1405-86-3
- Product Name：Glycyrrhizic acid
- Molecular Formula：C42H62O16
- Purity：99%
- Molecular Weight：
Product Details
Appearance:White powder
1405-86-3 Properties
- Molecular Formula:C42H62O16
- Molecular Weight:822.945
- Appearance/Colour:White powder
- Vapor Pressure:0mmHg at 25°C
- Melting Point:220ºC decomposes
- Refractive Index:61 ° (C=1.5, EtOH)
- Boiling Point:971.4 °C at 760 mmHg
- PKA:2.76±0.70(Predicted)
- Flash Point:288.1 °C
- PSA：267.04000
- Density:1.43 g/cm3
- LogP:2.24560
1405-86-3 Usage
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.
References
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4052927/ https://pubchem.ncbi.nlm.nih.gov/compound/Glycyrrhizic_acid#section=Top
Chemical Properties
White to off-white powder
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.
Uses
Glycyrrhizin 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.
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.
Uses
11beta-hydroxysteroid dehydrogenase inhibitor, antiinflammatory, expectorant, antihaemorrhagic, anti-HIV
Uses
Glycyrrhizic acid is a triterpene saponin used in the traditional Chinese medicinal preparation for its anti-inflammatory , antiulcerous and antiallergic effects.
Definition
ChEBI: A triterpenoid saponin that is the glucosiduronide derivative of 3beta-hydroxy-11-oxoolean-12-en-30-oic acid.
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.
InChI:InChI=1/C41H60O16.3H3N/c1-37(2)21-8-11-40(5)18-7-10-38(3)13-14-39(4,36(52)53)16-19(38)17(18)15-20(42)31(40)41(21,6)12-9-22(37)54-34-27(47)25(45)28(30(57-34)33(50)51)55-35-26(46)23(43)24(44)29(56-35)32(48)49;;;/h15,18-19,21-31,34-35,43-47H,7-14,16H2,1-6H3,(H,48,49)(H,50,51)(H,52,53);3*1H3/t18?,19-,21?,22-,23-,24-,25+,26+,27+,28-,29-,30-,31?,34+,35+,38-,39-,40-,41-;;;/m0.../s1
1405-86-3 Relevant articles
Syntheses of glycyrrhetic acid α-diglycosides and enol α-glycosides
Saito,Sumita,Kanda,Sasaki
, p. 1016 - 1027 (1994)
Glycyrrhetinate α-monoglycoside derivatives 8, 10 and 12, all having a trichloroacetyl group at the C-2 position of the pyranose ring, were treated with NH3-saturated ether at 0°C to give the corresponding alcohols 13, 15 and 17, accompanied by 2'-chloroderivatives, 14, 16 and 18, respectively. Glycosylations of the alcohols 13, 15 and 17 with methyl 2,3,4-tri-O-acetyl- α-D-glucuronatopyranosyl bromide 19 in the presence of AgOTf in dry CH2Cl2 gave the corresponding α-diglycosides 20, 22 and 24 together with the enol α-glycosides 21, 23 and 25, respectively. Glycosylations of the diglycoside derivatives 20, 22 and 35 having no reactive OH group in the molecules with 19 for longer reaction times gave quantitatively the enol α-glycoside derivatives 21, 23 and 36, respectively. Glycosylation of the monoglycoside derivative 37, which has a poorly reactive OH group at the C-4 position on the pyranose ring, with 19 gave an enol α-glycoside 38. The mechanism of the formation of enol α-glycosides was investigated. Removal of the protecting groups of 20, 22 and 24 by successive treatment with 1.5N NaOMe in MeOH and 5% KOH in EtOH-H2O (1:1) gave the free α-diglycosides 26-28, and removal of those of 31, 21, 23, 25 and 36 by treatment with 5% KOH in EtOH-H2O (1:1) under reflux gave the free enol α-glycosides 41-45, respectively.
A method for the preparation of trans-glycyrrhizic acid
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Paragraph 0018; 0021; 0024, (2019/07/04)
The invention takes the market glycyrrhizinate binds the raw material, the acid out-in and get the glycyrrhizic acid, glycyrrhetic acid according to the cis and trans glycyrrhizic acid in different solubility in a solvent, acetone or butanone recrystallization, cis glycyrrhizic acid remaining in the mother liquor, trans glycyrrhizic acid in the solvent precipitation, filtration can make the high purity of trans-glycyrrhizic acid, the invention solves the glycyrrhizic acid stereoisomers not easy to separate the key technical, with technological repeatability, the operation is simple, environmental protection, and the product obtained by the characteristic of high purity, is suitable for industrial production.
