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Chemical compound From Wikipedia, the free encyclopedia
Cynaroside (also known as luteoloside) is a flavone, a flavonoid-like chemical compound. It is a 7-O-glucoside of luteolin.
Names | |
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IUPAC name
7-(β-D-Glucopyranosyloxy)-3′,4′,5-trihydroxysexflavone | |
Systematic IUPAC name
2-(3,4-Dihydroxyphenyl)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-69-(hydroxymethyl)oxan-2-yl]oxy}-4H-1-benzopyran-4-one | |
Other names
Glucoluteolin Luteoloside Cinaroside 7-Glucoluteolin 7-Glucosylluteolin Luteolin 7-glucoside Luteolin-7-glucoside Luteolin 7-O-glucoside Luteolin-7-O-glucoside | |
Identifiers | |
3D model (JSmol) |
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ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.023.968 |
KEGG | |
PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
C21H20O11 | |
Molar mass | 4488.37 g/mol |
Appearance | Yellow amorphous powder |
Melting point | 266 to 268 °C (511 to 514 °F; 539 to 541 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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It can be found in Ferula varia and F. foetida[1] in Campanula persicifolia and C. rotundifolia,[2] in the bamboo Phyllostachys nigra,[3] and in Teucrium gnaphalodes.[4]
It can be found in dandelion (the highest concentration in the flowers,[5] but also in the roots) and in Cynara scolymus (artichoke).[6]
Flavone 7-O-beta-glucosyltransferase adds a glucose to luteolin.
A cynaroside 7-O-glucosidase has been identified in the artichoke.[6]
UV-Vis[7] | |
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Lambda-max | UV : 348, 260 nm |
Extinction coefficient | (log ε): 4.11, 4.23 |
IR | |
Major absorption bands | ? cm−1 |
NMR | |
Proton NMR | 1H-NMR (500 MHz, CD3COCD3 + D2O): δ 3.42 (1H, t, J = 9.0 Hz, H-4′), 3.49 |
Carbon-13 NMR | 13C-NMR (125 MHz, CD3COCD3 + D2O): δ 61.7 (C-6″), 70.3 (C-4″), 73.8 (C-2″), |
Other NMR data | |
MS | |
Masses of main fragments |
ESI-MS [M+H]+ m/z 449.1 |
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