Glycyrrhizin

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{{Metabolite
 
{{Metabolite
|SysName=(3.beta.,20.beta.)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-.beta.-D-glucopyranuronosyl-.alpha.-D-Glucopyranosiduronic acid
+
|SysName=(3beta,20beta)-20-Carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-beta-D-glucopyranuronosyl-alpha-D-glucopyranosiduronic acid
|Common Name=Glycyrrhizic acid (8CI)&& 30-Noroleanane, .alpha.-D-glucopyranosiduronic acid deriv.&& 18.beta.-Glycyrrhizic acid&& Glycyron&& Glycyrrhetinic acid glycoside&& Glycyrrhizin&& Glycyrrhizinic acid&& NSC 167409&& NSC 234419&& Potenlini&& .beta.-Glycyrrhizin
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|Common Name=&&Glycyrrhizin&&Glycyrrhizic acid&&30-Noroleanane alpha-D-glucopyranosiduronic acid deriv.&&18beta-Glycyrrhizic acid&& Glycyron&&Glycyrrhetinic acid glycoside&&Glycyrrhizinic acid&&Potenlini&&beta-Glycyrrhizin
 
|CAS=1405-86-3
 
|CAS=1405-86-3
 
|KNApSAcK=
 
|KNApSAcK=
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==Mass Spectral Data==
 
==Mass Spectral Data==
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 +
[[Image:Glycyrrhizin_PosMS.jpg|thumb|600px|left|Positive ESI ]]
 +
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[[Image:Glycyrrhizin_PosMS2.jpg|thumb|left|600px|Positive ESI MS<sup>2</sup> from 823.4038 (M+H)<sup>+</sup>
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]]
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[[Image:Glycyrrhizin_NegMS.jpg|thumb|600px|left|Negative ESI ]]
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[[Image:Glycyrrhizin_NegMS2.jpg|thumb|left|600px|Negative ESI MS<sup>2</sup> from 821.3656 (M-H)<sup>-</sup>
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]]
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{| class="wikitable" style="width:80%"
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|-
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| Instrument || Shimadzu LC-IT-TOF MS ESI
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|-
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| Column || Waters Atlantis T3 (2.1 mm x 150 mm)
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|-
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| Column Temperature|| 40 °C 
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|-
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| Solvent A || 5 mM Ammonium acetate solution
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|-
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| Solvent B || acetonitrile
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|-
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| Gradient || 10% to 100% Solvent B (0-30 min), 100% Solvent B (30-40 min)
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|-
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| Source voltage || – 3.5 kV (negative), 4.5 kV (positive)
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|-
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| Capillary temperature || 200 °C
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|-
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| Nebulizer gas || 1.5 l/min
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|}
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==Proposed Fragmentation Pathway==
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[[Image:Glycyrrhizin_fragment.jpg|thumb|900px|none|Meng et al., Chin.J.Chem., 27, 299-305 (2009)]]
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==Spectroscopic Data==
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{| class="wikitable" style="width:80%"
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|-
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| '''M.P.'''<sup>1</sup> || 217 °C (decomp.)
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|-
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| '''IR''' (KBr)<sup>1</sup> || 3400, 1720, 1640 cm<sup>-1</sup>
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|-
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| '''<sup>13</sup>C-NMR''' (CDCl<sub>3</sub>, 22.5MHz)<sup>2</sup>|| C-1) 40.15, (2) 26.96, (3) 90.74, (4) 40.47, (5) 56.40, (6) 18.34, (7) 32.87, (8) 44.49, (9) 62.99, (10) 37.89, (11) 202.52, (12) 128.79, (13) 171.90, (14) 46.64, (15) 27.48, (16) 27.32, (17) 32.87, (18) 49.77, (19) 42.27, (20) 44.47, (21) 31.92, (22) 38.91, (23) 28.20, (24) 16.78, (25) 16.97, (26) 19.27, (27) 23.83, (28) 28.72, (29) 29.15, (30) 180.26 '''GlcUA I''' (1) 106.01, (2) 83.78, (3) 77.03, (4) 72.85, (5) 76.05, (6) 172.29 '''GlcUA II''' (1) 105.10, (2) 76.05, (3) 77.35, (4) 72.75, (5) 77.09, (6) 172.29 
 +
|}
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<small>1) M.-T. Wang et al., Yaoxue Xuebao, 21, 510 (1986)., 2) G.A. Tolstikov et al., Khim.Prir.Soedin., 25, 500 (1989).</small>
 +
 +
== 関連項目 ==
 +
*[[CrudeDrug:Glycyrrhizae Radix]]
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*[[Glycyrrhizae Radix LC-MS]]

