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
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 433.389 g·mol−1
UV-vis (λmax) 505 nm
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

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

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. PMC 6268338. 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 from the original (PDF) on 2013-10-29. Retrieved 2014-02-09.)
  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.