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Glycyrrhizic acid
- Iupac Name：(3S,4S,5R,6R)-6-[(2S,3R,4S,5S)-2-[[(3S,6aR,6bS,8aS,11S,12aR,14aR,14bS)-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]-6-carboxy-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
- CAS No.: 1405-86-3
- Molecular Weight：822.942
- Modify Date.: 2022-10-28 09:16
- Introduction: Glycyrrhizic 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.
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1. Names and Identifiers
- 1.1 Name
- Glycyrrhizic acid
- 1.2 Synonyms
(3b,20b)-20-Carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-b-D-Glucopyranuronosyl-a-D-glucopyranosiduronic Acid (3Β)-30-Hydroxy-11,30-dioxoolean-12-en-3-yl 2-O-Β-D-glucopyranuronosyl-α-D-glucopyranosiduronic acid 20b-Carboxy-11-oxo-30-norolean-12-en-3b-yl-2-O-b-D-glucopyranuronosyl-a-D-glucopyranosiduronic Acid 30-Noroleanane, α-D-glucopyranosiduronic acid deriv 3-o-(2-o-beta-d-glucopyranuronosyl-alpha-d-glucopyranuronosyl)-18beta-g lycyrrhetinic acid DerMacrin EINECS 258-887-7 glycyron GLYCYRRHETINIC ACID GLYCOSIDE Glycyrrhitin Glycyrrhizate Glycyrrhizic Glycyrrhizic acid 1405-86-3 Glycyrrhizic acid,from licorice GLYCYRRHIZIN GLYCYRRHIZINATE Glycyrrhizine glycyrrhizinic acid GLYCYRRHYCIC ACID liquorice MFCD00167400 Olean-12-en-30-oic acid, 3-[(2-O-Β-D-glucopyranuronosyl-α-D-glucopyranuronosyl)oxy]-11-oxo-, (3Β)- Potenlini
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- 1.3 CAS No.
- 1405-86-3
- 1.4 CID
- 14982
- 1.5 EINECS(EC#)
- 215-785-7
- 1.6 Molecular Formula
- C42H62O16 (isomer)
- 1.7 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
- 1.8 InChIkey
- LPLVUJXQOOQHMX-QWBHMCJMSA-N
- 1.9 Canonical Smiles
- CC1(C2CCC3(C(C2(CCC1OC4C(C(C(C(O4)C(=O)O)O)O)OC5C(C(C(C(O5)C(=O)O)O)O)O)C)C(=O)C=C6C3(CCC7(C6CC(CC7)(C)C(=O)O)C)C)C)C
- 1.10 Isomers Smiles
- C[C@]12CC[C@](C[C@H]1C3=CC(=O)[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)O[C@@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)C(=O)O)O)O)O)C)(C)C(=O)O
2. Properties
- 2.1 Density
- 1.43
- 2.1 Melting point
- 220 deg C decomposes
- 2.1 Boiling point
- 971.4°Cat760mmHg
- 2.1 Refractive index
- 61 ° (C=1.5, EtOH)
- 2.1 Flash Point
- 288.1°C
- 2.1 Precise Quality
- 822.40400
- 2.1 PSA
- 267.04000
- 2.1 logP
- 2.24560
- 2.1 Appearance
- Crystals from glacial acetic acid. Obtained from licorice.
- 2.2 Chemical Properties
- White to off-white powder
- 2.3 Color/Form
- Powder
- 2.4 pKa
- 2.76±0.70(Predicted)
- 2.5 Water Solubility
- Insoluble
- 2.6 Spectral Properties
- Specific optical rotation: +46.2 deg @ 17 deg C/D (alcohol, 1.5%)
- 2.7 StorageTemp
- Inert atmosphere,2-8°C
3. Use and Manufacturing
- 3.1 Definition
- ChEBI: A triterpenoid saponin that is the glucosiduronide derivative of 3beta-hydroxy-11-oxoolean-12-en-30-oic acid.
- 3.2 Usage
-
Antiviral, hepatoprotective.
4. Safety and Handling
- 4.1 Risk Statements
- S22-S24/25
- 4.1 Safety Statements
- S22;S24/25
- 4.1 Exposure Standards and Regulations
- Substance added directly to human food affirmed as generally recognized as safe (GRAS). /Licorice and licorice derivatives/
- 4.2 Octanol/Water Partition Coefficient
- log Kow = 2.80
- 4.3 DisposalMethods
- SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
- 4.4 RIDADR
- NONH for all modes of transport
- 4.4 Safety Profile
- Poison by intravenous route. Moderately toxic by ingestion and intraperitoneal routes. Human systemic effects by ingestion: somnolence and changes in the metabolism of phosphorus, When heated to decomposition it emits acrid smoke and irritating fumes. Glycyrrhizic acid Preparation Products And Raw materials Raw materials
- 4.5 Formulations/Preparations
- For improved water solubility, an ammoniated salt is commonly used. ... either ammonium glycyrrhizinate or monoammonium glycyrrhizinate.
...MAIN CONSTITUENT /OF LICORICE/ IS GLYCYRRHIZIN (THE POTASSIUM-CALCIUM-MAGNESIUM SALT OF GLYCYRRHIZIC ACID); COMMERCIAL GLYCYRRHIZIN IS AMMONIUM SALT OF THE ACID.
- 4.6 WGK Germany
- 3
- 4.6 RTECS
- MD2025000
- 4.6 Safety
- Poison by intravenous route. Moderately toxic by ingestion and intraperitoneal routes. Human systemic effects by ingestion: somnolence and changes in the metabolism of phosphorus. When heated to decomposition it emits acrid smoke and irritating fumes.
