Glycyrrhetinic Acid

• CAS: 471-53-4
• Catalog Number: ACM471534-1
• Category: Material of Cosmetics
• Molecular Weight: 470.64
• Molecular Formula: C30H46O4
• Description: Effect on adrenocortical hormone ; Anti-inflammatory and immunization effect ; Effect on digestive system; Antitussive and expectorant effect; Anti-tumor effect; Antidiuretic activity; Influence on auditory sense; Inhibiting effect on acetylcholin esterase; Cleaning function on oxygen radical
• IUPAC Name: (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid
• SMILES: CC1(C2CCC3(C(C2(CCC1O)C)C(=O)C=C4C3(CCC5(C4CC(CC5)(C)C(=O)O)C)C)C)C
• InChI: InChI=1S/C30H46O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21-23,32H,8-15,17H2,1-7H3,(H,33,34)/t19-,21-,22-,23+,26+,27-,28-,29+,30+/m0/s1
• InChI Key: MPDGHEJMBKOTSU-YKLVYJNSSA-N
• Appearance: White powder
• Effective Constituent: Enoxolone

Case Study

Glycyrrhetinic Acid for Inducing Lipid Peroxidation-Associated Cell Death in Tobacco BY-2 Cells

Hirase K, et al. Biochemical and Biophysical Research Communications, 2025, 772, 52062.

Glycyrrhetinic acid (GA) has been investigated for its ability to induce programmed cell death in plant cell systems. In a study using tobacco BY-2 suspension cells, GA was applied to evaluate its impact on mitochondrial function and oxidative damage. BY-2 cells from a 7-day stationary culture were diluted 1:95 and 1 mL of the suspension was dispensed into each well of a 24-well plate. Subsequently, 1 μL of GA solution was added, while dimethyl sulfoxide served as the control. The cultures were incubated at 27 °C in the dark with shaking at 130 rpm. Mitochondrial membrane potential and lipid peroxidation were monitored using fluorescence probes. GA treatment caused a pronounced decrease in mitochondrial membrane potential and a concurrent increase in lipid peroxidation, demonstrating that glycyrrhetinic acid effectively triggers mitochondrial dysfunction-associated oxidative cell death in rapidly proliferating plant cells.

Glycyrrhetinic Acid for the Synthesis of Biguanide Conjugates and Construction of Drug-Delivery Nanoparticles

Wang Y, et al. Molecular Pharmaceutics, 2026, 23, 224-238.

Glycyrrhetinic acid (GA) has been employed as a structural scaffold for the preparation of multifunctional nanocarriers. In this approach, GA was conjugated with 1-(2-aminoethyl) biguanide through an amide coupling reaction. GA (800 mg) and the coupling reagent HATU were dissolved in a dichloromethane-methanol mixture (2:1), followed by dropwise addition of the amine component in the presence of DIPEA. The reaction was stirred for 8 h and the product was precipitated using 5% HCl, then purified by silica gel chromatography to obtain the glycyrrhetinic acid-biguanide conjugate (GABG). Nanoparticles were subsequently fabricated by emulsion solvent evaporation. GABG dissolved in dichloromethane-ethanol was emulsified with aqueous surfactant solution and sonicated, followed by solvent removal and filtration (0.22 μm). Paclitaxel-loaded nanoparticles were prepared by co-dissolving the drug with GABG, demonstrating the utility of glycyrrhetinic acid derivatives in nanoparticle-based drug delivery systems.

Custom Q&A

What is the molecular formula of Glycyrrhetinic Acid?

The molecular formula of Glycyrrhetinic Acid is C30H46O4.

What is the molecular weight of Glycyrrhetinic Acid?

The molecular weight of Glycyrrhetinic Acid is 470.7 g/mol.

What is the role of Glycyrrhetinic Acid?

Glycyrrhetinic Acid has a role as an immunomodulator and a plant metabolite.

What is the IUPAC Name of Glycyrrhetinic Acid?

The IUPAC Name of Glycyrrhetinic Acid is (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid.

In which organisms can enoxolone (glycyrrhetic acid) be found?

Enoxolone (glycyrrhetic acid) can be found in Glycyrrhiza, Echinopora lamellosa, and other organisms.

What is the InChIKey of Glycyrrhetinic Acid?

The InChIKey of Glycyrrhetinic Acid is MPDGHEJMBKOTSU-YKLVYJNSSA-N.

What is the CAS number for Glycyrrhetinic Acid?

The CAS number for Glycyrrhetinic Acid is 471-53-4.

What is the XLogP3-AA value of Glycyrrhetinic Acid?

The XLogP3-AA value of Glycyrrhetinic Acid is 6.4.

How many hydrogen bond donor counts are there in Glycyrrhetinic Acid?

Glycyrrhetinic Acid has 2 hydrogen bond donor counts.

What is the ChEMBL ID for Glycyrrhetinic Acid?

The ChEMBL ID for Glycyrrhetinic Acid is CHEMBL230006.