-tetrahydroxyflavone; digitoflavone; cyanidenon 1470
Percent Composition: C 62.94%, H 3.52%, ...
Literature References: Found in many plants in glycosidic combination, e.g., as the arabinoside: Perkin, J. Chem. Soc. 69, 800 (1896); Fleischer, Ber. 32, 1186 (1899); Perkin, Horsfall, J. Chem. Soc. 77, 1315 (1900); Hayashi, Inoue, Acta Phytochim. 15, 53 (1949); C.A. 43, 8450 (1949). Identity with digitoflavone: Kiliani, Mayer, Ber. 34, 3577 (1901). Synthesis: Hutchins, Wheeler, J. Chem. Soc. 1939, 91. See also Bioflavonoids.
CAS Name: 5,6,7,8-Tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinoline
Additional Names: 8-methoxy-5,6-methylenedioxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
Percent Composition: C 6...
Literature References: Found in mother liquors from morphine extraction. It is not certain whether it is formed from narcotine during the extraction or whether it exists in the poppy plant. May also be prepd by reduction of cotarnine: Topchiev, J. Appl. Chem. USSR 6, 529 (1933), C.A. 28, 2718 (1934); Schneider, Müller, Ann. 615, 34 (1958); Knabe, Arch. Pharm. 292, 652 (1959). Reduction of hydrocotarnine with sodium in alcohol leads to replacement of the methoxyl group by hydrogen, with formation of hydrohydrastinine. Review and bibliography: Small, Lutz, "Chemistry of the Opium Alkaloids," Suppl. No. 103, Public Health Reports, Washington (1932).
Additional Names: Urao; trona
Percent Composition: C 12.64%, H 0.53%, Na 36.30%, O 50.52%
Literature References: Found in nature as the dihydrate, e.g., Owens Lake, Searles Lake (U.S.A.); Lake Magadi (Kenya). Produced on a large scale from sodium carbonate and a slight excess of sodium bicarbonate: Schenk in Winnacker-Weingaertner, Chemische Technologie vol. I (München, 1950) p 427.
CAS Name: (5R)-5-Methyl-2-(1-methylethylidene)cyclohexanone
Additional Names: R-(+)-p-menth-4(8)-en-3-one; 1-methyl-4-isopropylidene-3-cyclohexanone
Percent Composition: C 78.90%, H 10.59%, ...
Literature References: Found in oils derived from plants of the Labiatae family as (+)-form. Readily isolated in quantity from the pennyroyal oils from Mentha pulegium L., M. longifolia (L.) Huds., and Hedeoma pulegioides (L.) Pers., Labiatae: Gildemeister, Hoffmann, Die ätherischen Ole Vol. I, p 560 (1928); Simonsen, The Terpenes Vol. I (2nd ed, 1947) p 370. Synthesis: Kuhn, Schinz, Helv. Chim. Acta 36, 161 (1953). Synthesis of the (±)-form: Black et al., J. Chem. Soc. 1956, 2971; Wolinsky et al., J. Org. Chem. 30, 3207 (1965); of the S(-)-form: E. J. Corey et al., ibid. 41, 380 (1976). Improved synthesis of the R(+)-form: T. Sato et al., Tetrahedron Lett. 1980, 3377. Conversion of the R(+) to the S(-)-form: H. E. Ensley, R. V. C. Carr, ibid. 1977, 513. Biosynthetic study: A. Akhila, D. V. Banthorpe, Z. Pflanzenphysiol. 99, 277 (1980), C.A. 94, 2073r (1981).
