
Additional Names: 6-Methylionone
Literature References: The fragrant principle of violets, best isolated from the rhizomes of iris or from orris oil: F. Tiemann, P. Kruger, Ber. 26, 2675 (1893); Ruzicka et al., Helv. Chim. Acta 16, 1143 (1933); Naves, Mazuyer, Les Parfums Naturels (Paris, 1939). Irone, as isolated, is an isomeric mixture of a-, b, and g-irones, q.q.v., with each having the same molecular formula, C14H22O. Synthesis of isomeric mixture: Eschinazi, US 3019265 (1962 to Givaudan).
Additional Names: Gum Ghatti; Indian gum
Literature References: The gummy exudate from stems of Anogeissus latifolia Wall., Combretaceae, abundant in India and Ceylon, cf. C. L. Mantell, The Water-Soluble Gums (New York, 1947). Name derived from the word ghats, meaning passes, and given to the gum because of its ancient mountain transportation routes. Structure is a complex water-soluble polysaccharide occurring as a calcium-magnesium salt; composed of L-arabinose, D-galactose, D-mannose, D-xylose, D-glucuronic acid, in a molar ratio of 10:6:2:1:2, and traces of 6-deoxyhexose: Aspinall et al., J. Chem. Soc. 1955, 1160. Early investigation of chemistry and mol wt: Shaw et al., Proc. S. D. Acad. Sci. 15, 46 (1935); 16, 34 (1936); 17, 27 (1937); 19, 130 (1939); 21, 78 (1941). Review: Meer et al., in Industrial Gums, R. L. Whistler, Ed. (Academic Press, New York, 2nd ed., 1973) pp 265-271.
CAS Name: (11b,16a)-21-(3,3-dimethyl-1-oxobutoxy)-9-fluoro-11-hydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione
Additional Names: 9-fluoro-11b,16a,17,21-tetrahydroxypregna...
Literature References: The hexacetonide ester of the potent glucocorticoid, triamcinolone, q.v. Prepn of syringeable suspension: Nash, Naeger, US 3457348 (1969 to Am. Cyanamid). Anti-inflammatory activity in rabbits: I. M. Hunneyball, Agents Actions 11, 490 (1981). Early clinical studies: Bilka, Minn. Med. 50, 483 (1967); Layman, Peterson, ibid. 669. Clinical studies of intra-articular therapy in arthritis: R. C. Allen et al., Arthritis Rheum. 29, 997 (1986); M. Talke, Fortschr. Med. 104, 742 (1986). Toxicity study: Tonelli, Steroids 8, 857 (1966). Comprehensive description: V. Zbinovsky, G. P. Chrekian, Anal. Profiles Drug Subs. 6, 579-595 (1977). For structure see Triamcinolone Acetonide.
CAS Name: 2-Piperidinecarboxylic acid
Additional Names: pipecolinic acid; hexahydropicolinic acid; homoproline; dihydrobaikiaine
Percent Composition: C 55.79%, H 8.58%, N 10.84%, O 24.77%
Literature References: The l-form occurs in plants: Phillips, Chem. Ind. (London) 1953, 127. Prepn: A. Ladenburg, Ber. 24, 640 (1891); Stevens, Ellman, J. Biol. Chem. 182, 75 (1950); V. Asher et al., Tetrahedron Lett. 22, 141 (1981). Synthesis of L-pipecolic acid from L-lysine: Fujii, Miyoshi, Bull. Chem. Soc. Jpn. 48, 1341 (1975). Synthesis of racemate: R. T. Shuman et al., J. Org. Chem. 55, 738 (1990).
CAS Name: N-(N-L-g-Glutamyl-L-cysteinyl)glycine
Additional Names: L-glutathione; glutathione-SH; GSH
Trademarks: Agifutol S (Kyorin); Copren (Fuso); Deltathione (Tobishi); Glutamed (Boehring...
