
CAS Name: (3b,5b,16b)-3,14,16-Trihydroxybufa-20,22-dienolide
Additional Names: desacetylbufotalin
Percent Composition: C 71.61%, H 8.51%, O 19.87%
Literature References: Isolated from the Chinese drug Ch'an Su which is prepd from Chinese toads (Bufo asiaticus = Bufo gargarizans Cantor); also obtained from bufotalin: Ruckstuhl, Meyer, Helv. Chim. Acta 40, 1270 (1957).
CAS Name: (2S-trans)-3-[3-(3-Hydroxy-2-piperidinyl)-2-oxopropyl]-4(3H)-quinazolinone
Additional Names: 3-[3-(3-hydroxy-2-piperidyl)acetonyl]-4(3H)-quinazolinone; 3-[b-keto-g-(3-hydroxy-2-piperi...
Literature References: Isolated from the Dichroa febrifuga Louv., Saxifragaceae and from the common hydrangea: Koepfli et al., J. Am. Chem. Soc. 71, 1048 (1949); Ablondi et al., J. Org. Chem. 17, 14 (1952). Identity with b-dichroine: Fu, Yang, C.A. 43, 1530a (1949). Structure: Koepfli et al., J. Am. Chem. Soc. 72, 3323 (1950). Synthesis: Baker et al., J. Org. Chem. 17, 132 (1952); 18, 178 (1953); Koepfli et al., US 2504847 (1950 to U.S. Gov't); Baker, Querry, US 2651632 (1953 to Am. Cyanamid). Config: Hill, Edwards, Chem. Ind. (London) 1962, 858. Revised stereochemistry: Barringer et al., J. Org. Chem. 38, 1937 (1973).
Percent Composition: C 32.39%, H 8.16%, O 21.58%, Si 37.87%
Literature References: Isolated from the hydrolysis product of dimethyldichlorosilane: Patnode, Wilcock, J. Am. Chem. Soc. 68, 358 (1946).
Percent Composition: C 32.39%, H 8.16%, O 21.58%, Si 37.87%
Literature References: Isolated from the hydrolysis product of dimethyldichlorosilane: Patnode, Wilcock, J. Am. Chem. Soc. 68, 358 (1946).
CAS Name: 3,5-Dihydroxy-4,4-dimethyl-2-(1-oxobutyl)-6-[[2,4,6-trihydroxy-3-methyl-5-(1-oxobutyl)phenyl]methyl]-2,5-cyclohexadien-1-one
Additional Names: 3'-[(5-butyryl-2,4-dihydroxy-3,3-dimethy...
Literature References: Isolated from the rhizomes of male fern: Boehm, Ann. 318, 253 (1901); 329, 310 (1903). Structure and synthesis: McGookin et al., J. Chem. Soc. 1953, 1828; Riedl, Ann. 585, 32 (1954); Aebi, Helv. Chim. Acta 39, 153 (1956). Crystal structure of a- and b-forms: Erämetsä, Penttilä, Acta Chem. Scand. 24, 3335 (1970). Toxicity study: Airaksinen et al., Acta Pharmacol. Toxicol. 25, 33 (1967).
CAS Name: 2,2,2-Trichloroethyl b-D-glucopyranosiduronic acid
Additional Names: 2,2,2-trichloroethyl b-D-glucosiduronic acid; b,b,b-trichloroethyl-D-glucuronide
Percent Composition: C 29.52%,...
Literature References: Isolated from urine of man and dog after ingestion of chloral hydrate: von Mering, Musculus, Ber. 8, 663 (1875); from urine of calves fed trichloroethylene: Seto, Schultze, J. Am. Chem. Soc. 78, 1616 (1956).
