
CAS Name: 6,7-Dihydroxy-2H-1-benzopyran-2-one
Additional Names: 6,7-dihydroxycoumarin; cichorigenin
Percent Composition: C 60.68%, H 3.39%, O 35.93%
Literature References: The aglucon of esculin and of cichoriin. By hydrolysis of esculin or of cichoriin: Merz, Arch. Pharm. 270, 486 (1932). By synthesis: Gattermann, Köbner, Ber. 32, 288 (1899); Bert, Compt. Rend. 214, 230 (1942). Review: Sethna, Shah, Chem. Rev. 36, 1 (1945).
CAS Name: 2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
Additional Names: 4',5,7-trihydroxyflavanone; naringetol; salipurpol; pelargidanon 1602
Percent Composition: C 6...
Literature References: The aglucon of naringin. Prepn by hydrolysis of naringin: Asahina, Inubuse, Ber. 61, 1514 (1928); Haley, Bassin, J. Am. Pharm. Assoc. 40, 111 (1951). From kino of Eucalyptus maculata Hook, Myrtaceae: Gell et al., Aust. J. Chem. 11, 372 (1958). Synthesis: Rosenmund, Rosenmund, Ber. 61, 2608 (1928); Zemplén, Bognár, Ber. 75, 648 (1942). Absolute configuration: Gaffield, Waiss, Chem. Commun. 1968, 29.
CAS Name: 7-Hydroxy-2H-1-benzopyran-2-one
Additional Names: 7-hydroxycoumarin; hydrangin; skimmetin
Percent Composition: C 66.67%, H 3.73%, O 29.60%
Literature References: The aglucon of skimmin. Present in many plants. Obtained by distillation of resins from umbelliferae: Zwenger, Ann. 115, 1, 15 (1860). Prepn: Bert, Compt. Rend. 214, 230 (1942); Austerweil, ibid. 248, 1810 (1959); Dressler, Reabe, US 3503996 (1970 to Koppers). Main product of metabolism of coumarin in man: Schilling et al., Nature 221, 664 (1969). Metabolism studies of umbelliferone: Indahl, Scheline, Xenobiotica 1, 13 (1971). Use in brain intracellular pH measurements: T. M. Sundt, R.E. Anderson, Brain Res. 186, 355 (1980); eidem, J. Neurophysiol. 44, 60 (1980). Use in fluorescent immunoassays: S. G. Thompson, J. F. Burd, Antimicrob. Agents Chemother. 18, 264 (1980); T. M. Li et al., Anal. Biochem. 118, 102 (1981).
CAS Name: 7-Hydroxy-6-methoxy-2H-1-benzopyran-2-one
Additional Names: 7-hydroxy-6-methoxycoumarin; 6-methoxyumbelliferone; b-methylesculetin; chrysatropic acid; gelseminic acid
Percent Compo...
Literature References: The aglucone of scopolin. Occurs in root of Scopolia japonica Maxim., Scopolia carniolica Jacq., Atropa belladonna L., Solanaceae, Convolvulus scammonia L., Convolvulaceae. Isoln: Eykman, Ber. 17 III, 442 (1884). Synthesis: Crosby, J. Org. Chem. 26, 1215 (1961); Desai, Desai, J. Indian Chem. Soc. 40, 456 (1963).
CAS Name: (2a,3b,5a,15b,25R)-Spirostan-2,3,15-triol
Percent Composition: C 72.28%, H 9.89%, O 17.83%
Literature References: The aglycon of digitonin: Tschesche, Ber. 68, 1090 (1935); Tschesche, Hagedorn, Ber. 69, 797 (1936). Structure and stereochemistry: Marker et al., J. Am. Chem. Soc. 64, 1843 (1942); Meystre et al., Helv. Chim. Acta 38, 381 (1955). Klass et al., J. Am. Chem. Soc. 77, 3829 (1955); and IR spectra: Djerassi et al., ibid. 78, 3166 (1956).
CAS Name: (3b,5b)-3,14-Dihydroxycard-20(22)-enolide
Additional Names: D20:22-3,14,21-trihydroxynorcholenic acid lactone; cerberigenin; echujetin; evonogenin
Trademarks: Thevetigenin
Perce...
