Licoricesaponin F3

Upper classes

IDs and Links
LipidBank	[1]
LipidMaps	[2]
CAS	118441-83-1
KEGG	{{{KEGG}}}
KNApSAcK	[3]
CDX file
MOL file	Licoricesaponin F3.mol

Licoricesaponin F3
Structural Information
Systematic Name	(3beta,20beta,22beta)-22,29-Epoxy-29-oxoolean-12-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-2)-O-beta-D-glucopyranuronosyl-(1-2)-beta-D-glucopyranosiduronic acid
Common Name	Licoricesaponin F3 Saponin F3 from licorice 4,2-(Epoxymethano)picene beta-D-glucopyranosiduronic acid deriv. Oleanane beta-D-glucopyranosiduronic acid deriv.
Symbol
Formula	C48H72O19
Exact Mass	952.4667801219999
Average Mass	953.07388
SMILES	CC(C1)(C9=O)CC(O9)C(C8)(C)C1C(=C7)C(C8)(C(C6C7)(CCC(C62C)C(C)(C)C(OC(O3)C(OC(C(OC(C(O)5)OC(C)C(C(O)5)O)4)OC(C(O)=O)C(O)C(O)4)C(O)C(C3C(O)=O)O)CC2)C)C
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

M.P.	215 - 217 °C
IR (KBr)2	3600-3200 (br), 2940, 1760, 1720, 1456, 1340 cm-1
1H-NMR (C5D5N, 500 MHz)2	0.71 (s, CH3), 0.75 (s, CH3), 1.11 (s, CH3), 1.14 (s, CH3), 1.26 (s, 2xCH3), 1.55 (d, J=6.4 Hz, 3xH-6 of Rha), 3.27 (dd, J=4.4, 16.8 Hz, H-3), 4.96 (d, J=7.6 Hz, H-1 of Glc I), 5.40 (brs, H-12), 5.68 (d, J=6.9 Hz, H-1 of Glc II), 6.10 (brs, H-1 of Rha)

Dimethyl ester

M.P.	207 - 209 °C
IR (KBr)	3420, 1745 cm-1
1H-NMR (C5D5N, 500 MHz)1	4.92 (d, J=7.2 Hz, H-1 of Glc I), 5.67 (d, J=7.3 Hz, H-1 of Glc II) , 6.20 (brs, H-1 of Rha)
13C-NMR (C5D5N, 22.5MHz)2	C-3) 89.9, (11) 23.6, (12) 124.8, (13) 140.6, (18) 44.1, (22) 84.3, (24) 16.3, (29) 28.0, (30) 180.1 GlcUA I (1) 104.7, (2) 79.1, (3) 76.3, (4) 72.2, (5) 77.9, (6) 170.1, GlcUA II (1)102.4, (2) 78.2, (3) 76.6, (4) 72.8, (5) 77.6, (6) 169.8 Rha (1) 101.6, (2) 71.8, (3) 72.8, (4) 73.9, (5) 69.1, (6) 18.5

1) M. Yoshikawa et al., Chem.Pharm.Bull., 39, 244 (1991). 2) M. Yoshikawa et al., Chem.Pharm.Bull., 41, 1337 (1993).