Resveratrol

Resveratrol
Chemical 9–69 structure of trans-resveratrol
Chemical structure of trans-resveratrol
Chemical structures of cis- and trans-resveratrols
Chemical structures of cis- ((Z)-resveratrol, left) and trans-resveratrol ((E)-resveratrol, right)[1]
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)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.121.386 Edit this at Wikidata
KEGG
RTECS number
  • CZ8987000
UNII
  • InChI=1S/C14H12O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h1-9,15-17H/b2-1+ checkY
    Key: LUKBXSAWLPMMSZ-OWOJBTEDSA-N checkY
  • InChI=1/C14H12O3/c15-
    12-5-3-10(4-6-12)
    1-2-11-7-13(16)9-
    14(17)8-11/h1-9,15-
    17H/b2-1+
  • Oc1ccc(cc1)\C=C\c2cc(O)cc(O)c2
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]
GHS07: Exclamation mark
Warning
H319
P264, P280, P305+P351+P338, P337+P313
Lethal dose or concentration (LD, LC):
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).
checkY verify (what is checkY☒N ?)

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]

  1. ^ a b Camont, Laurent; Cottart, Charles-Henry; Rhayem, Yara; et al. (February 2009). "Simple spectrophotometric assessment of the trans-/cis-resveratrol ratio in aqueous solutions". Anal. Chim. Acta. 634 (1): 121–128. Bibcode:2009AcAC..634..121C. doi:10.1016/j.aca.2008.12.003. PMID 19154820.
  2. ^ a b "Resveratrol MSDS on Fisher Scientific website". Archived from the original on 2012-11-03. Retrieved 2012-03-06.
  3. ^ Resveratrol MSDS on www.sigmaaldrich.com
  4. ^ Bechmann LP, Zahn D, Gieseler RK, 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.
  5. ^ GHS: Sigma-Aldrich R5010
  6. ^ "Resveratrol". Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis, OR. 11 June 2015. Retrieved 26 August 2019.
  7. ^ Fremont, Lucie (January 2000). "Biological Effects of Resveratrol". Life Sciences. 66 (8): 663–673. doi:10.1016/S0024-3205(99)00410-5. PMID 10680575.
  8. ^ 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.
  9. ^ Cite error: The named reference pe was invoked but never defined (see the help page).
  10. ^ "Resveratrol". MedlinePlus. 1 April 2019. Retrieved 22 September 2019.
  11. ^ Cite error: The named reference pmid21698226 was invoked but never defined (see the help page).
  12. ^ Sahebkar A, Serban C, Ursoniu S, 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.