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Delphinidin





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Delphinidin (also delphinidine[1][2]) is an anthocyanidin, a primary plant pigment, and also an antioxidant.[3] Delphinidin gives blue hues to flowers in the genera Viola and Delphinium. It also gives the blue-red color of the grape variety Cabernet Sauvignon, and can be found in cranberries and Concord grapes as well as pomegranates,[4] and bilberries.[5]

Delphinidin
Names
IUPAC name

3,3′,4′,5,5′,7-Hexahydroxyflavylium

Systematic IUPAC name

3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)-1λ4-1-benzopyran-1-ylium

Identifiers

CAS Number

  • 528-53-0 (chloride) checkY
  • 3D model (JSmol)

    ChEBI
    ChEMBL
  • ChEMBL276780 ☒N
  • ChemSpider
    ECHA InfoCard 100.007.671 Edit this at Wikidata
    E number E163b (colours)
    KEGG

    PubChem CID

    UNII
  • EM6MD4AEHE (chloride) checkY
  • CompTox Dashboard (EPA)

    • InChI=1S/C15H10O7.ClH/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6;/h1-5H,(H5-,16,17,18,19,20,21);1H checkY

      Key: FFNDMZIBVDSQFI-UHFFFAOYSA-N checkY

    • InChI=1/C15H10O7.ClH/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6;/h1-5H,(H5-,16,17,18,19,20,21);1H

      Key: FFNDMZIBVDSQFI-UHFFFAOYAW

    • C1=C(C=C(C(=C1O)O)O)C2=C(C=C3C(=CC(=CC3=[O+]2)O)O)O.[Cl-]

    Properties

    Chemical formula

    C15H11O7+
    Molar mass 303.24 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

    Delphinidin, like nearly all other anthocyanidins, is pH-sensitive, i.e. a natural pH indicator, and changes from blue in basic solution to red in acidic solution.

    Glycosides

    edit

    Several glycosides derived from delphinidin are known:

    See also

    edit

    References

    edit
    1. ^ "Delphinidine".
  • ^ "Delphinidine".
  • ^ Afaq, F.; Syed, D. N.; Malik, A.; Hadi, N.; Sarfaraz, S.; Kweon, M.-H.; Khan, N.; Zaid, M. A.; Mukhtar, H. (2007). "Delphinidin, an Anthocyanidin in Pigmented Fruits and Vegetables, Protects Human HaCaT Keratinocytes and Mouse Skin Against UVB-Mediated Oxidative Stress and Apoptosis". Journal of Investigative Dermatology. 127 (1): 222–232. doi:10.1038/sj.jid.5700510. PMID 16902416.
  • ^ Ribéreau-Gayon, J.; Ribéreau-Gayon, P. (1958). "The Anthocyans and Leucoanthocyans of Grapes and Wines". American Journal of Enology and Viticulture. 9: 1–9.
  • ^ Lätti AK, Riihinen KR, Kainulainen PS (2008). "Analysis of anthocyanin variation in wild populations of bilberry (Vaccinium myrtillus L.) in Finland". J Agric Food Chem. 56 (1): 190–6. doi:10.1021/jf072857m. PMID 18072741.
  • ^ CID 3083066 from PubChem
  • ^ Noda Y, Kneyuki T, Igarashi K, Mori A, Packer L (2000). "Antioxidant activity of nasunin, an anthocyanin in eggplant peels". Toxicology. 148 (2–3): 119–23. doi:10.1016/s0300-483x(00)00202-x. PMID 10962130.{{cite journal}}: CS1 maint: multiple names: authors list (link)

  • Retrieved from "https://en.wikipedia.org/w/index.php?title=Delphinidin&oldid=1152515695"
     



    Last edited on 30 April 2023, at 18:17  





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    This page was last edited on 30 April 2023, at 18:17 (UTC).

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