
Percent Composition: C 54.58%, H 7.21%, N 15.32%, O 20.19%, S 2.70%
Literature References: A hendecapeptide from the posterior salivary glands of eledone spp (small octopus spp): Anastasi, Erspamer, Br. J. Pharmacol. 19, 326 (1962); eidem, Experientia 18, 58 (1962). Synthesis: Sandrin, Boissonnas, ibid. 59; eidem, Helv. Chim. Acta 47, 1294 (1964); Lubke et al., Ann. 679, 195 (1964); GB 984810 (1965 to Farmitalia); solid-phase synthesis: P. G. Pietta et al., J. Org. Chem. 39, 44 (1974). Its physiologic action resembles that of the other tachykinins, substance P and physalaemin, q.q.v. Stimulates extravascular smooth muscle, acts as a potent vasodilator and hypotensive agent; in certain species causes salivation, and increases capillary permeability. Pharmacology: Erspamer, Erspamer, Br. J. Pharmacol. 19, 337 (1962); Sicuteri et al., Experientia 19, 44 (1963); G. Bertaccini, Pharmacol. Rev. 28, 127 (1976). Review: Erdös, Adv. Pharmacol. 4, 64-72 (1966).
CAS Name: Tetrafluoroethene homopolymer
Additional Names: tetrafluoroethylene polymer; polytetrafluoroethylene resin; polytef; PTFE
Trademarks: Fluon (ICI); Teflon (DuPont); Tetran (Elf Atoc...
Literature References: A highly stable thermoplastic tetrafluoroethylene, q.v., homopolymer. Composed of at least 20,000 C2F4 monomer units linked into very long unbranched chains. Prepd by polymerization of tetrafluoroethylene: Plunkett, US 2230654 (1941 to Kinetic Chem.); Brubaker, US 2393967; Joyce, US 2394243 (both 1946 to du Pont); Hanford, Joyce, J. Am. Chem. Soc. 68, 2082 (1946); Renfrew, US 2534058 (1950 to du Pont); C. E. Schildknecht, Vinyl and Related Polymers (Wiley, New York, 1952) pp 483-494. Account of discovery by Roy J. Plunkett: A. B. Garrett, J. Chem. Educ. 39, 288 (1962). Reviews: M. M. Renfrew, E. E. Lewis, Ind. Eng. Chem. 38, 870-877 (1946); R. W. Moncrieff, Man-Made Fibres (John Wiley, New York, 4th ed., 1963) pp 512-517; McCane in Encyclopedia of Polymer Science and Technology vol. 13, N. M. Bikales, Ed. (Interscience, New York, 1970) pp 623-654; S. V. Gangal in Kirk-Othmer Encyclopedia of Chemical Technology vol. 11 (Wiley-Interscience, New York, 4th ed., 1994) pp 621-644.
CAS Name: N2-L-Lysylbradykinin
Additional Names: kallidin-10; kallidin II
Percent Composition: C 56.60%, H 7.21%, N 20.04%, O 16.16%
Literature References: A hypotensive and smooth muscle-stimulating principle formed by the proteolysis of kininogen by glandular and other kallikreins, q.v. The decapeptide structure is a homologue of bradykinin, q.v.: Werle et al., Z. Physiol. Chem. 326, 174 (1961). Synthesis: Nicolaides et al., Biochem. Biophys. Res. Commun. 6, 210 (1961); Pless et al., Helv. Chim. Acta 45, 394 (1962).
CAS Name: 5-Oxo-L-prolyl-L-histidyl-L-prolinamide
Additional Names: thyrotropin-releasing factor; thyrotropin releasing hormone; TRF; protirelin; lopremone (rescinded USAN); TSH-releasing facto...
Literature References: A hypothalamic neurohormone which stimulates the release and synthesis of TSH, q.v., from the anterior pituitary via the hypophyseal portal system; the first of the hypothalamic regulatory hormones to be isolated, characterized, and synthesized. Isoln from bovine hypothalami: Schreiber et al., Experientia 18, 338 (1962); Schally et al., Endocrinology 78, 726 (1966). Purification from ovine hypothalami: Guillemin et al., C.R. Seances Acad. Sci. Ser. D 262, 2278 (1966). Isoln from porcine hypothalami and properties: Schally et al., Biochem. Biophys. Res. Commun. 25, 165 (1966); Schally et al., J. Biol. Chem. 244, 4077 (1969). Structural studies: Folkers et al., Biochem. Biophys. Res. Commun. 37, 123 (1969); Burgus et al., C.R. Seances Acad. Sci. Ser. D 269, 226 (1969). Identity of isolated TRH with synthetic tripeptide: Burgus et al., ibid. 1870; Bowers et al., Endocrinology 86, 573, 1143 (1970). Solubility: Burgus et al., Experientia 23, 417 (1967). Synthesis: Flouret, J. Med. Chem. 13, 843 (1970); Chang et al., ibid. 14, 481 (1971); E. Gross et al., Angew. Chem. Int. Ed. 12, 664 (1972); P. G. Pietta et al., J. Org. Chem. 39, 44 (1974). Review of synthetic methods: Rivier, Methods Enzymol. 37, 408 (1975). TRH is also believed to induce the secretion of the pituitary lactogenic hormone, prolactin, q.v.: Tasjian et al., Biochem. Biophys. Res. Commun. 43, 516 (1971); Bowers et al., ibid. 51, 512 (1973). It has been shown to block and reverse leukotriene-induced hypotension in the unanesthetized guinea pig: W. E. Lux et al., Nature 302, 822 (1983). Clinical studies: Hershman, N. Engl. J. Med. 290, 886 (1974). Reviews of TRH and other hypothalamic releasing hormones: Schally et al., Recent Prog. Horm. Res. 24, 497 (1968); Burgus, Guillemin, Annu. Rev. Biochem. 39, 499 (1970); Polypeptide Hormones, R. F. Beers, E. G. Bassett, Eds. (Raven Press, New York, 1980) pp 165-278.