Literature References: The major low mol wt thiol compound of the living plant or animal cell. Isoln from yeast: Hopkins, J. Biol. Chem. 84, 269 (1929). Synthesis: du Vigneaud, Miller, Biochem. Prep. 2, 87 (1952); Goldschmidt et al., Ber. 97, 2434 (1964); Y. Ozawa et al., Bull. Chem. Soc. Jpn. 53, 2592 (1980). Review of early syntheses: Jeschkeit et al., Pharmazie 18, 658 (1963). Review of metabolism: A. Meister, M. E. Anderson, Annu. Rev. Biochem. 52, 711-760 (1983); of metabolic role in antineoplastic chemotherapy: B. A. Arrick, C. F. Nathan, Cancer Res. 44, 4224-4232 (1984). Monographs: S. Colowick et al., Glutathione (Academic Press, New York, 1954); Glutathione, E. M. Crook, Ed., Biochem. Soc. Symposium No. 17, London, 1958 (Cambridge University Press, 1959); Glutathione, L. Flohe et al., Eds. (Academic Press, New York, 1974); Glutathione: Metabolism Function I. M. Arias, W. B. Jackoby, Eds. (Raven, New York, 1976).
CAS Name: (6aS)-5,6,6a,7-Tetrahydro-2,10,11-trimethoxy-6-methyl-4H-dibenzo[de,g]quinolin-1-ol
Additional Names: 2,10,11-trimethoxy-6aa-aporphin-1-ol; 1-hydroxy-2,10,11-trimethoxyaporphine
Pe...
Literature References: The methyl ether of corytuberine. Occurs in Corydalis cava (L.) Schweigg Körte (C. tuberosa DC), Fumariaceae, in the dextrorotatory form. Isoln: Gadamer, Ziegenbein, Arch. Pharm. 240, 94 (1902). Structure: Späth, Berger, Ber. 64, 2038 (1931). Synthesis: Hey, Palluel, J. Chem. Soc. 1957, 2926; Arumugam et al., Ber. 91, 40 (1958); Jackson, Martin, Chem. Commun. 1965, 142, 420; eidem, J. Chem. Soc. C 1966, 2222. uv spectrum: Shamma, Yao, J. Org. Chem. 36, 3253 (1971).
CAS Name: (3b)-1,6-Didehydro-14,17-dihydro-3-methoxy-16(15H)-oxaerythrinan-15-one
Additional Names: 12,13-didehydro-2,7,13,14-tetrahydro-a-erythroidine
Percent Composition: C 69.79%, H 7.69%...
Literature References: The more active of the two isomers that constitute the principal alkaloidal fraction of seeds from several Erythrina spp. In contrast to curare, q.v., it retains its ability to block neuromuscular transmission even when administered orally: K. Unna, J. G. Greslin, J. Pharmacol. 80, 53 (1944); K. Unna et al., ibid. 39. Prepd by catalytic hydrogenation of b-erythroidine or a salt of b-erythroidine: Folkers, Koniuszy, US 2370651 (1945 to Merck Co.). Structure: Boekelheide et al., J. Am. Chem. Soc. 75, 2550 (1953). Configuration: Hanson, Proc. Chem. Soc. London 1963, 52.
CAS Name: 1,2,3,6-Tetrahydro-2,3'-bipyridine
Additional Names: 2-(3-pyridyl)-1,2,3,6-tetrahydropyridine; 1,2,3,6-tetrahydro-2-(3-pyridyl)pyridine
Percent Composition: C 74.96%, H 7.55%, N 17...
Literature References: The most abundant of the minor alkaloids of tobacco: Späth, Kesztler, Ber. 70, 239, 704, 2450 (1937). Fresh Nicotiana tabacum, the species most commonly used for the production of cigarette tobacco, contains 3.9% anatabine. Configuration: Lukes et al., Collect. Czech. Chem. Commun. 27, 751 (1962). Total synthesis of dl-form: Quan et al., J. Org. Chem. 30, 2769 (1965). Biosynthesis: E. Leete, S. Slattery, J. Am. Chem. Soc. 98, 6326 (1976). Biomimetic synthesis: E. Leete, M. E. Mueller, ibid. 104, 6440 (1982).
