7451. Pinosylvin

Nomenclature

CAS number: 22139-77-1
(E)-5-(2-Phenylethenyl)-1,3-benzenediol; E-3,5-stilbenediol; 5-styrylresorcinol; trans-3,5-dihydroxystilbene.
C14H12O2; mol wt 212.24.
C 79.23%, H 5.70%, O 15.08%.

Description and references

Occurs together with its monomethyl and dimethyl ethers in the heartwood of pine and other woody plants. Naturally occurring pinosylvins have the trans configuration. Isoln from Pinus sylvestris L., Pinaceae: H. Erdtman, Ann. 539, 116 (1939); from other Pinus species: G. Lindstedt, Acta Chem. Scand. 3, 755-772 (1949); J. C. Alvarez-Novoa et al., ibid. 4, 444 (1950); from Alnus sieboldiana, Betulaceae: Y. Asakawa, Bull. Chem. Soc. Jpn. 44, 2761 (1971); from Polygonum nodosum, Polygonaceae: M. Kuroyanagi et al., Chem. Pharm. Bull. 30, 1602 (1982). Synthesis of pinosylvin: E. Sp"ath, F. Liebherr, Ber. 74, 869 (1941); of monomethyl ether: E. Sp"ath, K. Kromp, ibid. 1424; of dimethyl ether: G. Aulin-Erdtman, H. Erdtman, ibid. 50; of pinosylvin and derivatives: A. A. Loman, L. R. Snowdon, Can. J. Chem. 48, 1554 (1970). Biosynthesis: Birch, Fortschr. Chem. Org. Naturst. 14, 186 (1957). Toxicological study: K. O. Frykholm, Nature 155, 454 (1945). Use as antimicrobial agent: E. H. Sheers, DE 1952451; idem, US 3577230 (1970, 1971 both to Arizona Chem. Co.). Deterrent to feeding behavior of snowshoe hare: J. P. Bryant et al., Science 222, 1023 (1983).

Chemical structure

Properties

Fine needles from glacial acetic acid, mp 155.5-156°. uv max (ethanol): 305 nm (log ε 4.49). Practically insol in water. Sol in benzene, acetone, chloroform, glacial acetic acid.

Derivative

Monomethyl ether.
C15H14O2; mol wt 226.27.
C 79.62%, H 6.24%, O 14.14%.

Properties

Crystals, mp 122-123°. uv max (ethanol): 303 nm (log ε 4.26). More sol in benzene than pinosylvin. Also sol in methanol, glacial acetic acid.

Derivative

Dimethyl ether.
C16H16O2; mol wt 240.30.
C 79.97%, H 6.71%, O 13.32%.

Properties

Crystals from methanol-water, mp 55-56°. uv max (ethanol): 305 nm (log ε 4.39).