CAS Name: 2-Hexylcyclopropanedecanoic acid
Additional Names: 11,12-methyleneoctadecanoic acid; phytomonic acid
Percent Composition: C 76.97%, H 12.24%, O 10.79%
Literature References: A lipid constituent of various microorganisms. Isoln from Lactobacillus arabinosus: K. Hofmann, R. A. Lucas, J. Am. Chem. Soc. 72, 4328 (1950); from Agrobacterium tumefaciens and identity of phytomonic acid with lactobacillic acid: K. Hofmann, F. Tausig, J. Biol. Chem. 213, 425 (1955). Structure: K. Hofmann et al., J. Am. Chem. Soc. 80, 5717 (1958). Abs config: J. F. Tocanne, Tetrahedron 28, 363 (1972).
CAS Name: L-Lysine, homopolymer
Literature References: A lysine polypeptide or homopolymer, the chain length of which varies with the method of prepn. Prepn: Katchalski et al., J. Am. Chem. Soc. 69, 2564 (1947); 70, 2094 (1948); Fasman et al., ibid. 83, 709 (1961); Sela et al., Biopolymers 1, 517 (1963); Strojny, White, US 3215684 (1965 to Dow). For structure see Lysine.
CAS Name: N-(5-Amino-5-carboxypentyl)-L-glutamic acid
Additional Names: e-N-(L-glutar-2-yl)-L-lysine
Percent Composition: C 47.82%, H 7.30%, N 10.14%, O 34.74%
Literature References: A lysine precursor in the aminoadipic acid-lysine pathway in yeast: Darling, Larsen, Acta Chem. Scand. 15, 743 (1961); Kjaer, Larsen, ibid. 750; Kuo et al., Biochem. Biophys. Res. Commun. 8, 227 (1962); Trupin, Broquist, J. Biol. Chem. 240, 2524 (1965); Jones, Broquist, ibid. 241, 3430 sqq. (1966). Isoln from mycelium of the yeast Candida utilis: Marimoto, Yamano, Biochem. Z. 340, 155 (1964).
Additional Names: D-Glucose; dextrose; blood sugar; grape sugar; corn sugar
Trademarks: Dextropur; Dextrosol; Glucolin
Percent Composition: C 40.00%, H 6.71%, O 53.28%
Literature References: A main source of energy for living organisms. Occurs naturally and in the free state in fruits and other parts of plants. Combined in glucosides, in di- and oligosaccharides, in the polysaccharides cellulose and starch, and in glycogen. Normal human blood contains 0.08-0.1%. Manuf on a large scale from starch: Dean, Gottfried, Adv. Carbohydr. Chem. 5, 127 (1950). Below 50°, a-D-glucose hydrate is the stable cryst form, above 50° the anhydr form is obtained and at still higher temps b-D-glucose is formed: W. Pigman, The Carbohydrates (Academic Press, New York, 1957) p 92. Structure: Kjaer, Lindberg, Acta Chem. Scand. 13, 1713 (1959). Conformation: E. Percival, Structural Carbohydrate Chemistry (J. Garnet Miller, London, 1962) pp 51-57. Comprehensive monograph: H. Bartelheimer et al., D-Glucose und verwandte Verbindungen in Medizin und Biologie (Enke, Stuttgart, 1966) 1126 pp.
