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Contents

   



(Top)
 


1 Natural occurrences  





2 Chemistry  





3 Use as a marker in archaeology  





4 Glycosides  





5 See also  





6 References  














Malvidin






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From Wikipedia, the free encyclopedia
 


Malvidin
Names
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

Identifiers

CAS Number

3D model (JSmol)

ChEBI
ChEMBL
  • ChEMBL592005 checkY
  • ChemSpider
    KEGG

    PubChem CID

    UNII

    CompTox Dashboard (EPA)

    • InChI=1S/C17H14O7/c1-22-14-3-8(4-15(23-2)16(14)21)17-12(20)7-10-11(19)5-9(18)6-13(10)24-17/h3-7H,1-2H3,(H3-,18,19,20,21)/p+1 checkY

      Key: KZMACGJDUUWFCH-UHFFFAOYSA-O checkY

    • InChI=1/C17H14O7/c1-22-14-3-8(4-15(23-2)16(14)21)17-12(20)7-10-11(19)5-9(18)6-13(10)24-17/h3-7H,1-2H3,(H3-,18,19,20,21)/p+1

      Key: KZMACGJDUUWFCH-IKLDFBCSAG

    • Oc1cc2c(O)cc(O)cc2[o+]c1c3cc(OC)c(O)c(OC)c3

    Properties

    Chemical formula

    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).

    ☒N verify (what is checkY☒N ?)

    Infobox references

    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.

    Natural occurrences

    [edit]

    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

    [edit]

    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

    [edit]

    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

    [edit]

    See also

    [edit]

    References

    [edit]
    1. ^ "Phytochemicals: Malvidin". Top Cultures. Retrieved 2009-05-20.
  • ^ Mazza G (2005). "Compositional and functional properties of saskatoon berry and blueberry". International Journal of Fruit Science. 5 (3): 99–118. doi:10.1300/J492v05n03_10.
  • ^ Bakowska-barczak; Marianchuk, M; Kolodziejczyk, P (2007). "Survey of bioactive components in Western Canadian berries". Canadian Journal of Physiology and Pharmacology. 85 (11): 1139–52. doi:10.1139/y07-102. PMID 18066116.
  • ^ Nakayama, M; Roh, MS; Uchida, K; Yamaguchi, Y; Takano, K; Koshioka, M (2000). "Malvidin 3-rutinoside as the pigment responsible for bract color in Curcuma alismatifolia". Bioscience, Biotechnology, and Biochemistry. 64 (5): 1093–5. doi:10.1271/bbb.64.1093. PMID 10879491.
  • ^ Tatsuzawa, F (1999). "Acylated malvidin 3-rutinosides in dusky violet flowers of Petunia integrifolia subsp. Inflata". Phytochemistry. 52 (2): 351–355. doi:10.1016/S0031-9422(99)00095-3.
  • ^ Markham, Kenneth R.; Mitchell, Kevin A.; Boase, Murray R. (1997). "Malvidin-3-O-glucoside-5-O-(6-acetylglucoside) and its colour manifestation in 'Johnson's Blue' and other 'Blue' geraniums". Phytochemistry. 45 (2): 417–423. doi:10.1016/S0031-9422(96)00831-X.

  • Retrieved from "https://en.wikipedia.org/w/index.php?title=Malvidin&oldid=1170223366"

    Category: 
    O-methylated anthocyanidins
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    This page was last edited on 13 August 2023, at 20:36 (UTC).

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