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Revision as of 12:35, 12 November 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: StdInChI StdInChIKey.← Previous edit		Latest revision as of 19:55, 20 December 2023 edit undoJWBE (talk | contribs)Extended confirmed users10,126 edits removed Category:Vinylogous carboxylic acids using HotCat
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	{{Orphan|date=September 2009}}
	{{chembox		{{chembox
			| Verifiedfields = changed
			| Watchedfields = changed
			| verifiedrevid = 396306810
	| ImageFile = Caftaric acid.svg		| ImageFile = Caftaric acid.svg
	| ImageSize = 250		| ImageSize = 250
	| IUPACName = (2''R'',3''R'')-2-oxy-3-hydroxybutanedioic acid		| PIN = (2''R'',3''R'')-2-{oxy}-3-hydroxybutanedioic acid
	| OtherNames = Monocaffeyltartaric acid<br>Butanedioic acid, 2-(3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)-3-hydroxy-, (R-(R*,R*-(E)))-		| OtherNames = Monocaffeyltartaric acid<br>Butanedioic acid, 2-(3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)-3-hydroxy-, (R-(R*,R*-(E)))-<br>''trans''-Caftaric acid<br>''cis''-Caftaric acid<br>''trans''-Caffeoyl tartaric acid<br>''cis''-Caffeoyl tartaric acid
			| Reference =
	| Reference = <ref>, ].</ref>
		⚫	|Section1={{Chembox Identifiers
	|-
		⚫	| PubChem = 6440397
⚫	| Section1 = {{Chembox Identifiers
		⚫	| InChIKey = SWGKAHCIOQPKFW-JTNORFRNBW
⚫	| PubChem = 6440397
			| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫	| InChIKey = SWGKAHCIOQPKFW-JTNORFRNBW
	| StdInChIKey = SWGKAHCIOQPKFW-JTNORFRNSA-N		| StdInChIKey = SWGKAHCIOQPKFW-JTNORFRNSA-N
			| InChIKey1 = SWGKAHCIOQPKFW-JTNORFRNSA-N
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 4944664		| ChemSpiderID = 4944664
			| ChEMBL_Ref = {{ebicite|changed|EBI}}
⚫	| MeSHName = caftaric+acid
			| ChEMBL = 558557
⚫	| Canonical InChI = 1/C13H12O9/c14-7-3-1-6(5-8(7)15)2-4-9(16)22-11(13(20)21)10(17)12(18)19/h1-5,10-11,14-15,17H,(H,18,19)(H,20,21)/b4-2+/t10-,11-/m1/s1
			| CASNo_Ref = {{cascite|correct|CAS}}
			| CASNo = 67879-58-7
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = WCV7W3174L
		⚫	| MeSHName = caftaric+acid
		⚫	| InChI = 1S/C13H12O9/c14-7-3-1-6(5-8(7)15)2-4-9(16)22-11(13(20)21)10(17)12(18)19/h1-5,10-11,14-15,17H,(H,18,19)(H,20,21)/b4-2+/t10-,11-/m1/s1
			| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C13H12O9/c14-7-3-1-6(5-8(7)15)2-4-9(16)22-11(13(20)21)10(17)12(18)19/h1-5,10-11,14-15,17H,(H,18,19)(H,20,21)/b4-2+/t10-,11-/m1/s1		| StdInChI = 1S/C13H12O9/c14-7-3-1-6(5-8(7)15)2-4-9(16)22-11(13(20)21)10(17)12(18)19/h1-5,10-11,14-15,17H,(H,18,19)(H,20,21)/b4-2+/t10-,11-/m1/s1
	| SMILES = O=C(O)(O)(OC(=O)\C=C\c1cc(O)c(O)cc1)C(=O)O		| SMILES = O=C(O)(O)(OC(=O)\C=C\c1cc(O)c(O)cc1)C(=O)O
	| Isometric SMILES = C1=CC(=C(C=C1/C=C/C(=O)O((C(=O)O)O)C(=O)O)O)O		| SMILES1 = C1=CC(=C(C=C1/C=C/C(=O)O((C(=O)O)O)C(=O)O)O)O
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
			| C=13 | H=12 | O=9
	| Formula = C<sub>13</sub>H<sub>12</sub>O<sub>9</sub><small> (Basic formula)
			| BoilingPt =
	| MolarMass = 312.22898 g/mol
		⚫	| Solubility =
	| ExactMass = 312.048132
	| Complexity = 458
	| Heavy Atom Count = 22
	| BoilingPt = 618.2 °C at 760 mmHg
⚫	| Solubility =
	}}</small>
	| Section3 = {{Chembox Hazards
	| MainHazards =
⚫	| FlashPt = 236.3 °C
	| Autoignition =
	}}		}}
	| Section4 = {{Chembox Related		|Section3={{Chembox Hazards
	| OtherAnions =		| MainHazards =
		⚫	| FlashPt =
	| Function =
	| OtherFunctn =		| AutoignitionPt =
			}}
	| OtherCpds =
			|Section4={{Chembox Related
			| OtherAnions =
			| OtherFunction_label =
			| OtherFunction =
			| OtherCompounds =
	}}		}}
	}}		}}
	'''Caftaric acid''' is a non-] that impacts the color of ]. Many believe{{Who|date=June 2010}} this ] is responsible for the yellowish-gold color seen in some whites wines{{Citation needed|date=June 2010}}.