CAS Name: N-[(7S)-5,6,7,9-Tetrahydro-1,2,3,10-tetramethoxy-9-oxobenzo[a]heptalen-7-yl]acetamide
Percent Composition: C 66.15%, H 6.31%, N 3.51%, O 24.03%
Literature References: A major alkaloid of Colchicum autumnale L., Liliaceae. Extraction procedure: Chemnitius, J. Prakt. Chem. [II] 118, 29 (1928); F. E. Hamerslag, Technology and Chemistry of Alkaloids (New York, 1950) pp 66-80. Structure: Dewar, Nature 155, 141 (1945); King et al., Acta Crystallogr. 5, 437 (1952); Horowitz, Ullyot, J. Am. Chem. Soc. 74, 487 (1952). Crystal structure: L. Lessinger, T. N. Margulis, Acta Crystallogr. B34, 578 (1978). Total synthesis: Schreiber et al., Helv. Chim. Acta 44, 540 (1961); Van Tamelen et al., Tetrahedron 14, 8 (1961); Nakamura, Chem. Pharm. Bull. 8, 843 (1960); Sunagawa et al., ibid. 9, 81 (1961); 10, 281 (1962); Scott et al., Tetrahedron 21, 3605 (1965); Woodward, Harvey Lectures, Ser. 59 (Academic Press, New York, 1965) p 31; Kotani et al., Chem. Commun. 1974, 300; D. A. Evans et al., J. Am. Chem. Soc. 103, 5813 (1981). Biosynthesis: Leete, Tetrahedron Lett. 1965, 333; Battersby et al., J. Chem. Soc. 1964, 4257; Hill, Unrau, Can. J. Chem. 43, 709 (1965). Tubulin-binding activity: J. M. Andreu, S. N. Timasheff, Proc. Natl. Acad. Sci. USA 79, 6753 (1982). Toxicity: S. J. Rosenbloom, F. C. Ferguson, Toxicol. Appl. Pharmacol. 13, 50 (1968); R. P. Beliles, ibid. 23, 537 (1972). Clinical evaluations in cirrhosis of the liver: M. M. Kaplan et al., N. Engl. J. Med. 315, 1448 (1986); D. Kershenobich et al., ibid. 318, 1709 (1988). Bibliography of early literature: Eigsti, Lloydia 10, 65 (1947). Monograph: O. J. Eigsti, P. Dustin, Jr., Colchicine in Agriculture, Medicine, Biology and Chemistry (Iowa State College Press, Ames, Iowa, 1955). Reviews: Fleming, Selected Organic Syntheses (John Wiley, London, 1973) pp 183-207; G. Lagrue et al., Ann. Med. Interne 132, 496-500 (1981); F. D. Malkinson, Arch. Dermatol. 118, 453-457 (1982). Comprehensive description: D. K. Wyatt et al., Anal. Profiles Drug Subs. 10, 139-182 (1981).
CAS Name: (3a,5b,7a)-3,7-Dihydroxycholan-24-oic acid
Additional Names: 3a,7a-dihydroxy-5b-cholanic acid; anthropodesoxycholic acid; gallodesoxycholic acid; 17b-(1-methyl-3-carboxypropyl)etiocho...
Literature References: A major bile acid in many vertebrates, occurring as the N-glycine and/or N-taurine conjugate. With other bile acids, forms mixed micelles with lecithin in bile which solubilize cholesterol and thus facilitates its excretion. Facilitates fat absorption in the small intestine by micellar solubilization of fatty acids and monoglycerides. Has cathartic properties since it induces fluid secretion from large intestine. Main constituent of the bile of hens, geese and other fowl; occurs in appreciable amounts in the bile of hamster, hog, guinea pig, bear and man. Epimeric with ursodiol, q.v. Isoln: Windhaus et al., Z. Physiol. Chem. 140, 177 (1924); Wieland, Reveney, ibid. 186. Configuration: Lettré, Ber. 68, 766 (1935). Prepn from cholic acid: Fieser, Rajagopalan, J. Am. Chem. Soc. 72, 5530 (1950); Hauser et al., Helv. Chim. Acta 43, 1595 (1960); Hofmann, Acta Chem. Scand. 17, 173 (1963). Alternate prepns: Sato, Ikekawa, J. Org. Chem. 24, 1367 (1959); T. Iida, F. C. Chang, ibid. 46, 2786 (1981). Stereoselective total synthesis: T. Kametani et al., J. Am. Chem. Soc. 103, 2890 (1981). Asymmetric total synthesis of (+)-form: eidem, J. Org. Chem. 47, 2331 (1982). Dissolution of cholesterol gallstones: Danzinger et al., N. Engl. J. Med. 286, 1 (1972); Bell et al., Lancet II, 1213 (1972). Use in long-term treatment of cerebrotendinous xanthomatosis: V. M. Berginer et al., N. Engl. J. Med. 311, 1649 (1984). Monograph on bile acids: The Bile Acids, 2 vols., P. P. Nair, D. Kritchevsky, Eds. (Plenum Press, New York, 1971, 1973). Review of pharmacology and therapeutic use of chenodeoxycholic acid: J. H. Iser, A. Sali, Drugs 21, 90-119 (1981). Effect on cholesterol and bile acid metabolism: G. S. Tint et al., Gastroenterology 91, 1007 (1986).
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