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 | |
3D model (JSmol)
|
|
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.122.141 |
PubChem CID
|
|
| UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C16H16O3 | |
| Molar mass | 256.301 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Pterostilbene (/ˌtɛrəˈstɪlbiːn/) (trans-3,5-dimethoxy-4-hydroxystilbene) is a stilbenoid chemically related to resveratrol.[1] In plants, it serves a defensive phytoalexin role.[2]
Natural occurrence
Pterostilbene is found in almonds,[3] various Vaccinium berries (including blueberries[4][5][6]), grape leaves and vines,[2][7] and Pterocarpus marsupium heartwood.[5]
Research
Pterostilbene is being studied in laboratory and preliminary clinical research.[1] As of 2019[update], there are no published clinical studies on the safety or properties of pterostilbene when consumed by humans.[1]
Safety and regulation
Pterostilbene is considered to be a corrosive substance, is dangerous upon exposure to the eyes, and is an environmental toxin, especially to aquatic life.[1]
Its chemical relative, resveratrol, received FDA GRAS status in 2007,[8] and approval of synthetic resveratrol as a safe compound by the European Food Safety Authority (EFSA) in 2016.[9] Pterostilbene differs from resveratrol by exhibiting increased bioavailability (80% compared to 20% in resveratrol) due to the presence of two methoxy groups which cause it to exhibit increased lipophilic and oral absorption.[5]
See also
- Piceatannol, a stilbenoid related to both resveratrol and pterostilbene
References
- ^ a b c d "Pterostilbene, CID 5281727". PubChem, National Library of Medicine, US National Institutes of Health. 16 November 2019. Retrieved 18 November 2019.
- ^ a b Langcake, P.; Pryce, R. J. (1977). "A new class of phytoalexins from grapevines". Experientia. 33 (2): 151–2. doi:10.1007/BF02124034. PMID 844529.
- ^ 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.
- ^ "Pterostilbene's healthy potential". US Department of Agriculture, Online Magazine, Vol. 54, No. 11. 1 November 2006. Retrieved 2016-03-21.
- ^ a b c McCormack, Denise; McFadden, David (2013). "A review of pterostilbene antioxidant activity and disease modification". Oxidative Medicine and Cellular Longevity. 2013: 1–15. doi:10.1155/2013/575482. ISSN 1942-0900. PMC 3649683. PMID 23691264.
{{cite journal}}: CS1 maint: unflagged free DOI (link) - ^ 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.
- ^ 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. 2013 (7): 10587–600. doi:10.3390/molecules190710587. PMC 6271053. PMID 25050857.
{{cite journal}}: CS1 maint: unflagged free DOI (link) - ^ "GRAS Notice GRN 224: Resveratrol". US Food and Drug Administration, Food Ingredient and Packaging Inventories. 1 August 2007. Retrieved 7 February 2019.
- ^ "Safety of synthetic trans‐resveratrol as a novel food pursuant to Regulation (EC) No 258/97". EFSA Journal. 14 (1). European Food Safety Authority, EFSA Panel on Dietetic Products, Nutrition and Allergies: 4368. 12 January 2016. doi:10.2903/j.efsa.2016.4368.