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CAS No 90-65-3 , 2,5-Hexadienoic acid,3-methoxy-5-methyl-4-oxo-

  • Name: 2,5-Hexadienoic acid,3-methoxy-5-methyl-4-oxo-
  • Synonyms: NSC 402844; 3-Methoxy-5-methyl-4-oxo-2,5-hexadienoic acid;2,5-Hexadienoic acid,3-methoxy-5-methyl-4-oxo-;Penicillicacid (6CI); g-keto-b-Methoxy-d-methylene-Da-hexenoicacid;
  • CAS Registry Number:
  • Melting Point: 83-87 °C
  • Density: 1.157 g/cm3
  • Water Solubility: Soluble in DMSO, Ethanol, petrol ether. Not soluble in water
  • Safety Statements: Poison by intravenous, subcutaneous, and intraperitoneal routes. Moderately toxic by ingestion. An experimental teratogen. Experimental reproductive effects. Questionable carcinogen with experimental neoplastigenic data. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
  • Hazard Symbols: Xn: Harmful;T: Toxic;
  • EINECS: 202-008-1
  • Molecular Weight: 170.16
  • InChI: InChI=1S/C8H10O4/c1-5(2)8(11)6(12-3)4-7(9)10/h4H,1H2,2-3H3,(H,9,10)/b6-4+
  • Risk Statements: 36/37/38-20/21/22-22 23/24/25
  • Molecular Formula: C8H10O4
  • Molecular Structure:CAS No:90-65-3 2,5-Hexadienoic acid,3-methoxy-5-methyl-4-oxo-

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References of 2,5-Hexadienoic acid,3-methoxy-5-methyl-4-oxo-
Title: Penicillic Acid
CAS Registry Number: 90-65-3
CAS Name: 3-Methoxy-5-methyl-4-oxo-2,5-hexadienoic acid
Synonyms: g-keto-b-methoxy-d-methylene-Da-hexenoic acid
Molecular Formula: C8H10O4
Molecular Weight: 170.16
Percent Composition: C 56.47%, H 5.92%, O 37.61%
Literature References: Antibiotic mycotoxin produced by the following fungi: Penicillium puberulum, P. cyclopium, P. thomii, P. suaveolens, P. baarnense, Aspergillus ochraceus, A. melleus. Isoln: Alsberg, Black, USDA Bur. Plant Ind. Bull. 270, (1913); Birkinshaw et al., Biochem. J. 30, 394 (1936); Oxford et al., Chem. Ind. (London) 20, 22 (1942); Karow et al., Arch. Biochem. 5, 279 (1944); Burton, Nature 165, 274 (1950); Natori et al., Chem. Pharm. Bull. 18, 2259 (1970). Activity studies: Suzuki et al., Agric. Biol. Chem. 35, 287 (1971). Acid in tautomeric equilibrium with its lactone. Structure: Birkinshaw et al., loc. cit. Physical properties: Kovac, Solcaniova, Tetrahedron 25, 3617 (1969). Synthesis: Raphael, Nature 160, 261 (1947); J. Chem. Soc. 1948, 1508; C. L. Yeh et al., Tetrahedron Lett. 1978, 3987. Biosynthesis: Birch et al., J. Chem. Soc. 1958, 4582; Bentley, Keil, J. Biol. Chem. 237, 867 (1962). Physicochemical data: A. E. Pohland et al., Pure Appl. Chem. 54, 2219 (1982). Toxicity studies: P. K. Chan et al., Toxicol. Appl. Pharmacol. 52, 1 (1980); P. K. Chan, A. W. Hayes, J. Toxicol. Environ. Health 7, 169 (1981). Evaluation of carcinogenic risk: IARC Monographs 10, 211-216 (1976). Review: Ciegler et al., "Patulin, Penicillic Acid and Other Carcinogenic Lactones" in Microbial Toxins vol. VI, A. Ciegler et al., Eds. (Academic Press, New York, 1971) p 414.
Properties: Needles from petr ether, mp 83-84°. uv max: about 220 nm. Acid reaction, turns Congo red paper blue. Moderately sol in cold water (2 g/100 ml); freely sol in hot water, alcohol, ether, benzene, chloroform; slightly sol in hot petr ether. Practically insol in pentane-hexane. LD50 i.p. in mice: 90.00 mg/kg (Chan et al.).
Melting point: mp 83-84°
Absorption maximum: uv max: about 220 nm
Toxicity data: LD50 i.p. in mice: 90.00 mg/kg (Chan et al.)
 
Derivative Type: Monohydrate
Properties: Large transparent monoclinic or triclinic, rhombic crystals from water, mp 58-64°.
Melting point: mp 58-64°