			'''Caftaric acid''' is a non-flavonoid phenolic compound.
	Caftaric acid and ] are in a class of chemicals known as ]. Caftaric acid is formed when caffeic acid and ] undergo ]. But during ], caftaric acid is oxidized into its principle components.
			It is found in the juice of grapes<ref>{{cite journal |author1=C. Y. Lee |author2=A. Jaworski |year=1987 |title=Phenolic Compounds in White Grapes Grown in New York |journal=Am. J. Enol. Vitic. |volume=38 |issue=4 |pages=277–281 |doi=10.5344/ajev.1987.38.4.277 |s2cid=102310452 |url=http://ajevonline.org/content/38/4/277.short}}</ref><ref name="Understanding Wine Chemistry">{{cite book |last1=Waterhouse |first1=Andrew |last2=Sacks |first2=Gavin |last3=Jeffery |first3=David |title=Understanding Wine Chemistry |date=June 17, 2016 |publisher=Wiley Books |location=Adelaide |isbn=978-1-118-73072-0 |pages=112–113 |chapter=Chapter 13: Non‐flavonoid Phenolics}}</ref> (''Vitis vinifera'') and impacts the color of ].
⚫	==In wine==
⚫	] measure caftaric acid levels as their primary method to estimate the ] levels that a wine has undergone. For example, ], which undergo a high degree of oxidation{{Citation needed|date=December 2009}}, will have little to no caftaric acid.
			It is an esterified phenolic acid, composed of ], a ] produced by plants, and ], the principal organic acid found in grape berries. As such, caftaric acid is found in all grape juices and wines.<ref name="Understanding Wine Chemistry" /> During ] and ], the ester can be enzymatically hydrolysed, releasing the two constituents. Caffeic acid is susceptible to chemical oxidation, and subsequent redox reactions involving caffeic acid can contribute to wine ] over time, and the straw-gold color that can develop in some white wines after bottling.<ref name="Understanding Wine Chemistry" />
⚫	==References==
			Aside from wine, it is abundantly present in ]. It also occurs in ''Cichorium intybus'' (common ]) and is one of the bioactive components of '']'' (Eastern purple coneflower).<ref name=Vanzo>{{Cite journal |pmid=17300159| year=2007| last1=Vanzo |first1=A| last2=Cecotti |first2=R |last3=Vrhovsek |first3=U|last4=Torres |first4=AM|last5=Mattivi|first5=F| last6=Passamonti |first6=S |title=The fate of trans-caftaric acid administered into the rat stomach| volume=55 |issue=4| pages=1604–11| doi=10.1021/jf0626819|journal=Journal of Agricultural and Food Chemistry}}</ref>
			Caftaric acid has a good bioavailability when fed in rats. Intact trans-caftaric acid was detected in rat plasma along with its O-methylated derivative trans-].<ref name=Vanzo/>
		⚫	== In wine ==
		⚫	]s measure caftaric acid levels as their primary method to estimate the ] levels that a wine has undergone. For example, ], which undergo a high degree of oxidation{{Citation needed|date=December 2009}}, will have little to no caftaric acid.
			] (2-S glutathionyl caftaric acid) is an oxidation compound produced from caftaric acid and found in wine. ] alone is not oxidized in the presence of grape ] (PPO), whereas it is degraded in the presence of a crude grape PPO extract and of caftaric acid, forming ]s.<ref>{{Cite journal |last1=Sarni-Manchado |first1=Pascale |last2=Cheynier |first2=Véronique |last3=Moutounet |first3=Michel |date=August 1997 |year=1997 |title=Reactions of polyphenoloxidase generated caftaric acid o-quinone with malvidin 3-O-glucoside |url=https://linkinghub.elsevier.com/retrieve/pii/S0031942297001908 |journal=Phytochemistry |language=en |volume=45 |issue=7 |pages=1365–1369 |doi=10.1016/S0031-9422(97)00190-8}}</ref>
			== See also ==
			* ] (dicaffeoyltartaric acid)
		⚫	== References ==
	{{Reflist}}		{{Reflist}}
			{{Hydroxycinnamic acid}}
⚫	]
			]
		⚫	]