Licoricesaponin D3

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Upper classes



Licoricesaponin D3
Licoricesaponin D3.png
Structural Information
Systematic Name (3beta,20beta,22beta)-22-(Acetyloxy)-20-carboxy-30-norolean-12-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(12)-O-beta-D-glucopyranuronosyl-(12)-beta-D-glucopyranosiduronic acid
Common Name
  • Licoricesaponin D3
  • 30-Noroleanane beta-D-glucopyranosiduronic acid deriv.
Symbol
Formula C50H76O21
Exact Mass 1012.487909494
Average Mass 1013.1258399999999
SMILES C(O7)(C(OC(O8)C(O)C(C(O)C8C)O)C(C(O)C7C(O)=O)O)OC(C(OC(C6(C)C)CCC(C26)(C)C(C5)C(C(C4=C5)(CCC(C)(C43)C(OC(C)=O)CC(C)(C(O)=O)C3)C)(CC2)C)1)C(O)C(C(O1)C(O)=O)O
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation
Reflactive Index
Solubility
Spectral Information
Mass Spectra
UV Spectra
IR Spectra
NMR Spectra
Chromatograms





Spectroscopic Data

Free acid
IR (KBr) 3700-3200 (br, OH), 2940, 1730 (ester), 1712 (COOH), 1410, 1065 cm-1
1H-NMR (C5D5N-D2O, 500 MHz) 0.89 (s, CH3), 0.91 (s, CH3), 0.99 (s, CH3), 1.13 (s, CH3), 1.21 (s, CH3), 1.28 (s, CH3), 1.38 (s, CH3), 1.79 (d, J=5.7 Hz, 3xH-6 of Rha), 2.16 (s, OCOCH3), 3.28 (dd, J=4.2, 11.0 Hz, H-3alpha), 4.59 (dd, J=2.6, 3.4 Hz, H-22), 5.02 (d, J=7.4 Hz, H-1 of GlcUA I), 5.34 (d, J=7.6 Hz, H-1 of GlcUA II), 5.44 (brs, H-12), 6.30 (brs, H-1 of Rha)
Trimethyl ester
M.P. 221 - 223 °C
13C-NMR (C5D5N, 22.5MHz) C-3) 89.9, (11) 23.6, (12) 122.2, (13) 143.6, (18) 44.0, (22) 77.5, (24) 16.4, (29) 29.1, (30) 177.2, (OCOCH3) 21.8, (OCOCH3) 170.1, (COOCH3) 51.2, 51.2, 51.6 GlcUA I (1) 104.7, (2) 79.1, (3) 76.2, (4) 72.2, (5) 77.9, (6) 169.6 GlcUA II (1)102.4, (2) 78.2, (3) 76.7, (4) 72.9, (5) 77.5, (6) 169.8 Rha (1) 101.6, (2) 71.9, (3) 72.9, (4) 73.9, (5) 69.2, (6) 18.5

M. Yoshikawa et al., Chem.Pharm.Bull., 41, 1337 (1993).

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