Abresoline

A member of the Heimia group of alkaloids, abresoline occurs in Heimia salicijolia as a minor constituent and is found in the most polar alkaloidal fraction. So far it has been obtained only in low yields and forms a non-crystallizable solid having no definite melting point. The ultraviolet spectrum consists of two absorption maxima at 284 and 323 nm. The structure of this alkaloid represents a hitherto unknown structural variation in the series of Heimia alkaloids. Hydrogenation with Pd/C in MeOH furnishes the dihydro derivative which is also an amorphous white powder. The ultraviolet spectrum of this compound has an absorption maximum at 282 nm with an inflexion at 287 nm. Hydrolysis with 2N-NaOH yields trans-ferulic acid. Abresoline has been synthesized from pelletierine and 3-hydroxy-4-methoxybenzaldehyde as the starting materials.

Horhammer, Schwarting, Edwards, J. Org. Chem., 40, 656 (1975)