Hirsutidin

Hirsutidin
Names
IUPAC name
3,4′,5-Trihydroxy-3′,5′,7-trimethoxyflavylium
Systematic IUPAC name
3,5-Dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-7-methoxy-1λ4-benzopyran-1-ylium
Identifiers
CAS Number
  • 151776-57-7 checkY
  • (chloride): 4092-66-4 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:5728 ☒N
ChemSpider
  • 390303 ☒N
PubChem CID
  • 441694
UNII
  • VV9H579AR2 checkY
  • (chloride): UX37SFW7Y9 checkY
CompTox Dashboard (EPA)
  • DTXSID40961303 Edit this at Wikidata
InChI
  • InChI=1S/C18H16O7/c1-22-10-6-12(19)11-8-13(20)18(25-14(11)7-10)9-4-15(23-2)17(21)16(5-9)24-3/h4-8H,1-3H3,(H2-,19,20,21)/p+1 ☒N
    Key: JGPCLGHKWGCWNO-UHFFFAOYSA-O ☒N
  • InChI=1/C18H16O7/c1-22-10-6-12(19)11-8-13(20)18(25-14(11)7-10)9-4-15(23-2)17(21)16(5-9)24-3/h4-8H,1-3H3,(H2-,19,20,21)/p+1
    Key: JGPCLGHKWGCWNO-IKLDFBCSAS
  • Oc1cc2c(O)cc(OC)cc2[o+]c1c3cc(OC)c(O)c(OC)c3
Properties
Chemical formula
 C18H17O7+
Molar mass 345.32 g/mol
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

Hirsutidin is an O-methylated anthocyanidin, a chemical compound belonging to the anthocyanins. It can be found in Catharanthus roseus[1] (Madagascar periwinkle) where it is the prominent compound in petals and can also be found in callus cultures.[2]

Glycosides

3-O-(6-O-p-coumaroyl) glucoside of hirsutidin can also be found in Catharanthus roseus.[3]

References

  1. ^ Characterization of the anthocyanins of Catharanthus roseus (L.) G. Don in vivo and in vitro by electrospray ionization ion trap mass spectrometry, Anna Piovan, Raffaella Filippini, Donata Favretto, 1998
  2. ^ Catharanthus flavonoids on Schroeder page, uni. Freiburg, Germany
  3. ^ Piovan, Anna; Filippini, Raffaella (2007). "Anthocyanins in Catharanthus roseus in vivo and in vitro: A review". Phytochemistry Reviews. 6 (2–3): 235–242. Bibcode:2007PChRv...6..235P. doi:10.1007/s11101-006-9052-y. S2CID 676724.
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Anthocyanidins and their anthocyanin glucosides
3-Hydroxyanthocyanidins3-DeoxyanthocyanidinsO-Methylated anthocyanidins
Anthocyanins
(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