Pinosylvin

Chemical compound From Wikipedia, the free encyclopedia

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]

Quick facts Names, Identifiers ...
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
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.208.695 Edit this at Wikidata
UNII
  • 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+ â˜’N
    Key: YCVPRTHEGLPYPB-VOTSOKGWSA-N â˜’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
  • C1=CC=C(C=C1)\C=C\C2=CC(=CC(=C2)O)O
Properties
C14H12O2
Molar mass 212.248 g·mol−1
Appearance white solid
Melting point 153 to 155 Â°C (307 to 311 Â°F; 426 to 428 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 Â°C [77 Â°F], 100 kPa).
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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]

References

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