CAS Name: 1,3,5-Benzenetriol
Additional Names: 1,3,5-trihydroxybenzene; phloroglucin
Percent Composition: C 57.14%, H 4.80%, O 38.06%
Literature References: Isolation as dimer from phloretin, q.v.: H. Hlasiwetz, Ann. 96, 118 (1855). Prepn: J. R. Hwu, S.-C. Tsay, J. Org. Chem. 55, 5987 (1990). GC-MS determn in human plasma: C. Lartigue-Mattei et al., J. Chromatogr. 617, 140 (1993). Clinical evaluation: G. Cargill et al., Presse Med. 21, 19 (1992). Toxicology: R. Cahen et al., Therapie 17, 1349 (1962); J. Am. Coll. Toxicol. 14, 468 (1995). Review: G. Leston in Kirk-Othmer Encyclopedia of Chemical Technology vol. 19 (Wiley-Interscience, New York, 4th ed., 1996) pp 792-812. Biosynthesis study: J. Achkar et al., J. Am. Chem. Soc. 127, 5332 (2005).
CAS Name: (3b,5a,11b)-3,11,21-Trihydroxypregnan-20-one
Additional Names: 3b,11b,21-trihydroxy-20-oxo-5a-pregnane; Reichstein's substance R
Percent Composition: C 71.96%, H 9.78%, O 18.26%
Literature References: Isolation from adrenal glands: Reichstein, von Euw, Helv. Chim. Acta 21, 1197 (1938); Reichstein, ibid. 1490. Partial synthesis by hydrogenation of corticosterone acetate: Pataki et al., J. Biol. Chem. 195, 751 (1952). Prepn from 3b,11b-dihydroxyalloetiocholanic acid: Lardon, Reichstein, Helv. Chim. Acta 37, 443 (1954); from hydrocortisone: Mancera et al, J. Am. Chem. Soc. 77, 5669 (1955); from 3b,21-diacetoxy-17(20)-allopregnene + osmium tetroxide and triethylamine oxide peroxide: Schneider, Hanze, US 2769823 (1956 to Upjohn).
CAS Name: [1R-(1a,4ab,4ba,10aa)]-1,2,3,4,4a,4b,5,9,10,10a-Decahydro-1,4a-dimethyl-7-(1-methylethyl)-1-phenanthrenecarboxylic acid
Additional Names: 13-isopropylpodocarpa-8(14),12-dien-15-oic ac...
Literature References: Isolation from American pine oleoresin: Palkin, Harris, J. Am. Chem. Soc. 55, 3677 (1933); from French galipot, from Pinus maritima: Ruzicka, Bacon, Helv. Chim. Acta 20, 1542 (1937); from Pinus palustris: Harris, Sanderson, J. Am. Chem. Soc. 70, 334, 3671 (1948). Structure: Ruzicka, Kaufmann, Helv. Chim. Acta 23, 1346 (1940): cf. Arbuzov, Chem. Zentralbl. 1942, II, 893. Stereochemistry: Schuller, Lawrence, J. Am. Chem. Soc. 83, 2563 (1961); Burgstahler et al., ibid. 83, 4660 (1961); Weiss et al., Chem. Ind. (London) 1962, 1286; Dauben, Coates, J. Org. Chem. 28, 1698 (1963). Conformation: Burgstahler et al., Chem. Commun. 1971, 121; Weiss et al., ibid. 1972, 17.
CAS Name: 3,20-Dihydroxycevan-6-one
Additional Names: raddeamine; sipeimine
Percent Composition: C 75.48%, H 10.09%, N 3.26%, O 11.17%
Literature References: Isolation from bulb of Fritillaria imperialis L., Liliaceae: Fragner, Ber. 21, 3284 (1888); Boit, ibid. 87, 472 (1954); from Petilium eduardi: Shakirov et al., C.A. 60, 13280h (1964). Identity with sipeimine and raddeamine: Chu et al., C.A. 53, 7503e (1959); Nurridinov, Yunusov, C.A. 57, 15165h (1962). Structure: Nuriddinov et al., Khim. Prir. Soedin. 3, 316 (1967); C.A. 68, 69168g (1968). Prepn of the b-D-glucopyranoside: Shakirov et al., C.A. 63, 1858e (1965). Isolation and structure of the b-D-glucopyranoside: eidem, C.A. 63, 3007f (1965). Absolute configuration: S. Itô et al., Tetrahedron Lett. 1976, 3161.
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