Cynaroside

Cynaroside (also known as luteoloside) is a flavone, a flavonoid-like chemical compound. It is a 7-O-glucoside of luteolin.

Cynaroside

Names
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
CAS Number	5373-11-5 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:27994 N
ChemSpider	4444241 N
ECHA InfoCard	100.023.968
KEGG	C03951 Y
PubChem CID	5280637
UNII	98J6XDS46I Y
CompTox Dashboard (EPA)	DTXSID50949617
InChI InChI=1S/C21H20O11/c22-7-16-18(27)19(28)20(29)21(32-16)30-9-4-12(25)17-13(26)6-14(31-15(17)5-9)8-1-2-10(23)11(24)3-8/h1-6,16,18-25,27-29H,7H2/t16-,18-,19+,20-,21-/m1/s1 N Key: PEFNSGRTCBGNAN-QNDFHXLGSA-N N InChI=1/C21H20O11/c22-7-16-18(27)19(28)20(29)21(32-16)30-9-4-12(25)17-13(26)6-14(31-15(17)5-9)8-1-2-10(23)11(24)3-8/h1-6,16,18-25,27-29H,7H2/t16-,18-,19+,20-,21-/m1/s1 Key: PEFNSGRTCBGNAN-QNDFHXLGBE
SMILES C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O
Properties
Chemical formula	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). N verify (what is YN ?) Infobox references

Natural occurrences

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]

In food

It can be found in dandelion (the highest concentration in the flowers,^[5] but also in the roots) and in Cynara scolymus (artichoke).^[6]

Metabolism

Flavone 7-O-beta-glucosyltransferase adds a glucose to luteolin.

A cynaroside 7-O-glucosidase has been identified in the artichoke.^[6]

Spectral data

UV-Vis[7]
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 (1H, t, J = 9.0 Hz, H-2″), 3.56 (1H, t, J = 9.0 Hz, H-3″), 3.60 (1H, m, H-5″) , 3.68 (1H, dd, J = 12.2, 5.6 Hz, H-6a″), 3.85 (1H, dd, J = 12.2, 1.8 Hz, H-6b″), 5.10 (1H, d, J = 7.8 Hz, H-1″), 6.44 (1H, d, J = 1.8 Hz, H-6), 6.63 (1H, s, H-3), 6.83 (1H, d, J = 1.8 Hz, H-8), 6.95 (1H, d, J = 8.0 Hz, H-5′), 7.41 (1H, d, J = 8.0 Hz, H-6′), 7.43 (1H, bs, H-2′)
Carbon-13 NMR	13C-NMR (125 MHz, CD3COCD3 + D2O): δ 61.7 (C-6″), 70.3 (C-4″), 73.8 (C-2″), 76.8 (C-3″), 77.4 (C-5″), 95.8 (C-8), 100.5 (C-6), 100.7 (C-1″), 103.7 (C-3), 106.3 (C-10), 113.8 (C-2″), 116.5 (C-5′), 120.3 (C-6′), 122.6 (C-1′), 146.3(C-3′), 150.4 (C-4′), 158.0 (C-9), 161.8 (C-5), 163.9 (C-7), 165.8(C-2), 183.1 (C-4)
Other NMR data
MS
Masses of main fragments	ESI-MS [M+H]+ m/z 449.1