Polymorphic forms of lupane triterpenoid betulonic aldehyde (betulonal)

Abstract

The lupane triterpenoid betulonic aldehyde [also known as betulonal; systematic name: lup-20(29)-en-28-al-3-one, C30H46O2] is a product of betulin oxidation. Crystals were obtained from hexane [form (I)] and dimethyl sulfoxide [form (II)] solutions. Forms (I) and (II) are both orthorhombic. The molecular geometric parameters in the two forms are similar, but the structures are different with respect to the crystal packing. Polymorph (I) contains two independent molecules in the asymmetric unit, while polymorph (II) contains only one molecule, which has a disordered aldehyde group [the disorder ratio is 0.769 (4):0.231 (4)]. In each molecule, the six-membered rings have chair conformations, whereas the cyclopentane ring in each molecule adopts an envelope conformation. All the rings in the lupane nucleus aretrans-fused. The extended structures of both polymorphs are stabilized by weak intermolecular C—H...O and van der Waals interactions. Weak intramolecular C—H...O interactions are also observed.