Glycyrrhetic acid 3-O-β-D-glucuronide - ≥98% , CAS No.34096-83-8

CAS: 34096-83-8 Cat. No.: G646871 Molecular Weight: 646.81 PubChem CID: 161800

GRADE & PURITY ≥98%

Synonyms

A-D-Glucuronide | Glycyrrhetic Acid 3-O- | glycyrrhetinic acid 3-O-monoglucuronide | MS-30945 | 3-(Monoglucuron-1'-yl)-18-glycyrrhetic acid | Monazon | 3-MGA | 3-monoglucuronyl glycyrrhetinic acid | 3-O-beta-D-glucuronopyranosyl-18beta-glycyrrhetinic acid

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Glycyrrhetic acid 3-O-β-D-glucuronide, isolated from glycyrrhiza , is an important derivative of glycyrrhizin (GL) with an anti -allergic activity. 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 .Glycyrrhetic acid 3-O-β-D-glucuronide is valuable as a sweetener.

In Vitro

Glycyrrhetic acid 3-O-β-D-glucuronide can inhibit the release of β‐hexosaminidase from RBL‐2H3 cells with an IC 50 value of 0.28 mM. Glycyrrhetic acid 3-O-β-D-glucuronide (GAMG) significantly reduces the nitrite concentration in a dose-dependent manner with an IC 50 value of 120 μM in LPS‐induced RAW264.7 cells. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Form:Solid

Specifications

Synonyms

A-D-Glucuronide | Glycyrrhetic Acid 3-O- | glycyrrhetinic acid 3-O-monoglucuronide | MS-30945 | 3-(Monoglucuron-1'-yl)-18-glycyrrhetic acid | Monazon | 3-MGA | 3-monoglucuronyl glycyrrhetinic acid | 3-O-beta-D-glucuronopyranosyl-18beta-glycyrrhetinic acid

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Glycyrrhetic acid 3-O-β-D-glucuronide, isolated from glycyrrhiza , is an important derivative of glycyrrhizin (GL) with an anti -allergic activity. Glycyrrhetic acid 3-O-β-D-glucuronide (GAMG) shows that β‐glucuronidases (β‐GUS) are key GAMG-producin

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CC1(C2CCC3(C(C2(CCC1OC4C(C(C(C(O4)C(=O)O)O)O)O)C)C(=O)C=C5C3(CCC6(C5CC(CC6)(C)C(=O)O)C)C)C)C
• IUPAC 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
• InChIKey: HLDYLAJAWSKPFZ-QDPIGISRSA-N
• INCHI: 1S/C36H54O10/c1-31(2)21-8-11-36(7)27(34(21,5)10-9-22(31)45-29-25(40)23(38)24(39)26(46-29)28(41)42)20(37)16-18-19-17-33(4,30(43)44)13-12-32(19,3)14-15-35(18,36)6/h16,19,21-27,29,38-40H,8-15,17H2,1-7H3,(H,41,42)(H,43,44)/t19-,21-,22-,23-,24-,25+,26-,27+,29+,32+,33-,34-,35+,36+/m0/s1
• Isomeric SMILES: C[C@]12CC[C@](C[C@H]1C3=CC(=O)[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O)O)C)(C)C(=O)O
• PubChem CID: 161800
• Molecular Weight: 646.81

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Terpene glycosides
        • Level5 Triterpene glycosides
          • Level6 Triterpene saponins

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Terpene glycosides
• Intermediate Tree Nodes: Triterpene glycosides
• Direct Parent: Triterpene saponins
• Alternative Parents: Triterpenoids O-glucuronides Hexoses O-glycosyl compounds Cyclohexenones Beta hydroxy acids and derivatives Pyrans Oxanes Dicarboxylic acids and derivatives Secondary alcohols Polyols Oxacyclic compounds Carboxylic acids Acetals Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Triterpene saponin - Triterpenoid - O-glucuronide - 1-o-glucuronide - Glucuronic acid or derivatives - Hexose monosaccharide - O-glycosyl compound - Glycosyl compound - Cyclohexenone - Beta-hydroxy acid - Pyran - Oxane - Monosaccharide - Hydroxy acid - Dicarboxylic acid or derivatives - Secondary alcohol - Ketone - Oxacycle - Organoheterocyclic compound - Polyol - Carboxylic acid - Carboxylic acid derivative - Acetal - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Alcohol - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: DMSO : 250 mg/mL (386.51 mM; Need ultrasonic)
• Molecular Weight: 646.800 g/mol
• XLogP3: 5.100
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 4
• Exact Mass: 646.372 Da
• Monoisotopic Mass: 646.372 Da
• Topological Polar Surface Area: 171.000 Ų
• Heavy Atom Count: 46
• Formal Charge: 0
• Complexity: 1340.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 14
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1