Title: Akuammicine
CAS Registry Number: 639-43-0
CAS Name: 2,16,19-20-Tetradehydrocuran-17-oic acid methyl ester
Molecular Formula: C20H22N2O2
Molecular Weight: 322.40
Percent Composition: C 74.51%, H 6.88%, N 8.69%, O 9.93%
Literature References: From the seeds of Picralima klaineana, Pierre, Apocynaceae found in the Gold Coast: Henry, Sharp, J. Chem. Soc. 1927, 1950; Henry, ibid. 1932, 2759. Structure: Aghoramurthy, Robinson, Tetrahedron 1, 172 (1957); Bernauer et al., Helv. Chim. Acta 43, 717 (1960); Edwards, Smith, J. Chem. Soc. 1961 152. Derivs: Robinson, Thomas, ibid. 1955, 2049. Total synthesis: Kutney, Fuller, Heterocycles 3, 197 (1975).
Properties: Plates from ethanol+ water, mp 182°. [a]D16 -745° (c = 0.994 in ethanol). pKa 7.45. uv max (ethanol): 227, 300, 330 nm (log e 4.09, 4.07, 4.24).
Melting point: mp 182°
pKa: pKa 7.45
Optical Rotation: [a]D16 -745° (c = 0.994 in ethanol)
Absorption maximum: uv max (ethanol): 227, 300, 330 nm (log e 4.09, 4.07, 4.24)
Derivative Type: Hydrochloride dihydrate
Molecular Formula: C20H22N2O2.HCl.2H2O
Molecular Weight: 394.89
Percent Composition: C 60.83%, H 6.89%, N 7.09%, O 16.21%, Cl 8.98%
Properties: Leaflets from alcohol or water, mp 171°. [a]D21 -610° (c = 1.430 in ethanol).
Melting point: mp 171°
Optical Rotation: [a]D21 -610° (c = 1.430 in ethanol)
Derivative Type: Perchlorate monohydrate
Molecular Formula: C20H22N2O2.HClO4.H2O
Molecular Weight: 440.87
Percent Composition: C 54.49%, H 5.72%, N 6.35%, O 25.40%, Cl 8.04%
Properties: Needles from ethanol + water, mp 134-136°.
Melting point: mp 134-136°
Derivative Type: Hydriodide monohydrate
Molecular Formula: C20H22N2O2.HI.H2O
Molecular Weight: 468.33
Percent Composition: C 51.29%, H 5.38%, N 5.98%, O 10.25%, I 27.10%
Properties: Square plates from water, mp 128°.
Melting point: mp 128°
Derivative Type: Methiodide
Properties: Crystals from water, mp 252°.
Melting point: mp 252°
Derivative Type: Nitrate
Properties: Needles from hot water, mp 182.5°.
Melting point: mp 182.5°
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