Resveratrol

Resveratrol
	Chemical structures of cis- ((Z)-resveratrol, left) and trans-resveratrol ((E)-resveratrol, right)
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
CAS Number	501-36-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:45713 ;
ChEMBL	ChEMBL165 ;
ChemSpider	392875 ;
DrugBank	DB02709 ;
ECHA InfoCard	100.121.386
KEGG	C03582 ;
PubChem CID	445154;
RTECS number	CZ8987000;
UNII	Q369O8926L ;
CompTox Dashboard (EPA)	DTXSID4031980 ;
	InChI 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+ Key: LUKBXSAWLPMMSZ-OWOJBTEDSA-N ; 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+;
	SMILES Oc1ccc(cc1)\C=C\c2cc(O)cc(O)c2;
Properties
Chemical formula	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)
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)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H319
Precautionary statements	P264, P280, P305+P351+P338, P337+P313
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	23.2 μM (5.29 g)
Safety data sheet (SDS)	Fisher Scientific; Sigma Aldrich
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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 pe was invoked but never defined (see the help page).
^ "Resveratrol". MedlinePlus. 1 April 2019. Retrieved 22 September 2019.
^ Cite error: The named reference pmid21698226 was 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.

[Camont-1] 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.

[FisherScientificMSDS-2] "Resveratrol MSDS on Fisher Scientific website". Archived from the original on 2012-11-03. Retrieved 2012-03-06.

[SigmaAldrichMSDS-3] Resveratrol MSDS on www.sigmaaldrich.com

[pmid19207580-4] 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.

[5] GHS: Sigma-Aldrich R5010

[lpi-6] "Resveratrol". Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis, OR. 11 June 2015. Retrieved 26 August 2019.

[7] Frémont L (January 2000). "Biological effects of resveratrol". Life Sciences. 66 (8): 663–673. doi:10.1016/S0024-3205(99)00410-5. PMID 10680575.

[Jansiski2013-8] 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.

[pe-9] Cite error: The named reference pe was invoked but never defined (see the help page).

[MLP-10] "Resveratrol". MedlinePlus. 1 April 2019. Retrieved 22 September 2019.

[pmid21698226-11] Cite error: The named reference pmid21698226 was invoked but never defined (see the help page).

[pmid25885871-12] 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.

[1]

[2]

[5]

[4]

[3]

[6]

[7]

[8]

[9]

[10]

[11]

[12]