Title: Pinosylvin
CAS Registry Number: 22139-77-1
CAS Name: (E)-5-(2-Phenylethenyl)-1,3-benzenediol
Additional Names: E-3,5-stilbenediol; 5-styrylresorcinol; trans-3,5-dihydroxystilbene
Molecular Formula: C14H12O2
Molecular Weight: 212.24
Percent Composition: C 79.23%, H 5.70%, O 15.08%
Literature 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. Späth, F. Liebherr, Ber. 74, 869 (1941); of monomethyl ether: E. Späth, 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).
Properties: Fine needles from glacial acetic acid, mp 155.5-156°. uv max (ethanol): 305 nm (log e 4.49). Practically insol in water. Sol in benzene, acetone, chloroform, glacial acetic acid.
Melting point: mp 155.5-156°
Absorption maximum: uv max (ethanol): 305 nm (log e 4.49)
Derivative Type: Monomethyl ether
Molecular Formula: C15H14O2
Molecular Weight: 226.27
Percent Composition: C 79.62%, H 6.24%, O 14.14%
Properties: Crystals, mp 122-123°. uv max (ethanol): 303 nm (log e 4.26). More sol in benzene than pinosylvin. Also sol in methanol, glacial acetic acid.
Melting point: mp 122-123°
Absorption maximum: uv max (ethanol): 303 nm (log e 4.26)
Derivative Type: Dimethyl ether
Molecular Formula: C16H16O2
Molecular Weight: 240.30
Percent Composition: C 79.97%, H 6.71%, O 13.32%
Properties: Crystals from methanol-water, mp 55-56°. uv max (ethanol): 305 nm (log e 4.39).
Melting point: mp 55-56°
Absorption maximum: uv max (ethanol): 305 nm (log e 4.39)

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