Title: Isopilosine
CAS Registry Number: 491-88-3
CAS Name: (3S,4R)-Dihydro-3-[(R)-hydroxyphenylmethyl]-4-[(1-methyl-1H-imidazol-5-yl)methyl]-2(3H)-furanone
Additional Names: carpiline; carpidine
Molecular Formula: C16H18N2O3
Molecular Weight: 286.33
Percent Composition: C 67.12%, H 6.34%, N 9.78%, O 16.76%
Literature References: This compound was originally called pilosine (the cis-isomer of isopilosine): H. W. Voigtländer, W. Rosenberg, Arch. Pharm. 292, 579 (1959). Isoln from leaves of Pilocarpus microphyllus Stapf, Rutaceae: F. L. Pyman, J. Chem. Soc. 101, 2260 (1912). Synthesis and abs config: Link, Bernauer, Helv. Chim. Acta 55, 1053 (1972). Crystal structure: W. E. Oberhaensli, Cryst. Struct. Commun. 1, 203 (1972).
Properties: Needles from alcohol, mp 182-182.5°. [a]D20 +37.6° (alcohol).
Melting point: mp 182-182.5°
Optical Rotation: [a]D20 +37.6° (alcohol)
Derivative Type: Pilosine
CAS Registry Number: 13640-28-3
Properties: Needles from alcohol, mp 179°. [a]D20 +83.9° (alcohol). uv max (alcohol): 210 nm (log e 4.10).
Melting point: mp 179°
Optical Rotation: [a]D20 +83.9° (alcohol)
Absorption maximum: uv max (alcohol): 210 nm (log e 4.10)
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