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HomeProduct name listGlycyrrhizic acid

Glycyrrhizic acid

Synonym(s):3-O-(2-O-β-D-Glucopyranuronosyl-α-D-glucopyranuronosyl)-18β-glycyrrhetinic acid;GL;Glycyrrhetinic acid glycoside;Glycyrrhizic acid;Glycyrrhizinic acid

  • CAS NO.:1405-86-3
  • Empirical Formula: C42H62O16
  • Molecular Weight: 822.94
  • MDL number: MFCD00065194
  • EINECS: 215-785-7
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-12-18 13:37:16
Glycyrrhizic acid Structural

What is Glycyrrhizic acid?

Absorption

Glycyrrhizic acid is mainly absorbed after presystemic hydrolysis and formation of glycyrrhetinic acid. Therefore, after oral administration of a dose of 100 mg of glycyrrhizic acid, this major metabolite appears in plasma in a concentration of 200 ng/ml while glycyrrhizic acid cannot be found. The finding of a minimal amount of glycyrrhizic acid in urine suggests the existence of a partial absorption in the gastrointestinal tract.

Toxicity

Glycyrrhizic acid is thought to generate inhibition of 11-beta-hydroxysteroid dehydrogenase in the kidney which leads to elevated cortisol levels in the kidney. Intravenous administration of the ammoniated form was shown to produce convulsions and hemolysis.
Preclinical overdose studies have been shown to produce mineralocorticoid excess. The LD50 in preclinical studies was reported to be in the range of 308-12700 mg/kg.
Glycyrrhizic acid has been proven to not have mutagenic, genotoxic, teratogenic nor carcinogenic effects.

Chemical properties

White to off-white powder

Chemical properties

Glycyrrhizin, also known as glycyrrhizic acid, is a glycoside isolated from the roots of licorice, Glycyrrhiza glabra L. For improved water solubility, an ammoniated salt is commonly used. This can be in the form of either ammonium glycyrrhizinate or monoammonium glycyrrhizinate.

The Uses of Glycyrrhizic acid

Glycyrrhizic acid is a triterpene saponin used in the traditional Chinese medicinal preparation for its anti-inflammatory , antiulcerous and antiallergic effects.

The Uses of Glycyrrhizic acid

11beta-hydroxysteroid dehydrogenase inhibitor, antiinflammatory, expectorant, antihaemorrhagic, anti-HIV

The Uses of Glycyrrhizic acid

glycyrrhizic acid is a hydrolyzed glycyrrhizin. It is credited with antiinflammatory and anti-allergenic properties. Studies comparing glycyrrhizin with hydrocortisone found glycyrrhizin to be somewhat milder but longer lasting in effectiveness. once the application of hydrocortisone is suspended, the symptoms return. This does not appear to be the case with glycyrrhizin. It does not have side effects and is chemically stable so it can be safely used on a continuing basis.

The Uses of Glycyrrhizic acid

Glycyrrhizin is a flavorant and foaming agent derived from the separation of flavonoids found in the whole licorice extract from the licorice root glycyrrhiza glabra. It is 50–100 times as sweet as sugar, is soluble in water, and has a licorice taste. It has good heat stability but prolonged heating can result in some degradation. It is stable within ph 4–9; below ph 4 there could be precipitation. It has foaming and emulsifying properties in water, being used in cocktail mixes and soft drinks. It is used as a flavorant in bacon and imitation whipped products. It is synergistic with sugar, the sweetness being amplified to 100 times that of cane sugar alone. It is used as a sweetener in sugar-free chewing gum and low-fat sugar-free frozen desserts. It is also termed ammoniated glycyrrhizin. Monoammonium glycyrrhizinate is obtained by additional refinement.

Background

Glycyrrhizic acid is extracted from the root of the licorice plant; Glycyrrhiza glabra. It is a triterpene glycoside with glycyrrhetinic acid that possesses a wide range of pharmacological and biological activities. When extracted from the plant, it can be obtained in the form of ammonium glycyrrhizin and mono-ammonium glycyrrhizin. Glycyrrhizic acid has been developed in Japan and China as a hepatoprotective drug in cases of chronic hepatitis. From January 2014, glycyrrhizic acid as part of the licorice extract was approved by the FDA as an existing food sweetener. It was approved by Health Canada to be used in over-the-counter products but all the products are currently on the status canceled post marketed.

Indications

Glycyrrhizic acid is widely applied in foods as a natural sweetener. As a therapeutic agent, is has been used in a vast variety of formulations as it is reported to be anti-inflammatory, anti-ulcer, anti-allergic, antioxidant, anti-tumor, anti-diabetic and hepatoprotective. Due to this properties, its indications have been: treatment of premenstrual syndrome, treatment of viral infections, anti-lipidemic and antihyperglycemic. It is also known to be used as a remedy for peptic ulcer and other stomach diseases.

What are the applications of Application

Glycyrrhizic acid is a triterpene saponin

Definition

ChEBI: A triterpenoid saponin that is the glucosiduronide derivative of 3beta-hydroxy-11-oxoolean-12-en-30-oic acid.

Pharmacokinetics

Glycyrrhizic acid was reported to present antiallergic, antiviral and anti-inflammatory activities as well as improvements in glucose tolerance.
The effect of glycyrrhizic acid in metabolic syndrome generates a significant decrease in blood glucose, fasting blood glucose and mean serum insulin concentration.

Safety Profile

Poison by intravenous route. Moderately toxic by ingestion and intraperitoneal routes. Human systemic effects by ingestion: somnolence and changes in the metabolism of phosphorus, When heated to decomposition it emits acrid smoke and irritating fumes.

Metabolism

When orally administered, glycyrrhizic acid is almost completely hydrolyzed by intestinal bacteria for the formation of glycyrrhetinic acid, which is an active metabolite and can enter systemic circulation, and two molecules of glucuronic acid. This metabolite is transported and taken in the liver for its metabolization to form glucuronide and sulfate conjugates.

Properties of Glycyrrhizic acid

Melting point: 220°C (rough estimate)
Boiling point: 681.01°C (rough estimate)
alpha  D17 +46.2° (c = 1.5 in alc)
Density  1.1442 (rough estimate)
refractive index  61 ° (C=1.5, EtOH)
storage temp.  under inert gas (nitrogen or Argon) at 2-8°C
solubility  DMSO (Slightly), Ethanol (Slightly), Methanol (Sparingly), Pyridine (Slightly)
form  Solid
pka 2.76±0.70(Predicted)
color  White to Light Yellow
Odor at 100.00 %. mild spicy
Merck  14,4505
Stability: Hygroscopic
CAS DataBase Reference 1405-86-3
EPA Substance Registry System Glycyrrhizin (1405-86-3)

Safety information for Glycyrrhizic acid

Computed Descriptors for Glycyrrhizic acid

InChIKey BXFBITNYMHAJGT-KYXJNIQISA-N

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