References of 2,4,6,8-Decatetraenedioicacid,1-[(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methyl-2-buten-1-yl)-2-oxiranyl]-1-oxaspiro[2.5]oct-6-yl]ester, (2E,4E,6E,8E)-
Title: Fumagillin
CAS Registry Number: 23110-15-8
CAS Name: (2
E,4
E,6
E,8
E)-2,4,6,8-Decatetraenedioic acid mono[(3
R,4
S,5
S,6
R)-5-methoxy-4-[(2
R,3
R)-2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-1-oxaspiro[2.5]oct-6-yl] ester
Synonyms: 2,4,6,8-decatetraenedioic acid mono[4-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-5-methoxy-1-oxaspiro[2.5]oct-6-yl] ester
Molecular Formula: C26H34O7
Molecular Weight: 458.54
Percent Composition: C 68.10%, H 7.47%, O 24.42%
Literature References: Antibiotic substance produced by
Aspergillus fumigatus: T. E. Eble, F. R. Hanson,
Antibiot. Chemother. 1, 55 (1951); F. R. Hanson, T. E. Eble,
US 2652356 (1953 to Upjohn). Purification: D. S. Tarbell
et al., J. Am. Chem. Soc. 77, 5613 (1955). Structure:
eidem, ibid. 82, 1005 (1960);
83, 3096 (1961). Stereochemistry: N. J. McCorkindale, J. G. Sime,
Proc. Chem. Soc. London 1961, 331; J. R. Turner, D. S. Tarbell,
Proc. Natl. Acad. Sci. USA 48, 733 (1962). Biosynthesis: A. J. Birch, S. F. Hussain,
J. Chem. Soc. C 1969, 1473. Total synthesis of (±)-form: E. J. Corey, B. B. Snider,
J. Am. Chem. Soc. 94, 2549 (1972). Anti-amebic activity: M. C. McCowen
et al., Science 113, 202 (1951). Acute toxicity: J. A. DiPaolo
et al., Antibiot. Annu. 1958-1959, 541. HPLC determn in trout muscle: J. Guyonnet
et al., J. Chromatogr. B 666, 354 (1995). Field trial in honey bees: T. C. Webster,
J. Econ. Entomol. 87, 601 (1994); in rainbow trout: R. le Gouvello
et al., Aquaculture 171, 27 (1999). Clinical evaluation in intestinal microsporidiosis in immunocompromised patients: J.-M. Molina
et al., N. Engl. J. Med. 346, 1963 (2002).
Properties: Yellow needles from methanol, mp 194-195°. [a]D25 -26.6° (c = 1 in 95% ethanol). Absorptivity: 156.0 at 335 nm and 146.5 at 351 nm (soln of 100 mg in 10 ml chloroform diluted with alcohol to 0.0004% fumagillin and 0.04% chloroform). Practically insol in water, dil acids, satd hydrocarbons. Sol in most other organic solvents, in aq solns of bicarbonates and alkali hydroxides. Best stored in dark, evacuated ampuls at low temps. Stability data: T. E. Eble, E. R. Garrett,
J. Am. Pharm. Assoc. 43, 536 (1954); E. R. Garrett,
ibid. 539. LD50 in mice (mg/kg): ~800 s.c. (DiPaolo).
Melting point: mp 194-195°
Optical Rotation: [a]D25 -26.6° (c = 1 in 95% ethanol)
Toxicity data: LD50 in mice (mg/kg): ~800 s.c. (DiPaolo)
Derivative Type: Dicyclohexylamine salt
CAS Registry Number: 41567-78-6
Synonyms: Bicyclohexylammonium fumagillin
Trademarks: Fumidil B (Sanofi)
Therap-Cat: Antiprotozoal.
Therap-Cat-Vet: Antiprotozoal. Control of
Nosema apis in honey bees.
Keywords: Antiamebic.
![CAS No:23110-15-8 2,4,6,8-Decatetraenedioicacid,1-[(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methyl-2-buten-1-yl)-2-oxiranyl]-1-oxaspiro[2.5]oct-6-yl]ester, (2E,4E,6E,8E)-](/structure/cas-231/23110-15-8.png)
