Piceatannol

Piceatannol

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Names
Systematic IUPAC name 4-[(E)-2-(3,5-Dihydroxyphenyl)ethenyl]benzene-1,2-diol
Other names 3',4',3,5-Tetrahydroxy-trans-stilbene Astringinin
Identifiers
CAS Number	10083-24-6 Y
ChEBI	CHEBI:28814 N
ChemSpider	581006 N
Jmol 3D model	Interactive image
PubChem	667639
InChI InChI=1S/C14H12O4/c15-11-5-10(6-12(16)8-11)2-1-9-3-4-13(17)14(18)7-9/h1-8,15-18H/b2-1+ N Key: CDRPUGZCRXZLFL-OWOJBTEDSA-N N InChI=1/C14H12O4/c15-11-5-10(6-12(16)8-11)2-1-9-3-4-13(17)14(18)7-9/h1-8,15-18H/b2-1+ Key: CDRPUGZCRXZLFL-OWOJBTEDBC
SMILES C1=CC(=C(C=C1C=CC2=CC(=CC(=C2)O)O)O)O
Properties
Chemical formula	C14H12O4
Molar mass	244.25 g·mol−1
Appearance	Light tan to yellow powder
Vapor pressure	{{{value}}}
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

Piceatannol is a stilbenoid, a type of phenolic compound.

Natural occurrences

Piceatannol and its glucoside, astringin, are phenolic compounds found in mycorrhizal and non-mycorrhizal roots of Norway spruces (Picea abies). It can also be found in the seeds of the palm Aiphanes horrida and in Gnetum cleistostachyum. The chemical structure of piceatannol was established by Cunningham et al. as being an analog of resveratrol.

In food

Piceatannol is a metabolite of resveratrol found in red wine, grapes, passion fruit, white tea, and Japanese knotweed. Astringin, a piceatannol glucoside, is also found in red wine.

Biochemical study

A 1989 in vitro study found that piceatannol blocked LMP2A, a viral protein-tyrosine kinase implicated in leukemia, non-Hodgkin's lymphoma and other diseases associated with Epstein-Barr virus. In 2003, this prompted research interest in piceatannol and its effect on these diseases.

Injected in rats, piceatannol shows a rapid glucuronidation and a poor bioavailability, according to a 2006 study.

A 2012 Purdue University study found that fat cells in culture, in the presence of piceatannol, alters the timing of gene expressions, gene functions and insulin action, resulting in the delay or complete inhibition of adipogenesis.

See also

• Pterostilbene
• List of phytochemicals in food