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Malvidin





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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.

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

    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

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    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"
     



    Last edited on 13 August 2023, at 20:36  





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    This page was last edited on 13 August 2023, at 20:36 (UTC).

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