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Glycyrrhizin

Main sweet-tasting constituent of liquorice


Main sweet-tasting constituent of liquorice

FieldValue
drug_nameGlycyrrhizic acid
IUPAC_name(3β,20β)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-β-D-glucopyranuronosyl-α-D-glucopyranosiduronic acid
imageGlycyrrhizic Acid.svg
image_classskin-invert-image
width280px
image2Glycyrrhizin zwitterion ball-and-stick xtal 2009.png
image_class2bg-transparent
width2250px
tradenameEpigen, Glycyron
Drugs.com
legal_status
routes_of_administrationOral, intravenous
metabolismHepatic and by intestinal bacteria
elimination_half-life6.2–10.2 hours
excretionFaeces, urine (0.31–0.67%)
UNII6FO62043WK
KEGGD00157
PubChem14982
StdInChI_Ref
StdInChI1S/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
StdInChIKey_Ref
StdInChIKeyLPLVUJXQOOQHMX-QWBHMCJMSA-N
CAS_number1405-86-3
CAS_supplemental(α-D-Glucopyranosiduronic acid), (β-D-Glucopyranosiduronic acid)
ChemSpiderID_Ref
ChemSpiderID14263
ChEMBL_Ref
ChEMBL441687
ChEBI_Ref
ChEBI15939
ATC_prefixA05
ATC_suffixBA08
ATC_supplementalQA05BA08 (vet)
C42H=62O=16
solubility1–10
smilesO=C(O)[C@H]7OC@@HC@HC@@H[C@@H]7O

| Drugs.com =

| elimination_half-life = 6.2–10.2 hours

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. 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.

Pharmacological action

The polypharmacological effect of glycyrrhizinic acid, which has at least 12 types of activity (antitumor, hepatoprotective, immunomodulatory, antidiabetic, nephroprotective, cardioprotective, neuroprotective, atheroprotective, anti-inflammatory, antithrombotic, etc.), is closely related to its interaction with various cellular targets. Approximately 88 cellular proteins have been experimentally identified as potential targets of glycyrrhizic acid, including cytochromes P450, UDP-glucouronosyltransferases, oxidoreductases, and proteins involved in amino acid metabolism and steroid hormone biosynthesis.

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.

References

References

  1. (December 1999). "Pharmacokinetics of intravenous glycyrrhizin after single and multiple doses in patients with chronic hepatitis C infection". Clinical Therapeutics.
  2. (May 2001). "The pharmacokinetics of glycyrrhizic acid evaluated by physiologically based pharmacokinetic modeling". Drug Metabolism Reviews.
  3. (2012). "Excretion profile of glycyrrhizin metabolite in human urine". Food Chemistry.
  4. (September 2025). "Glycyrrhizic acid: novel potential protein targets". Biomeditsinskaia Khimiia.
  5. (November 2017). "Glycyrrhizic acid: A promising carrier material for anticancer therapy". Biomedicine & Pharmacotherapy.
  6. (June 2025). "Glycyrrhizic acid promotes liver regeneration through activating β-catenin in acetaminophen-induced liver injury". Journal of Ethnopharmacology.
  7. (1 April 2017). "Sec. 184.1408 Licorice and licorice derivatives". US Food and Drug Administration, Code of Federal Regulations Title 21, 21CFR184.1408.
  8. "Glycyrrhizic Acid". National Institutes of Health.
  9. (30 October 2017). "Black Licorice: Trick or Treat?". US Food and Drug Administration.
  10. (November 2017). "The association between consistent licorice ingestion, hypertension and hypokalaemia: a systematic review and meta-analysis". Journal of Human Hypertension.
  11. "Too much candy: Man dies from eating bags of black licorice". AP News.
  12. (September 2020). "Case 30-2020: A 54-Year-Old Man with Sudden Cardiac Arrest". The New England Journal of Medicine.
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