CAS Name: (5Z,11a,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-oic acid
Additional Names: 7-[3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl]-5-heptenoic acid; dinoprostone; PGE2Trademar...
Literature References: The most common and most biologically potent of mammalian prostaglandins. Isoln from sheep prostate: S. Bergström, J. Sjövall, GB 851827; eidem, US 3598858 (1960, 1971); from sheep seminal vesicle tissue: S. Bergström et al., Acta Chem. Scand. 16, 501 (1962). Total synthesis of the dl-form: W. P. Schneider, Chem. Commun. 1969, 304; E. J. Corey et al., J. Am. Chem. Soc. 91, 5675 (1969); E. J. Corey et al., Tetrahedron Lett. 1970, 307; W. P. Schneider, DE 2011969 (1970 to Upjohn), C.A. 74, 87486n (1971); J. Fried et al., J. Am. Chem. Soc. 94, 4342 (1972). Synthesis of naturally occurring form: E. J. Corey et al., ibid. 92, 397, 2586 (1970); J. B. Heather et al., Tetrahedron Lett. 1973, 2313; from Plexaura homomalla prostaglandin intermediates: G. L. Bundy et al., J. Am. Chem. Soc. 94, 2123 (1972); W. P. Schneider et al., Chem. Commun. 1973, 254. Biosynthesis: D. A. Van Dorp et al., Biochim. Biophys. Acta 90, 204 (1964); S. Bergström et al., ibid. 207; NL 6505799 (1965 to Unilever), C.A. 65, 7584h (1966). Metabolism: E. Anggard, B. Samuelsson, Mem. Soc. Endocrinol., no. 14, 107 (1966); M. Hamberg, B. Samuelsson, J. Biol. Chem. 246, 6713 (1971). Several reviews in Prostaglandin Symp. Worcester Found. Exp. Biol., P. Ramwell, Ed. (Interscience, New York, 1968). For general refs see Prostaglandins.
CAS Name: (1R-trans)-2,3,5,7a-Tetrahydro-1-hydroxy-1H-pyrrolizine-7-methanol
Percent Composition: C 61.91%, H 8.44%, N 9.03%, O 20.62%
Literature References: The most common base portion of pyrrolizidine alkaloids. "Necine" bases are 1-methylpyrrolizidines of different stereochemical configurations and degrees of hydroxylation that occur in the form of esters in alkaloids of Senecio, Crotalaria and a number of genera of the Boraginaceae. Retronecine occurs in nature in the (+)-form. It is the necine base of monocrotaline, senecionine, seneciphylline, retrorsine, q.q.v., and numerous other hepatotoxic pyrrolizidine alkaloids. Structure: R. Adams, E. F. Rogers, J. Am. Chem. Soc. 63, 228 (1941). Total synthesis: T. A. Geissman, A. C. Waiss, J. Org. Chem. 27, 139 (1962). Stereospecific synthesis: E. Vedejs, G. R. Martinez, J. Am. Chem. Soc. 102, 7993 (1980); H. Niwa et al., Tetrahedron Lett. 27, 4605 (1986). Total synthesis of (-)-form: J. Cooper et al., Chem. Commun. 1988, 509. Toxicity data: P. N. Harris et al., J. Pharmacol. Exp. Ther. 75, 78 (1942). Biosynthesis: D. J. Robins, J. R. Sweeney, Chem. Commun. 1979, 120; G. Grue Sorensen, I. D. Spenser, J. Am. Chem. Soc. 103, 3208 (1981). Comprehensive reviews on retronecine and other necine bases: F. L. Warren, Fortschr. Chem. Org. Naturst. 12, 198-269 (1955); 24, 329-406 (1966); D. J. Robins, ibid. 41, 115-203 (1982); F. L. Warren in Alkaloids Vol. XII, R. H. F. Manske, Ed. (Academic Press, New York, 1970) pp 245-331.
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