Glycyrrhizin

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Glycyrrhizin
IUPAC name	(3β,18α)-30-hydroxy-11,30-dioxoolean-12-en-3-yl 2-O-β-D-glucopyranuronosyl-β-D-glucopyranosiduronic acid
Other names	Glycyrrhizin Glycyrrhizinic acid Glycyrrhizic acid
Identifiers
CAS number	1405-86-3 Y
EC number	215-785-7
ATC code	A05BA08,[1]
SMILES	O=C(O)[C@H]7O[C@@H](O[C@@H]6[C@@H](O)[C@H](O)[C@H](O[C@H]6O[C@H]2CC[C@]3(C)[C@H]4C(=O)C=C1[C@H]5C[C@](C)(CC[C@]5(C)CC[C@@]1(C)[C@]4(C)CC[C@H]3C2(C)C)C(=O)O)C(=O)O)[C@H](O)[C@@H](O)[C@@H]7O
ChemSpider ID	14263
Properties
Molecular formula	C42H62O16
Molar mass	822.93 g mol−1
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.

Chemically, glycyrrhizin is a triterpenoid saponin glycoside of glycyrrhizic (or glycyrrhizinic) acid.^[2] 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, 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 that people should not consume any more than 100 mg of glycyrrhizic acid a day,^[3] equivalent to approximately 50g of liquorice sweets.^[4]

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.^{[citation needed]}

Health effects

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.^[5] Thus, consumption of black licorice can mimic disorders of excess aldosterone.

Glycyrrhizin and other licorice root products have been used for numerous medical purposes, particularly treatment of peptic ulcers and as an expectorant. The triterpene derivative of hydrolyzed glycyrrhizin, glycyrrhetinic acid, is itself effective in treatment of peptic ulcer.^{[citation needed]}

Although licorice may produce anti-inflammatory effects, it is uncertain whether that is due to glycyrrhizin, glycyrrhetinic acid, or some other licorice derivative.

Recently researchers have demonstrated that 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.^[6]

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.^[7]

See also

• Glycyrrhetinic acid

References