
Additional Names: Bis[methylmercapto]methane; methylenebis[methyl sulfide]
Percent Composition: C 33.29%, H 7.45%, S 59.25%
Literature References: Odorous principle of the white truffle Tuber magnatum (Pico) Vitt., Tuberaceae. Isoln: Fiecchi et al., Tetrahedron Lett. 1967, 1681. Synthesis from methyl mercaptan: Böhme, Marx, Ber. 74, 1672 (1941).
CAS Name: 2-(1,3-Dithiol-2-ylidene)-1,3-dithiole
Additional Names: D 2,2'-bi-1,3-dithiole; bis-1,3-dithiole; 1,4,5,8-tetrathiafulvalene; TTF
Percent Composition: C 35.26%, H 1.97%, S 62.76%
Literature References: Of interest in solid state chemistry as a conductor, catalyst or sensor due to its unusual electronic and magnetic properties. Primarily used as the parent compound for supramolecular assemblies. Prepn: F. Wudl et al., Chem. Commun. 1970, 1453. In combination with TCNQ (tetracyano-p-quinodimethane) to form first "organic metal": J. Ferraris et al., J. Am. Chem. Soc. 95, 948 (1973); electronic structure: R. Gleiter et al., J. Electron. Spectrosc. Relat. Phenom. 2, 207 (1973). Use as a catalyst in radical reactions: R. J. Fletcher et al., J. Chem. Soc. Perkin Trans. 1 1995, 623; J. A. Murphy, S. J. Roome, ibid. 1349. TTF-mediated biosensors for glucose: T. Yu et al., J. Appl. Polym. Sci. 58, 973 (1995); for NADH: X. Zhang et al., Anal. Commun. 33, 111 (1996); for gln and glu: A. Mulchandani, A. S. Bassi, Biosens. Bioelectron. 11, 271 (1996). Review: T. Jorgensen et al., Chem. Soc. Rev. 23, 41-51 (1994). Review of electrical properties and structural data of unsymmetric TTF cmpds: J. M. Fabre et al., Synth. Met. 35, 57-64 (1990); of role in superconductors: M. R. Bryce, J. Mater. Chem. 5, 1481-1496 (1995).
CAS Name: (2S-trans)-5-Methyl-2-(1-methylethyl)cyclohexanone
Additional Names: (1R,4S)-(-)-p-menthan-3-one; 1-methyl-4-isopropylcyclohexan-3-one
Percent Composition: C 77.87%, H 11.76%, O 10...
Literature References: Of the four optically active isomers of methone, the one occurring most frequently in nature. Found in various volatile oils, such as pennyroyal, peppermint, geranium: Simonsen, The Terpenes vol. I (University Press, Cambridge, 2nd ed., 1947) pp 314-327. Prepd by chromic acid oxidation of l-menthol: Hussey, Baker, J. Org. Chem. 25, 1434 (1960); Brown, Garg, J. Am. Chem. Soc. 83, 2952 (1961).
Trademarks: Robecote (Robeco)
Literature References: Oil expressed from the livers of sharks and other Elasmobranchii species. Constit: Squalene, pristane, vitamins A and D, esters of fatty acids (esp. palmitic and oleic), glycerol ethers, triglycerides, cholesterol and fatty alcohols. Isoln: A. Ehrenreich, GB 284657 (1927); C. E. Brown, S. A. Reed, GB 1021542 (1966 to Marfleet Refining Co. Ltd.). Composition: N. A. Sörensen, J. Mehlum, Acta Chem. Scand. 2, 140 (1948); E. Gelpi, J. Oro, J. Am. Oil Chem. Soc. 45, 144 (1968); R. Lombardi et al., Ann. Pharm. Fr. 29, 429 (1971). Comparison with cod liver oil: A. O. Banjo, J. Food Technol. 14, 107 (1979).