Literature References: The aglycon of digitoxin, thevetin, cerberin, echujin, evomonosid. Prepn by refluxing digitoxin in a mixture of water + alcohol + HCl: Cloetta, Arch. Exp. Pathol. Pharmakol. 88, 113 (1920); Stoll, Kreiss, Helv. Chim. Acta 17, 592 (1934). Structure: Jacobs, Hoffmann, J. Biol. Chem. 67, 333 (1926); Jacobs, Gustus, ibid. 78, 573; 79, 533 (1928); 82, 402 (1929); Jacobs, Elderfield, ibid. 108, 497 (1935); Elderfield, Chem. Rev. 17, 187 (1935). Stereochemistry: Meyer, Helv. Chim. Acta 30, 1976 (1947). Synthesis: Danieli et al., Tetrahedron 22, 3189 (1966); W. Fritsch et al., Ann. 1974, 621; S. F. Donovan et al., Tetrahedron Lett. 1979, 3287; R. Marinibettolo et al., Can. J. Chem. 59, 1403 (1981); T. Milkova et al., Tetrahedron Lett. 23, 413 (1982). Biosynthesis from neriifolin, q.v.: A. Cruz et al., J. Org. Chem. 42, 3580 (1977).
CAS Name: (3b,5b,16b)-3,14,16-Trihydroxycard-20(22)-enolide
Additional Names: D20,22-3,14,16,21-tetrahydroxynorcholenic acid lactone
Percent Composition: C 70.74%, H 8.78%, O 20.49%
Literature References: The aglycon of gitoxin. By refluxing gitoxin in a mixture of water + alcohol + HCl: Smith, J. Chem. Soc. 1931, 23. Structure: Jacobs, Elderfield, J. Biol. Chem. 100, 671 (1933); Elderfield, Chem. Rev. 17, 217 (1935); Henderson, Chen, J. Med. Pharm. Chem. 5, 988 (1962). Configuration: Moore, Helv. Chim. Acta 37, 659 (1954); Repke, Klesczewski, Arch. Exp. Pathol. Pharmakol. 239, 131 (1960). Cf. ref under Digoxigenin.
CAS Name: 5,7-Dihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one
Additional Names: 5,7-dihydroxy-4'-methoxyflavone; apigenin-4'-methyl ether
Percent Composition: C 67.60%, H 4.26%, O 28.14%
Literature References: The aglycon of linarin, q.v., and of acaciin. Isoln from linarin: Zemplén, Bognar, Ber. 74B, 1818 (1941). From acaciin: Hattori, Acta Phytochim. 2, 105 (1925). Isoln from Robinia pseudoacacia L., Leguminosae: Nakazawa, Matsuura, J. Pharm. Soc. Jpn. 73, 481 (1953). Structure: Baker et al., J. Chem. Soc. 1951, 691. Synthesis: Robinson, Venkataraman, ibid. 1926, 2348; Zemplén, Bognar, Ber. 76B, 452 (1943); Narasimhachari, Seshadri, Proc. Indian Acad. Sci. 30A, 151 (1949); Simpson, Sci. Proc. R. Dublin Soc. 27, 111 (1956), C.A. 51, 8082a (1957).
CAS Name: (3b,5b)-3,5,14-Trihydroxycard-20(22)-enolide
Additional Names: desoxostrophanthidin
Percent Composition: C 70.74%, H 8.78%, O 20.49%
Literature References: The aglycon of periplocin and periplocymarin; accompanies strophanthidin in Strophanthus eminii Asch. et Pax., Apocynaceae. Isoln: Lehmann, Arch. Pharm. 235, 157 (1897); Jacobs, Hoffmann, J. Biol. Chem. 79, 519 (1928); Stoll, Renz, Helv. Chim. Acta 22, 1193 (1939); Lardon, ibid. 33, 639 (1950). Structure: Speiser, Reichstein, Experientia 3, 323 (1947); eidem, Helv. Chim. Acta 30, 2143 (1947); 31, 622 (1948). Synthesis: Deghenghi, Gaudry, Tetrahedron Lett. 1963, 2045; Kamano et al., J. Org. Chem. 39, 2319 (1974).
CAS Name: 3-(1,3-Benzodioxol-5-yl)-7-hydroxy-4H-1-benzopyran-4-one
Additional Names: 7-hydroxy-3',4'-(methylenedioxy)isoflavone
Percent Composition: C 68.09%, H 3.57%, O 28.34%
Literature References: The aglycon of pseudobaptisin. Prepn by hydrolysis of natural pseudobaptisin: Gorter, Arch. Pharm. 235, 494 (1897). Structure: Späth, Schmidt, Monatsh. Chem. 53, 454 (1929). Syntheses: Späth, Lederer, Ber. 63, 743 (1930); Mahal et al., J. Chem. Soc. 1934, 1771; Baker et al., ibid. 1937, 805; 1953, 1852; Farkas, Ber. 91, 2858 (1958); Dhoubhadel, Joshi, J. Indian Chem. Soc. 52, 440 (1975).
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