Glycyrrhizin
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| Glycyrrhizin | |
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| IUPAC name | (3-β,20-β)-20-Carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-β-D-glucopyranuronosyl-α-D-glucopyranosiduronic acid |
| Other names | Glycyrrhizin Glycyrrhizinic acid Glycyrrhizic acid |
| Identifiers | |
| CAS number | [1405-86-3] |
| EINECS number | |
| SMILES | OC1C(O)C(O)C (OC2C(O)C(O)C (C(O)=O)OC2OC3 [C@] (C)(C)[C@@] (CC[C@]([C@@] (CC[C@]7(C)[C@@] ([H])6C[C@@](C)(C(O)=O)CC7) (C)C6=C5)(C) [C@@]([H])4 C5=O) ([H])[C@]4(C) CC3)OC1C(O)=O |
| Properties | |
| Molecular formula | C42H62O16 |
| Molar mass | 822.94 g/mol |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Glycyrrhizin is the active principle of liquorice root. It is a powerful sweetener, 30–50 times as potent as sucrose (table sugar).
Chemically, glycyrrhizin is a triterpenoid saponin glycoside being either the Ca2+ or K+ salt 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 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. Additionally, its characteristic licorice flavor makes it unsuitable as a direct flavor substitute for sugar. 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 100mg of glycyrrhizic acid a day, [2], approximately 50 g 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, glycyrrhizin appears to have some pharmacological side effects, and the Japanese government has asked its citizens to limit their consumption to 200 milligrams per day.
[edit] 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. [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, 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.[5]
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.[citation needed]
[edit] See also
[edit] References
- ^ Saponin Glycosides, by Georges-Louis Friedli, URL accessed Dec 2007.
- ^ Opinion of the Scientific Committee on Food on Glycyrrhizinci Acid and its Ammonium Salt (opinion expressed on 4 April 2003), European Commission, 4 April 2003, accessed online 7 June 2008
- ^ Størmer, FC; Reistad R, Alexander J. (1993). "Glycyrrhizic acid in liquorice - evaluation of health hazard". Food Chem Toxicol 31 (4): 303-12.
- ^ Ferrari, P; at al (2001). "In vivo 11beta-HSD-2 activity: variability, salt-sensitivity, and effect of licorice.". Hypertension 38 (6): 1330-6. PMID 11751713.
- ^ Glycyrrhiza: Licorice root and testosterone
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