Licoricesaponin G2

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{{Metabolite
 
{{Metabolite
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|SysName=(3.beta.,4.beta.,20.beta.)-20-carboxy-23-hydroxy-11-oxo-30-norolean-12-en-3-yl 2-O-.beta.-D-glucopyranuronosyl-.beta.-D-Glucopyranosiduronic acid
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|SysName=(3beta,4beta,20beta)-20-Carboxy-23-hydroxy-11-oxo-30-norolean-12-en-3-yl 2-O-beta-D-glucopyranuronosyl-beta-D-glucopyranosiduronic acid
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|Common Name=&&Licoricesaponin G2&&30-Noroleanane, .beta.-D-glucopyranosiduronic acid deriv.&& 24-Hydroxyglycyrrhizin&& Saponin G2, from licorice
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|Common Name=&&Licoricesaponin G2&&30-Noroleanane beta-D-glucopyranosiduronic acid deriv.&&24-Hydroxyglycyrrhizin&&Saponin G2 from licorice&&
 
|CAS=118441-84-2
 
|CAS=118441-84-2
 
|KNApSAcK=
 
|KNApSAcK=
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==Mass Spectral Data==
 
==Mass Spectral Data==
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==Spectroscopic Data==
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{| class="wikitable" style="width:80%"
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'''Free acid'''
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|-
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| '''M.P.'''<sup>1</sup> || 229 - 230 °C
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|-
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| '''IR''' (KBr)<sup>2</sup>|| 3500-3000 (br), 2910, 1720, 1648, 1385, 1040 cm<sup>-1</sup>
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|-
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| '''<sup>1</sup>H-NMR''' (C<sub>5</sub>D<sub>5</sub>N, 500 MHz)<sup>2</sup>|| 0.78 (s, CH3), 1.05 (s, CH3), 1.20 (s, CH3), 1.34 (s, CH3), 1.43 (s, CH3), 1.48 (s, CH3), 2.99 (brd, ''J''=''ca.'' 14.0 Hz, H-18), 3.52 (dd, ''J''=4.8, 11.0 Hz, H-3), 4.58 (d, ''J''=10.6 Hz, H-24A), 4.68 (d, ''J''=10.6 Hz, H-24B), 5.64 (d, ''J''=7.0 Hz, H-1 of GlcUA II), 5.94 (s, H-12)
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|-
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| '''<sup>13</sup>C-NMR''' (C<sub>5</sub>D<sub>5</sub>N, 22.5MHz)<sup>2</sup>|| 63.1 (C-24), 104.4, 104.9 (C-1 of Glc-I and C-1 of GlcII)
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|}
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{| class="wikitable" style="width:80%"
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'''Trimethyl ester'''
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|-
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| '''M.P.'''<sup>1</sup> || 176 - 178 °C
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|-
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| '''IR''' (KBr)<sup>1</sup>|| 3367, 1720, 1648 cm<sup>-1</sup>
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|-
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| '''<sup>1</sup>H-NMR''' (C<sub>5</sub>D<sub>5</sub>N, 500 MHz)<sup>1</sup>|| 4.94 (d, ''J''=7.9 Hz, H-1 of Glc I), 5.56 (d, ''J''=7.6 Hz, H-1 of Glc II)
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|-
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| '''<sup>13</sup>C-NMR''' (C<sub>5</sub>D<sub>5</sub>N, 22.5MHz)<sup>2</sup>|| C-3) 89.9, (11) 198.9, (12) 128.6, (13) 168.7, (18) 44.2, (22) 38.2, (24) 63.1, (29) 28.0, (30) 176.5 '''GlcUA I''' (1) 104.1, (2) 81.9, (3) 75.2, (4) 72.2, (5) 77.2, (6) 169.6 '''GlcUA II''' (1)105.6, (2) 76.5, (3) 76.8, (4) 72.2, (5) 77.2, (6) 169.6 
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|}
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<small>1) M. Yoshikawa et al., Chem.Pharm.Bull., 39, 244 (1991). 2) M. Yoshikawa et al., Chem.Pharm.Bull., 41, 1337 (1993).</small>

Revision as of 11:45, 9 February 2010



Upper classes



IDs and Links
LipidBank [1]
LipidMaps [2]
CAS 118441-84-2
KEGG {{{KEGG}}}
KNApSAcK

[3]

CDX file
MOL file Licoricesaponin G2.mol
Licoricesaponin G2
Licoricesaponin G2.png
Structural Information
Systematic Name (3beta,4beta,20beta)-20-Carboxy-23-hydroxy-11-oxo-30-norolean-12-en-3-yl 2-O-beta-D-glucopyranuronosyl-beta-D-glucopyranosiduronic acid
Common Name
  • Licoricesaponin G2
  • 30-Noroleanane beta-D-glucopyranosiduronic acid deriv.
  • 24-Hydroxyglycyrrhizin
  • Saponin G2 from licorice
Symbol
Formula C42H62O17
Exact Mass 838.398700558
Average Mass 838.93148
SMILES CC(C71)(CCC(C7=6)(C(C(C(C6)=O)2)(CCC(C(C)3CO)C2(C)CCC(OC(O5)C(C(C(C(C(O)=O)5)O)O)OC(C(O)4)OC(C(O)=O)C(O)C4O)3)C)C)CCC(C(O)=O)(C)C1
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation
Reflactive Index
Solubility
Spectral Information
Mass Spectra
UV Spectra
IR Spectra
NMR Spectra
Chromatograms




Glycyrrhizae Radix LC-MS


Mass Spectral Data

Spectroscopic Data

Free acid
M.P.1 229 - 230 °C
IR (KBr)2 3500-3000 (br), 2910, 1720, 1648, 1385, 1040 cm-1
1H-NMR (C5D5N, 500 MHz)2 0.78 (s, CH3), 1.05 (s, CH3), 1.20 (s, CH3), 1.34 (s, CH3), 1.43 (s, CH3), 1.48 (s, CH3), 2.99 (brd, J=ca. 14.0 Hz, H-18), 3.52 (dd, J=4.8, 11.0 Hz, H-3), 4.58 (d, J=10.6 Hz, H-24A), 4.68 (d, J=10.6 Hz, H-24B), 5.64 (d, J=7.0 Hz, H-1 of GlcUA II), 5.94 (s, H-12)
13C-NMR (C5D5N, 22.5MHz)2 63.1 (C-24), 104.4, 104.9 (C-1 of Glc-I and C-1 of GlcII)
Trimethyl ester
M.P.1 176 - 178 °C
IR (KBr)1 3367, 1720, 1648 cm-1
1H-NMR (C5D5N, 500 MHz)1 4.94 (d, J=7.9 Hz, H-1 of Glc I), 5.56 (d, J=7.6 Hz, H-1 of Glc II)
13C-NMR (C5D5N, 22.5MHz)2 C-3) 89.9, (11) 198.9, (12) 128.6, (13) 168.7, (18) 44.2, (22) 38.2, (24) 63.1, (29) 28.0, (30) 176.5 GlcUA I (1) 104.1, (2) 81.9, (3) 75.2, (4) 72.2, (5) 77.2, (6) 169.6 GlcUA II (1)105.6, (2) 76.5, (3) 76.8, (4) 72.2, (5) 77.2, (6) 169.6

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

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