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Glycyrrhizin information


Glycyrrhizic acid
Clinical data
Trade namesEpigen, Glycyron
AHFS/Drugs.comInternational Drug Names
Routes of
administration
Oral, intravenous
ATC code
  • A05BA08 (WHO) QA05BA08 (vet)
Pharmacokinetic data
MetabolismHepatic and by intestinal bacteria
Elimination half-life6.2–10.2 hours[1]
ExcretionFaeces, urine (0.31–0.67%)[2]
Identifiers
IUPAC name
  • (3β,20β)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-β-D-glucopyranuronosyl-α-D-glucopyranosiduronic acid
CAS Number
  • 1405-86-3 (α-D-Glucopyranosiduronic acid), 103000-77-7 (β-D-Glucopyranosiduronic acid)
PubChem CID
  • 128229
ChemSpider
  • 14263 checkY
UNII
  • 6FO62043WK
KEGG
  • D00157
ChEBI
  • CHEBI:15939 checkY
ChEMBL
  • ChEMBL441687 checkY
E numberE958 (glazing agents, ...) Edit this at Wikidata
CompTox Dashboard (EPA)
  • DTXSID8047006 Edit this at Wikidata
ECHA InfoCard100.014.350 Edit this at Wikidata
Chemical and physical data
FormulaC42H62O16
Molar mass822.942 g·mol−1
3D model (JSmol)
  • Interactive image
Solubility in water1–10 mg/mL (20 °C)
SMILES
  • O=C(O)[C@H]7O[C@@H](O[C@@H]6[C@@H](O)[C@H](O)[C@H](O[C@@H]6O[C@@H]2C(C)(C)[C@@H]3CC[C@@]1(C)[C@]5(C(=C/C(=O)[C@@H]1[C@@]3(C)CC2)\[C@@H]4C[C@](C(=O)O)(C)CC[C@]4(C)CC5)C)C(=O)O)[C@H](O)[C@@H](O)[C@@H]7O
InChI
  • 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.

  1. ^ van Rossum TG, Vulto AG, Hop WC, Schalm SW (December 1999). "Pharmacokinetics of intravenous glycyrrhizin after single and multiple doses in patients with chronic hepatitis C infection". Clinical Therapeutics. 21 (12): 2080–2090. doi:10.1016/S0149-2918(00)87239-2. hdl:1765/73160. PMID 10645755.
  2. ^ Ploeger B, Mensinga T, Sips A, Seinen W, Meulenbelt J, DeJongh J (May 2001). "The pharmacokinetics of glycyrrhizic acid evaluated by physiologically based pharmacokinetic modeling". Drug Metabolism Reviews. 33 (2): 125–147. doi:10.1081/DMR-100104400. PMID 11495500. S2CID 24778157.

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Glycyrrhizin

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Glycyrrhizin (glycyrrhizic acid or glycyrrhizinic acid) is the chief sweet-tasting constituent of Glycyrrhiza glabra (liquorice) root. Structurally, it...

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Liquorice

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Flavonoids account for the yellow root color. The principal glycoside, glycyrrhizin, exists in content of 7% to 10%, depending on cultivation practices....

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Sweetener

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produced food and drink. Natural non-sugar sweeteners also exist, such as glycyrrhizin found in liquorice. Sugar Sugar alcohol Sucrose, or glucose-fructose...

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Deglycyrrhizinated licorice

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duodenal ulcers. It is made from licorice from which the glycyrrhizin has been removed. Glycyrrhizin is known to cause undesirable side effects, such as hypertension...

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Glycyrrhiza uralensis

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Shanxi, Gansu and Xinjiang regions of China. Liquorice root contains glycyrrhizin, which may affect blood pressure, blood potassium levels or have untoward...

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Glycyrrhiza lepidota

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potato)." American licorice is not sweet from sugar but from glycyrrhizin. Glycyrrhizin may increase blood pressure (aka hypertension) by interfering...

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Saponin

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them their useful soap properties. Some examples of these chemicals are glycyrrhizin (licorice flavoring) and quillaia (alt. quillaja), a bark extract used...

