Glycyrrhizin

Glycyrrhizic acid
Clinical data
Trade namesEpigen, Glycyron
AHFS/Drugs.comInternational Drug Names
Routes of
administration
Oral, intravenous
ATC code
Pharmacokinetic data
MetabolismHepatic and by intestinal bacteria
Elimination half-life6.2–10.2 hours
ExcretionFaeces, urine (0.31–0.67%)
Identifiers
  • (3β,20β)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-β-D-glucopyranuronosyl-α-D-glucopyranosiduronic acid
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
E numberE958 (glazing agents, ...) Edit this at Wikidata
CompTox Dashboard (EPA)
ECHA InfoCard100.014.350 Edit this at Wikidata
Chemical and physical data
FormulaC42H62O16
Molar mass822.942 g·mol−1
3D model (JSmol)
Solubility in water1–10 mg/mL (20 °C)
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  • InChI=1S/C42H62O16/c1-37(2)21-8-11-42(7)31(20(43)16-18-19-17-39(4,36(53)54)13-12-38(19,3)14-15-41(18,42)6)40(21,5)10-9-22(37)55-35-30(26(47)25(46)29(57-35)33(51)52)58-34-27(48)23(44)24(45)28(56-34)32(49)50/h16,19,21-31,34-35,44-48H,8-15,17H2,1-7H3,(H,49,50)(H,51,52)(H,53,54)/t19-,21-,22-,23-,24-,25-,26-,27+,28-,29-,30+,31+,34-,35-,38+,39-,40-,41+,42+/m0/s1 checkY
  • Key:LPLVUJXQOOQHMX-QWBHMCJMSA-N checkY

Glycyrrhizin (glycyrrhizic acid or glycyrrhizinic acid) is the chief sweet-tasting constituent of Glycyrrhiza glabra (liquorice) root. Structurally, it is a saponin used as an emulsifier and gel-forming agent in foodstuffs and cosmetics. Its aglycone is enoxolone.

Pharmacokinetics

After oral ingestion, glycyrrhizin is hydrolysed 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.[quantify] 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 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 in manufactured foods, beverages, candies, dietary supplements, and seasonings. It is 30 to 50 times as sweet as sucrose (table sugar).

Adverse effects

The most widely reported side effect of glycyrrhizin use via consumption of black liquorice is reduction of blood potassium levels, which can affect body fluid balance and function of nerves. Chronic consumption of black licorice, even in moderate amounts, is associated with an increase in blood pressure, may cause irregular heart rhythm, and may have adverse interactions with prescription drugs. In extreme cases, death can occur as a result of excess consumption.

See also


This page was last updated at 2023-11-18 08:06 UTC. Update now. View original page.

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