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{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 396312933 | verifiedrevid = 440125119
| name = Chrysanthemin | Name = Chrysanthemin
| ImageFile = Cyanidin 3-O-glucoside.svg | ImageFile = Chrysanthemin_chloride.svg
| ImageSize = 300px | ImageSize = 300px
| IUPACName = <nowiki>(2S,3R,4S,5S,6R)-2-oxy-6-(hydroxymethyl)oxane-3,4,5-triol chloride</nowiki> | IUPACName = <nowiki>(2S,3R,4S,5S,6R)-2-oxy-6-(hydroxymethyl)oxane-3,4,5-triol chloride</nowiki>
| OtherNames = Chrysontenin<br>Glucocyanidin<br>Asterin<br>Chrysanthemin<br>Purple corn color<br>Kuromanin chloride<br>Cyanidin 3-glucoside<br>Cyanidol 3-glucoside<br>Cyanidine 3-glucoside<br>Cyanidin 3-O-glucoside<br>cyanidin-3-O-beta-D-glucoside<br>Cyanidin 3-monoglucoside | OtherNames = Chrysontenin<br>Glucocyanidin<br>Asterin<br>Chrysanthemin<br>Purple corn color<br>Kuromanin<br>Kuromanin chloride<br>Cyanidin 3-glucoside<br>Cyanidol 3-glucoside<br>Cyanidine 3-glucoside<br>Cyanidin 3-O-glucoside<br>cyanidin-3-O-beta-D-glucoside<br>Cyanidin 3-monoglucoside<br>C3G
| Section1={{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 170681 | ChemSpiderID = 170681
| 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 | 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
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| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 7084-24-4 | CASNo = 7084-24-4
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem = 197081
| UNII = 8X15R84UEM
⚫ | SMILES = .O(c1c(c2c(c1)c(O)cc(O)c2)c3ccc(O)c(O)c3)4O((O)(O)4O)CO
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C08604
⚫ | PubChem = 197081
⚫ | SMILES = .O(c1c(c2c(c1)c(O)cc(O)c2)c3ccc(O)c(O)c3)4O((O)(O)4O)CO
}} }}
|Section2={{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>21</sub>H<sub>21</sub>O<sub>11</sub><sup>+</sup>, Cl<sup>-</sup><br>C<sub>21</sub>H<sub>21</sub>ClO<sub>11</sub> | Formula = C<sub>21</sub>H<sub>21</sub>O<sub>11</sub><sup>+</sup>, Cl<sup>−</sup><br>C<sub>21</sub>H<sub>21</sub>ClO<sub>11</sub>
| MolarMass = 484.83 g/mol (chloride)<br>449.38 g/mol | MolarMass = 484.83 g/mol (chloride)<br>449.38 g/mol
| Appearance =
| ExactMass = 484.077239 (chloride)<br>449.108387
| Appearance = | Density =
| Density = | MeltingPt =
| MeltingPt = | BoilingPt =
| BoilingPt = | Solubility =
| Solubility =
}} }}
|Section3={{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
}} }}
}} }}
]
'''Chrysanthemin''' is an ]. It is the 3-] of ]. It has been detected in ] pomace, ], Japanaese ],<ref>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}}</ref> '']'',<ref>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}}</ref> ],<ref>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}}</ref> and ].<ref>{{cite journal |author=Del Pozo-Insfran D, Brenes CH, Talcott ST |title=Phytochemical composition and pigment stability of Açai (Euterpe oleracea Mart.) |journal=J. Agric. Food Chem. |volume=52 |issue=6 |pages=1539–45 |year=2004 |month=March |pmid=15030208 |doi=10.1021/jf035189n |url=}}</ref> The biosynthesis of cyanidin 3-O-glucoside in '']'' was demonstrated by mean of metabolic genetic engineering.<ref>{{cite journal |author=Yan Y, Chemler J, Huang L, Martens S, Koffas MA |title=Metabolic engineering of anthocyanin biosynthesis in Escherichia coli |journal=Appl. Environ. Microbiol. |volume=71 |issue=7 |pages=3617–23 |year=2005 |pmid=16000769 |doi=10.1128/AEM.71.7.3617-3623.2005}}</ref>
'''Chrysanthemin''' is an ]. It is the 3-] of ] ('''kuromanin''').<ref name="PubChem">{{cite web | title = Cyanidin 3-glucoside| work = ] | publisher = ] | url = https://pubchem.ncbi.nlm.nih.gov/compound/Cyanidin-3-glucoside | accessdate = 2024-04-07 }}</ref>


== Natural occurrences ==
⚫ ==References==
Chrysanthemin can be found in the ] (''Hibiscus sabdariffa'', Malvaceae), different Japanese ]s,<ref>{{cite journal | doi = 10.1007/BF02490176 | volume=85 | title=A survey of anthocyanins in sprouting leaves of some Japanese angiosperms studies on anthocyanins, LXV | year=1972 | journal=The Botanical Magazine Tokyo | pages=303–306 | last1 = Yoshitama | first1 = Kunijiro| issue=4 | s2cid=46453668 }}</ref> '']'' (Asteraceae),<ref>{{cite journal | doi = 10.1007/BF00565267 | volume=14 | title=Chrysanthemin and cyanin in species of the genusRhaponticum | year=1978 | journal=Chemistry of Natural Compounds | pages=450–451 | last1 = Vereskovskii | first1 = VV| issue=4 | s2cid=4817423 }}</ref> The fruits of the smooth arrowwood ('']'', Caprifoliaceae) appear blue. One of the major pigments is cyanidin 3-glucoside, but the total mixture is very complex.<ref>{{cite journal | doi = 10.1080/10408398909527503 | volume=28 | title=Food colorants: Anthocyanins | year=1989 | journal=Critical Reviews in Food Science and Nutrition | pages=273–314 | last1 = Francis | first1 = FJ | issue=4 | pmid=2690857}}</ref>

