rac-Osyrol® (3,7-dimethyl-7-methoxyoctane-2-ol), a commercially important sandalwood odorant has been prepared from dihydromyrcene in three steps. The key steps in the synthesis are the epoxidation of terminal double bond using urea hydrogen peroxide (UHP) and regioselective reduction of epoxide using Vitride®. The same strategy has been applied to the synthesis of its ethoxy homologue.

In the title crystal structure, C10H16O2, inversion-related mol­ecules are linked by pairs of O—H⋯O hydrogen bonds involving carboxyl groups to form R 2 2(8) dimers. The cyclo­hexene ring displays a half-chair conformation.

In the crystal of the title compound C10H17NO, synthesized by the reaction of β-cyclo­citral with hydroxyl­amine hydro­chloride, inversion-related mol­ecules are linked by a pair of O—H⋯N hydrogen-bonding inter­actions between the oxime functionalities, forming R 2 2(6) loops. The molecular conformation is stabilized by intra­molecular methyl C—H⋯N inter­actions. The cyclohexene ring has the typical half-chair conformation.