Glycyrrhetic acid 3-O-mono-beta-D-glucuronide

Modify Date: 2024-01-02 15:43:11

Glycyrrhetic acid 3-O-mono-beta-D-glucuronide Structure
Glycyrrhetic acid 3-O-mono-beta-D-glucuronide structure
Common Name Glycyrrhetic acid 3-O-mono-beta-D-glucuronide
CAS Number 34096-83-8 Molecular Weight 646.80800
Density 1.31g/cm3 Boiling Point 785ºC at 760mmHg
Molecular Formula C36H54O10 Melting Point N/A
MSDS N/A Flash Point 240.7ºC

 Use of Glycyrrhetic acid 3-O-mono-beta-D-glucuronide


Glycyrrhetic acid 3-O-β-D-glucuronide, isolated from glycyrrhiza, is an important derivative of glycyrrhizin (GL) with an anti -allergic activity[1]. Glycyrrhetic acid 3-O-β-D-glucuronide (GAMG) shows that β‐glucuronidases (β‐GUS) are key GAMG-producing enzymes, displaying a high potential to convert GL directly into GAMG[2].Glycyrrhetic acid 3-O-β-D-glucuronide is valuable as a sweetener.

 Names

Name (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Synonym More Synonyms

  Biological Activity

Description Glycyrrhetic acid 3-O-β-D-glucuronide, isolated from glycyrrhiza, is an important derivative of glycyrrhizin (GL) with an anti -allergic activity[1]. Glycyrrhetic acid 3-O-β-D-glucuronide (GAMG) shows that β‐glucuronidases (β‐GUS) are key GAMG-producing enzymes, displaying a high potential to convert GL directly into GAMG[2].Glycyrrhetic acid 3-O-β-D-glucuronide is valuable as a sweetener.
Related Catalog
In Vitro Glycyrrhetic acid 3-O-β-D-glucuronide can inhibit the release of β‐hexosaminidase from RBL‐2H3 cells with an IC50 value of 0.28 mM[2]. Glycyrrhetic acid 3-O-β-D-glucuronide (GAMG) significantly reduces the nitrite concentration in a dose-dependent manner with an IC50 value of 120 μM in LPS‐induced RAW264.7 cells[2].
References

[1]. Park HY,et al. Anti-allergic activity of 18beta-glycyrrhetinic acid-3-O-beta-D-glucuronide.Arch Pharm Res. 2004 Jan;27(1):57-60.

[2]. Lichun Guo,et al. Glycyrrhetic Acid 3‐O‐Mono‐β‐d‐glucuronide (GAMG): An Innovative High‐Potency Sweetener with Improved Biological Activities. Comprehensive Reviews in Food Science and Food Safety 

 Chemical & Physical Properties

Density 1.31g/cm3
Boiling Point 785ºC at 760mmHg
Molecular Formula C36H54O10
Molecular Weight 646.80800
Flash Point 240.7ºC
Exact Mass 646.37200
PSA 170.82000
LogP 4.32910

 Synthetic Route

~93%

Glycyrrhetic acid 3-O-mono-beta-D-glucuronide Structure

Glycyrrhetic ac...

CAS#:34096-83-8

Literature: Ruiz, Maria Carmen del Ruiz; Amer, Hassan; Stanetty, Christian; Beseda, Igor; Czollner, Laszlo; Shah, Priti; Jordis, Ulrich; Kueenburg, Bernhard; Classen-Houben, Dirk; Hofinger, Andreas; Kosma, Paul Carbohydrate Research, 2009 , vol. 344, # 9 p. 1063 - 1071

~93%

Glycyrrhetic acid 3-O-mono-beta-D-glucuronide Structure

Glycyrrhetic ac...

CAS#:34096-83-8

Literature: Kanaoka; Yano; Kato; Nakada Chemical and Pharmaceutical Bulletin, 1986 , vol. 34, # 12 p. 4978 - 4983

~%

Glycyrrhetic acid 3-O-mono-beta-D-glucuronide Structure

Glycyrrhetic ac...

CAS#:34096-83-8

Literature: Chemical and Pharmaceutical Bulletin, , vol. 34, # 12 p. 4978 - 4983

~%

Glycyrrhetic acid 3-O-mono-beta-D-glucuronide Structure

Glycyrrhetic ac...

CAS#:34096-83-8

Literature: Chemical and Pharmaceutical Bulletin, , vol. 37, # 2 p. 551 - 553

~%

Glycyrrhetic acid 3-O-mono-beta-D-glucuronide Structure

Glycyrrhetic ac...

CAS#:34096-83-8

Literature: Bioscience, biotechnology, and biochemistry, , vol. 58, # 3 p. 554 - 555

 Synonyms

Glycyrrhetyl 3-monoglucuronide
Glycyrrhetic Acid 3-O-Glucuronide
3-monoglucuronylglycyrrhetinic acid
Starrhizin
3-MGA
glycyrrhetic acid mono-glucuronide
Glycyrrhetinic acid 3-O-mono-beta-D-glucuronide