Chrysanthemin

Chrysanthemin

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 chloride Cyanidin 3-glucoside Cyanidol 3-glucoside Cyanidine 3-glucoside Cyanidin 3-O-glucoside cyanidin-3-O-beta-D-glucoside Cyanidin 3-monoglucoside
Identifiers
CAS number	7084-24-4^Y
PubChem	197081
ChemSpider	170681^Y
Jmol-3D images	Image 1
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
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
Properties
Molecular formula	C₂₁H₂₁O₁₁⁺, Cl^- C₂₁H₂₁ClO₁₁
Molar mass	484.83 g/mol (chloride) 449.38 g/mol
Exact mass	484.077239 (chloride) 449.108387
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Chrysanthemin is an anthocyanin. It is the 3-glucoside of cyanidin. It has been detected in blackcurrant pomace, roselle plant, Japanaese angiosperm,^[1] Rhaponticum,^[2] victoria plum,^[3] and açaí.^[4] The biosynthesis of cyanidin 3-O-glucoside in Escherichia coli was demonstrated by mean of metabolic genetic engineering.^[5]

References

^ A survey of anthocyanins in sprouting leaves of some Japanese angiosperms studies on anthocyanins, LXV. Kunijiro Yoshitama, Makiko Ozaku, Michiko Hujii and Kôzô Hayashi, Journal of plant research, Volume 85, Number 4, pp. 303-306, doi:10.1007/BF02490176
^ Chrysanthemin and cyanin in species of the genus Rhaponticum. V. V. Vereskovskii and I. I. Chekalinskaya, Chemistry of natural compounds, Volume 14, Number 4, pp. 450-451, doi:10.1007/BF00565267
^ The chemical constituents of victoria plums: Chrysanthemin, acid and pectin contents. D. Dickinson and Joy H. Gawler, Journal of the Science of Food and Agriculture, Volume 7, Issue 11, November 1956, pp. 699–705 doi:10.1002/jsfa.2740071103
^ Del Pozo-Insfran D, Brenes CH, Talcott ST (March 2004). "Phytochemical composition and pigment stability of Açai (Euterpe oleracea Mart.)". J. Agric. Food Chem. 52 (6): 1539–45. doi:10.1021/jf035189n. PMID 15030208.
^ Yan Y, Chemler J, Huang L, Martens S, Koffas MA (2005). "Metabolic engineering of anthocyanin biosynthesis in Escherichia coli". Appl. Environ. Microbiol. 71 (7): 3617–23. doi:10.1128/AEM.71.7.3617-3623.2005. PMID 16000769.

Anthocyanidins and their anthocyanin glucosides

3-hydroxyanthocyanidins	5-Desoxy-peonidin \| Aurantinidin \| Cyanidin \| 6-Hydroxycyanidin \| Delphinidin \| Fisetinidin \| Guibourtinidin \| Pelargonidin \| Robinetinidin

3-deoxyanthocyanidins	Apigeninidin \| Columnidin \| Diosmetinidin \| Gesneridin \| Luteolinidin \| Tricetinidin

O-methylated anthocyanidins	5-Desoxy-malvidin \| Capensinidin \| Europinidin \| Hirsutidin \| Malvidin \| Peonidin \| Petunidin \| Pulchellidin \| Rosinidin

Anthocyanins	Antirrhinin \| Chrysanthemin \| Malvin \| Myrtillin \| Oenin \| Primulin \| Pulchellidin 3-glucoside \| Pulchellidin 3-rhamnoside \| Tulipanin

Acetylated glycosides	Cyanidin-3-(di-p-coumarylglucoside)-5-glucoside (found in Dark opal basil) Violdelphin (found in Aconitum chinense)

Misc.	Metalloanthocyanins (Commelinin \| Cyanosalvianin \| Protocyanin \| Protodelphin) \| Pyranoanthocyanins \| Copigmentation