(2S)-2,3-dihydrobilobetin

(2S)-2,3-dihydrobilobetin

Common Name: (2S)-2,3-dihydrobilobetin

Synonyms: (2S)-2,3-dihydro-4′-O-methylamentoflavone

CAS Registry Number: 1126431-68-2

InChI:

InChIKey:

Formula: C31H22O10

Molecular Weight: 554.507

Exact Mass: 554.1213

NMR Solvent: acetone-d6

MHz: 400 (1H), 100 (13C)

Calibration: Chemical shifts were standardized to the solvent resonances (CDCl3 7.24 ppm, CD3OD 4.78, 3.31ppm, acetone-d6 2.05 ppm, and DMSO-d6 2.5ppm).

NMR references: Moawad, A., Hetta, M., Zjawiony, J., Jacob, M., Hifnawy, M., Ferreira, D. (2010). Phytochemical Investigation of Cycas circinalis and Cycas revoluta Leaflets: Moderately Active Antibacterial Biflavonoids. Planta Med. 76, 796-802.

Species: Cycas circinalis - Moawad, A., Hetta, M., Zjawiony, J., Jacob, M., Hifnawy, M., Ferreira, D. (2010). Phytochemical Investigation of Cycas circinalis and Cycas revoluta Leaflets: Moderately Active Antibacterial Biflavonoids. Planta Med. 76, 796-802.

Notes:

Proton NMR Peaks

Position PPM Peak Type J (Hz)
2 5.6 dt 13, 2.8
3-ax 3.38 m
3-ax 3.21 m
3-eq 2.9 m
3-eq 2.73 m
6 5.96 s
8 5.99 s
2' 7.71 m
5' 7.24 d 9.1
6' 7.62 m
3" 6.65 s
6" 6.43 s
2''' 7.6 dd 8, 5.2
3''' 6.97 m
5''' 6.85 m
6''' 7.6 dd 8, 5.2
5-OH 12.18 s
5"-OH 13.12 s
4'-OCH3 3.79 s

Carbon NMR Peaks

Position PPM
2 79.08
2 79
3 43.06
3 42.7
4 196.23
4 196.2
5 164.4
6 96.1
7 166.5
8 95.1
9 (may be interchanged with 7") 163.5
10 102.3
1' 130.91
1' 130.76
2' 131.5
2' 131.31
3' 121.02
3' 120.93
4' 158.3
4' 158.26
5' 111.23
5' 111.15
6' 127.99
6' 127.95
2" 164.01
2" 163.98
3" 102.68
3" 102.63
4" 182.6
5" 161.5
6" 98.8
7" (may be interchanged with 9) 161.4
8" 104.7
9" 154.8
10" 104.5
1''' 122.3
2''' 128.24
2''' 128.19
3''' 115.9
4''' 161
5''' 115.9
6''' 128.24
6''' 128.19
4'-OCH3 55.2