Protoapigenone-(8-3")-apigenin

Protoapigenone-(8-3")-apigenin

Common Name: Protoapigenone-(8-3")-apigenin

Synonyms: [3,​8'-​Bi-​4H-​1-​benzopyran]​-​4,​4'-​dione, 5,​5',​7,​7'-​tetrahydroxy-​2'-​(1-​hydroxy-​4-​oxo-​2,​5-​ cyclohexadien-​1-​yl)​-​2-​(4-​hydroxyphenyl)​-

CAS Registry Number: 1344034-52-1

InChI:

InChIKey:

Formula: C30H18O11

Molecular Weight: 554.46

Exact Mass: 554.0849

NMR Solvent: acetone-d6

MHz: 200 (1H), 400(13C)

Calibration: TMS

NMR references: Hunyadi, A., Chuang, D., Danko, B., Chiang, M., Lee, C., Wang, H., Wu, C., Chang, F., Wu, Y. (2011). Direct Semi-Synthesis of the Anticancer Lead-Drug Protoapigenone from Apigenin, and Synthesis of Further New Cytotoxic Protoflavone Derivatives. PLoS ONE 6, e23922.

Species: synthesis - Hunyadi, A., Chuang, D., Danko, B., Chiang, M., Lee, C., Wang, H., Wu, C., Chang, F., Wu, Y. (2011). Direct Semi-Synthesis of the Anticancer Lead-Drug Protoapigenone from Apigenin, and Synthesis of Further New Cytotoxic Protoflavone Derivatives. PLoS ONE 6, e23922.

Notes:

Proton NMR Peaks

Position PPM Peak Type J (Hz)
3 6.57 s
5-OH 12.65 s
6 6.3 s
2', 6' 6.81 dd 10, 3.2
2', 6' 6.76 dd 9.6, 3.2
3', 5' 6.08 dd 10, 2
3', 5' 5.85 dd 10, 1.6
5"-OH 12.87 s
6" 6.29 d 2
8" 6.5 d 2
2''', 3''' 7.38 d 8.8
3''', 5''' 6.78 d 8.8

Carbon NMR Peaks

Position PPM
2 168.8
3 108
4 184.1
10 106.1
5 163.5
6 100.5
7, 5" 163.9
8 101.3
9 164
1' 71.3
2', 6' 148.1
2', 6' 148
3', 5' 130.6
3', 5' 130.5
4' 185.2
2" 165.4
3" 111.3
4" 182.5
10'' 105.3
6" 100.3
7" 165.8
8" 95.4
9'' 159.5
1''' 125.3
2''', 6''' 131.6
3''', 5''' 116.7
4''' 161.4