Pinosylvin

Pinosylvin
Names
	IUPAC name 5-[(E)-2-Phenylethenyl]benzene-1,3-diol
	Other names (E)-3,5-Stilbenediol; trans-3,5-Dihydroxystilbene
Identifiers
CAS Number	102-61-4 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL101506 ;
ECHA InfoCard	100.208.695
PubChem CID	5280457;
CompTox Dashboard (EPA)	DTXSID00895857 ;
	SMILES C1=CC=C(C=C1)\C=C\C2=CC(=CC(=C2)O)O;
Properties
Chemical formula	C14H12O2
Molar mass	212.244 g/mol
Melting point	153–155 °C
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Pinosylvin is a pre-infectious stilbenoid toxin (i.e. synthesized prior to infection), contrary to phytoalexins which are synthesized during infection. It is present in the heartwood of Pinaceae.^[1] It is a fungitoxin protecting the wood from fungal infection.^[2]

Injected in rats, pinosylvin shows a rapid glucuronidation and a poor bioavailability.^[3]

Biosynthesis

Pinosylvin synthase is an enzyme that catalyzes the chemical reaction 3 malonyl-CoA + cinnamoyl-CoA → 4 CoA + pinosylvin + 4 CO₂

References

^ Screening Analyses of Pinosylvin Stilbenes, Resin Acids and Lignans in Norwegian Conifers. Hanne Hovelstad, Ingebjorg Leirset, Karin Oyaas and Anne Fiksdahl, Molecules, 2006, 11(1), pages 103-114, doi:10.3390/11010103
^ Antibacterial and antifungal activity of pinosylvin, a constituent of pine. S.K. Lee, H.J. Lee, H.Y. Min, E.J. Park, K.M. Lee, Y.H. Ahn, Y.J. Cho and J.H. Pyee, Fitoterapia, Volume 76, Issue 2, March 2005, Pages 258–260, doi:10.1016/j.fitote.2004.12.004
^ Pharmacokinetics of selected stilbenes: rhapontigenin, piceatannol and pinosylvin in rats. Kathryn A. Roupe, Jaime A. Yáñez, Xiao Wei Teng and Neal M. Davies, Journal of Pharmacy and Pharmacology, November 2006, Volume 58, Issue 11, pages 1443–1450, doi:10.1211/jpp.58.11.0004

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[1] Screening Analyses of Pinosylvin Stilbenes, Resin Acids and Lignans in Norwegian Conifers. Hanne Hovelstad, Ingebjorg Leirset, Karin Oyaas and Anne Fiksdahl, Molecules, 2006, 11(1), pages 103-114, doi:10.3390/11010103

[2] Antibacterial and antifungal activity of pinosylvin, a constituent of pine. S.K. Lee, H.J. Lee, H.Y. Min, E.J. Park, K.M. Lee, Y.H. Ahn, Y.J. Cho and J.H. Pyee, Fitoterapia, Volume 76, Issue 2, March 2005, Pages 258–260, doi:10.1016/j.fitote.2004.12.004

[3] Pharmacokinetics of selected stilbenes: rhapontigenin, piceatannol and pinosylvin in rats. Kathryn A. Roupe, Jaime A. Yáñez, Xiao Wei Teng and Neal M. Davies, Journal of Pharmacy and Pharmacology, November 2006, Volume 58, Issue 11, pages 1443–1450, doi:10.1211/jpp.58.11.0004

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