| Glycyrrhizin | |
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(3β,18α)-30-hydroxy-11,30-dioxoolean-12-en-3-yl 2-O-β-D-glucopyranuronosyl-β-D-glucopyranosiduronic acid |
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Other names
Glycyrrhizin |
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| Identifiers | |
| CAS number | 1405-86-3 |
| PubChem | 14982 |
| ChemSpider | 14263 |
| UNII | 6FO62043WK |
| EC number | 215-785-7 |
| ChEBI | CHEBI:15939 |
| ATC code | A05 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C42H62O16 |
| Molar mass | 822.93 g mol−1 |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Glycyrrhizin is the main sweet-tasting compound from liquorice root. It is 30–50 times as sweet as sucrose (table sugar). Pure glycyrrhizin is odorless.
In chemical terms, glycyrrhizin is a triterpenoid saponin glycoside of glycyrrhizic (or glycyrrhizinic) acid.[1] Upon hydrolysis, the glycoside loses its sweet taste and is converted to the aglycone glycyrrhetinic acid plus two molecules of glucuronic acid. The acid form is not particularly water-soluble, but its ammonium salt is soluble in water at pH greater than 4.5.
Although sweet, the taste sensation of glycyrrhizin is different from that of sugar. The sweetness of glycyrrhizin has a slower onset than sugar has, and lingers in the mouth for some time. Unlike the artificial sweetener aspartame, glycyrrhizin maintains its sweetness under heating.
In the United States, glycyrrhizin is classified as "generally recognized as safe" as a flavoring agent, although not as a sweetener. Glycyrrhizin is used as a flavoring in some candies, pharmaceuticals, and tobacco products.
The European Union suggests people should not consume any more than 100 mg of glycyrrhizic acid a day,[2] equivalent to approximately 50 g of liquorice sweets.[3]
In Japan, where concern over the safety of artificial sweeteners during the 1970s led to a shift towards plant-derived sugar substitutes, glycyrrhizin is a commonly used sweetener, often used in combination with another plant-based sweetener, stevia. However, the Japanese government has asked its citizens to limit their consumption to 200 milligrams per day.
The most widely reported side-effects of glycyrrhizin use are hypertension and edema (water retention). These effects are related to the inhibition of cortisol metabolism within the kidney, and the subsequent stimulation of the mineralocorticoid receptors.[4] Thus, consumption of black licorice can mimic disorders of excess aldosterone.
Glycyrrhizin and other licorice root products have been used for numerous medical purposes, in particular, treatment of peptic ulcers and as an expectorant. The triterpene derivative of hydrolyzed glycyrrhizin glycyrrhetinic acid is itself effective in treatment of peptic ulcer. According to MedlinePlus and the Natural Medicines Comprehensive Database, licorice is "possibly effective" for dyspepsia in combination with other herbs, but there is "insufficient evidence" to rate its effectiveness for other conditions.[5] Regarding stomach ulcers, specifically, there is "some evidence...that specially prepared licorice will speed the healing of stomach ulcers".[5]
An un-blinded study of 82 patients from the early 1980s, published in the British Medical Journal, reported that Caved-S had a therapeutic effect is similar to that of cimetidine in the treatment of gastric ulcers.[6]
Although licorice may produce anti-inflammatory effects, it is uncertain as to whether that is due to glycyrrhizin, glycyrrhetinic acid, or some other licorice derivative.
Researchers have recently demonstrated doses of licorice root extract, delivering the constituent glycyrrhizin in amounts similar to that contained in standard medical doses of the root, rapidly and significantly lowered levels of circulating testosterone in males.[7]
Glycyrrhizin inhibits liver cell injury caused by many chemicals and is used in the treatment of chronic hepatitis and cirrhosis in Japan. It also inhibits the growth of several DNA and RNA viruses, inactivating herpes simplex virus particles irreversibly.[8]
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