Columnidin

Columnidin
Chemical structure of columnidin
Names
IUPAC name
3′,4′,5,7,8-Pentahydroxyflavylium
Preferred IUPAC name
2-(3,4-Dihydroxyphenyl)-5,7,8-trihydroxy-1λ4-benzopyran-1-ylium
Identifiers
3D model (JSmol)
  • Interactive image
ChemSpider
  • 30780721 ☒N
PubChem CID
  • 57459464
CompTox Dashboard (EPA)
  • DTXSID101028787 Edit this at Wikidata
InChI
  • InChI=1S/C15H10O6/c16-9-3-1-7(5-11(9)18)13-4-2-8-10(17)6-12(19)14(20)15(8)21-13/h1-6H,(H4-,16,17,18,19,20)/p+1 ☒N
    Key: USQSSTLNPXPPHA-UHFFFAOYSA-O ☒N
  • InChI=1/C15H10O6/c16-9-3-1-7(5-11(9)18)13-4-2-8-10(17)6-12(19)14(20)15(8)21-13/h1-6H,(H4-,16,17,18,19,20)/p+1
    Key: USQSSTLNPXPPHA-IKLDFBCSAT
  • C1=CC(=C(C=C1C2=[O+]C3=C(C=C2)C(=CC(=C3O)O)O)O)O
Properties
Chemical formula
C15H11O6
Molar mass 287.244
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Chemical compound

Columnidin is an orange red pigment, belonging to the 3-deoxyanthocyanidins[1] found in red-flowered western-hemisphere gesneriad species such as episcias, columneas, sarmientas, and sinningias.

The columnidin is named after the gesneriad genus Columnea in which it is found,[2] notably in Columnea hybrida.[3]

References

  1. ^ "Gesneriaceae and Scrophulariaceae : Robert Brown and now, Anton Weber, 2004" (PDF). Archived from the original (PDF) on 2015-09-24. Retrieved 2009-08-26.
  2. ^ Sinningia Pollinators
  3. ^ "Studies on columnidin biosynthesis with flower extracts from Columnea hybrida, Stich, K.; Forkmann, G.; Z. Naturforsch. C 43, 311-314 (1988)". Archived from the original on 2012-10-25. Retrieved 2009-08-26.
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Anthocyanidins and their anthocyanin glucosides
3-Hydroxyanthocyanidins3-DeoxyanthocyanidinsO-Methylated anthocyanidinsAnthocyanins
(anthocyaninidin glycosides)
Glucosides:
  • Callistephin (Pelargonidin 3-O-glucoside)
  • Chrysanthemin (Cyanidin 3-O-glucoside)
  • Myrtillin (Delphinidin 3-O-glucoside)
  • Oenin (Malvidin 3-O-glucoside)
  • Peonidin 3-O-glucoside
  • Petunidin 3-O-glucoside
  • Pulchellidin 3-glucoside

Diglucosides:

  • Cyanin (Cyanidin 3,5-O-diglucoside)
  • Delphin (Delphinidin 3,5-O-diglucoside)
  • Malvin (Malvidin 3,5-diglucoside)
  • Pelargonin (Pelargonidin 3,5-O-diglucoside)
  • Peonin (Peonidin 3,5-O-diglucoside)
  • Petunin (Petunidin 3,5-O-diglucoside)

Others glycosides:

  • Antirrhinin (Cyanidin 3-O-rutinoside)
  • Ideain (Cyanidin 3-O-galactoside)
  • Delphinidin 3-O-rhamnoside
  • Petunidin 3-O-arabinoside
  • Petunidin 3-O-galactoside
  • Petunidin 3-O-rhamnoside
  • Petunidin 3-O-rutinoside
  • Primulin (Malvidin 3-O-galactoside)
  • Pulchellidin 3-rhamnoside
  • Tulipanin (Delphinidin 3-O-rutinoside)
Acylated anthocyanins
Acetylated anthocyanins
  • Cyanidin 3-O-(6-acetyl)glucoside
  • Delphinidin 3-O-(6-acetyl)glucoside
  • Malvidin 3-O-(6-acetyl)glucoside
  • Petunidin 3-O-(6-acetyl)galactoside
  • Petunidin 3-O-(6-acetyl)glucoside
  • Peonidin 3-O-(6-acetyl)glucoside
  • Coumaroylated anthocyanins
    (cis- and trans-)
    • Cyanidin 3-O-(6-p-coumaroyl)glucoside
    • Delphinidin 3-O-(6-p-coumaroyl)glucoside
    • Malvidin 3-O-(6-p-coumaroyl)glucoside
    • Petunidin 3-O-(6-p-coumaroyl)glucoside
    • Peonidin 3-O-(6-p-coumaroyl)glucoside
    Caffeoylated anthocyanins
    • Malvidin 3-O-(6-p-caffeoyl)glucoside
    • Peonidin 3-O-(6-p-caffeoyl)glucoside
    Malonylated anthocyanins
    • Malonylmalvin (malvidin 3-(6″-malonylglucoside)-5-glucoside)
    Acylated anthocyanin diglycosides
    • Cyanidin 3-O-(di-p-coumarylglucoside)-5-glucoside
    • Gentiodelphin (delphinidin 3-''O''-glucosyl-5-''O''-(6-''O''-caffeoyl-glucosyl)-3′-''O''-(6-''O''-caffeoyl-glucoside))
    • Nasunin (Delphinidin 3-(p-coumaroylrutinoside)-5-glucoside)
    • Petanin (petunidin 3-[6-O-(4-O-(E)-p-coumaroyl-O-α-l-rhamnopyranosyl)-β-D-glucopyranoside]-5-O-β-D-glucopyranoside)
    • Violdelphin (Delphinidin 3-rutinoside-7-O-(6-O-(4-(6-O-(4-hydroxybenzoyl)-β-D-glucosyl)oxybenzoyl)-β-D-glucoside)
    Flavanol-anthocyanin adducts
    • Malvidin glucoside-ethyl-catechin
    • Catechin(4α→8)pelargonidin 3-O-β-glucopyranoside
    • Epicatechin(4α→8)pelargonidin 3-O-β-glucopyranoside
    • Afzelechin(4α→8)pelargonidin 3-O-β-glucopyranoside
    • Epiafzelechin(4α→8)pelargonidin 3-O-β-glucopyranoside
    Miscellaneous