Chrysanthemin: Difference between revisions

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	\| 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
	\| InChIKey = YTMNONATNXDQJF-UBNZBFALBB		\| InChIKey = YTMNONATNXDQJF-UBNZBFALBB
			\| StdInChI = 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
			\| StdInChIKey = YTMNONATNXDQJF-UBNZBFALSA-N
	\| CASNo_Ref = {{cascite\|correct\|CAS}}		\| CASNo_Ref = {{cascite\|correct\|CAS}}
	\| CASNo = 7084-24-4		\| CASNo = 7084-24-4

Revision as of 13:23, 12 November 2010

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	7084-24-4
3D model (JSmol)	Interactive image
ChemSpider	170681
ECHA InfoCard	100.027.622
PubChem CID	197081
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

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.

http://www.springerlink.com/content/p16q653041217g00/
http://www.springerlink.com/content/nv56926774865781/
http://www3.interscience.wiley.com/journal/113319245/abstract?CRETRY=1&SRETRY=0
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)
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)

3-Hydroxyanthocyanidins

O-Methylated anthocyanidins

Anthocyanins
(anthocyaninidin glycosides)

Glucosides:

Diglucosides:

Cyanin (Cyanidin 3,5-O-diglucoside)
Delphin (Delphinidin 3,5-O-diglucoside)
Malvin (Malvidin 3,5-diglucoside)
Pelargonin (Pelargonidin 3,5-O-diglucoside)
Peonin (Peonidin 3,5-O-diglucoside)
Petunin (Petunidin 3,5-O-diglucoside)

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-)	Cyanidin 3-O-(6-p-coumaroyl)glucoside Delphinidin 3-O-(6-p-coumaroyl)glucoside Malvidin 3-O-(6-p-coumaroyl)glucoside Petunidin 3-O-(6-p-coumaroyl)glucoside Peonidin 3-O-(6-p-coumaroyl)glucoside
Caffeoylated anthocyanins	Malvidin 3-O-(6-p-caffeoyl)glucoside Peonidin 3-O-(6-p-caffeoyl)glucoside
Malonylated anthocyanins	Malonylmalvin (malvidin 3-(6″-malonylglucoside)-5-glucoside)
Acylated anthocyanin diglycosides	Cyanidin 3-O-(di-p-coumarylglucoside)-5-glucoside Gentiodelphin (delphinidin 3-''O''-glucosyl-5-''O''-(6-''O''-caffeoyl-glucosyl)-3′-''O''-(6-''O''-caffeoyl-glucoside)) Nasunin (Delphinidin 3-(p-coumaroylrutinoside)-5-glucoside) Petanin (petunidin 3--5-O-β-D-glucopyranoside) Violdelphin (Delphinidin 3-rutinoside-7-O-(6-O-(4-(6-O-(4-hydroxybenzoyl)-β-D-glucosyl)oxybenzoyl)-β-D-glucoside)

Miscellaneous