METHOD FOR PRODUCING GLYCYRRHIZINIC ACID AND GALACTURO GLYCYRRHIZINIC ACID, AND INTERMEDIATE USED FOR THE PRODUCTION METHOD
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, (2018/07/28)
PROBLEM TO BE SOLVED: To provide a synthesis method that makes it possible to produce high-purity glycyrrhizinic acid or galacturo glycyrrhizinic acid, simply and in high yields. SOLUTION: A production method includes performing glycosylation of position-3 hydroxy group of glycyrrhetinic acid, then performing selective galactosylation or glycosylation at position-2', and through deprotection, performing selective oxidation of a primary hydroxy group. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
Methyl isoglycyrrhizinate refining method
-
Paragraph 0016, (2018/04/02)
According to the present invention, a methyl isoglycyrrhizinate crude product is used as a raw material and is refined to obtain the methyl isoglycyrrhizinate fine product, wherein the impurity A content can be controlled at less than 0.3%, and the single impurity content in the magnesium isoglycyrrhizinate can be controlled at less than 0.1%; and the preparation method has advantages of simpleness, good process reproducibility, simple operation, high yield and high product purity, and is suitable for industrial large-scale production.
Acyclovir transdermal delivery system
-
, (2008/06/13)
A transdermal formulation for providing antiviral effect in dermis or epidermis, wherein comprising (a) 0.01 to 30 weight percent of antiviral drug; (b) 0.05 to 20 weight percent of a Chinese medicine enhancer; and (c) a pharmaceutical acceptable vehicles. The antiviral drug is selected from the group consisting of ACV(Acyclovir), Carbovir, DDA(2',3'-Dideoxyadnosine), HPMPA(1-(3-Hydroxy-2-phosphonylmethoxylpropyl)-adenosine), DHPG(Ganciclovir), Desciclovir, IDC (5-Iodo-2'-deoxy-cytidine), Vidarabine(Ara-A), DDI(2',3'-Dideoxyinosine), Cordycepin, Cytarabine, Deoxyguanosine, d4T(2',3'-Didehydro-3'-deoxythymidine), FIAC(2'-Fluoro-5-iodoaracytosine), AZT(ZDV, Zidovudine), Ara-T(1- beta -D-Ara-binofuranosylthymine), Deoxythymidine, Ribavirin, EDU(5-Ethyl-2'-deoxy-uridine), Enviroxime, Amantadine, Arildone, HPMPC(9-(3-Hydroxy-2-phosphonyl-methoxyl-propyl)cytidine), Riboxamide, Rimantidine, Tromantadine, Foscamet sodium, Moroxydine, F3T(5-Trifluoro-methyl-2'-deoxy-uridine), BVDU (Bromovinyldeoxyuridine). Preferably, the Chinese medicine enhancer is oleanolic acid, and the pharmaceutical acceptable vehicles is polyethylene glycols.
1405-86-3 Process route
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diammonium glycyrrhizinate
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- 1405-86-3
glycyrrhizin
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18α-glycyrrhizic acid
| Conditions | Yield |
|---|---|
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With sulfuric acid; In methanol; at 0 ℃; pH=3; Overall yield = 98 g;
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56.25 % de |
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C45H68O15
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- 1405-86-3
glycyrrhizin
| Conditions | Yield |
|---|---|
|
With sodium hydroxide; for 2h; Reflux;
|
8.5 g |
1405-86-3 Upstream products
-
30430-55-8
trimethyl glycyrrhizate
-
149553-79-7
C42H62O12
-
60192-37-2
C55H78O21
-
68340-31-8
2-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl-11-oxoolean-12-en-30-oate
1405-86-3 Downstream products
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53-96-3
2-acetylaminofluorene
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147218-57-3
18β-glycyrrhetinic acid α-D-glucuronic acid
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1200807-21-1
C72H102N4O20
-
1200807-19-7
C68H96N2O18
