Chimarrhoside

Chimarrhoside

Common Name: Chimarrhoside

Synonyms: 5-hydroxy-7-((5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-7-yl)oxy)-2-(4-hydroxyphenyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

CAS Registry Number: 887503-97-1

InChI:

InChIKey:

Formula: C54H58O29

Molecular Weight: 1171.029

Exact Mass: 1170.3064

NMR Solvent: CD3OD

MHz: 500 (1H), 125 (13C)

Calibration: residual proton solvent resonance (CD3OD at δ 3.33 and 49.0 for 1H and 13C NMR, respectively)

NMR references: Cardoso, C., Silva, D., Castro-Gamboa, I., Bolzani, V. (2005). New Biflavonoid and Other Flavonoids from the Leaves of Chimarrhis turbinata and their Antioxidant Activities. J. Braz. Chem. Soc. 16, 1353-1359.

Species: Chimarrhis turbinata - Cardoso, C., Silva, D., Castro-Gamboa, I., Bolzani, V. (2005). New Biflavonoid and Other Flavonoids from the Leaves of Chimarrhis turbinata and their Antioxidant Activities. J. Braz. Chem. Soc. 16, 1353-1359.

Notes: *positions have a 1H ppm range of 3.00-4.00

Proton NMR Peaks

Position PPM Peak Type J (Hz)
6 6.13 br s
8 6.31 br s
2' 8.08 d 8.9
3' 6.88 d 8.9
1" 5.12 d 7.7
2"* 3.5 m
3"* 3.5 m
4"* 3.5 m
5"* 3.5 m
6" 3.64 dd 9, 5.5
6'' 3.79 dd 9, 6
1''' 4.4 br s
2'''* 3.5 m
3'''* 3.5 m
4'''* 3.5 m
5'''* 3.5 m
6''' 1.17 d 6.2
6 6.13 br s
8 6.31 br s
2' 8.05 d 8.9
3' 6.87 d 8.9
1" 5.02 d 7.7
2"* 3.5 m
3"* 3.5 m
4"* 3.5 m
5"* 3.5 m
6" 2.64 s
1''' 4.6 br s
2'''* 3.5 m
3'''* 3.5 m
4'''* 3.5 m
5'''* 3.5 m
6''' 1.11 d 6.2

Carbon NMR Peaks

Position PPM
2 157.1
3 134.2
4 179
5 161.5
6 98.5
7 164.6
8 93.4
9 158.5
10 105.6
1' 126.3
2' 130.9
3' 114.6
4' 161.1
5' 114.6
6' 130.9
1" 103.1
2" 74.3
3" 76.6
4" 70.1
5" 75.7
6" 67.1
1''' 100.9
2''' 70.8
3''' 70.6
4''' 72.4
5''' 68.6
6''' 16.4
2 157.1
3 134.2
4 179.1
5 161.5
6 98.5
7 164.6
8 93.4
9 158.2
10 105.9
1' 126.3
2' 130.9
3' 114.6
4' 160.9
5' 114.6
6' 130.9
1" 104
2" 71.5
3" 73.6
4" 68.2
5" 73.9
6" 65.9
1''' 100.4
2''' 69.9
3''' 71.5
4''' 72.5
5''' 68.2
6''' 16.6