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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 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
3D model (JSmol)	Interactive image
ChemSpider	170681
ECHA InfoCard	100.027.622
KEGG	C08604
PubChem CID	197081
UNII	8X15R84UEM
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./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). Y verify (what is  ?) Infobox references

Chrysanthemin is an anthocyanin. It is the 3-glucoside of cyanidin (kuromanin).

Natural occurrences

Chrysanthemin can be found in the roselle plant (Hibiscus sabdariffa, Malvaceae), different Japanese angiosperms, Rhaponticum (Asteraceae), 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.

In food

Chrysanthemin has been detected in blackcurrant pomace, in European elderberry, in red raspberries, in soybean seed coats, in Victoria plum, in peach, lychee and açaí. It is found in red oranges and black rice.

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.

Biosynthesis

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

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.

References

1. "Cyanidin 3-glucoside". PubChem. United States National Library of Medicine. Retrieved 2024-04-07.
2. Yoshitama, Kunijiro (1972). "A survey of anthocyanins in sprouting leaves of some Japanese angiosperms studies on anthocyanins, LXV". The Botanical Magazine Tokyo. 85 (4): 303–306. doi:10.1007/BF02490176. S2CID 46453668.
3. Vereskovskii, VV (1978). "Chrysanthemin and cyanin in species of the genusRhaponticum". Chemistry of Natural Compounds. 14 (4): 450–451. doi:10.1007/BF00565267. S2CID 4817423.
4. Francis, FJ (1989). "Food colorants: Anthocyanins". Critical Reviews in Food Science and Nutrition. 28 (4): 273–314. doi:10.1080/10408398909527503. PMID 2690857.
5. Foods in which the polyphenol Cyanidin 3-O-glucoside is found, http://www.phenol-explorer.eu/contents/polyphenol/9
6. Choung, Myoung-Gun; Baek, In-Youl; Kang, Sung-Taeg; Han, Won-Young; Doo-Chull, Shin; Moon, Huhn-Pal; Kang, Kwang-Hee (2001). "Isolation and Determination of Anthocyanins in Seed Coats of Black Soybean (Glycine max (L.) Merr.)". Journal of Agricultural and Food Chemistry. 49 (12): 5848–5851. doi:10.1021/jf010550w. PMID 11743773.
7. Dickinson, D (1956). "The chemical constituents of victoria plums: Chrysanthemin, acid and pectin contents". Journal of the Science of Food and Agriculture. 7 (11): 699–705. doi:10.1002/jsfa.2740071103.
8. Postharvest sensory and phenolic characterization of 'Elegant Lady and 'Carson' peaches. Rodrigo Infante, Loreto Contador, Pía Rubio, Danilo Aros and Álvaro Peña-Neira, Chilean Journal of Agricultural Research, 71(3), July–September 2011, pages 445–451 (article)
9. 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.
10. Felgines, C; Texier, O; Besson, C; Vitaglione, P; Lamaison, JL; Fogliano, V; Scalbert, A; Vanella, L; Galvano, F (2008). "Influence of glucose on cyanidin 3-glucoside absorption in rats". Mol Nutr Food Res. 52 (8): 959–64. doi:10.1002/mnfr.200700377. PMID 18646002.
11. Um, Min Young; Ahn, Jiyun; Ha, Tae Youl (2013-09-01). "Hypolipidaemic effects of cyanidin 3-glucoside rich extract from black rice through regulating hepatic lipogenic enzyme activities". Journal of the Science of Food and Agriculture. 93 (12): 3126–3128. doi:10.1002/jsfa.6070. ISSN 1097-0010. PMID 23471845.
12. Anthocyanins isolated from purple corn (Zea mays L.). Hiromitsu Aoki, Noriko Kuze and Yoshiaki Kato (article Archived 2013-10-29 at the Wayback Machine)
13. 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. Bibcode:2005ApEnM..71.3617Y. doi:10.1128/AEM.71.7.3617-3623.2005. PMC 1169036. PMID 16000769.
14. Yonekura-Sakakibara, Keiko; Fukushima, Atsushi; Nakabayashi, Ryo; Hanada, Kousuke; Matsuda, Fumio; Sugawara, Satoko; Inoue, Eri; Kuromori, Takashi; Ito, Takuya; Shinozaki, Kazuo; Wangwattana, Bunyapa; Yamazaki, Mami (2012). "Two glycosyltransferases involved in anthocyanin modi?cation delineated by transcriptome independent component analysis in Arabidopsis thaliana". The Plant Journal. 69 (1): 154–167. doi:10.1111/j.1365-313X.2011.04779.x. PMC 3507004. PMID 21899608.

• Anthocyanins
• Flavonoid glucosides