| Revision as of 10:59, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 464319253 of page Malvidin for the Chem/Drugbox validation project (updated: 'CASNo'). |
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{{distinguish|Malvidine}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 440126448 |
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| ImageFile=malvidin.png |
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| verifiedrevid = 464371038 |
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| ImageFile=malvidin.svg |
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| ImageSize=250px |
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| ImageSize=250px |
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| IUPACName=3,5,7-trihydroxy-2-(4-hydroxy- 3,5-dimethoxyphenyl)chromenium |
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| IUPACName=3,4′,5,7-Tetrahydroxy-3′,5′-dimethoxyflavylium |
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| SystematicName=3,5,7-Trihydroxy-2-(4-hydroxy-3,5-dimethoxy)-1λ<sup>4</sup>-benzopyran-1-ylium |
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|Section1= {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 140095 |
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| ChemSpiderID = 140095 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 6674 |
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| ChEMBL2_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL2 = 592005 |
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| ChEMBL2 = 592005 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = KZMACGJDUUWFCH-UHFFFAOYSA-O |
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| StdInChIKey = KZMACGJDUUWFCH-UHFFFAOYSA-O |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 643-84-5 --> |
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| CASNo=643-84-5 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem=159287 |
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| UNII = GL5KGZ4D8U |
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| SMILES = O(c1cc(cc(OC)c1O)c3c2cc(O)cc(O)c2cc3O)C |
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| KEGG = C08716 |
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| PubChem=159287 |
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| SMILES = Oc1cc2c(O)cc(O)cc2c1c3cc(OC)c(O)c(OC)c3 |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>17</sub>H<sub>15</sub>O<sub>7</sub>+ |
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| Formula=C<sub>17</sub>H<sub>15</sub>O<sub>7</sub>+ |
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| MolarMass = 331.2968 g/mol |
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| MolarMass = 331.2968 g/mol |
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| ExactMass = 331.081778 |
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'''Malvidin''' is an ], the 3',5'-methoxy derivative of ]. As a primary ], its ]s are highly abundant in nature. |
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== Natural occurrences == |
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Malvidin is responsible for the blue color found in petals of the '']'' plants of the ''polyanthus'' group. Blue flowers of the blue pimpernel ('']'') have also a higher concentration of malvidin. |
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It is responsible primarily for the color of red wine, '']'' being one of its sources.<ref>{{cite web|url=http://www.phytochemicals.info/phytochemicals/malvidin.php|archive-url=https://web.archive.org/web/20100401100651/http://www.phytochemicals.info/phytochemicals/malvidin.php|url-status=usurped|archive-date=April 1, 2010|title=Phytochemicals: Malvidin|publisher=Top Cultures|accessdate=2009-05-20}}</ref> It is also present in other berries, such as blueberries ('']'') or the saskatoon berries ('']'').<ref name=mazza05>{{cite journal | last1 = Mazza | first1 = G |name-list-style=vanc | year = 2005 | title = Compositional and functional properties of saskatoon berry and blueberry | journal = International Journal of Fruit Science| volume = 5 | issue = 3| pages = 99–118 | doi = 10.1300/J492v05n03_10 | doi-access = free }}</ref><ref>{{cite journal |pmid=18066116 |year=2007 |author1=Bakowska-barczak |first2=M |first3=P |title=Survey of bioactive components in Western Canadian berries |volume=85 |issue=11 |pages=1139–52 |doi=10.1139/y07-102 |journal=Canadian Journal of Physiology and Pharmacology |last2=Marianchuk |last3=Kolodziejczyk}}</ref> |
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== Chemistry == |
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Slightly ] and ] solutions of malvidin are characteristically of a red color, while ] solutions of malvidin yield a blue color. |
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The breakdown of malvidin releases ]. |
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== Use as a marker in archaeology == |
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The breakdown of malvidin releases ] as revealed in the examination of jars containing ], a drink of Ancient Egypt. Malvidin is also present in the site of the ], a 6,100-year-old winery discovered in 2007 in the Areni-1 cave complex in the village of Areni in the Vayots Dzor province of ]. |
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== Glycosides == |
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* ] is a malvidin di]. |
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* ] is the malvidin-3-glucoside. |
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* ] is the 3-O-] of malvidin. |
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* ] is a pigment responsible for bract color in '']'' (the Siam tulip).<ref>{{Cite journal|pmid=10879491|year=2000|last1=Nakayama|first1=M|last2=Roh|first2=MS|last3=Uchida|first3=K|last4=Yamaguchi|first4=Y|last5=Takano|first5=K|last6=Koshioka|first6=M|title=Malvidin 3-rutinoside as the pigment responsible for bract color in Curcuma alismatifolia|volume=64|issue=5|pages=1093–5|journal=Bioscience, Biotechnology, and Biochemistry|doi=10.1271/bbb.64.1093|doi-access=free}}</ref> ]s are responsible for the violet color of '']''.<ref>{{Cite journal|doi=10.1016/S0031-9422(99)00095-3|title=Acylated malvidin 3-rutinosides in dusky violet flowers of Petunia integrifolia subsp. Inflata|year=1999|last1=Tatsuzawa|first1=F|journal=Phytochemistry|volume=52|issue=2|pages=351–355|bibcode=1999PChem..52..351T }}</ref> |
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* ] is a pigment responsible for the blue color in 'Johnson's Blue' and other 'blue' ]s<ref>{{Cite journal|doi=10.1016/S0031-9422(96)00831-X|title=Malvidin-3-O-glucoside-5-O-(6-acetylglucoside) and its colour manifestation in 'Johnson's Blue' and other 'Blue' geraniums|year=1997|last1=Markham|first1=Kenneth R.|last2=Mitchell|first2=Kevin A.|last3=Boase|first3=Murray R.|journal=Phytochemistry|volume=45|issue=2|pages=417–423|bibcode=1997PChem..45..417M }}</ref> |
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== See also == |
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* ] |
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* ] |
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== References == |
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{{Reflist}} |
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{{Anthocyanins}} |
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] |