Callistephin

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

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
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • 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
C21H21O10+
Molar mass 433.38 g/mol
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

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. Anthocyanins and Their Variation in Red Wines I. Monomeric Anthocyanins and Their Color Expression. Fei He, Na-Na Liang, Lin Mu, Qiu-Hong Pan, Jun Wang, Malcolm J. Reeves and Chang-Qing Duan, Molecules, 2012, 17, pages 1571-1601, doi:10.3390/molecules17021571
  2. Evolution of juice anthocyanins during ripening of new selected pomegranate (Punica granatum) clones. F. Hernández, P. Melgarejo, F. A. Tomás-Barberán and F. Artés, European Food Research and Technology, November 1999, Volume 210, Issue 1, pages 39-42, doi:10.1007/s002170050529
  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. Anthocyanins isolated from purple corn (Zea mays L.). Hiromitsu Aoki, Noriko Kuze and Yoshiaki Kato (article Archived 2013-10-29 at the Wayback Machine)
  5. Mass-spectrometry evidence confirming the presence of pelargonidin-3-O-glucoside in the berry skins of Cabernet Sauvignon and Pinot Noir (Vitis vinifera L.). F. HE, J.-J. HE, Q.-H. PAN and C.-Q. DUAN, Australian Journal of Grape and Wine Research, October 2010, Volume 16, Issue 3, pages 464–468, doi:10.1111/j.1755-0238.2010.00107.x


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