Callistephin - Misplaced Pages

Callistephin
Names

IUPAC name 5,7‐Dihydroxy‐2‐(4‐hydroxyphenyl)‐3‐{oxy}‐1λ‐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
3D model (JSmol)	Interactive image
ChEBI	CHEBI:31967
ChemSpider	391782
KEGG	C12137
PubChem CID	443648
UNII	W623YHH61A
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/s1Key: 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/s1Key: ABVCUBUIXWJYSE-OAYIZRCEBP
SMILES C1=CC(=CC=C1C2=C3=CC(=CC(=C3C=C2O4((((O4)CO)O)O)O)O)O)O
Properties
Chemical formula	C₂₁H₂₁O₁₀
Molar mass	433.389 g·mol
UV-vis (λ_max)	505 nm
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

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.).

References

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.
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.
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.
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)
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.

3-Hydroxyanthocyanidins

O-Methylated anthocyanidins

Anthocyanins
(anthocyaninidin glycosides)

Glucosides:

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:

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--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)

Miscellaneous

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