
CAS Name: (3b,5a)-3-[(2-O-b-D-Glucopyranosyl-b-D-glucopyranosyl)oxy]-14-hydroxycard-20(22)-enolide
Percent Composition: C 60.16%, H 7.79%, O 32.05%
Literature References: Isoln from the dried root of a Gomphocarpus sp, Asclepiadaceae: Windaus, Haack, Ber. 63, 1377 (1930); Tschesche, Brathge, ibid. 85, 1042 (1952); Schmid et al., Helv. Chim. Acta 42, 72 (1959). Yields uzarigenin by enzymic cleavage. Structure: Tschesche, Bohle, Ber. 68, 2252 (1935). Structure of uzarigenin: Rangaswami, Reichstein, Helv. Chim. Acta 32, 939 (1949); Russel et al., ibid. 44, 1320 (1961). Unlike all other known cardiac glycosides, has the A/B-trans configuration: L. F. Fieser, M. Fieser, Steroids (Reinhold, New York, 1959) pp 762-763. Review: Heusser, Fortschr. Chem. Org. Naturst. 7, 101 (1950).
CAS Name: 9-b-D-Ribofuranosyl-9H-purine
Percent Composition: C 47.62%, H 4.80%, N 22.21%, O 25.37%
Literature References: Isoln from the mushroom Clitocybe nebularis (Batsch.) Quel., Agaricaceae: Ehrenberg et al., Sven. Kem. Tidskr. 58, 269 (1946); Löfgren et al., Acta Chem. Scand. 8, 670 (1954); from a streptomycete: Isono, Suzuki, J. Antibiot. 13A, 270 (1960). In vitro toxicity towards sarcoma 180 cells, mouse embryonic fibroblasts and epithelial cells: J. J. Biescle et al., Cancer 8, 87 (1955). Synthesis: Brown, Weliky, J. Biol. Chem. 204, 1019 (1953); Fox et al., J. Am. Chem. Soc. 80, 1669 (1958); Hashizume, Iwamura, Tetrahedron Lett. 1966, 643; eidem, J. Org. Chem. 33, 1796 (1968). Crystal structure: T. Takeda, Acta Crystallogr. 30B, 825 (1974). Alternate syntheses: V. Nair, S. G. Richardson, Tetrahedron Lett. 1979, 1181; P. K. Gupta, D. S. Bhakuni, Indian J. Chem. 20B, 534 (1981). Toxicity studies: Truant, D'Amato, Fed. Proc. 14, 391 (1955).
CAS Name: 2-Methyl-1,3-butadiene
Percent Composition: C 88.16%, H 11.84%
Literature References: Isoln from the products of the pyrolysis of natural rubber: Williams, Trans. R. Soc. London 150, 241 (1860); Boonstra, van Amerongen, Ind. Eng. Chem. 41, 161 (1949). Structure: Euler, Ber. 30, 1989 (1897). Prepn from turpentine: Tilden, J. Chem. Soc. 45, 410 (1884); Bibb, US 2386537 (1945 to Newport Ind.); from terpenes: Davis et al., Ind. Eng. Chem. 38, 53 (1946); Bourbon, US 2547684 (1951 to Manufacture de Caoutchouc Michelin); by condensation of isobutylene and formaldehyde in acetic acid: Blomquist, Verdol, J. Am. Chem. Soc. 77, 78 (1955); Chaffe et al., FR 1294716 (1962 to Inst. Francais du Petrole); by dehydrogenation of isoamylenes from cracked gasolines: GB 875346 (Apr. 21, 1960 to Shell Int. Res. Maatschappij); Voge et al., US 3110746 (1963 to Shell); by dimerization of propylene followed by pyrolysis of the resulting 2-methyl-2-pentene: Gorin, Oblad, US 2404056 (1946 to Socony-Vacuum Oil); GB 913852 (1962 to Goodyear); by dehydrogenation of isopentane: Dempsey, US 2914588 (1959 to Sun Oil); Owen, US 2982795 (1961 to Phillips Petroleum); Stevenson, US 3088986 (1963 to Air Products Chem.); by reacting isoamylenes with methanol and pyrolizing and dehydrogenating the resulting tertiary ethers: Verdol, Walker, US 2972645 (1961 to Sinclair Refining). Toxicity: Gostinskii, C.A. 62, 15338a (1965). Reviews of isoprene and its polymers: Bean et al., "Isoprene Polymers" in Encyclopedia of Polymer Science and Technology vol. 7 (Interscience, New York, 1967) pp 782-855; Bailey, "Isoprene" in Vinyl and Diene Monomers (part 2), E. C. Leonard, Ed. (Wiley-Interscience, New York, 1971) pp 997-1148; W. M. Saltman in Kirk-Othmer Encyclopedia of Chemical Technology vol. 13 (Wiley-Interscience, New York, 3rd ed., 1981) pp 818-837; of carcinogenic risk: IARC Monographs 60, 215-232 (1994).
