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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
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
C 21 H 21 O 10
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).
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
^ 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
3-Deoxyanthocyanidins O -Methylated anthocyanidins
Anthocyanins (anthocyaninidin glycosides) Glucosides:
Diglucosides:
Others glycosides:
Acylated anthocyanins
Acetylated anthocyanins Coumaroylated anthocyanins (cis - and trans -) Caffeoylated anthocyanins Malonylated anthocyanins Acylated anthocyanin diglycosides
Flavanol-anthocyanin adducts Miscellaneous