3679. α-Erythroidine
Nomenclature
CAS number: 466-80-8
(3β,12β)-1,2,6,7-Tetradehydro-12,17-dihydro-3-methoxy-16(15H)-oxaerythrinan-15-one. C16H19NO3; mol wt 273.33.
C 70.31%, H 7.01%, N 5.12%, O 17.56%.
Description and 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 α- to β-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°. [α]D27 +136° (c = 0.5 in water). Unstable on exposure to air.Derivative
Hydrochloride.C16H20ClNO3; mol wt 309.79.
C 62.03%, H 6.51%, Cl 11.44%, N 4.52%, O 15.49%.
Properties
Prisms from ethanol, dec 226-228°. [α]D32 +118° (c = 0.5 in water). uv max (ethanol): 224 nm (log ε 4.55).Derivative
Methiodide.C17H22INO3; mol wt 415.27.
C 49.17%, H 5.34%, I 30.56%, N 3.37%, O 11.56%.