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Glucuronolactone

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X; An, R (September 2018). "Protective effects of compound ammonium glycyrrhizin, L‑arginine, silymarin and glucurolactone against liver damage induced...

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Hyperaldosteronism

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genus of plants that contain the triterpenoid saponin glycoside known as glycyrrhizin can lead to pseudohyperaldosteronism. Licorice and closely related plants...

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Sugar substitute

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solutions to sweet Erythritol 0.65 14 0.05 Fructooligosaccharide 0.4 Glycyrrhizin 40 Glycerol 0.6 0.55 1.075 E422 Hydrogenated starch hydrolysates 0.65...

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National Brain Research Centre

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process genetically for treating nerve injuries in humans in future. Glycyrrhizin prevents SARS-CoV-2 S1 and Orf3a induced high mobility group box 1 (HMGB1)...

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Tapioca pearl

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Acetate, etc. Sweetener D-Sorbitol, 70% D-SorbitolSolution, D-Xylitol, Glycyrrhizin, Trisodium Glycyrrhizinate, D-Mannitol, Aspartame, Licorice Extracts...

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Onepharm

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Minophagen, a major supplier of pharmaceutical-grade glycyrrhizin and marketer of a glycyrrhizin-based drug. By this time, the company had secured an...

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E number

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E957 Thaumatin (sweetener) flavour enhancer Approved in the EU. E958 Glycyrrhizin (sweetener) flavour enhancer E959 Neohesperidine dihydrochalcone (sweetener)...

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Anaphrodisiac

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decreasing performance, similar to alcohol. A 2003 study has found that glycyrrhizin, the compound in liquorice root, can lower levels of testosterone. The...

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Ganghwa Island

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medicine. Its leaves have vitamins, and its roots contain tryptophan and glycyrrhizin. Said to have anticancer activity, the turnip helps cure skin diseases...

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Hypokalemia

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excess syndrome—can either be congenital or caused by consumption of glycyrrhizin, which is contained in extract of licorice, sometimes found in herbal...

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Digitonin

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Kaplan, Gideon; Weisenberg, Emil (April 1977). "The protective action of glycyrrhizin against saponin toxicity". Biochemical Pharmacology. 26 (7): 643–645...

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Sweetness

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concentrations much lower than common sugars. The most well-known example is glycyrrhizin, the sweet component of licorice root, which is about 30 times sweeter...

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Metabolic alkalosis

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the aldosterone escape to excrete sodium and chloride in urine. Excess glycyrrhizin consumption Low levels of magnesium in the blood Severely high levels...

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Neohesperidin dihydrochalcone

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and the pH of the product. Like other highly sweet glycosides, such as glycyrrhizin and those found in stevia, NHDC's sweet taste has a slower onset than...

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Taste

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alcohols like anethol, glycerol and propylene glycol, saponins such as glycyrrhizin, artificial sweeteners (organic compounds with a variety of structures)...

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Chinese herbology

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products containing Reynoutria multiflora (synonym Polygonum multiflorum), glycyrrhizin, Senecio and Symphytum. The evidence suggests that hepatotoxic herbs...

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Traditional Chinese medicine

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products containing Reynoutria multiflora (synonym Polygonum multiflorum), glycyrrhizin, Senecio and Symphytum. The herbs indicated as being hepatotoxic included...

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Glycyrrhiza inflata

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licochalcone D are chalconoids isolated from root of G. inflata as well as glycyrrhizin. Trudy Glavnago Botanicheskago Sada. Acta Horti Petropolitani. Petrograd...

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Paeoniflorin

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Okamura, Takashi; Yaginuma, Tsutomu (1991). "Effect of Paeoniflorin, Glycyrrhizin and Glycyrrhetic acid on Ovarian Androgen Production". The American Journal...

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Enoxolone

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Medicine. Badam L (June 1997). "In vitro antiviral activity of indigenous glycyrrhizin, licorice and glycyrrhizic acid (Sigma) on Japanese encephalitis virus"...

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List of additives in cigarettes

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phenylacetate Ginger oil and oleoresin L-Glutamic acid L-Glutamine Glycerol Glycyrrhizin ammoniated Grape juice concentrate Guaiac wood oil Guaiacol Guar gum...

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