MOLECULE

alpha-Pinene oxide

Alpha-pinene oxide has been exploited as an abundant and a cheap terpene substrate and precursor for the biosynthesis of desirable oxygenated terpene derivatives such as limonen. While these can be produced chemically, biosynthesis of oxygenated terpenes is the more desirable process since it proceeds under mild conditions, it does not generate toxic waste and the products can be labelled as ‘natural’. Some Pseudomonads utilized alpha-terpene, beta-pinene and alpha-pinene oxide as their sole carbon source, suggesting that they have an active metabolic pathway to use it. Using alpha-pinene oxide as a substrate, resting cells of Pseudomonas fluorescens NCIMB 11671 produced isonovalal (cis-2-methyl-5-isopropylhexa-2,5-dienal), which is a fragrance. Another study demonstrated that alpha-pinene oxide was consumed by both Pseudomonas flueoescens and rhodesiae with P. rhodesiae being more efficient in converting alpha-pinene oxide to isonovalal (doi:10.1111/j.1365-2672.2008.03923.x). The enzyme alpha-pinene lyase metabolizes alpha-pine oxide to (Z)-2-methyl-5-isopropylhexa-2,5-dienal ( alpha-Cedrene (PMID: 3667522). Alpha-pinene oxide can also be metabolized to carveol then carvone, thujune and borneol. Alpha-pinene oxide was quantified in labdanum oil (0.23%) and detected in formosan juniper, lemon balm, lamb's lettuce, calabash nutmeg, ocotea floribunda and pepper (http://www.thegoodscentscompany.com/data/rw1218571.html#tooccur). Alpha-pinene oxide is also found in cannabis (PMID: 6991645).