- 4.7 Toxicity
-
CHEMICAL IDENTIFICATION
- RTECS NUMBER :
- MD2025000
- CHEMICAL NAME :
- Glycyrrhizinic acid
- CAS REGISTRY NUMBER :
- 1405-86-3
- BEILSTEIN REFERENCE NO. :
- 0077922
- LAST UPDATED :
- 199706
- DATA ITEMS CITED :
- 10
- MOLECULAR FORMULA :
- C42-H62-O16
- MOLECULAR WEIGHT :
- 823.04
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Human
- DOSE/DURATION :
- 280 mg/kg/4W
- TOXIC EFFECTS :
- Behavioral - somnolence (general depressed activity)
Nutritional and Gross Metabolic - changes in phosphorus
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Human - man
- DOSE/DURATION :
- 662 mg/kg/1Y-I
- TOXIC EFFECTS :
- Behavioral - convulsions or effect on seizure threshold
Behavioral - muscle weakness
Nutritional and Gross Metabolic - changes in potassium
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 3 gm/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 2 gm/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD - Lethal dose
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- >300 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 4320 mg/kg
- TOXIC EFFECTS :
- Lungs, Thorax, or Respiration - respiratory stimulation
Lungs, Thorax, or Respiration - other changes
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 1 gm/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 589 mg/kg
- TOXIC EFFECTS :
- Lungs, Thorax, or Respiration - respiratory stimulation
Lungs, Thorax, or Respiration - other changes
MUTATION DATA
- TYPE OF TEST :
- Micronucleus test
- TEST SYSTEM :
- Rodent - hamster Ovary
- DOSE/DURATION :
- 100 umol/L
- REFERENCE :
- MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE
Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 367,99,1996
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5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Not classified.
2.2 GHS label elements, including precautionary statements
| Pictogram(s) | No symbol. |
| Signal word | No signal word. |
| Hazard statement(s) | none |
| Precautionary statement(s) | |
| Prevention | none |
| Response | none |
| Storage | none |
| Disposal | none |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
1405-86-3Total: 3 Synthesis Route
9. Other Information
- 9.0 Merck
- 14,4505
- 9.1 Description
- Glycyrrhizic 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.
- 9.2 References
- https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4052927/
https://pubchem.ncbi.nlm.nih.gov/compound/Glycyrrhizic_acid#section=Top
- 9.3 Chemical Properties
- White to off-white powder
- 9.4 Uses
- 11beta-hydroxysteroid dehydrogenase inhibitor, antiinflammatory, expectorant, antihaemorrhagic, anti-HIV
- 9.5 Uses
- Glycyrrhizic acid is a triterpene saponin used in the traditional Chinese medicinal preparation for its anti-inflammatory , antiulcerous and antiallergic effects.
- 9.6 Uses
- glycyrrhizic 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.
- 9.7 Definition
- ChEBI: A triterpenoid saponin that is the glucosiduronide derivative of 3beta-hydroxy-11-oxoolean-12-en-30-oic acid.
- 9.8 Safety Profile
- Poison by intravenous route. Moderately toxic by ingestion and intraperitoneal routes. Human systemic effects by ingestion: somnolence and changes in the metabolism of phosphorus, When heated to decomposition it emits acrid smoke and irritating fumes.
- 9.9 Chemical Properties
- Glycyrrhizin, also known as glycyrrhizic acid, is a glycoside isolated from the roots of licorice, Glycyrrhiza glabra L. For improved water solubility, an ammoniated salt is commonly used. This can be in the form of either ammonium glycyrrhizinate or monoammonium glycyrrhizinate.
10. Computational chemical data
- Molecular Weight: 822.942g/mol
- Molecular Formula: C42H62O16
- Compound Is Canonicalized: True
- XLogP3-AA: 3.7
- Exact Mass: 822.40378589
- Monoisotopic Mass: 822.40378589
- Complexity: 1730
- Rotatable Bond Count: 7
- Hydrogen Bond Donor Count: 8
- Hydrogen Bond Acceptor Count: 16
- Topological Polar Surface Area: 267
- Heavy Atom Count: 58
- Defined Atom Stereocenter Count: 19
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADcfB8PgAAAAAAAAAAAAAAAAAAAAAAAAA0aMGCAAAAAADAAAAAGgAACAAADxSwgAMCCAAABgCIAqDSCAIAAAAgAAAACAFAAEgREBYAAQQiQAAFoAAPAQPK7PzPgAAAAAAAAADAAAYAADAAAAAAAAAAAA==
11. Question & Answer
-
Glycyrrhizic acid A is an effective ingredient extracted from licorice, with various pharmacological effects commonly used in traditional Chinese medicine and health products. When purchasing Glycyrrh..
-
Glycyrrhizic acid, a perennial herbaceous plant in the legume family, has been used for thousands of years in Asian countries such as China, India, and Japan. It is now widely used in Europe, the Midd..
-
Glycyrrhizic acid is a pentacyclic triterpene glycoside that exists in two stereoisomers, 18α and 18β2. It is a white needle crystal with an extremely sweet taste. It can be hydrolyzed into glycyrrh..
-
Glycyrrhizic acid preparations have non-specific anti-inflammatory effects similar to glucocorticoids, which can effectively inhibit the progression of liver inflammation, protect liver cells, improve..
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13. Realated Product Infomation
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