Callistephin

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
ChEBI	CHEBI:31967
ChemSpider	391782
Jmol interactive 3D	Image
KEGG	C12137
PubChem	443648
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
SMILES 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	433.38 g/mol
UV-vis (λ_max)	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

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]

References

↑ 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
↑ 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
↑ 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.
↑ Anthocyanins isolated from purple corn (Zea mays L.). Hiromitsu Aoki, Noriko Kuze and Yoshiaki Kato (article)
↑ 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

Anthocyanidins and their anthocyanin glucosides

3-hydroxyanthocyanidins

3-deoxyanthocyanidins

O-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)-beta-D-glucosyl)oxybenzoyl)-beta-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

Misc.

Metalloanthocyanins (Commelinin
Cyanosalvianin
Protocyanin
Protodelphin)
Pyranoanthocyanins
Copigmentation
Anthocyanone A (degradation product of oenin)
Malvone (oxidation product of malvin)

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Callistephin

See also

References