Resveratrolのソースを表示

{{Short description|Polyphenol with a stilbene skeleton}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{chembox
| Watchedfields = changed
| verifiedrevid = 477172311
| Name = Resveratrol
| ImageFile = resveratrol.svg
| ImageSize = 250px
| ImageClass = skin-invert
| ImageName = Chemical 9–69 structure of ''trans''-resveratrol
| ImageFile1 = Resveratrol3d.png
| ImageSize1 = 180px
| ImageName1 = Chemical structure of ''trans''-resveratrol
| ImageFile2 = Cis_and_trans_resveratrol_notext.svg
| ImageSize2 = 250px
| ImageClass2 = skin-invert
| ImageName2 = Chemical structures of ''cis-'' and ''trans''-resveratrols
| ImageCaption2 = Chemical structures of ''cis-'' ((''Z'')-resveratrol, left) and ''trans''-resveratrol ((''E'')-resveratrol, right)<ref name=Camont>{{cite journal | vauthors = Camont L, Cottart CH, Rhayem Y, Nivet-Antoine V, Djelidi R, Collin F, Beaudeux JL, Bonnefont-Rousselot D | title = Simple spectrophotometric assessment of the trans-/cis-resveratrol ratio in aqueous solutions | journal = Analytica Chimica Acta | volume = 634 | issue = 1 | pages = 121–128 | date = February 2009 | pmid = 19154820 | doi = 10.1016/j.aca.2008.12.003 | bibcode = 2009AcAC..634..121C }}</ref>
| PIN = 5-[(''E'')-2-(4-Hydroxyphenyl)ethen-1-yl]benzene-1,3-diol
| OtherNames = ''trans''-3,5,4′-Trihydroxystilbene;<br />3,4′,5-Stilbenetriol;<br />''trans''-Resveratrol;<br />(''E'')-5-(''p''-Hydroxystyryl)resorcinol;<br />(''E'')-5-(4-hydroxystyryl)benzene-1,3-diol
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 501-36-0
| PubChem = 445154
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 392875
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 165
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB02709
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = Q369O8926L
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 45713
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C03582
| RTECS = CZ8987000
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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+
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LUKBXSAWLPMMSZ-OWOJBTEDSA-N
| SMILES = Oc1ccc(cc1)\C=C\c2cc(O)cc(O)c2
| InChI =1/C14H12O3/c15-<br />12-5-3-10(4-6-12)<br />1-2-11-7-13(16)9-<br />14(17)8-11/h1-9,15-<br />17H/b2-1+
 }}
|Section2={{Chembox Properties
| C=14 | H=12 | O=3
| Appearance = white powder with<br /> slight yellow cast
| MeltingPtC = 261 to 263
| MeltingPt_ref = <ref name=FisherScientificMSDS>{{Cite web |url=http://www.fishersci.com/ecomm/servlet/msdsproxy?productName=AC430075000&productDescription=RESVERATROL+99%25+500MG&catNo=AC43007-5000&vendorId=VN00032119&s |title=Resveratrol MSDS on Fisher Scientific website |access-date=2012-03-06 |archive-date=2012-11-03 |archive-url=https://web.archive.org/web/20121103030802/http://www.fishersci.com/ecomm/servlet/msdsproxy?productName=AC430075000&productDescription=RESVERATROL+99%25+500MG&catNo=AC43007-5000&vendorId=VN00032119&s |url-status=dead }}</ref>
| Solubility1 = 0.03 g/L
| Solvent1 = water
| Solubility2 = 16 g/L
| Solvent2 = Dimethyl sulfoxide{{!}}DMSO
| Solubility3 = 50 g/L
| Solvent3 = ethanol
| LambdaMax = 304nm (trans-resveratrol, in water)<br />286nm (cis-resveratrol, in water)<ref name=Camont/>
 }}
|Section7={{Chembox Hazards
| ExternalSDS = Fisher Scientific<ref name=FisherScientificMSDS/><br />Sigma Aldrich<ref name=SigmaAldrichMSDS>[http://www.sigmaaldrich.com/catalog/DisplayMSDSContent.do Resveratrol MSDS on www.sigmaaldrich.com]</ref>
| MainHazards =
| NFPA-H =
| NFPA-F =
| NFPA-R =
| NFPA-S =
| GHSPictograms = {{GHS07}}
| GHSSignalWord = warning
| HPhrases      = {{HPhrases|H319}}
| PPhrases      = {{PPhrases|P264 | P280 | P305 + P351 + P338 | P337 + P313}}
| GHS_ref       = <ref>GHS: [https://www.sigmaaldrich.com/product/SIGMA/R5010 Sigma-Aldrich R5010]</ref>
| FlashPt =
| AutoignitionPt =
| ExploLimits =
| LD50 = 23.2 μM (5.29 g)<ref name="pmid19207580">{{cite journal | vauthors = Bechmann LP, Zahn D, Gieseler RK, Fingas CD, Marquitan G, Jochum C, Gerken G, Friedman SL, Canbay A | title = Resveratrol amplifies profibrogenic effects of free fatty acids on human hepatic stellate cells | journal = Hepatology Research | volume = 39 | issue = 6 | pages = 601–608 | date = June 2009 | pmid = 19207580 | pmc = 2893585 | doi = 10.1111/j.1872-034X.2008.00485.x }}</ref>
| PEL =
 }}
}}

'''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 [[pathogen]]s, such as [[bacterium|bacteria]] or [[fungus|fungi]].<ref name="lpi">{{cite web | title=Resveratrol | publisher = Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis, OR |date=11 June 2015 | url = http://lpi.oregonstate.edu/infocenter/phytochemicals/resveratrol/ |access-date=26 August 2019}}</ref><ref>{{cite journal | vauthors = Frémont L | title = Biological effects of resveratrol | journal = Life Sciences | volume = 66 | issue = 8 | pages = 663–673 | date = January 2000 | pmid = 10680575 | doi = 10.1016/S0024-3205(99)00410-5 }}</ref> Sources of resveratrol in food include the skin of [[grape]]s, [[blueberries]], [[raspberries]], [[mulberries]], and [[peanut]]s.<ref name="Jansiski2013">{{cite journal | vauthors = Jasiński M, Jasińska L, Ogrodowczyk M | title = Resveratrol in prostate diseases - a short review | journal = Central European Journal of Urology | volume = 66 | issue = 2 | pages = 144–149 | date = August 2013 | pmid = 24579014 | pmc = 3936154 | doi = 10.5173/ceju.2013.02.art8 }}</ref><ref name="pe" />

Although commonly used as a [[dietary supplement]] and studied in laboratory models of human diseases,<ref name="MLP">{{cite web |title=Resveratrol |url=https://medlineplus.gov/druginfo/natural/307.html |publisher=MedlinePlus |access-date=22 September 2019 |date=1 April 2019}}</ref> there is no [[evidence-based medicine|high-quality evidence]] that resveratrol improves [[longevity|lifespan]] or has a substantial effect on any human disease.<ref name=pmid21698226/><ref name="pmid25885871">{{cite journal | vauthors = Sahebkar A, Serban C, Ursoniu S, Wong ND, Muntner P, Graham IM, Mikhailidis DP, Rizzo M, Rysz J, Sperling LS, Lip GY, Banach M | title = 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 | journal = International Journal of Cardiology | volume = 189 | pages = 47–55 | year = 2015 | pmid = 25885871 | doi = 10.1016/j.ijcard.2015.04.008 }}</ref>
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