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Revision as of 04:41, 17 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 477272822 of page Ellagic_acid for the Chem/Drugbox validation project (updated: '').		Latest revision as of 01:44, 10 December 2024 edit Citation bot (talk | contribs)Bots5,429,149 edits Added bibcode. | Use this bot. Report bugs. | Suggested by Dominic3203 | Linked from User:Marbletan/sandbox | #UCB_webform_linked 907/2664
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			{{Short description|Natural phenol antioxidant}}
	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
			{{Use mdy dates|date=September 2022}}
	{{chembox		{{chembox
			| Watchedfields = changed
	| verifiedrevid = 443720904
			| verifiedrevid = 477313805
	| Name = Ellagic acid
	| ImageFile = Ellagic acid.svg		| Name = Ellagic acid
			| ImageFile = Ellagic acid.svg
			| ImageSize = 220
	| ImageName = Ellagic acid
			| ImageAlt = Skeletal formula of ellagic acid
	| IUPACName = 2,3,7,8-Tetrahydroxy-chromenochromene-5,10-dione
			| ImageFile1 = Ellagic acid 3D spacefill.png
	| OtherNames = 4,4′,5,5′,6,6′-] 2,6,2′,6′-dilactone
			| ImageAlt1 = Space-filling model of the ellagic acid molecule
	| Section1 = {{Chembox Identifiers
			| PIN = 2,3,7,8-Tetrahydroxybenzopyranobenzopyran-5,10-dione
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| OtherNames = 4,4′,5,5′,6,6′-] 2,6,2′,6′-dilactone
			|Section1={{Chembox Identifiers
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 4445149		| ChemSpiderID = 4445149
	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
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	| StdInChIKey = AFSDNFLWKVMVRB-UHFFFAOYSA-N		| StdInChIKey = AFSDNFLWKVMVRB-UHFFFAOYSA-N
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 476-66-4		| CASNo = 476-66-4
	| PubChem = 5281855		| PubChem = 5281855
	| DrugBank_Ref = {{drugbankcite|correct|drugbank}}		| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
	| DrugBank = DB08468		| DrugBank = DB08468
	| ChEBI_Ref = {{ebicite|correct|EBI}}		| ChEBI_Ref = {{ebicite|correct|EBI}}
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	| SMILES = O=C1Oc3c2c4c1cc(O)c(O)c4OC(=O)c2cc(O)c3O		| SMILES = O=C1Oc3c2c4c1cc(O)c(O)c4OC(=O)c2cc(O)c3O
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| Formula = C<sub>14</sub>H<sub>6</sub>O<sub>8</sub>		| Formula = C<sub>14</sub>H<sub>6</sub>O<sub>8</sub>
	| MolarMass = 302.197 g/mol		| MolarMass = 302.197 g/mol
			| Density = 1.67 g/cm<sup>3</sup>
	| ExactMass = 302.006267
			| MeltingPtC =
	| Density = 1.67 g/cm³
			| MeltingPt_notes = >360 °C
	| MeltingPt =
	| BoilingPt =		| BoilingPt =
	}}		}}
	}}		}}
			]
			'''Ellagic acid''' is a ] found in numerous fruits and vegetables. It is the ] of ].
			==Name==
			The name comes from the French term ''acide ]'', from the word ''galle'' spelled backward<ref>{{Cite web |url=http://artflx.uchicago.edu/cgi-bin/dicos/pubdico1look.pl?strippedhw=ellagique&dicoid=LITTRE1872 |title=ellagique |last=Littré |first=Émile |website=Dictionnaire de la langue française}}</ref> because it can be obtained from ''noix de galle'' (]s), and to distinguish it from ''acide gallique'' (]). The molecule structure resembles to that of two gallic acid molecules being assembled "head to tail" and bound together by a C–C bond (as in ], or in ]) and two ] links (cyclic ]s).
