Malvidin
Chemical compound
From Wikipedia, the free encyclopedia
Malvidin is an O-methylated anthocyanidin, the 3',5'-methoxy derivative of delphinidin. As a primary plant pigment, its glycosides are highly abundant in nature.
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| IUPAC name
3,4′,5,7-Tetrahydroxy-3′,5′-dimethoxyflavylium | |
| Systematic IUPAC name
3,5,7-Trihydroxy-2-(4-hydroxy-3,5-dimethoxy)-1λ4-benzopyran-1-ylium | |
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| Properties | |
| C17H15O7+ | |
| Molar mass | 331.2968 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Natural occurrences
Malvidin is responsible for the blue color found in petals of the Primula plants of the polyanthus group. Blue flowers of the blue pimpernel (Anagallis monelli) have also a higher concentration of malvidin.
It is responsible primarily for the color of red wine, Vitis vinifera being one of its sources.[1] It is also present in other berries, such as blueberries (Vaccinium corymbosum) or the saskatoon berries (Amelanchier alnifolia).[2][3]
Chemistry
Slightly acidic and neutral solutions of malvidin are characteristically of a red color, while basic solutions of malvidin yield a blue color.
The breakdown of malvidin releases syringic acid.
Use as a marker in archaeology
The breakdown of malvidin releases syringic acid as revealed in the examination of jars containing shedeh, a drink of Ancient Egypt. Malvidin is also present in the site of the Areni-1 winery, 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 Armenia.
Glycosides
- Malvin is a malvidin diglucoside.
- Oenin is the malvidin-3-glucoside.
- Primulin is the 3-O-galactoside of malvidin.
- Malvidin 3-rutinoside is a pigment responsible for bract color in Curcuma alismatifolia (the Siam tulip).[4] Acylated malvidin 3-rutinosides are responsible for the violet color of Petunia integrifolia subsp. inflata.[5]
- Malvidin-3-O-glucoside-5-O-(6-acetylglucoside) is a pigment responsible for the blue color in 'Johnson's Blue' and other 'blue' geraniums[6]