Pterostilbene

Pterostilbene

Names
IUPAC name 4-[(E)-2-(3,5-Dimethoxyphenyl)ethenyl]phenol
Other names 3',5'-Dimethoxy-4-stilbenol 3,5-Dimethoxy-4'-hydroxy-E-stilbene 3',5'-dimethoxy-resveratrol
Identifiers
CAS Number	537-42-8
ChEBI	CHEBI:8630
ChEMBL	ChEMBL83527
ChemSpider	4445042
IUPHAR/BPS	2681
Jmol interactive 3D	Image
PubChem	5281727
InChI InChI=1S/C16H16O3/c1-18-15-9-13(10-16(11-15)19-2)4-3-12-5-7-14(17)8-6-12/h3-11,17H,1-2H3/b4-3+ Key: VLEUZFDZJKSGMX-ONEGZZNKSA-N InChI=1S/C16H16O3/c1-18-15-9-13(10-16(11-15)19-2)4-3-12-5-7-14(17)8-6-12/h3-11,17H,1-2H3/b4-3+ Key: VLEUZFDZJKSGMX-ONEGZZNKBK Key: VLEUZFDZJKSGMX-ONEGZZNKSA-N
SMILES O(c1cc(cc(OC)c1)\C=C\c2ccc(O)cc2)C
Properties
Chemical formula	C16H16O3
Molar mass	256.296 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Pterostilbene is a stilbenoid chemically related to resveratrol. In plants, it serves a defensive phytoalexin role.^[1]

Natural occurrences

Pterostilbene is found in almonds,^[2] various Vaccinium berries,^[3] grape leaves and vines ^[1][4] and blueberries.^[5][6]

While resveratrol is under research for its potential properties from consuming wine and other foods or beverages, pterostilbene is not found in wine.^[7]

Basic research

The possible biological effects of pterostilbene are being examined in basic research involving laboratory models of several disorders, including age-related cognitive decline.^[8]

See also

• Piceatannol, a stilbenoid related to both resveratrol and pterostilbene

References

1. Langcake, P.; Pryce, R. J. (1977). "A new class of phytoalexins from grapevines". Experientia 33 (2): 151–2. doi:10.1007/BF02124034. PMID 844529.
2. Xie L, Bolling BW (2014). "Characterisation of stilbenes in California almonds (Prunus dulcis) by UHPLC-MS". Food Chem 148 (Apr 1): 300–6. doi:10.1016/j.foodchem.2013.10.057. PMID 24262561.
3. Rimando AM, Kalt W, Magee JB, Dewey J, Ballington JR (2004). "Resveratrol, pterostilbene, and piceatannol in vaccinium berries". J Agric Food Chem 52 (15): 4713–9. doi:10.1021/jf040095e. PMID 15264904.
4. Becker L, Carré V, Poutaraud A, Merdinoglu D, Chaimbault P (2014). "MALDI mass spectrometry imaging for the simultaneous location of resveratrol, pterostilbene and viniferins on grapevine leaves". Molecules 19 (7): 10587–600. doi:10.3390/molecules190710587. PMID 25050857.
5. "USDA ARS Online Magazine Vol. 54, No. 11". agresearchmag.ars.usda.gov. Retrieved 2016-03-21.
6. McCormack, Denise; McFadden, David (2013-01-01). "A Review of Pterostilbene Antioxidant Activity and Disease Modification". Oxidative Medicine and Cellular Longevity 2013. doi:10.1155/2013/575482. ISSN 1942-0900. PMC 3649683. PMID 23691264.
7. M. Adrian, P. Jeandet, A. C. Breuil, D. Levite, S. Debord and R. Bessis (2000). "Assay of Resveratrol and Derivative Stilbenes in Wines by Direct Injection High Performance Liquid Chromatography". Am J Enol Vitic 51 (1): 37–41.
8. Poulose SM, Thangthaeng N, Miller MG, Shukitt-Hale B (2015). "Effects of pterostilbene and resveratrol on brain and behavior". Neurochem Int. (in press): 227–33. doi:10.1016/j.neuint.2015.07.017. PMID 26212523.