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	22139-77-1 (E isomer) N 102-61-4 (Mixture of E & Z) N
3D model (Jmol)	Interactive image
ChemSpider	4444110 N
ECHA InfoCard	100.208.695
PubChem CID	5280457
InChI InChI=1S/C14H12O2/c15-13-8-12(9-14(16)10-13)7-6-11-4-2-1-3-5-11/h1-10,15-16H/b7-6+ N Key: YCVPRTHEGLPYPB-VOTSOKGWSA-N N InChI=1/C14H12O2/c15-13-8-12(9-14(16)10-13)7-6-11-4-2-1-3-5-11/h1-10,15-16H/b7-6+ Key: YCVPRTHEGLPYPB-VOTSOKGWBH
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 to 155 °C (307 to 311 °F; 426 to 428 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
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. It is a fungitoxin protecting the wood from fungal infection. It is also found in Gnetum cleistostachyum.

Injected in rats, pinosylvin shows a rapid glucuronidation and a poor bioavailability.

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

This biosynthesis is noteworthy because plant biosyntheses employing cinnamic acid as a starting point are rare compared to the more common use of p-coumaric acid. Only a few identified compounds, such as anigorufone and curcumin, use cinnamic acid as their start molecule.