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CAS No 315-22-0 , Monocrotaline

  • Name: Monocrotaline
  • Synonyms: 2H-[1,6]Dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione,4,5,8,10,12,13,13a,13b-octahydro-4,5-dihydroxy-3,4,5-trimethyl-,[3R-(3R*,4R*,5R*,13aR*,13bR*)]-; NSC 28693;Monocrotaline; (-)-Monocrotaline; Monocrotaline (6CI,7CI,8CI);20-Norcrotalanan-11,15-dione,14,19-dihydro-12,13-dihydroxy-, (13a,14a)-;2H-[1,6]Dioxacycloundecino[2,3,4-gh]pyrrolizine, 20-norcrotalanan-11,15-dionederiv.; Monocrotalin;
  • CAS Registry Number:
  • Transport: UN 1544 6.1/PG 3
  • Melting Point: 204 °C (dec.)(lit.)
  • Flash Point: 278.7°C
  • Boiling Point: 537.3°Cat760mmHg
  • Density: 1.35g/cm3
  • Alpha: -54.8o (C=5 IN CHLOROFORM)
  • Safety Statements: Suspected carcinogen with experimental carcinogenic data. Poison by ingestion, intravenous, intraperitoneal, and subcutaneous routes. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
  • Hazard Symbols: T: Toxic;
  • Flash Point: 278.7°C
  • Molecular Weight: 325.36
  • InChI: InChI=1S/C16H23NO6/c1-9-13(18)23-11-5-7-17-6-4-10(12(11)17)8-22-14(19)16(3,21)15(9,2)20/h4,9,11-12,20-21H,5-8H2,1-3H3
  • Risk Statements: 25-40
  • Molecular Formula: C16H23NO6
  • Molecular Structure:CAS No:315-22-0 Monocrotaline

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315-22-0 3914.16 CROTALINE

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315-22-0 Monocrotaline

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References of Monocrotaline
Title: Monocrotaline
CAS Registry Number: 315-22-0
CAS Name: (13a,14a)-14,19-Dihydro-12,13-dihydroxy-20-norcrotolanan-11,15-dione
Synonyms: crotaline; MCT
Manufacturers' Codes: NSC-28693; NCI-C56462
Molecular Formula: C16H23NO6
Molecular Weight: 325.36
Percent Composition: C 59.06%, H 7.13%, N 4.30%, O 29.50%
Literature References: Toxic pyrrolizidine alkaloid isolated from Crotalaria spp. Isoln: R. Adams, E. F. Rogers, J. Am. Chem. Soc. 61, 2815 (1939); R. B. Tinker, W. M. Lauter, Econ. Bot. 10, 254 (1956); C. C. J. Culvenor, L. W. Smith, Aust. J. Chem. 16, 239 (1963). Structure: R. Adams et al., J. Am. Chem. Soc. 74, 5612 (1952). Stereochemistry: D. J. Robins, D. H. G. Crout, J. Chem. Soc. C 1969, 1386. Crystal structure: H. Stoeckli-Evans, Acta Crystallogr. B35, 231 (1979). Stereoselective synthesis: H. Niwa et al., Tetrahedron 48, 10531 (1992). ELISA measurment: M. A. Bober et al., Toxicon 27, 1059 (1989). Toxicology: P. M. Newberne et al., Toxicol. Appl. Pharmacol. 18, 387 (1971); R. A. Roth et al., ibid. 60, 193 (1981). Review of carcinogenicity studies: IARC Monographs 10, 291-302, 333-342 (1976). Comprehensive reviews: L. Bull et al., The Pyrrolizidine Alkaloids (North-Holland, Amsterdam, 1968) 293 pp; D. J. Robins, Fortschr. Chem. Org. Naturst. 41, 115-203 (1982). Review of pulmonary toxicity: D. W. Wilson et al., Crit. Rev. Toxicol. 22, 307-325 (1992).
Properties: White prisms from abs ethanol, mp 197-198° (dec). [a]D26 -54.7° (c = 5.054 in chloroform). Also reported as colorless crystals from ethanol, mp 187-190° (dec). [a]D12 -55.0° (c = 0.16 in CHCl3). uv max (96% ethanol): 217 nm (log e 3.32), Simánek et al., Collect. Czech. Chem. Commun. 34, 1832 (1969). LD50 orally in rats: 71 mg/kg (Newberne).
Melting point: mp 197-198° (dec); mp 187-190° (dec)
Optical Rotation: [a]D26 -54.7° (c = 5.054 in chloroform); [a]D12 -55.0° (c = 0.16 in CHCl3)
Absorption maximum: uv max (96% ethanol): 217 nm (log e 3.32), Simánek et al., Collect. Czech. Chem. Commun. 34, 1832 (1969)
Toxicity data: LD50 orally in rats: 71 mg/kg (Newberne)
 
Derivative Type: Hydrochloride
Molecular Formula: C16H23NO6.HCl
Molecular Weight: 361.82
Percent Composition: C 53.11%, H 6.69%, N 3.87%, O 26.53%, Cl 9.80%
Properties: mp 184° (dec). [a]D28 -38.4° (c = 5.2 in water).
Melting point: mp 184° (dec)
Optical Rotation: [a]D28 -38.4° (c = 5.2 in water)
 
Derivative Type: Methiodide
Molecular Formula: C16H23NO6.CH3I
Molecular Weight: 467.30
Percent Composition: C 43.69%, H 5.61%, N 3.00%, O 20.54%, I 27.16%
Properties: mp 205° (dec). [a]D28 +23.4° (c = 3.1 in methanol).
Melting point: mp 205° (dec)
Optical Rotation: [a]D28 +23.4° (c = 3.1 in methanol)
 
Use: For inducing pulmonary diseases in rats.