Pinosylvin

Pinosylvin is an organic compound with the formula C₆H₅CH=CHC₆H₃(OH)₂. A white solid, it is related to trans-stilbene, but with two hydroxy groups on one of the phenyl substituents. It is very soluble in many organic solvents, such as acetone.^[1]

Pinosylvin

Names
Preferred IUPAC name 5-[(1E)-2-Phenylethen-1-yl]benzene-1,3-diol
Other names (E)-3,5-Stilbenediol trans-3,5-Dihydroxystilbene
Identifiers
CAS Number	22139-77-1 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL101506 N
ChemSpider	4444110 N
ECHA InfoCard	100.208.695
PubChem CID	5280457
UNII	881R434AIB Y
CompTox Dashboard (EPA)	DTXSID00895857
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	212.248 g·mol−1
Appearance	white solid
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 verify (what is YN ?) Infobox references

Occurrence

Pinosylvin is produced in plants in response to fungal infections, ozone-induced stress, and physical damage for example.^[2] It is a fungitoxin protecting the wood from fungal infection.^[3] It is present in the heartwood of Pinaceae^[2] and also found in Gnetum cleistostachyum.^[4]

Injected in rats, pinosylvin undergoes rapid glucuronidation and a poor bioavailability.^[5]

Biosynthesis

Pinosylvin synthase, an enzyme, catalyzes the biosynthesis of pinosylvin from malonyl-CoA and cinnamoyl-CoA:

3 malonyl-S-CoA + cinnamoyl-S-CoA → 4 CoA-SH + 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. Two other compounds produced from cinnamic acid are anigorufone and curcumin.^[6][7]