CAS Name: Mithramycin
Additional Names: aureolic acid; mithracin; mitramycin; aurelic acid; antibiotic LA-7017
Percent Composition: C 57.55%, H 7.06%, O 35.39%
Literature References: Oligosaccharide antibiotic produced by Streptomyces argillaceus n. sp. and S. tanashiensis. Isoln: Grundy et al., Antibiot. Chemother. 3, 1215 (1953); Philip, Schenck, ibid. 1218; Rao et al., ibid. 12, 182 (1962). Identity of aureolic acid with mithramycin: Berlin et al., Nature 218, 193 (1968). Prepn: Gado et al., HU 155679 (1969 to Gyogyszerkutato Intezet), C.A. 70, 118093f (1969). Similar to the chromomycins and olivomycins, q.q.v. Structural elucidation of the aglycone, chromomycinone, and the carbohydrate moieties: Bakhaeva et al., Tetrahedron Lett. 1968, 3595; Berlin et al., Khim. Prir. Soedin. 1972, 537, 542, C.A. 78, 16436t, 16443t (1973). Revised structure: J. Thiem, B. Meyer, Tetrahedron 37, 551 (1981). NMR and fluorometric characterization: N. R. Krishna et al., J. Antibiot. 43, 1543 (1990). Metabolic studies: Kennedy et al., Cancer Res. 27, 1534 (1967). Mode of action studies: Kushch et al., Antibiotiki 17, 504 (1972). Toxicity study: M. Slavik, S. K. Carter, Adv. Pharmacol. Chemother. 12, 1 (1975). Review: J. D. Skarbek, M. K. Speedie in Antitumor Compounds of Natural Origin vol. 1, A. Aszalos, Ed. (CRC Press, Boca Raton, 1981) pp 191-235.
CAS Name: b-D-Fructofuranosyl O-a-D-galactopyranosyl-(1®6)-O-a-D-galactopyranosyl(1®6)-O-a-D-galactopyranosyl-(1®6)-a-D-glucopyranoside
Additional Names: O-a-D-galactopyranosyl-(1®6)-[O-a-D-gal...
Literature References: Oligosaccharide isolated from roots of mullein Verbascum thapsus L., Scrophulariaceae: Bourquelot, Bridel, Compt. Rend. 151, 760 (1910); from birch wood, Betula verrucosa Ehrh., Betulaceae: Lindberg, Selleby, Acta Chem. Scand. 12, 1512 (1958). Structure: Wickström et al., Bull. Soc. Chim. Fr. 1956, 827. Review: D. French "The Raffinose Family of Oligosaccharides" in Adv. Carbohydr. Chem. 9, 180-181 (1954).
CAS Name: O-2-Amino-2-deoxy-a-D-glucopyranosyl-(1®4)-O-[O-2,6-diamino-2,6-dideoxy-b-L-idopyranosyl-(1®3)-b-D-ribofuranosyl-(1®5)]-2-deoxy-D-streptamine
Additional Names: O-2,6-diamino-2,6-dideo...
Literature References: Oligosaccharide-type antibiotic isolated from various Streptomyces. From S. rimosus forma paromomycinus: Frohardt et al., US 2916485 (1959 to Parke, Davis); from S. catenulae: Davisson, Finlay, US 2895876 (1959 to Pfizer); from S. chrestomyceticus: Canevazzi, Scotti, G. Microbiol. 7, 242 (1959); Arcamone et al., ibid. 251. Identity of paromomycin, catenulin, hydroxymycin and aminosidine: Schillings, Schaffner, Antimicrob. Agents Chemother. 1961, 274. Structure: Haskell et al., J. Am. Chem. Soc. 81, 3480, 3482 (1959); Rinehart et al., ibid. 84, 3218 (1962); Hichens, Rinehart, ibid. 85, 1547 (1963). Probable identity with zygomycin A: Horii, J. Antibiot. 15A, 187 (1962). Identity with monomycin A: Konstantinova, Brazhnikova, Antibiotiki 10(1), 34 (1965); with neomycin E: Hessler et al., J. Antibiot. 23, 464 (1970). Toxicity data: A. DiMarco, C. Bertazzoli, Antibiot. Chemother. 11, 2 (1963). Review of antimicrobial activity: G. L. Coffey et al., ibid. 9, 730 (1959). Review of pharmacology: Gasparini, Pignatelli, Veterinaria (Milan) 21, 7 (1972).
