5199. Isopilosine

Nomenclature

CAS number: 491-88-3
(3S,4R)-Dihydro-3-[(R)-hydroxyphenylmethyl]-4-[(1-methyl-1H-imidazol-5-yl)methyl]-2(3H)-furanone; carpiline; carpidine.
C16H18N2O3; mol wt 286.33.
C 67.12%, H 6.34%, N 9.78%, O 16.76%.

Description and references

This compound was originally called pilosine (the cis-isomer of isopilosine): H. W. Voigtlnder, 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).

Chemical structure

Properties

Needles from alcohol, mp 182-182.5°. [α]D20 +37.6° (alcohol).

Derivative

Pilosine.

Nomenclature

CAS number: 13640-28-3

Properties

Needles from alcohol, mp 179°. [α]D20 +83.9° (alcohol). uv max (alcohol): 210 nm (log ε 4.10).