
Additional Names: 2-Amino-4-hydroxybutanoic acid; 2-amino-4-hydroxybutyric acid; a-amino-g-hydroxy-n-butyric acid
Percent Composition: C 40.33%, H 7.62%, N 11.76%, O 40.29%
Literature References: Principal free amino acid occurring in pea plants: A. I. Virtanen, Acta Chem. Scand. 7, 1423 (1953); J.A. Bakhuis, Nature 180, 713 (1957). Prepn: Fischer, Blumenthal, Ber. 40, 106 (1907); Armstrong J. Am. Chem. Soc. 70, 1756 (1948); Birnbaum, Greenstein, Arch. Biochem. Biophys. 42, 212 (1953); M. Frankel, Y. Knobler, J. Am. Chem. Soc. 80, 3147 (1958). Review of homoserine production by fermentation: T. Nara in Microbial Prod. Amino Acids, K. Yamada, Ed. (Wiley, New York, 1972) pp 417-434.
CAS Name: (11b)-11,17,21-Trihydroxypregn-4-ene-3,20-dione
Additional Names: cortisol; 4-pregnene-11b,17a,21-triol-3,20-dione; 17-hydroxycorticosterone; anti-inflammatory hormone; Kendall's comp...
Literature References: Principal glucocorticoid hormone produced by the adrenal cortex. Biosynthesis stimulated by ACTH, q.v. Circulates in plasma primarily bound to corticosteroid-binding globulin, also known as transcortin, and to albumin. Isoln from adrenal glands: Reichstein, Helv. Chim. Acta 20, 953 (1937); Mason et al., J. Biol. Chem. 124, 459 (1938); from urine: Mason, Sprague, ibid. 175, 451 (1948); from blood: Reich et al., ibid. 187, 411 (1950). Configuration: von Euw, Reichstein, Helv. Chim. Acta 25, 988 (1942); 30, 205 (1947). Synthesis: N. L. Wendler et al., J. Am. Chem. Soc. 72, 5793 (1950). Biosynthesis by isolated adrenal glands: O. Hechter et al., Arch. Biochem. Biophys. 25, 457 (1950); A. Zaffaroni et al., J. Am. Chem. Soc. 73, 1390 (1951). Prepn by microbial transformation: H. C. Murray, D. H. Peterson, US 2602769 (1952 to Upjohn); D. R. Colingsworth et al., J. Biol. Chem. 203, 807 (1953). Total biosynthesis in yeast: F. M. Szczebara et al., Nat. Biotechnol. 21, 143 (2003). Comprehensive description: K. Florey, Anal. Profiles Drug Subs. 12, 277-324 (1983). Review of clinical use in dermatoses: A. M. Kligman, K. H. Kaidbey, Cutis 22, 232-244 (1978). Review of clinical assays in serum and urine: A. Moore et al., Ann. Clin. Biochem. 22, 435-454 (1985). Physiological role in immunity: W. M. Jefferies, Med. Hypotheses 34, 198-208 (1991); in fetal maturation: G. C. Liggins, Reprod. Fertil. Dev. 6, 141-150 (1994).
CAS Name: 4-(3-Hydroxy-1-propenyl)-2-methoxyphenyl b-D-glucopyranoside
Additional Names: 4-hydroxy-3-methoxy-1-(g-hydroxypropenyl)benzene-4-D-glucoside; abietin; laricin
Percent Composition:...
Literature References: Principal glucoside of the conifers. Also in comfrey root, sugar beet, and asparagus. Extraction from the cambium layer of fir: Solntsev, C.A. 38, 3780 (1944). Synthesis: Pauley, Feuerstein, Ber. 60, 1031 (1927). Hydrolysis by emulsin yields coniferyl alcohol and D-glucose. Yields lignin-like material by enzymatic dehydrogenation and polymerization: Freudenberg et al., Ber. 85, 641 (1952); Freudenberg, Rasenack, Ber. 86, 756 (1953).
CAS Name: 1-[2,3-Dihydro-2-(1-methylethenyl)-5-benzofuranyl]ethanone
Additional Names: 2,3-dihydro-2-isopropenyl-5-benzofuranyl methyl ketone; 2-isopropenyl-2,3-dihydro-5-acetylbenzofuran
Pe...
Literature References: Principal ketone suspected of being the active toxin of Eupatorium urticaefolium Reichard, Compositae (white snakeroot). Isoln and structure: Bonner, DeGraw, Tetrahedron 18, 1295 (1962). Synthesis of dihydrotremetone: DeGraw, Bonner, ibid. 1311. Synthesis of racemic tremetone: DeGraw et al., ibid. 19, 19 (1963); Bohlmann, Buehmann, Ber. 105, 863 (1972). Abs config: Bonner et al., Tetrahedron 20, 1419 (1964). Review: Christensen, Econ. Bot. 19, 293-300 (1965).
CAS Name: (E)-1-[6-[(3-Acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-8-yl]-3-phenyl-2-propen-1-one
Additional Names: 5,7-dihydroxy-2,2-dimethyl-6-(2,...
