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Chrysanthemin

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Chrysanthemin
Names
IUPAC name (2S,3R,4S,5S,6R)-2-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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.027.622 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
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./s1Key: YTMNONATNXDQJF-UBNZBFALSA-N
  • 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./s1Key: YTMNONATNXDQJF-UBNZBFALBB
SMILES
  • .O(c1c(c2c(c1)c(O)cc(O)c2)c3ccc(O)c(O)c3)4O((O)(O)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 , 100 kPa). checkverify (what is  ?) Infobox references
Chemical compound

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

References

  1. 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
  2. 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
  3. 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
  4. Del Pozo-Insfran D, Brenes CH, Talcott ST (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  5. 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
Anthocyanidins and their anthocyanin glucosides
3-Hydroxyanthocyanidins
3-Deoxyanthocyanidins
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-)
    Caffeoylated anthocyanins
    Malonylated anthocyanins
    Acylated anthocyanin diglycosides
    Flavanol-anthocyanin adducts
    Miscellaneous
    Categories: