Structural Formula Vector Image
Title: Helminthosporal
CAS Registry Number: 723-61-5
CAS Name: (1R,4R,5S,8S)-1,7-Dimethyl-4-(1-methylethyl)bicyclo[3.2.1]oct-6-ene-6,8-dicarboxaldehyde
Molecular Formula: C15H22O2
Molecular Weight: 234.33
Percent Composition: C 76.88%, H 9.46%, O 13.66%
Literature References: Toxin produced as (-)-form by the fungus Bipolaris sarokiniana Shoemaker (Helminthosporium sativum). Isoln: deMayo et al., Can. J. Chem. 39, 1608 (1961). Structure: deMayo et al., J. Am. Chem. Soc. 84, 494 (1962). Stereochemistry: deMayo et al., Can. J. Chem. 41, 2996 (1963). Total synthesis and absolute configuration: Corey, Nozoe, J. Am. Chem. Soc. 87, 5728 (1965); (+)-form: E. Piers, H. P. Isenring, Can. J. Chem. 55, 1039 (1977); of (±)-form: M. Yanagiya et al., Tetrahedron Lett. 1979, 1761.
Properties: Crystals from light petr, mp 56-59°. [a]D -49° (c = 1.18 in CHCl3). bp0.015 115-120°. uv max (ethanol): 266 nm (e 11000).
Melting point: mp 56-59°
Boiling point: bp0.015 115-120°
Optical Rotation: [a]D -49° (c = 1.18 in CHCl3)
Absorption maximum: uv max (ethanol): 266 nm (e 11000)
Derivative Type: Bis-oxime
Molecular Formula: C15H24N2O2
Molecular Weight: 264.36
Percent Composition: C 68.15%, H 9.15%, N 10.60%, O 12.10%
Properties: Crystals from alc, mp 177-182°.
Melting point: mp 177-182°
Status: This monograph has been retired and is no longer subject to revision or update.

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