CAS Name: 2-[[2,4-Dihydroxy-6-methoxy-3-(1-oxobutyl)phenyl]methyl]-3,5-dihydroxy-4,4-dimethyl-6-(1-oxobutyl)-2,5-cyclohexadien-1-one
Additional Names: 3'-[(5-butyryl-2,4-dihydroxy-3,3-dimethyl-...
Literature References: Isoln from the rhizome of Dryopteris austriaca (Jacq.) Wojnar, Polypodiaceae: Aebi et al., Helv. Chim. Acta 40, 266 (1957); from D. caucasica (A. Br.) Fraser-Jenkins et Corley: Widén et al., ibid. 56, 831 (1973). Structure: Aebi et al., ibid. 40, 572 (1957). Toxicity study: Airaksinan et al., Acta Pharmacol. Toxicol. 25, 33 (1967).
CAS Name: (8b)-8-methoxy-16-methyl-2,3:10,11-bis[methylenebis(oxy)]rheadan
Additional Names: rhoeadine
Percent Composition: C 65.79%, H 5.52%, N 3.65%, O 25.04%
Literature References: Isoln from the seed capsules of corn poppy (Papaver rhoeas L., Papaveraceae): Hesse, Ann. 140, 145 (1866); Arch. Pharm. 228, 7 (1890); Awe, ibid. 274, 439 (1936); Awe, Winkler, ibid. 290, 367 (1957); Nemecková, Santavy, Collect. Czech. Chem. Commun. 27, 1210 (1962). Structure and stereochemistry: Santavy et al., ibid. 30, 3479 (1965); 32, 4452 (1967). Total synthesis: Klotzer et al., Helv. Chim. Acta 54, 2057 (1971); 55, 2228 (1972); Irie et al., J. Chem. Soc. Perkin Trans. 1 1972, 2986.
Additional Names: D-manno-Ketoheptose
Percent Composition: C 40.00%, H 6.71%, O 53.29%
Literature References: Isoln from the wet pulp of the fruit of the avocado tree, Persea gratissima Gaertn. f. (P. americana Mill.), Lauraceae: LaForge, J. Biol. Chem. 28, 511 (1917); Montgomery, Hudson, J. Am. Chem. Soc. 61, 1654 (1939); Richtmyer in Methods in Carbohydrate Chemistry R. L. Whistler et al., Eds. vol. 1, 173 (1962).
CAS Name: 3-[2-(Dimethylamino)ethyl]-1H-indol-5-ol
Additional Names: 3-(2-dimethylaminoethyl)-5-indolol; 5-hydroxy-N,N-dimethyltryptamine; N,N-dimethylserotonin; 3-(b-dimethylaminoethyl)-5-hydr...