Latest revision as of 08:58, 9 February 2010



Upper classes



Glycyrrhizin
Glycyrrhizin.png
Structural Information
Systematic Name (3beta,20beta)-20-Carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-beta-D-glucopyranuronosyl-alpha-D-glucopyranosiduronic acid
Common Name
  • Glycyrrhizin
  • Glycyrrhizic acid
  • 30-Noroleanane alpha-D-glucopyranosiduronic acid deriv.
  • 18beta-Glycyrrhizic acid
  • Glycyron
  • Glycyrrhetinic acid glycoside
  • Glycyrrhizinic acid
  • Potenlini
  • beta-Glycyrrhizin
Symbol
Formula C42H62O16
Exact Mass 822.4037859360001
Average Mass 822.93208
SMILES C(C7(C)2)(=CC(C(C7(C)6)C(C5CC6)(CCC(C5(C)C)OC(C(OC(O4)C(O)C(O)C(O)C4C(O)=O)3)OC(C(O)C3O)C(O)=O)C)=O)C(C1(CC2)C)CC(CC1)(C)C(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




Contents

[edit] Mass Spectral Data

Positive ESI
Positive ESI MS2 from 823.4038 (M+H)+
Negative ESI


Negative ESI MS2 from 821.3656 (M-H)-
Instrument Shimadzu LC-IT-TOF MS ESI
Column Waters Atlantis T3 (2.1 mm x 150 mm)
Column Temperature 40 °C
Solvent A 5 mM Ammonium acetate solution
Solvent B acetonitrile
Gradient 10% to 100% Solvent B (0-30 min), 100% Solvent B (30-40 min)
Source voltage – 3.5 kV (negative), 4.5 kV (positive)
Capillary temperature 200 °C
Nebulizer gas 1.5 l/min


[edit] Proposed Fragmentation Pathway

Meng et al., Chin.J.Chem., 27, 299-305 (2009)


[edit] Spectroscopic Data

M.P.1 217 °C (decomp.)
IR (KBr)1 3400, 1720, 1640 cm-1
13C-NMR (CDCl3, 22.5MHz)2 C-1) 40.15, (2) 26.96, (3) 90.74, (4) 40.47, (5) 56.40, (6) 18.34, (7) 32.87, (8) 44.49, (9) 62.99, (10) 37.89, (11) 202.52, (12) 128.79, (13) 171.90, (14) 46.64, (15) 27.48, (16) 27.32, (17) 32.87, (18) 49.77, (19) 42.27, (20) 44.47, (21) 31.92, (22) 38.91, (23) 28.20, (24) 16.78, (25) 16.97, (26) 19.27, (27) 23.83, (28) 28.72, (29) 29.15, (30) 180.26 GlcUA I (1) 106.01, (2) 83.78, (3) 77.03, (4) 72.85, (5) 76.05, (6) 172.29 GlcUA II (1) 105.10, (2) 76.05, (3) 77.35, (4) 72.75, (5) 77.09, (6) 172.29

1) M.-T. Wang et al., Yaoxue Xuebao, 21, 510 (1986)., 2) G.A. Tolstikov et al., Khim.Prir.Soedin., 25, 500 (1989).

[edit] 関連項目

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