Title: Isopilosine
CAS Registry Number: 491-88-3
CAS Name: (3
S,4
R)-Dihydro-3-[(
R)-hydroxyphenylmethyl]-4-[(1-methyl-1
H-imidazol-5-yl)methyl]-2(3
H)-furanone
Synonyms: 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. Voigtl?nder, 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)