Pinosylvin dimethyl ether

Rowe, J. W., C. L. Bower, and E. R. Wagner Extractives of jack pine bark Occurrence of cis- and /ran -pinosylvin dimethyl ether and ferulic acid esters. Phytochemistry 8, 235—241 (1969). 

Most stilbenes isolated from natural sources are of trans E) configuration. However, Rowe et al. (98) have isolated the cis (Z) isomer of pinosylvin dimethyl ether from the bark of Pinus banksiana. The bark contains a mixture of the cis/trans isomers with the trans isomer as the major compound. 

Plant phenolics of stilbene type are also reported to contribute to the insect resitance of the wood. Thus wood samples impregnated with pinosylvin monomethyl ether are resistant to the attack of the West Indian termite Cryp-totermes brevis (123, 124). Pinosylvin dimethyl ether and dihydropinosylvin were less effective. Sandermann and co-workers (103) have also found that pinosylvin and related hydroxystilbenes as well as some other phenolic wood extractives contribute to the termite and insect resistance of wood. However, our knowledge on this topic is still limited, and further studies shall reveal useful information. 

Canadian chemists3 report that attempted demethylation of the dimethyl ether of pinosylvin (1) with boron tribromide gave the monodemethylated product in... 

Pinosylvin (3,5-stilbenediol) ( )-form needles, insoluble in water, soluble in acetone. )- and (Z)-isomers occur together with the corresponding mono- and dimethyl ethers in pines, firs, and conifers. Pinosylvin has antifungal and antibacterial activities and protects the wood against rot, as a disinfectant it is 30-times stronger than phenol and is highly toxic for fish. As a result of condensation with lignin, pinosylvin prevents sulfite dissolution of wood. Pinosylvin monomethyl ether acts as an antifeedant for certain rabbit species. ... 

A common oxygenation pattern of the natural stilbenes is the 3,5-dioxy substitution. Thus, the first natural stilbenes to be isolated from wood - pinosylvin and its monomethyl and dimethyl ethers-carry 3,5-dioxy substituents (35). 

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