Ajaconine

Title: Ajaconine
CAS Registry Number: 545-61-9
Molecular Formula: C22H33NO3
Molecular Weight: 359.50
Percent Composition: C 73.50%, H 9.25%, N 3.90%, O 13.35%
Literature References: From seeds of larkspur, Delphinium ajacis L., Ranunculaceae: Keller, Volker, Arch. Pharm. 251, 207 (1913); Goodson, J. Chem. Soc. 1945, 245. Structure: Dvornik, Edwards, Tetrahedron 14, 54 (1961); Nabors et al., Tetrahedron Lett. 1969, 2445. Stereochemistry: Solo, Pelletier, Chem. Ind. (London) 1960, 1108; Whalley, Tetrahedron 18, 43 (1962). Synthetic studies: Nabors et al., ibid. 27, 2385 (1971). Rearrangement: S. W. Pelletier, N. V. Mody, J. Am. Chem. Soc. 101, 492 (1979).
Properties: Prisms from dil alcohol, mp 172°. [a]D18 -119° (c = 2 in anhydr alcohol).
Melting point: mp 172°
Optical Rotation: [a]D18 -119° (c = 2 in anhydr alcohol)
Derivative Type: Sulfate heptahydrate
Properties: Hexagonal plates from dil acetone, mp 113°. [a]D20 +5.5° (c = 2).
Melting point: mp 113°
Optical Rotation: [a]D20 +5.5° (c = 2)
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