CAS Name: 1-Phenazinol
Additional Names: a-hydroxyphenazine; 1-hydroxy-5,10-diazoanthracene; pyoxanthose
Percent Composition: C 73.46%, H 4.11%, N 14.28%, O 8.15%
Literature References: Found in old cultures of Pseudomonas pyocyanea. Isoln: Fordos, Compt. Rend. 56, 1128 (1863). Prepd from pyocyanine by the action of 2% NaOH: Wrede, Strack, Z. Physiol. Chem. 140, 12 (1924); by the reaction of pyrogallol monomethyl ether and o-phenylenediamine followed by demethylation of the formed a-methoxyphenazine: Surrey, Org. Synth. coll. vol. III, 753 (1955). Alternate syntheses: Hegedüs, Helv. Chim. Acta 33, 766 (1950); Vivian, Nature 178, 753 (1956).
CAS Name: 5,6-Dimethoxy-2H-furo[2,3-h]-1-benzopyran-2-one
Additional Names: 4-hydroxy-6,7-dimethoxy-5-benzofuranacrylic acid d-lactone
Percent Composition: C 63.41%, H 4.09%, O 32.49%
Literature References: Found in Pimpinella saxifraga L., Heracleum spondylium L., H. lanatum Michx., and H. panaces L., Umbelliferae. Isoln: Heut, Arch. Pharm. 236, 162 (1898); Herzog, Hancu, ibid. 246, 402 (1908); Wessely, Kallab, Monatsh. Chem. 59, 161 (1932); Späth, Simon, ibid. 67, 344 (1936); Fujita, Furuya, J. Pharm. Soc. Jpn. 74, 795 (1954); 76, 535 (1956); Svendsen, Ottestad, Pharm. Acta Helv. 32, 457 (1957); Svendsen, C.A. 52, 2173g (1958); Svendsen et al., Planta Med. 7, 113 (1959); Pharm. Acta Helv. 34, 33 (1959); Jastrzebski, C.A. 54, 1205b (1960). Synthesis: M. W. Reed, H. W. Moore, J. Org. Chem. 53, 4166 (1988).
CAS Name: (3b,16b,17a,18b,20a)-11,17-Dimethoxy-18-[[1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]oxy]-3,20-yohimban-16-carboxylic acid methyl ester
Additional Names: 3,4,5-trimethoxycinnamic aci...
Literature References: Found in Rauwolfia serpentina Benth., Apocynaceae: Haack et al., Naturwissenschaften 41, 214 (1954); Ordway, Guercio, US 2876228 (1959 to Pfizer); Klohs et al., US 2974144 (1961 to Riker); from Rauwolfia spp: Banes et al., J. Am. Pharm. Assoc. 47, 625 (1958). Identity with reserpinine: Haack et al., Naturwissenschaften 42, 47 (1955). Structure: Klohs et al., J. Am. Chem. Soc. 77, 2241 (1955). LC-ED determn in urine: J. Wang, M. Bonakdar, J. Chromatogr. 382, 343 (1986). LC determn in rauwolfia preparations: U. R. Cieri, J. AOAC Int. 81, 373 (1998).
CAS Name: 2,3,4,13-Tetrahydro-1H-benz[g]indolo[2,3-a]quinolizin-6-ium
Additional Names: 3,4,5,6,14,15,20,21-octadehydroyohimbanium; sempervirene
Percent Composition: C 83.79%, H 5.92%, N 10....
Literature References: Found in rhizome and roots of Carolina jessamine (yellow jessamine) Gelsemium sempervirens (L.) Ait. f., Loganiaceae: Stevenson, Sayre, J. Am. Pharm. Assoc. 4, 60 (1915); 8, 708 (1919); Hasenfratz, Bull. Soc. Chim. Fr. [4] 53, 1084 (1933); Forsyth et al., J. Chem. Soc. 1945, 579; Prelog, Helv. Chim. Acta 31, 588 (1948). Believed to exist primarily as inner salt depicted below: Woodward, Witkop, J. Am. Chem. Soc. 71, 379 (1949). Synthesis: Woodward, McLamore, ibid. 379; Swan, J. Chem. Soc. 1958, 2039; Ban, Seo, Tetrahedron 16, 11 (1961); Potts, Mattingly, J. Org. Chem. 33, 3985 (1968).
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