Callistephin

Callistephin
Chemical structure of callistephin
Names
IUPAC name
5,7‐Dihydroxy‐2‐(4‐hydroxyphenyl)‐3‐{[(2S,3R,4S,5S,6R)‐3,4,5‐trihydroxy‐6‐(hydroxymethyl)oxan‐2‐yl]oxy}‐1λ4‐chromen‐1‐ylium
Systematic IUPAC name
5,7-Dihydroxy-2-(4-hydroxyphenyl)-3-chromeniumyl β-D-glucopyranoside
Other names
Pelargonidin-3-O-glucoside
Identifiers
CAS Number
  • 47684-27-5 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:31967
ChemSpider
  • 391782
KEGG
  • C12137
PubChem CID
  • 443648
UNII
  • W623YHH61A checkY
InChI
  • InChI=1S/C21H20O10/c22-8-16-17(26)18(27)19(28)21(31-16)30-15-7-12-13(25)5-11(24)6-14(12)29-20(15)9-1-3-10(23)4-2-9/h1-7,16-19,21-22,26-28H,8H2,(H2-,23,24,25)/p+1/t16-,17-,18+,19-,21-/m1/s1
    Key: ABVCUBUIXWJYSE-GQUPQBGVSA-O
  • InChI=1/C21H20O10/c22-8-16-17(26)18(27)19(28)21(31-16)30-15-7-12-13(25)5-11(24)6-14(12)29-20(15)9-1-3-10(23)4-2-9/h1-7,16-19,21-22,26-28H,8H2,(H2-,23,24,25)/p+1/t16-,17-,18+,19-,21-/m1/s1
    Key: ABVCUBUIXWJYSE-OAYIZRCEBP
  • C1=CC(=CC=C1C2=[O+]C3=CC(=CC(=C3C=C2O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O
Properties
Chemical formula
 C21H21O10
Molar mass 433.389 g·mol−1
UV-vis (λmax) 505 nm[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound

Callistephin is an anthocyanin. It is the 3-O-glucoside of pelargonidin.

It is found in pomegranate juice,[2] in strawberries,[3] and in purple corn.[4] It is also found in the berry skins of Cabernet Sauvignon and Pinot Noir grapes (Vitis vinifera L.).[5]

See also

References

  1. ^ He, Fei; Liang, Na-Na; Mu, Lin; Pan, Qiu-Hong; Wang, Jun; Reeves, Malcolm J.; Duan, Chang-Qing (2012). "Anthocyanins and Their Variation in Red Wines I. Monomeric Anthocyanins and Their Color Expression". Molecules. 17 (2): 1571–1601. doi:10.3390/molecules17021571. PMID 22314380.
  2. ^ Hernández, F.; Melgarejo, P.; Tomás-Barberán, F. A.; Artés, F. (1999). "Evolution of juice anthocyanins during ripening of new selected pomegranate ( Punica granatum ) clones". European Food Research and Technology. 210: 39–42. doi:10.1007/s002170050529. S2CID 16524540.
  3. ^ Mullen, William; Edwards, Christine A.; Serafini, Mauro; Crozier, Alan (2008). "Bioavailability of Pelargonidin-3-O-glucoside and Its Metabolites in Humans Following the Ingestion of Strawberries with and without Cream". Journal of Agricultural and Food Chemistry. 56 (3): 713–9. doi:10.1021/jf072000p. PMID 18211024.
  4. ^ Hiromitsu Aoki, Noriko Kuze and Yoshiaki Kato. "Anthocyanins isolated from purple corn (Zea mays L.)" (PDF). Agricultural and Food Sciences. Archived 2013-10-29 at the Wayback Machine)
  5. ^ He, F.; He, J.-J.; Pan, Q.-H.; Duan, C.-Q. (2010). "Mass-spectrometry evidence confirming the presence of pelargonidin-3-O-glucoside in the berry skins of Cabernet Sauvignon and Pinot Noir (Vitis vinifera L.)". Australian Journal of Grape and Wine Research. 16 (3): 464–468. doi:10.1111/j.1755-0238.2010.00107.x.
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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
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