Title: Carpaine
CAS Registry Number: 3463-92-1
Molecular Formula: C28H50N2O4
Molecular Weight: 478.71
Percent Composition: C 70.25%, H 10.53%, N 5.85%, O 13.37%
Literature References: Found in Carica papaya L. and in Vasconcellosia hastata Caruel, Caricaceae. Isoln from papaya leaves: Greshoff, Mededeel. uit's Lands. Plant., Buitenzorg. No. 7, 5 (1890); Rapoport, Baldridge, J. Am. Chem. Soc. 73, 343 (1951). Reportedly causes bradycardia, CNS depression: Kakowski, Arch. Int. Pharm. 15, 84 (1905). Structure and stereochemistry: Govindachari et al., Tetrahedron Lett. 1965, 1907. Absolute configuration: Coke, Rice, J. Org. Chem. 30, 3420 (1965). Review of structural studies: Govindachari, J. Indian Chem. Soc. 45, 945 (1968).
Properties: Monoclinic prisms from acetone, mp 119-120°. Sublimes at 120° under 0.05 mm pressure. [a]D12 +24.7° (c = 1.07 in ethanol). Slightly sol in water. Sol in most organic solvents except petr ether.
Melting point: mp 119-120°
Optical Rotation: [a]D12 +24.7° (c = 1.07 in ethanol) |