			== Metabolism ==
			=== Biosynthesis ===
			Plants produce ellagic acid from hydrolysis of ] such as ] and ].<ref name="Seigler1998">{{Cite book |last=Seigler |first=David S. |url=https://books.google.com/books?id=hmYbjbGU-EgC |title=Plant Secondary Metabolism |date=December 31, 1998 |publisher=Springer Science & Business Media |isbn=978-0-412-01981-4 |page=208}}</ref>
			=== Biodegradation ===
			]s are ] human metabolites of dietary ellagic acid derivatives.<ref>{{Cite journal |last1=Larrosa |first1=M. |last2=González Sarrías |first2=A. |last3=García Conesa |first3=M. T. |last4=Tomás Barberán |first4=F. A. |last5=Espín |first5=J. C. |year=2006 |title=Urolithins, ellagic acid-derived metabolites produced by human colonic microflora, exhibit estrogenic and antiestrogenic activities |journal=Journal of Agricultural and Food Chemistry |volume=54 |issue=5 |pages=1611–1620 |doi=10.1021/jf0527403 |pmid=16506809|bibcode=2006JAFC...54.1611L }}</ref><ref name="pmid30614249">{{cite journal | vauthors=Luca SV, Macovei I, Bujor A, Trifan A | title=Bioactivity of dietary polyphenols: The role of metabolites | journal=] | volume=60 | issue=4 | pages=626–659 | year=2020 | doi = 10.1080/10408398.2018.1546669 | pmid=30614249| s2cid=58651581 }}</ref> Ellagic acid has low bioavailability, with 90% remaining unabsorbed from the intestines until metabolized by microflora to the more bioavailable urolithins.<ref name="pmid30614249" />
			== History ==
			Ellagic acid was first discovered by chemist ] in 1831.<ref name="Grasser">{{Cite book |last1=Grasser |first1=Georg |url=https://archive.org/details/synthetictannins032496mbp |title=Synthetic Tannins |last2=Enna |first2=F. G. A. |date=1922 |isbn=9781406773019 |page=|publisher=Read Books }}</ref> ] prepared this substance from ], ], oak bark, ], ], and ] in 1905.<ref name=Grasser/> He also suggested its formation from galloyl-glycine by '']'' in 1915.<ref>{{Cite journal |last=Nierenstein |first=M. |year=1915 |title=The Formation of Ellagic Acid from Galloyl-Glycine by ''Penicillium'' |journal=The Biochemical Journal |volume=9 |issue=2 |pages=240–244 |doi=10.1042/bj0090240 |pmc=1258574 |pmid=16742368}}</ref> ] was the first person to synthesize ellagic acid by heating ] with ] or silver oxide.<ref name=Grasser/><ref>{{Cite journal |last=Löwe |first=Julius |date=1868 |title=Über die Bildung von Ellagsäure aus Gallussäure |trans-title=On the synthesis of ellagic acid from gallic acid |journal=Zeitschrift für Chemie |volume=4 |page=603}}</ref>
			== Natural occurrences ==
			Ellagic acid is found in edible nuts.<ref>{{cite journal |doi=10.1021/acs.jafc.9b07160 |title=Phenolic Compounds from Nuts: Extraction, Chemical Profiles, and Bioactivity |date=2020 |last1=Bodoira |first1=Romina |last2=Maestri |first2=Damián |journal=Journal of Agricultural and Food Chemistry |volume=68 |issue=4 |pages=927–942 |pmid=31910006 |bibcode=2020JAFC...68..927B }}</ref> It is also found in oak species such as the North American white oak ('']'') and European red oak ('']'').<ref>{{Cite journal |last1=Mämmelä |first1=P. |last2=Savolainen |first2=H. |last3=Lindroos |first3=L. |last4=Kangas |first4=J. |last5=Vartiainen |first5=T. |year=2000 |title=Analysis of oak tannins by liquid chromatography-electrospray ionisation mass spectrometry |journal=Journal of Chromatography A |volume=891 |issue=1 |pages=75–83 |doi=10.1016/S0021-9673(00)00624-5 |pmid=10999626}}</ref>
			The macrophyte '']'' produces ellagic acid.<ref name="Nakai">{{Cite journal |last=Nakai |first=S. |year=2000 |title=Myriophyllum spicatum-released allelopathic polyphenols inhibiting growth of blue-green algae ''Microcystis aeruginosa'' |journal=Water Research |volume=34 |issue=11 |pages=3026–3032 |doi=10.1016/S0043-1354(00)00039-7|bibcode=2000WatRe..34.3026N }}</ref>
			Ellagic acid can be found in the ] '']''.<ref name="pmid18827365">{{Cite journal |last1=Lee |first1=Y.-S. |last2=Kang |first2=Y.-H. |last3=Jung |first3=J.-Y. |last4=Lee |first4=S. |last5=Ohuchi |first5=K. |last6=Shin |first6=K.-H. |last7=Kang |first7=I.-J. |last8=Park |first8=J.-H. |last9=Shin |first9=H.-K. |last10=Lim |first10=S.-S. |year=2008 |title=Protein glycation inhibitors from the fruiting body of ''Phellinus linteus'' |journal=Biological and Pharmaceutical Bulletin |volume=31 |issue=10 |pages=1968–1972 |doi=10.1248/bpb.31.1968 |pmid=18827365 |doi-access=free}}</ref>
			=== In food ===
