Reaction: myrcene + [reduced NADPHhemoprotein reductase] + O2 = (R)-ipsdienol + [oxidized NADPHhemoprotein reductase] + H2O
For diagram of reaction click here.
Glossary: myrcene = 7-methyl-3-methyleneocta-1,6-diene
ipsdienol = 2-methyl-6-methyleneocta-2,7-dien-4-ol
Other name(s): myrcene hydroxylase; CYP9T2; CYP9T3
Systematic name: myrcene,NADPHhemoprotein reductase:O2 oxidoreductase (hydroxylating)
Comments: A cytochrome P-450 heme-thiolate protein. Involved in the insect aggregation pheromone production. Isolated from the pine engraver beetle, Ips pini. A small amount of (S)-ipsdienol is also formed. In vitro it also hydroxylated (+)- and ()-α-pinene, 3-carene, and (+)-limonene, but not α-phellandrene, ()-β-pinene, γ-terpinene, or terpinolene.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number:
1. Sandstrom, P., Welch, W.H., Blomquist, G.J. and Tittiger, C. Functional expression of a bark beetle cytochrome P450 that hydroxylates myrcene to ipsdienol. Insect Biochem. Mol. Biol. 36 (2006) 835-845. [PMID: 17046597]
2. Song, M., Kim, A.C., Gorzalski, A.J., MacLean, M., Young, S., Ginzel, M.D., Blomquist, G.J. and Tittiger, C. Functional characterization of myrcene hydroxylases from two geographically distinct Ips pini populations. Insect Biochem. Mol. Biol. 43 (2013) 336-343. [PMID: 23376633]