=== In food ===
Chrysanthemin has been detected in ] pomace, in ],<ref>Foods in which the polyphenol Cyanidin 3-O-glucoside is found, http://www.phenol-explorer.eu/contents/polyphenol/9</ref> in ], in ] ],<ref>{{cite journal|last1=Choung|first1=Myoung-Gun|last2=Baek|first2=In-Youl|last3=Kang|first3=Sung-Taeg|last4=Han|first4=Won-Young|last5=Doo-Chull|first5=Shin|last6=Moon|first6=Huhn-Pal|last7=Kang|first7=Kwang-Hee|title=Isolation and Determination of Anthocyanins in Seed Coats of Black Soybean (Glycine max (L.) Merr.)|journal=Journal of Agricultural and Food Chemistry|date=2001|volume=49|issue=12|pages=5848–5851|doi=10.1021/jf010550w|pmid=11743773}}</ref> in ],<ref>{{cite journal | doi = 10.1002/jsfa.2740071103 | volume=7 | title=The chemical constituents of victoria plums: Chrysanthemin, acid and pectin contents | year=1956 | journal=Journal of the Science of Food and Agriculture | pages=699–705 | last1 = Dickinson | first1 = D| issue=11 }}</ref> in ],<ref>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 ()</ref> ] and ].<ref>{{cite journal |vauthors=Del Pozo-Insfran D, Brenes CH, Talcott ST |title=Phytochemical composition and pigment stability of Açai (''Euterpe oleracea'' Mart.) |journal=J. Agric. Food Chem. |volume=52 |issue=6 |pages=1539–45 |date=March 2004 |pmid=15030208 |doi=10.1021/jf035189n }}</ref> It is found in ]s<ref>{{cite journal | pmid = 18646002 | doi=10.1002/mnfr.200700377 | volume=52 | title=Influence of glucose on cyanidin 3-glucoside absorption in rats | year=2008 | journal=Mol Nutr Food Res | pages=959–64 | last1 = Felgines | first1 = C | last2 = Texier | first2 = O | last3 = Besson | first3 = C | last4 = Vitaglione | first4 = P | last5 = Lamaison | first5 = JL | last6 = Fogliano | first6 = V | last7 = Scalbert | first7 = A | last8 = Vanella | first8 = L | last9 = Galvano | first9 = F| issue=8 }}</ref> and black rice.<ref>{{Cite journal|last1=Um|first1=Min Young|last2=Ahn|first2=Jiyun|last3=Ha|first3=Tae Youl|date=2013-09-01|title=Hypolipidaemic effects of cyanidin 3-glucoside rich extract from black rice through regulating hepatic lipogenic enzyme activities|journal=Journal of the Science of Food and Agriculture|volume=93|issue=12|pages=3126–3128|doi=10.1002/jsfa.6070|issn=1097-0010|pmid=23471845|doi-access=free}}</ref>

It is the major anthocyanin in ] (''Zea mays''). Purple corn is approved in Japan and listed in the "]" as ''purple corn color''.<ref>Anthocyanins isolated from purple corn (''Zea mays'' L.). Hiromitsu Aoki, Noriko Kuze and Yoshiaki Kato ( {{Webarchive|url=https://web.archive.org/web/20131029210237/http://www.ffcr.or.jp/zaidan/ffcrhome.nsf/7bd44c20b0dc562649256502001b65e9/c6698773361b42b249256ba60018e581/$FILE/anthocyanin-FFIJ199.pdf |date=2013-10-29 }})</ref>

== Biosynthesis ==
The biosynthesis of cyanidin 3-O-glucoside in '']'' was demonstrated by means of genetic engineering.<ref>{{cite journal |vauthors=Yan Y, Chemler J, Huang L, Martens S, Koffas MA |title=Metabolic engineering of anthocyanin biosynthesis in ''Escherichia coli'' |journal=Appl. Environ. Microbiol. |volume=71 |issue=7 |pages=3617–23 |year=2005 |pmid=16000769 |doi=10.1128/AEM.71.7.3617-3623.2005 |pmc=1169036|bibcode=2005ApEnM..71.3617Y }}</ref>

In '']'', a ], UGT79B1, is involved in the anthocyanin biosynthetic pathway. UGT79B1 protein converts cyanidin 3-O-glucoside to cyanidin 3-O-xylosyl(1→2)glucoside.<ref>{{cite journal | last1 = Yonekura-Sakakibara | first1 = Keiko | last2 = Fukushima | first2 = Atsushi | last3 = Nakabayashi | first3 = Ryo | last4 = Hanada | first4 = Kousuke | last5 = Matsuda | first5 = Fumio | last6 = Sugawara | first6 = Satoko | last7 = Inoue | first7 = Eri | last8 = Kuromori | first8 = Takashi | last9 = Ito | first9 = Takuya | last10 = Shinozaki | first10 = Kazuo | last11 = Wangwattana | first11 = Bunyapa | last12 = Yamazaki | first12 = Mami | year = 2012 | title = Two glycosyltransferases involved in anthocyanin modi?cation delineated by transcriptome independent component analysis in ''Arabidopsis thaliana'' | journal = The Plant Journal | volume = 69 | issue = 1| pages = 154–167 | doi = 10.1111/j.1365-313X.2011.04779.x | pmid = 21899608 | pmc=3507004}}</ref>

⚫ == References ==
{{Reflist}} {{Reflist}}


{{Anthocyanins}} {{Anthocyanins}}


] ]
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