Title: a-Erythroidine
CAS Registry Number: 466-80-8
CAS Name: (3b,12b)-1,2,6,7-Tetradehydro-12,17-dihydro-3-methoxy-16(15H)-oxaerythrinan-15-one
Molecular Formula: C16H19NO3
Molecular Weight: 273.33
Percent Composition: C 70.31%, H 7.01%, N 5.12%, O 17.56%
Literature References: Isoln from Erythrina spp, Leguminosae: Folkers, Major, US 2373952 (1945 to Merck & Co.); Boekelheide, Grundon, J. Am. Chem. Soc. 75, 2563 (1953). Structure: Godfrey et al., ibid. 77, 3342 (1955). Absolute configuration: Hill, Shearer, J. Org. Chem. 27, 921 (1962); Wenzinger, Boekelheide, Proc. Chem. Soc. London 1963, 53. Conversion of a- to b-erythroidine: Boekelheide, Morrison, J. Am. Chem. Soc. 80, 3905 (1958). Biosynthesis studies: Leete, Ahmad, ibid. 88, 4722 (1966).
Properties: Needles from pentane, mp 58-60°. [a]D27 +136° (c = 0.5 in water). Unstable on exposure to air.
Melting point: mp 58-60°
Optical Rotation: [a]D27 +136° (c = 0.5 in water)
Derivative Type: Hydrochloride
Molecular Formula: C16H20ClNO3
Molecular Weight: 309.79
Percent Composition: C 62.03%, H 6.51%, Cl 11.44%, N 4.52%, O 15.49%
Properties: Prisms from ethanol, dec 226-228°. [a]D32 +118° (c = 0.5 in water). uv max (ethanol): 224 nm (log e 4.55).
Optical Rotation: [a]D32 +118° (c = 0.5 in water)
Absorption maximum: uv max (ethanol): 224 nm (log e 4.55)
Derivative Type: Methiodide
Molecular Formula: C17H22INO3
Molecular Weight: 415.27
Percent Composition: C 49.17%, H 5.34%, I 30.56%, N 3.37%, O 11.56%
Properties: Yellow prisms from ethanol, mp 219-220°.
Melting point: mp 219-220°
|