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 Chemical structures of cis- ((Z)-resveratrol, left) and trans-resveratrol ((E)-resveratrol, right)[1]
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| Names | |
|---|---|
| Preferred IUPAC name
5-[(E)-2-(4-Hydroxyphenyl)ethen-1-yl]benzene-1,3-diol | |
| Other names
trans-3,5,4′-Trihydroxystilbene;
3,4′,5-Stilbenetriol; trans-Resveratrol; (E)-5-(p-Hydroxystyryl)resorcinol; (E)-5-(4-hydroxystyryl)benzene-1,3-diol | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.121.386 |
| KEGG | |
PubChem CID
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| RTECS number |
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C14H12O3 | |
| Molar mass | 228.247 g·mol−1 |
| Appearance | white powder with slight yellow cast |
| Melting point | 261 to 263 °C (502 to 505 °F; 534 to 536 K)[2] |
| Solubility in water | 0.03 g/L |
| Solubility in DMSO | 16 g/L |
| Solubility in ethanol | 50 g/L |
| UV-vis (λmax) | 304nm (trans-resveratrol, in water) 286nm (cis-resveratrol, in water)[1] |
| Hazards | |
| GHS labelling:[5] | |
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| Warning | |
| H319 | |
| P264, P280, P305+P351+P338, P337+P313 | |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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23.2 μM (5.29 g)[4] |
| Safety data sheet (SDS) | Fisher Scientific[2] Sigma Aldrich[3] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Resveratrol (3,5,4′-trihydroxy-trans-stilbene) is a stilbenoid, a type of natural phenol or polyphenol and a phytoalexin produced by several plants in response to injury or when the plant is under attack by pathogens, such as bacteria or fungi.[6][7] Sources of resveratrol in food include the skin of grapes, blueberries, raspberries, mulberries, and peanuts.[8][9]
Although commonly used as a dietary supplement and studied in laboratory models of human diseases,[10] there is no high-quality evidence that resveratrol improves lifespan or has a substantial effect on any human disease.[11][12]
- ^ a b Camont L, Cottart CH, Rhayem Y, Nivet-Antoine V, Djelidi R, Collin F, et al. (February 2009). "Simple spectrophotometric assessment of the trans-/cis-resveratrol ratio in aqueous solutions". Analytica Chimica Acta. 634 (1): 121–128. Bibcode:2009AcAC..634..121C. doi:10.1016/j.aca.2008.12.003. PMID 19154820.
- ^ a b "Resveratrol MSDS on Fisher Scientific website". Archived from the original on 2012-11-03. Retrieved 2012-03-06.
- ^ Resveratrol MSDS on www.sigmaaldrich.com
- ^ Bechmann LP, Zahn D, Gieseler RK, Fingas CD, Marquitan G, Jochum C, et al. (June 2009). "Resveratrol amplifies profibrogenic effects of free fatty acids on human hepatic stellate cells". Hepatology Research. 39 (6): 601–608. doi:10.1111/j.1872-034X.2008.00485.x. PMC 2893585. PMID 19207580.
- ^ GHS: Sigma-Aldrich R5010
- ^ "Resveratrol". Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis, OR. 11 June 2015. Retrieved 26 August 2019.
- ^ Frémont L (January 2000). "Biological effects of resveratrol". Life Sciences. 66 (8): 663–673. doi:10.1016/S0024-3205(99)00410-5. PMID 10680575.
- ^ Jasiński M, Jasińska L, Ogrodowczyk M (August 2013). "Resveratrol in prostate diseases - a short review". Central European Journal of Urology. 66 (2): 144–149. doi:10.5173/ceju.2013.02.art8. PMC 3936154. PMID 24579014.
- ^ Cite error: The named reference
pewas invoked but never defined (see the help page). - ^ "Resveratrol". MedlinePlus. 1 April 2019. Retrieved 22 September 2019.
- ^ Cite error: The named reference
pmid21698226was invoked but never defined (see the help page). - ^ Sahebkar A, Serban C, Ursoniu S, Wong ND, Muntner P, Graham IM, et al. (2015). "Lack of efficacy of resveratrol on C-reactive protein and selected cardiovascular risk factors--Results from a systematic review and meta-analysis of randomized controlled trials". International Journal of Cardiology. 189: 47–55. doi:10.1016/j.ijcard.2015.04.008. PMID 25885871.