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Delphinidin

From Wikipedia, the free encyclopedia
(Redirected fromNasunin)
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.007.671Edit this at Wikidata
E numberE163b(colours)
KEGG
UNII
  • 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
C15H11O7+
Molar mass303.24 g/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Delphinidin (alsodelphinidine[1][2]) is ananthocyanidin, a primaryplant pigment, and also anantioxidant.[3] Delphinidin gives blue hues to flowers in the generaViola andDelphinium. It also gives the blue-red color of thegrape varietyCabernet Sauvignon, and can be found incranberries andConcord grapes as well aspomegranates,[4] andbilberries.[5]

Delphinidin, like nearly all other anthocyanidins, ispH-sensitive, i.e. anatural pH indicator, and changes from blue in basicsolution to red inacidic solution.

Glycosides

[edit]

Severalglycosides derived from delphinidin are known:

See also

[edit]

References

[edit]
  1. ^"Delphinidine".
  2. ^"Delphinidine".
  3. ^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.
  4. ^Ribéreau-Gayon, J.; Ribéreau-Gayon, P. (1958). "The Anthocyans and Leucoanthocyans of Grapes and Wines".American Journal of Enology and Viticulture.9:1–9.
  5. ^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.
  6. ^CID 3083066 fromPubChem
  7. ^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)
Anthocyanidins and their anthocyaninglucosides
3-Hydroxyanthocyanidins
3-Deoxyanthocyanidins
O-Methylated anthocyanidins
Anthocyanins
(anthocyaninidin glycosides)
Glucosides:

Diglucosides:

Others glycosides:

Acylated anthocyanins
Acetylated anthocyanins
Coumaroylated anthocyanins
(cis- andtrans-)
Caffeoylated anthocyanins
Malonylated anthocyanins
Acylated anthocyanin diglycosides
Flavanol-anthocyanin adducts
Miscellaneous
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