			The highest levels of ellagic acid are found in raw ], ]s, ]s, ], ], ], and grapes, as well as ]s.<ref name="vattem">{{Cite journal |last1=Vattem |first1=D. A. |last2=Shetty |first2=K. |year=2005 |title=Biological Function of Ellagic Acid: A Review |journal=Journal of Food Biochemistry |volume=29 |issue=3 |pages=234–266 |doi=10.1111/j.1745-4514.2005.00031.x}}</ref> It is also found in ]es<ref>{{Cite journal |last1=Infante |first1=R. |last2=Contador |first2=L. |last3=Rubio |first3=P. |last4=Aros |first4=D. |last5=Peña Neira |first5=Á. |date=2011 |title=Postharvest sensory and phenolic characterization of 'Elegant Lady' and 'Carson' peaches |url=http://www.scielo.cl/pdf/chiljar/v71n3/at16.pdf |journal=Chilean Journal of Agricultural Research |volume=71 |issue=3 |pages=445–451 |doi=10.4067/S0718-58392011000300016|doi-access=free }}</ref> and ].<ref>{{Cite journal |last1=Usta |first1=C. |last2=Özdemir |first2=S. |last3=Schiariti |first3=M. |last4=Puddu |first4=P. E. |date=November 2013 |title=The pharmacological use of ellagic acid-rich pomegranate fruit |journal=International Journal of Food Sciences and Nutrition |volume=64 |issue=7 |pages=907–913 |doi=10.3109/09637486.2013.798268 |pmid=23700985|s2cid=10798834 }}</ref>
			{| class="wikitable"
			!Dietary source
			!Ellagic acid<ref>{{Cite journal |last=Landete |first=J.M. |year=2011 |title=Ellagitannins, ellagic acid and their derived metabolites: A review about source, metabolism, functions and health |journal=Food Research International |volume=44 |issue=5 |pages=1150–1160 |doi=10.1016/j.foodres.2011.04.027}}</ref>
			|-
			|-
			!colspan="2" |Fruits (mg/100g fresh weight)
			|-
			|]
			|150
			|-
			|]
			|90
			|-
			|]
			|70
			|-
			|]
			|315.1
			|-
			|Pomegranate
			|269.9<ref name=":20">{{Cite journal |last1=García-Villalba |first1=Rocío |last2=Espín |first2=Juan Carlos |last3=Tomás-Barberán |first3=Francisco A. |year=2016 |title=Chromatographic and spectroscopic characterization of urolithins for their determination in biological samples after the intake of foods containing ellagitannins and ellagic acid |journal=Journal of Chromatography A |volume=1428 |pages=162–175 |doi=10.1016/j.chroma.2015.08.044 |pmid=26341594}}</ref>
			|-
			|Raspberries
			|270
			|-
			|]
			|109.6
			|-
			|Strawberries
			|77.6
			|-
			|Strawberry jam
			|24.5
			|-
			|Yellow raspberries
			|1900
			|-
			|-
			!colspan="2" |Nuts (mg/100g fresh weight)
			|-
			|Pecans
			|33
			|-
			|Walnuts
			|59
			|-
			|-
			!colspan="2" |Beverages (mg/L)
			|-
			|Pomegranate juice
			|811.1<ref name=":20" />
			|-
			|]
			|31–55
			|-
			|]
			|33
			|-
			|]
			|1.2
			|-
			|-
			!colspan="2" |Seeds (mg/g)
			|-
			|Black raspberries
			|6.7
			|-
			|Red raspberries
			|8.7
			|-
			|Boysenberries
			|30
			|-
			|]
			|1.2
			|}
			== Research and health claims ==
			Ellagic acid has been marketed as a ] with various claimed benefits against cancer, heart disease, and other diseases. In the 21st century, numerous U.S.-based supplement companies received ]s for promoting ellagic acid with false ] that violate the ].<ref name="vita">{{cite web |author1=Miriam R. Burbach |title=Warning letter:VitaPurity Corporation |url=https://www.fda.gov/inspections-compliance-enforcement-and-criminal-investigations/warning-letters/vitapurity-corporation-514472-05122017 |publisher=US Food and Drug Administration |access-date=December 2, 2021 |date=May 12, 2017}}</ref><ref name="fda">{{Cite web |url=https://www.fda.gov/Drugs/GuidanceComplianceRegulatoryInformation/EnforcementActivitiesbyFDA/ucm171057.htm |title=187 Fake Cancer 'Cures' Consumers Should Avoid |publisher=U.S. ] |archive-url=https://web.archive.org/web/20170502034227/https://www.fda.gov/drugs/guidancecomplianceregulatoryinformation/enforcementactivitiesbyfda/ucm171057.htm |archive-date=May 2, 2017 |access-date=June 17, 2008}}</ref><ref>{{Cite news|last=|first=|date=June 17, 2008|title=FDA Cracks Down On Unproved Cancer Cures|work=CBS News|url=https://www.cbsnews.com/news/fda-cracks-down-on-unproved-cancer-cures/|url-status=live|access-date=February 16, 2021|archive-url=https://web.archive.org/web/20180629181344/https://www.cbsnews.com/news/fda-cracks-down-on-unproved-cancer-cures/|archive-date=June 29, 2018}}</ref> Ellagic acid has been identified by the FDA as a "fake cancer 'cure'".<ref name="fda"/> There is no ] to support the claims that ellagic acid can treat or prevent cancer.<ref name=fda/>
			==See also==
			*]
			== References ==
			{{reflist}}
			{{Ellagitannins}}
			{{Xenobiotic-sensing receptor modulators}}
			{{Unproven and disproven cancer treatments}}
			]
			]
			]
			]
			]
			]
			]
			]
			]
			]