Chrysanthemin

Chrysanthemin is an anthocyanin. It is the 3-glucoside of cyanidin (kuromanin).^[1]

Chrysanthemin

Names
IUPAC name (2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol chloride
Other names Chrysontenin Glucocyanidin Asterin Chrysanthemin Purple corn color Kuromanin Kuromanin chloride Cyanidin 3-glucoside Cyanidol 3-glucoside Cyanidine 3-glucoside Cyanidin 3-O-glucoside cyanidin-3-O-beta-D-glucoside Cyanidin 3-monoglucoside C3G
Identifiers
CAS Number	7084-24-4 Y
3D model (JSmol)	Interactive image
ChemSpider	170681 Y
ECHA InfoCard	100.027.622
KEGG	C08604 Y
PubChem CID	197081
UNII	8X15R84UEM Y
CompTox Dashboard (EPA)	DTXSID401028798
InChI InChI=1S/C21H20O11.ClH/c22-7-16-17(27)18(28)19(29)21(32-16)31-15-6-10-12(25)4-9(23)5-14(10)30-20(15)8-1-2-11(24)13(26)3-8;/h1-6,16-19,21-22,27-29H,7H2,(H3-,23,24,25,26);1H/t16-,17-,18+,19-,21-;/m1./s1 Y Key: YTMNONATNXDQJF-UBNZBFALSA-N Y InChI=1/C21H20O11.ClH/c22-7-16-17(27)18(28)19(29)21(32-16)31-15-6-10-12(25)4-9(23)5-14(10)30-20(15)8-1-2-11(24)13(26)3-8;/h1-6,16-19,21-22,27-29H,7H2,(H3-,23,24,25,26);1H/t16-,17-,18+,19-,21-;/m1./s1 Key: YTMNONATNXDQJF-UBNZBFALBB
SMILES [Cl-].O(c1c([o+]c2c(c1)c(O)cc(O)c2)c3ccc(O)c(O)c3)[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O)CO
Properties
Chemical formula	C21H21O11+, Cl− C21H21ClO11
Molar mass	484.83 g/mol (chloride) 449.38 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

UV visible spectrum of cyanidin 3-O-glucoside

Natural occurrences

Chrysanthemin can be found in the roselle plant (Hibiscus sabdariffa, Malvaceae), different Japanese angiosperms,^[2] Rhaponticum (Asteraceae),^[3] The fruits of the smooth arrowwood (Viburnum dentatum, Caprifoliaceae) appear blue. One of the major pigments is cyanidin 3-glucoside, but the total mixture is very complex.^[4]

In food

Chrysanthemin has been detected in blackcurrant pomace, in European elderberry,^[5] in red raspberries, in soybean seed coats,^[6] in Victoria plum,^[7] in peach,^[8] lychee and açaí.^[9] It is found in red oranges^[10] and black rice.^[11]

It is the major anthocyanin in purple corn (Zea mays). Purple corn is approved in Japan and listed in the "Existing Food Additive List" as purple corn color.^[12]

Biosynthesis

The biosynthesis of cyanidin 3-O-glucoside in Escherichia coli was demonstrated by means of genetic engineering.^[13]

In Arabidopsis thaliana, a glycosyltransferase, UGT79B1, is involved in the anthocyanin biosynthetic pathway. UGT79B1 protein converts cyanidin 3-O-glucoside to cyanidin 3-O-xylosyl(1→2)glucoside.^[14]