ChEBI: Alpha-pinene oxide is an epoxide of alpha-pinene. It has a role as a fragrance, a bacterial xenobiotic metabolite and a human metabolite. It is a pinane monoterpenoid and an epoxide. It derives from a hydride of an alpha-pinene.
An industrially important reaction of optically
active a-pinene oxide is rearrangement to
campholene aldehyde (e.g., in the presence of
zinc bromide). Subsequent aldol condensation
with lower aliphatic aldehydes or ketones (e.g.,
propionaldehyde, butyraldehyde, or acetone)
provides unsaturated aldehydes or ketones that can be reduced to the corresponding
saturated alcohols. These are used in
the fragrance industry as a sandalwood scent.