Literature References: Principal phenolic component of kamala, q.v., an anthelmintic dye obtained from Mallotus philippinensis (Lam.) Muell. Arg. (also known as Rottlera tinctoria Roxb.), Euphorbiaceae. Isoln: H. Telle, Arch. Pharm. 244, 446 (1906); S. Dutt, J. Chem. Soc. 127, 2044 (1925); A. McGookin et al., ibid. 1937, 748. Structure: Brockmann, Maier, Ann. 535, 149 (1938); A. McGookin et al., J. Chem. Soc. 1939, 1579. Synthesis of tetrahydrorottlerin: Backhouse et al., ibid. 1948, 113. Review of isoln and chemistry: M. Lounasmaa et al., Planta Med. 28, 16 (1975). Activity as protein kinase inhibitor: M. Gschwendt et al., Biochem. Biophys. Res. Commun. 199, 93 (1994). HPTLC determn in serum and pharmacokinetics: V. D. Mody et al., J. Pharm. Technol. 10, 71 (1994).
CAS Name: (1S,1'S,3S,3'S,4S,4'S,4aS,4'aS,9aR,9'aR)-1,1',3,3',4,4',9a,9'a-Octahydro-4,4',8,8',9a,9'a-hexahydroxy-3,3'-dimethyl-[7,7'-bi-1,4a-(epoxymethano)-4aH-xanthene]-9,9',11,11'(2H,2'H)-tetrone...
Literature References: Principal pigment from ergot: Freeborn, Pharm. J. 88, 568 (1912); Eglinton et al., J. Chem. Soc. 1958, 1833. Structure: McPhail et al., ibid. 1966, Sect. B, 18. Review of ergoflavin and other ergochromes: Franck, Flasch in Fortschr. Chem. Org. Naturst. 30, 151-206 (1973).
CAS Name: (3b,24S)-Stigmast-5-en-3-ol
Additional Names: clionasterol
Percent Composition: C 83.99%, H 12.15%, O 3.86%
Literature References: Principal sterol of soybean oil: Bonstedt, Z. Physiol. Chem. 176, 269 (1928). Isoln from corn oil: Anderson, Shriner, J. Am. Chem. Soc. 48, 2976 (1926); from venom of Chinese toad, Bufo gargarizans: Rukstuhl, Meyer, Helv. Chim. Acta 40, 1270 (1957). Differs from b-sitosterol in spatial configuration at C-24: Bergmann, Low, J. Org. Chem. 12, 67 (1947). Structure: Pavanaram, Helv. Chim. Acta 46, 1377 (1963). Stereospecific synthesis: W. Sucrow, M. Slopianka, Ber. 108, 3721 (1975).
CAS Name: 9,10-Dihydro-3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-2-anthracenecarboxylic acid
Additional Names: C.I. Natural Red 3; C.I. 75460
Percent Composition: C 58.19%, H 3.05%, O 38.76%
Literature References: Principle constituent of kermes, one of the oldest known insect dyes. Isoln and characterization: O. Dimroth, Ber. 43, 1387 (1910); O. Dimroth, W. Scheurer, Ann. 399, 43 (1913). Structure: O. Dimroth, R. Fick, Ann. 411, 315 (1916). Revised structure: D. D. Gadgil et al., Tetrahedron Lett. 1968, 2223. Synthesis: D. W. Cameron et al., Chem. Commun. 1978, 688; eidem, Aust. J. Chem. 34, 2401 (1981).
Trademarks: Puerzym (Firma)
Literature References: Principle digestive enzyme of gastric juice; controls the degradation of proteins to proteoses and peptones. Distinctive among enzymes for having a very low isoelectric point and a very low pH optimum. Hydrolyzes only peptide linkages. The N.F. grade digests not less than 3000 or more than 3500 times its wt of freshly coagulated and disintegrated egg albumin in 2½ hours at 52° in water acidulated with HCl. Isoln from gastric juice of swine and beef: Northrup, J. Gen. Physiol. 13, 739 (1930); 16, 615 (1933); from salmon and tuna: Norris, Edam, J. Biol. Chem. 134, 443 (1940); 204, 673 (1953). Amino acid composition: Brand in Crystalline Enzymes, J. H. Northrup et al. (Columbia Univ. Press, New York, 2nd ed., 1948) p 26. Active site: Herriott, J. Gen. Physiol. 45, Suppl., 57 (1962). Review: Bovey, Yanari in The Enzymes vol. 4, P. D. Boyer et al., Eds. (Academic Press, New York, 1960) pp 63-92.
CAS Name: 5-Amino-4-oxopentanoic acid hexyl ester
Additional Names: 5-aminolevulinic acid hexyl ester; hexyl 5-aminolevulinate
Percent Composition: C 61.37%, H 9.83%, N 6.51%, O 22.29%
Literature References: Prodrug of d-aminolevulinic acid, q.v.; induces production of intracellular protoporphyrin IX. Prepn: H. Takeya, JP Kokai 92 9360 (1992 to Cosmo Sogo Kenkyusho); and use as photosensitizer: K. E. Gierskcky et al., WO 9628412 (1996 to Norwegian Radium Res. Found.); eidem, US 6034267 (2000 to PhotoCure). Synthesis and pharmacology: C. J. Whitaker et al., Anti-Cancer Drug Des. 15, 161 (2000). Clinical evaluation for photodetection of bladder cancer: N. Lange et al., Br. J. Cancer 80, 185 (1999).
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