Basic information
- CAS
1405-86-3- Standard SMILES
CC1(C(=O)O)CCC2(C)CCC3(C)C(=CC(=O)C4C5(C)CCC(OC6OC(C(=O)O)C(O)C(O)C6OC6OC(C(=O)O)C(O)C(O)C6O)C(C)(C)C5CCC43C)C2C1- InChIKey
LPLVUJXQOOQHMX-UHFFFAOYSA-N- Molecular formula
- C42H62O16
- Average molar mass
- 822.9 g/mol
- Monoisotopic mass
- 822.40378589
Overview
liquorice has been reported in Glycyrrhiza uralensis and Glycyrrhiza glabra with data available.
Names & identifiers
- Preferred name
- 29-Hydroxy-11,29-dioxoolean-12-en-3-yl 2-O-hexopyranuronosylhexopyranosiduronic acid
- IUPAC
- 6-[6-carboxy-2-[(11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl)oxy]-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
- English name
- Glycyrrhizic acid
- Molecular formula
- C42H62O16
- Molecular weight
- 822.94
Names & synonyms
DTXSID5085964129-Hydroxy-11,29-dioxoolean-12-en-3-yl 2-O-hexopyranuronosylhexopyranosiduronic acidRefChem:1064937DTXCID001966541970133-70-0Glycyrrhizinate5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-6-[(11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl)oxy]-3,4-dihydroxyoxane-2-carboxylic acid6-((6-carboxy-2-((11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl)oxy)-4,5-dihydroxytetrahydro-2h-pyran-3-yl)oxy)-3,4,5-trihydroxytetrahydro-2h-pyran-2-carboxylic acidC42H62O1618Alpha-Glycyrrhizic acidGlycrrhizinGlycyrrhitin
Show more names
GLYCYRRHIZINDeglycyrrhizinated Licoriceliquorice18β-Glycyrrhizic acidGlycyrrhizicGlycyrrhizic acid 1405-86-3GlycyrrhizineGLYCYRRHYCIC ACID
Properties
Computed structural properties
- XLogP
- 3.7
- Topological polar surface area
- 267 Ų
- Hydrogen bond donors
- 8
- Hydrogen bond acceptors
- 16
- Rotatable bonds
- 7
- Heavy atoms
- 58
- Formal charge
- 0
- Complexity
- 1,730
Experimental & physicochemical properties
LogP2.80
Boiling Point970.00 to 972.00 °C. @ 760.00 mm Hg
Melting Point220 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 220 °C · 220°C (rough estimate)
- Boiling point
- 681.01 °C · 681.01°C (rough estimate)
- alpha
- 17 · D17 +46.2° (c = 1.5 in alc)
- Density
- 1.1442 · 1.1442 (rough estimate)
- refractive index
- 61 ° · 61 ° (C=1.5, EtOH)
- FLAVIS Number
- 16.012 · 16.012 | Glycyrrhizic acid
- storage temp.
- 2 · under inert gas (nitrogen or Argon) at 2-8°C
- solubility
- DMSO (Slightly), Ethanol (Slightly), Methanol (Sparingly), Pyridine (Slightly)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- MD2025000
- hs_code
- 29389090
- Toxicity
- human,TDLo,oral,5571ug/kg/3D- (5.571mg/kg),KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION,Toxicologist. Vol. 54, Pg. 109, 2000.
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
- Hazardous Substances Data
- 1405-86-3(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Applications
DescriptionGlycyrrhizic acid is a kind of anti-inflammatory triterpene glycoside extracted from the licorice root. Inside the body, it can be metabolized to glycyrrhetinic acid which inhibits the 11-beta-hydroxysteroid dehydrogenase and some other enzymes related to the corticosteroid metabolism. Glycyrrhizic acid has various pharmacological effects including suppressing hepatic apoptosis and necrosis, anti-inflammatory and immune regulatory actions, antiviral effects, antineoplastic and anticancer effects. It is the active ingredient of licorice root which is commonly used in the treatment of acute and chronic liver injury, viral hepatitis, hepatic steatosis, liver fibrosis, hepatoma, viral myocarditis and other diseases such as psoriasis or prostate cancer. Glycyrrhizic acid is also widely used as a sweetening and flavoring agent in food.
Usesglycyrrhizic acid is a hydrolyzed glycyrrhizin. It is credited with antiinflammatory and anti-allergenic properties. Studies comparing glycyrrhizin with hydrocortisone found glycyrrhizin to be somewhat milder but longer lasting in effectiveness. once the application of hydrocortisone is suspended, the symptoms return. This does not appear to be the case with glycyrrhizin. It does not have side effects and is chemically stable so it can be safely used on a continuing basis.
Uses11beta-hydroxysteroid dehydrogenase inhibitor, antiinflammatory, expectorant, antihaemorrhagic, anti-HIV
UsesGlycyrrhizic acid is a triterpene saponin used in the traditional Chinese medicinal preparation for its anti-inflammatory , antiulcerous and antiallergic effects.
UsesGlycyrrhizin is a flavorant and foaming agent derived from the separation of flavonoids found in the whole licorice extract from the licorice root glycyrrhiza glabra. It is 50–100 times as sweet as sugar, is soluble in water, and has a licorice taste. It has good heat stability but prolonged heating can result in some degradation. It is stable within ph 4–9; below ph 4 there could be precipitation. It has foaming and emulsifying properties in water, being used in cocktail mixes and soft drinks. It is used as a flavorant in bacon and imitation whipped products. It is synergistic with sugar, the sweetness being amplified to 100 times that of cane sugar alone. It is used as a sweetener in sugar-free chewing gum and low-fat sugar-free frozen desserts. It is also termed ammoniated glycyrrhizin. Monoammonium glycyrrhizinate is obtained by additional refinement.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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