Literature References: Isoln from toads: Wieland et al., Ann. 513, 1 (1934); Wieland, Wieland, ibid. 528, 239 (1937); from toadstools: Wieland, Motzel, ibid. 581, 10 (1953). Isoln from Piptadenia peregrina Benth., Leguminosae: Stromberg, J. Am. Chem. Soc. 76, 1707 (1954). Synthesis: Hoshino, Shimodaira, Ann. 520, 19 (1935); Harley-Mason, Jackson, Chem. Ind. (London) 1952, 954; see also Serotonin; and Speetor, US 2708197 (1955 to Upjohn); Stoll et al., Helv. Chim. Acta 38, 1452 (1955). Activity: Bhattacharya, Sanyal, Indian J. Physiol. Pharmacol. 15, 133 (1971). Crystal and molecular structure: G. Falkenberg, Acta Crystallogr. 28B, 3219 (1972).
CAS Name: 3,7,11-Trimethyl-1,3,6,10-dodecatetraene
Additional Names: 2,6,10-trimethyl-2,6,9,11-dodecatetraene; farnesene
Percent Composition: C 88.16%, H 11.84%
Literature References: Isoln of (E,E)-form from natural coating of apples: Huelin, Murray, Nature 210, 1260 (1966); Murray, Aust. J. Chem. 22, 197 (1969); from Dufour's gland in ants: Cavill et al., Tetrahedron Lett. 1967, 2201. Isoln of (Z,E)-form from oil of perilla: T. Sakai, Y. Hirose, Bull. Chem. Soc. Jpn. 42, 3615 (1969). Oxidation products of farnesene are believed to cause scald, a serious storage disorder of apples. Four possible geometric isomers. Synthetic studies: Ruzicka, Helv. Chim. Acta 6, 490, 501 (1923); Ruzicka, Capato, ibid. 8, 267 (1925). Configuration of (E,E)-form confirmed by synthesis from trans-b-farnesene: Brieger et al., J. Org. Chem. 34, 3789 (1969). Stereospecific synthesis of (E,Z)- and (Z,Z)-isomers: Anet, Aust. J. Chem. 23, 2101 (1970). Synthesis of (E,E)-form: Tanaka et al., J. Am. Chem. Soc. 97, 3252 (1975). (E,E)- and (Z,E)-forms are components of aphid alarm pheromones: J. A. Pickett, D. C. Griffiths, J. Chem. Ecol. 6, 349 (1980); of the trail pheromone of red imported fire ants: R. K. Vandermeer et al., Tetrahedron Lett. 22, 1651 (1981).
CAS Name: 2-Amino-2,6-dideoxygalactose
Percent Composition: C 44.17%, H 8.03%, N 8.58%, O 39.22%
Literature References: Isoln of D-form from lipopolysaccharide of Chromobacterium violaceum: Crumpton, Davies, Biochem. J. 70, 729 (1958); from Bacillus licheniformis: Sharon et al., ibid. 93, 210 (1964). Isoln of L-form from type V Pneumococcus capsular polysaccharide: Barker et al., Nature 189, 303 (1961). Synthesis of L-form: Kuhn et al., Ann. 628, 186 (1959); J. Lehmann et al., Ber. 112, 1470 (1979); of D-form: Zehavi, Sharon, J. Org. Chem. 29, 3654 (1964).
CAS Name: 3-Methylene-6-(1-methylethyl)cyclohexene
Additional Names: p-mentha-1(7),2-diene; 3-isopropyl-6-methylene-1-cyclohexene; 4-isopropyl-1-methylene-2-cyclohexene
Percent Composition: ...
Literature References: Isoln of d-form from oil of water fennel (Phellandrium aquaticum L., Umbelliferae): Berry et al., J. Chem. Soc. 1937, 1448. Isoln of l-form from Canada balsam oil: Macbeth et al., ibid. 1938, 119. Structure: Wallach, Ann. 343, 28 (1905). Synthesis of dl-form: Deorha, Sareen, Rec. Trav. Chim. 82, 137 (1965); B. Singaram, J. Verghese, Indian J. Chem. 14B, 1003 (1976).
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