CAS Name: (4Z,7Z,10Z,13Z,16Z,19Z)-4,7,10,13,16,19-Docosahexaenoic acid
Additional Names: cervonic acid; doconexent; DHA
Percent Composition: C 80.44%, H 9.82%, O 9.74%
Literature References: Omega-3 fatty acid found in marine fish oils and in many phospholipids. Major structural component of excitable membranes of the retina and brain; synthesized in the liver from a-linolenic acid, q.v. Isoln from oil of Sardina ocellata J. and structure: J. M. Whitcutt, Biochem. J. 67, 60 (1957). Improved isoln from cod liver oil: S. W. Wright et al., J. Org. Chem. 52, 4399 (1987). Effect on brain and behavioral development: P. E. Wainwright, Neurosci. Biobehav. Rev. 16, 193 (1992). Review of uptake and metabolism by retinal cells: N. G. Bazan, E. B. Rodriguez de Turco, J. Ocul. Pharmacol. 10, 591-603 (1994). Review of clinical studies in infant formula supplementation: M. Makrides et al., Lipids 31, 115-119 (1996).
CAS Name: (E)-10-Propyl-5,9-tridecadien-1-ol acetate
Additional Names: trans-1-acetoxy-10-(n-propyl)trideca-5,9-diene; 10-propyl-trans-5,9-tridecadienyl acetate
Percent Composition: C 77.09%...
Literature References: Once thought to be the sex pheromone of the pink bollworm moth, Pectinophora gossypiella (Saunders), a destructive cotton pest: H. E. Hummel et al., Science 181, 873 (1973), cf. Gossyplure. Reported as the first known natural product possessing di-n-propyl branching. Isoln, structure, and synthesis: Jones et al., Science 152, 1516 (1966). Improved total syntheses: Pattenden, J. Chem. Soc. C 1968, 2385; Meyers, Collington, Tetrahedron 27, 5979 (1971); Vig et al., J. Indian Chem. Soc. 50, 39 (1973); K. Utimoto et al., Tetrahedron Lett. 1975, 4233. Photochemical synthesis: Kossanyi et al., ibid. 1973, 3459. Stereoselective synthesis: A. Alexakis et al., ibid. 1978, 2027. trans-Propylure is rendered inactive by the presence of 15% of the cis-isomer: Jacobson, Science 163, 190 (1969).
CAS Name: (2S)-N-[(1S,2R,3E,5E,7S,9E,11E,13S,15R,19R)-13-(Acetyloxy)-7-hydroxy-1,4,10,19-tetramethyl-17,18-dioxo-16-oxabicyclo[13.2.2]nonadeca-3,5,9,11-tetraen-2-yl]-2-oxopropanamide
Additional...
Literature References: One of 7 components of antibiotic T-2636. First isolated as bundlin B from Streptomyces griseofuscus: J. M. J. Sakamoto et al., J. Antibiot. A15, 98 (1962). Isoln from S. rochei var volubilis: NL 6807119; E. Higashide et al., US 3626055 (1968, 1971 both to Takeda); eidem, J. Antibiot. 24, 1 (1971); S. Harada et al., ibid. 13. Similar to lankacidin which is isolated from S. violaceoniger with lankamycin. Structure, absolute configuration and identity with bundlin B: H. Harada et al., Tetrahedron Lett. 10, 2239 (1969); K. Kamiya et al., ibid. 2245; M. Uramoto et al., ibid. 2249. Enzymatic conversion to other lankacidins: T. Fugono et al., Experientia 26, 26 (1970). Antibacterial activity: K. Tsuchiya et al., J. Antibiot. 24, 29 (1971). Mass spectra: M. Uramoto et al., Agric. Biol. Chem. 38, 855 (1974). Biosynthetic studies: eidem, J. Am. Chem. Soc. 100, 3616 (1978); K. Kakinima et al., Tetrahedron Lett. 23, 5303 (1982). Synthetic study: M. J. Fray, E. J. Thomas, Tetrahedron 40, 673 (1984). Activity against Treponema hyodysenteriae (swine dysentery): BE 891275; N. Narukawa et al., US 4425356 (1982, 1984 both to Takeda).
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