Antirrhinin

Antirrhinin
Names

IUPAC name (2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxane-3,4,5-triol chloride
Other names Keracyanin Prunicyanin Sambucin Cyaninoside Keraciannai Keracyanine Keracyaninum Cyanidin 3-rutinoside Cyanidin 3-O-rutinoside Keracyanin chloride cyanidin-3-rhamnoglucoside
Identifiers
CAS Registry Number	18719-76-1^N
ChEBI	CHEBI:16726^Y
ChEMBL	ChEMBL592218^Y
ChemSpider	27186^Y
InChI InChI=1S/C27H30O15.ClH/c1-9-19(32)21(34)23(36)26(39-9)38-8-18-20(33)22(35)24(37)27(42-18)41-17-7-12-14(30)5-11(28)6-16(12)40-25(17)10-2-3-13(29)15(31)4-10;/h2-7,9,18-24,26-27,32-37H,8H2,1H3,(H3-,28,29,30,31);1H/t9-,18+,19-,20+,21+,22-,23+,24+,26+,27+;/m0./s1^Y Key: ADZHXBNWNZIHIX-XYGAWYNKSA-N^Y InChI=1S/C27H30O15.ClH/c1-9-19(32)21(34)23(36)26(39-9)38-8-18-20(33)22(35)24(37)27(42-18)41-17-7-12-14(30)5-11(28)6-16(12)40-25(17)10-2-3-13(29)15(31)4-10;/h2-7,9,18-24,26-27,32-37H,8H2,1H3,(H3-,28,29,30,31);1H/t9-,18+,19-,20+,21+,22-,23+,24+,26+,27+;/m0./s1
Jmol-3D images	Image
PubChem	29231
SMILES [Cl-].O(C[C@H]4O[C@@H](Oc2cc3c(O)cc(O)cc3[o+]c2c1ccc(O)c(O)c1)[C@H](O)[C@@H](O)[C@@H]4O)[C@@H]5O[C@H]([C@H](O)[C@@H](O)[C@H]5O)C
Properties
Chemical formula	C₂₇H₃₁O₁₅⁺, Cl⁻
Molar mass	630.97 g/mol (chloride) 595.52 g/mol (cation)
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
Infobox references

Antirrhinin is an anthocyanin. It is the 3-rutinoside of cyanidin.

Natural occurrences

It can be found in Antirrhinum majus (common snapdragon),^[1]^[2] in blackcurrant,^[3] in açaí^[4] or in litchi pericarp.^[5]

Cyanidin 3-O-rutinoside 5-O-glucosyltransferase uses UDP-glucose and cyanidin 3-O-rutinoside (antirrhinin) to produce UDP and cyanidin 3-O-rutinoside 5-O-beta-D-glucoside.

↑ Scott-Moncrieff, R (1930). "Natural anthocyanin pigments: The magenta flower pigment of Antirrhinum majus". Biochemical Journal 24 (3): 753–766. PMC 1254517. PMID 16744416.
↑ Gilbert, R.I. (1971). "An unusual anthocyanin in Antirrhinum majus". Phytochemistry 10 (11): 2848. doi:10.1016/S0031-9422(00)97309-6.
↑ Slimestad, Rune; Solheim, Haavard (2002). "Anthocyanins from Black Currants (Ribes nigrumL.)". Journal of Agricultural and Food Chemistry 50 (11): 3228–31. doi:10.1021/jf011581u. PMID 12009991.
↑ Gallori, S.; Bilia, A. R.; Bergonzi, M. C.; Barbosa, W. L. R.; Vincieri, F. F. (2004). "Polyphenolic Constituents of Fruit Pulp of Euterpe oleracea Mart. (Açai palm)". Chromatographia 59 (11–12). doi:10.1365/s10337-004-0305-x.
↑ Sarni-Manchado, Pascale; Le Roux, Erwan; Le Guernevé, Christine; Lozano, Yves; Cheynier, Véronique (2000). "Phenolic Composition of Litchi Fruit Pericarp". Journal of Agricultural and Food Chemistry 48 (12): 5995–6002. doi:10.1021/jf000815r. PMID 11312772.

3-hydroxyanthocyanidins

O-methylated anthocyanidins

Anthocyanins
(anthocyaninidin glycosides)

Glucosides:

Diglucosides:

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 Cyanidin-3-O-(di-p-coumarylglucoside)-5-glucoside Delphinidin-3-O-(6-p-coumaroyl)glucoside Malvidin-3-O-(6-p-coumaroyl)glucoside Petanin (petunidin 3-[6-O-(4-O-E-p-coumaroyl-O-α-l-rhamnopyranosyl)-β-d-glucopyranoside]-5-O-β-d-glucopyranoside) 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 Gentiodelphin (delphinidin 3-O-glucosyl-5-O-(6-O-caffeoyl-glucosyl)-3′-O-(6-O-caffeoyl-glucoside))

p-hydroxybenzoylated anthocyanins	Violdelphin

Malonylated anthocyanins	Malonylmalvin (malvidin 3-(6″-malonylglucoside)-5-glucoside)

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.