Glycyrrhizinic Acid
   HOME

TheInfoList



OR:

Glycyrrhizin (or glycyrrhizic acid or glycyrrhizinic acid) is the chief sweet-tasting constituent of ''Glycyrrhiza glabra'' (
liquorice Liquorice (British English) or licorice (American English) ( ; also ) is the common name of ''Glycyrrhiza glabra'', a flowering plant of the bean family Fabaceae, from the root of which a sweet, aromatic flavouring can be extracted. The liqu ...
) root. Structurally, it is a
saponin Saponins (Latin "sapon", soap + "-in", one of), also selectively referred to as triterpene glycosides, are bitter-tasting usually toxic plant-derived organic chemicals that have a foamy quality when agitated in water. They are widely distributed ...
used as an
emulsifier An emulsion is a mixture of two or more liquids that are normally immiscible (unmixable or unblendable) owing to liquid-liquid phase separation. Emulsions are part of a more general class of two-phase systems of matter called colloids. Altho ...
and
gel A gel is a semi-solid that can have properties ranging from soft and weak to hard and tough. Gels are defined as a substantially dilute cross-linked system, which exhibits no flow when in the steady-state, although the liquid phase may still di ...
-forming agent in foodstuffs and
cosmetics Cosmetics are constituted mixtures of chemical compounds derived from either natural sources, or synthetically created ones. Cosmetics have various purposes. Those designed for personal care and skin care can be used to cleanse or protect ...
. Its
aglycone An aglycone (aglycon or genin) is the compound remaining after the glycosyl group on a glycoside is replaced by a hydrogen atom. For example, the aglycone of a cardiac glycoside would be a steroid molecule. Detection A way to identify aglycone ...
is
enoxolone Enoxolone (INN, BAN; also known as glycyrrhetinic acid or glycyrrhetic acid) is a pentacyclic triterpenoid derivative of the beta-amyrin type obtained from the hydrolysis of glycyrrhizic acid, which was obtained from the herb liquorice. It is u ...
.


Pharmacokinetics

After oral ingestion, glycyrrhizin is
hydrolysed Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysis ...
to 18β-glycyrrhetinic acid (enoxolone) by intestinal bacteria. After absorption from the gut, 18β-glycyrrhetinic acid is metabolised to 3β-monoglucuronyl-18β-glycyrrhetinic acid in the liver. This metabolite circulates in the bloodstream. Consequently, its oral bioavailability is poor. Most of it is eliminated by bile and only a minor part (0.31–0.67%) by urine. After oral ingestion of 600 mg of glycyrrhizin the metabolite appeared in urine after 1.5 to 14 hours. Maximal concentrations (0.49 to 2.69 mg/L) were achieved after 1.5 to 39 hours and metabolite can be detected in the urine after 2 to 4 days.


Flavouring properties

Glycyrrhizin is obtained as an
extract An extract is a substance made by extracting a part of a raw material, often by using a solvent such as ethanol, oil or water. Extracts may be sold as tinctures, absolutes or in powder form. The aromatic principles of many spices, nuts, h ...
from licorice root after maceration and boiling in water. Licorice extract (glycyrrhizin) is sold in the United States as a liquid, paste, or spray-dried powder. When in specified amounts, it is approved for use as a flavor and
aroma An odor (American English) or odour (Commonwealth English; see spelling differences) is caused by one or more volatilized chemical compounds that are generally found in low concentrations that humans and animals can perceive via their sense ...
in manufactured foods, beverages, candies,
dietary supplement A dietary supplement is a manufactured product intended to supplement one's diet by taking a pill, capsule, tablet, powder, or liquid. A supplement can provide nutrients either extracted from food sources or that are synthetic in order ...
s, and
seasoning Seasoning is the process of supplementing food via herbs, spices, salts, and/or sugar, intended to enhance a particular flavour. General meaning Seasonings include herbs and spices, which are themselves frequently referred to as "seasonings". Ho ...
s. It is 30 to 50 times as sweet as
sucrose Sucrose, a disaccharide, is a sugar composed of glucose and fructose subunits. It is produced naturally in plants and is the main constituent of white sugar. It has the molecular formula . For human consumption, sucrose is extracted and refined ...
(table sugar).


Adverse effects

The most widely reported side effect of glycyrrhizin use via consumption of
black licorice Liquorice (British English) or licorice (American English) ( ) is a confectionery, confection usually flavoured and coloured black with the extract of the roots of the liquorice plant ''Glycyrrhiza glabra''. A wide variety of liquorice sweets ar ...
is reduction of blood
potassium Potassium is the chemical element with the symbol K (from Neo-Latin ''kalium'') and atomic number19. Potassium is a silvery-white metal that is soft enough to be cut with a knife with little force. Potassium metal reacts rapidly with atmosphe ...
levels, which can affect body
fluid balance Fluid balance is an aspect of the homeostasis of organisms in which the amount of water in the organism needs to be controlled, via osmoregulation and behavior, such that the concentrations of electrolytes (salts in solution) in the various body ...
and function of
nerve A nerve is an enclosed, cable-like bundle of nerve fibers (called axons) in the peripheral nervous system. A nerve transmits electrical impulses. It is the basic unit of the peripheral nervous system. A nerve provides a common pathway for the e ...
s. Chronic consumption of black licorice, even in moderate amounts, is associated with an increase in
blood pressure Blood pressure (BP) is the pressure of circulating blood against the walls of blood vessels. Most of this pressure results from the heart pumping blood through the circulatory system. When used without qualification, the term "blood pressure" r ...
, may cause irregular heart rhythm, and may have adverse interactions with
prescription drug A prescription drug (also prescription medication or prescription medicine) is a pharmaceutical drug that legally requires a medical prescription to be dispensed. In contrast, over-the-counter drugs can be obtained without a prescription. The rea ...
s. In extreme cases, death can occur as a result of excess consumption.


See also

*
11α-Hydroxyprogesterone 11α-Hydroxyprogesterone (11α-OHP), or 11α-hydroxypregn-4-ene-3,20-dione is an endogenous steroid and metabolite of progesterone. It is a weak antiandrogen, and is devoid of androgenic, estrogenic, and progestogenic activity. 11α-OHP was in ...
*
Glycyrrhetinic acid Enoxolone (International Nonproprietary Name, INN, British Approved Name, BAN; also known as glycyrrhetinic acid or glycyrrhetic acid) is a pentacyclic triterpenoid derivative of the beta-amyrin type obtained from the hydrolysis of glycyrrhizic ac ...
*
List of unusual deaths This list of unusual deaths includes unique or extremely rare circumstances of death recorded throughout history, noted as being unusual by multiple sources. Antiquity Middle Ages Renaissance Early modern period 19th centur ...


References


External links

{{Navboxes , title =
Corticosteroid Corticosteroids are a class of steroid hormones that are produced in the adrenal cortex of vertebrates, as well as the synthetic analogues of these hormones. Two main classes of corticosteroids, glucocorticoids and mineralocorticoids, are involv ...
ics , list1 = {{Glucocorticoidics {{Mineralocorticoidics 11β-Hydroxysteroid dehydrogenase inhibitors Triterpene glycosides Sugar substitutes Saponins