| Glycyrrhizin | |
|---|---|
 |
|
| 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. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to The EINECS number (for European Inventory of Existing Chemical Substances) is a registry number given to each Chemical substance commercially available in the A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 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 |
|
Glycyrrhizin is the active principle of liquorice root. In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly Liquorice (UK or licorice (US (see spelling differences;, or) is the root of Glycyrrhiza glabra, from which a sweet flavour can be extracted It is a powerful sweetener, 30–50 times as potent as sucrose (table sugar). A sweetener is a Food additive which adds the Basic taste of Sweetness to a food artificial sweeteners are Sugar substitutes Solubility of Pure SucroseTemperature(Cg Solubility of Pure SucroseTemperature(Cg
Chemically, glycyrrhizin is a triterpenoid saponin glycoside being either the Ca2+ or K+ salt of glycyrrhizic (or glycyrrhizinic) acid. The terpenoids, sometimes referred to as isoprenoids, are a large and diverse class of naturally-occurring organic chemicals similar to Terpenes derived Saponins are a class of chemical compounds one of very many Secondary metabolites found in natural sources with saponins found in particular abundance in various plant [1] Upon hydrolysis, the glycoside loses its sweet taste and is converted to the aglycone glycyrrhetinic acid plus two molecules of glucuronic acid. A aglycon or aglycone is the non-sugar compound remaining after replacement of the glycosyl group from a Glycoside by a hydrogen atom Glycyrrhetinic acid is a pentacyclic Triterpenoid derivative of the Beta-amyrin type obtained from the Hydrolysis of Glycyrrhizic acid, Glucuronic acid (from Greek γλυκερός - "sweet" is a Carboxylic acid. The acid form is not particularly water soluble, but its ammonium salt is soluble in water at pH greater than 4. Ammonium is also an old name for the Siwa Oasis in western Egypt. A salt, in Chemistry, is defined as the product formed from the neutralisation reaction of Acids and bases. pH is the measure of the acidity or alkalinity of a Solution. 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. Aspartame (or APM) (ˈæspɚteɪm or /əˈspɑrteɪm/ is the name for an artificial non- Saccharide Sweetener, aspartyl-phenylalanine-1-methyl
In the United States, glycyrrhizin is classified as "generally recognized as safe" as a flavoring agent, although not as a sweetener. The United States of America —commonly referred to as the Generally Recognized as Safe ( GRAS) is a United States of America Food and Drug Administration (FDA designation that a chemical or substance added to food Glycyrrhizin is used as a flavoring in some candies, pharmaceuticals, and tobacco products. Candy, specifically sugar candy, is a confection made from a concentrated solution of sugar in water to which a variety of flavorings and colorants is added Tobacco is an Agricultural product recognized as an addictive drug processed from the fresh Leaves of plants in the genus Nicotiana.
The European Union suggests that people should not consume any more than 100mg of glycyrrhizic acid a day, [2], approximately 50 g liquorice sweets. The European Union ( EU) is a political and economic union of twenty-seven member states, located primarily in [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. For a topic outline on this subject see List of basic Japan topics. This article is about the Decade 1970-1979 For the Year 1970 see 1970. Stevia is a Genus of about 240 Species of herbs and Shrubs in the sunflower family ( Asteraceae) native to Subtropical 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.
Health effects
The most widely reported side effects of glycyrrhizin use are hypertension and edema (water retention). Hypertension, also referred to as high blood pressure, HTN or HPN, is a medical condition in which the Blood pressure is chronically elevated Oedema (or Edema in American English formerly known as dropsy or hydropsy, is the increase of Interstitial fluid in any organ &mdash swelling Water is a common Chemical substance that is essential for the survival of all known forms of Life. These effects are related to the inhibition of cortisol metabolism within the kidney, and the subsequent stimulation of the mineralocorticoid receptors. Cortisol is a Corticosteroid Hormone produced by the Adrenal gland (in the Zona fasciculata of the Adrenal cortex) Mineralocorticoids are a class of Steroid hormones characterised by their similarity to Aldosterone and their influence on salt and water balance [4] Thus, consumption of black licorice can mimic disorders of excess aldosterone. Aldosterone is a hormone that causes the tubules of the kidneys to retain sodium and water
Glycyrrhizin and other licorice root products have been used for numerous medical purposes, particularly treatment of peptic ulcers and as an expectorant. A peptic ulcer, also known as PUD or peptic ulcer disease, is an Ulcer (defined as mucosal erosions equal to or greater than 0 A mucolytic agent is any agent which dissolves thick Mucus usually used to help relieve respiratory difficulties The triterpene derivative of hydrolyzed glycyrrhizin, glycyrrhetinic acid, is itself effective in treatment of peptic ulcer. Hydrolysis is a Chemical reaction during which one or more water molecules are split into hydrogen and hydroxide ions which may go on to participate in further reactions Glycyrrhetinic acid is a pentacyclic Triterpenoid derivative of the Beta-amyrin type obtained from the Hydrolysis of Glycyrrhizic acid,
Although licorice may produce anti-inflammatory effects, it is uncertain whether that is due to glycyrrhizin, glycyrrhetinic acid, or some other licorice derivative. Anti-inflammatory refers to the property of a substance or treatment that reduces Inflammation.
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. Hepatitis (plural hepatitides) implies injury to the Liver characterized by the presence of Inflammatory cells in the tissue of Cirrhosis is a consequence of chronic Liver Disease characterized by replacement of liver tissue by fibrous Scar tissue as well as regenerative It also inhibits the growth of several DNA and RNA viruses, inactivating herpes simplex virus particles irreversibly. Herpes simplex is a Viral disease caused by Herpes simplex viruses both herpes simplex virus 1 (HSV-1 and herpes simplex virus 2 (HSV-2 cause herpes simplex
See also
References
- ^ Saponin Glycosides, by Georges-Louis Friedli, URL accessed Dec 2007. Glycyrrhetinic acid is a pentacyclic Triterpenoid derivative of the Beta-amyrin type obtained from the Hydrolysis of Glycyrrhizic acid,
- ^ 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
Dapyx Software network: MP3 Explorer | Ebook Manager | Zenithic