Glycyrrhizic acid ammonium salt

Glycyrrhizic acid ammonium salt Basic information
Product Name:Glycyrrhizic acid ammonium salt
Synonyms:monoammoniumglycyrrhetat;Monoammoniumglycyrrhetate;(2S,3S,4S,5R,6S)-6-[[(3S,4aS,6aR,6bS,8aR,11S,12aR,14aS,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]-5-[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxy-oxan-2-yl]oxy-3,4-dihydroxyoxane-2-carboxylic acid azane;alpha-D-Glucopyranosiduronic acid, (3-beta,20-beta)-20-carboxy-11-oxo-30-norolean-12-en- 3-yl 2-O-beta-D-glucopyranuronosyl-, ammoniate;20β-Carboxy-11-oxo-30-noroleana-12-ene-3β-yl 2-O-(β-D-glucopyranuronosyl)-α-D-glucopyranosiduronic acid/ammonia,(1:x);Glycyrrhizine ammonium salt;AMMONIUM 10-[6-CARBOXY-3-(6-CARBOXY-3,4,5-TRIHYDROXY-OXAN-2-YL)OXY-4,5-DIHYDROXY-OXAN-2-YL]OXY-2,4A,6A,6B,9,9,12A-HEPTAMETHYL-13-OXO-3,4,5,6,6A,7,8,8A,10,11,12,14B-DODECAHYDRO-1H-PICENE-2-CARBOXYLATE;AMMONIATED GLYCYRRHIZIN
CAS:53956-04-0
MF:C42H65NO16
MW:839.97
EINECS:258-887-7
Product Categories:API;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Herb extract;Pyridines;Inhibitors;Natural Plant Extract;The group of Liquorice;Biochemistry;Disaccharides;Glycosides;Sugars;Organics;53956-04-0
Mol File:53956-04-0.mol
Glycyrrhizic acid ammonium salt Structure
Glycyrrhizic acid ammonium salt Chemical Properties
Melting point >200°C (dec.)
Boiling point 768.56°C (rough estimate)
density 1.1846 (rough estimate)
refractive index 49 ° (C=1.5, EtOH)
FEMA 2528 | GLYCYRRHIZIN, AMMONIATED (GLYCYRRHIZA SPP.)
storage temp. 2-8°C
solubility Slightly soluble in water, very slightly soluble in anhydrous ethanol, practically insoluble in acetone. It dissolves in dilute solutions of acids and of alkali hydroxides.
form Powder or Crystals
color Yellow to yellow-green
Odorbland
optical activity[α]20/D +48±4°, c = 1% in ethanol: water (1:1)
BRN 3897076
Stability:Hygroscopic
InChIKeyILRKKHJEINIICQ-YDYGGSECSA-N
LogP-0.9
CAS DataBase Reference53956-04-0
EPA Substance Registry System.alpha.-D-Glucopyranosiduronic acid, (3.beta.,20.beta.)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-.beta.-D-glucopyranuronosyl-, monoammonium salt (53956-04-0)
Safety Information
RIDADR UN 3077 9 / PGIII
WGK Germany 2
RTECS LZ6500000
3-10
HS Code 29389090
Glycyrrhizic acid ammonium salt Usage And Synthesis
Description§ 184.1408(a)(1) Licorice (glycyrrhiza) root is the dried and ground rhizome and root portions of Glycyrrhiza glabra or other species of glycyrrhiza. Licorice extract is that portion of the licorice root that is, after maceration, extracted by boiling water. The extract can be further purified by filtration and by treatment with acids and ethyl alcohol. Licorice extract is sold as a liquid paste ("block"), or spraydried powder. (2) Ammoniated glycyrrhizin is prepared from the water extract of licorice root by acid precipitation followed by neutralization with dilute ammonia. Monoammonium glycyrrhizinate (C42H61016NH45H2O ) is prepared from ammoniated glycyrrhizin by solvent extraction and separation techniques.
Chemical PropertiesLicorice (glycyrrhiza) root is the dried and ground rhizome and root portions of Glycyrrhiza glabra or other species of glycyrrhiza Ammoniated glycyrrhizin is prepared from the water extract of licorice root by acid precipitation, followed by neutral- ization with dilute ammonia Monoammonium glycyrrhizinate (C42H62O16NH45H2O) is prepared from ammoniated glycyrrhizin by solvent extraction and separation techniques.
Chemical Propertieswhite to slightly yellow powder
Usespharmaceutical excipient, GRAS, sweetener
Usesanti-cancer agent
UsesAmmonium Glycyrrhizinate is used in the synthesis of polyion complex nanocarriers which may act as a template for the design of other negatively charged water-soluble drugs. Particularly for anti-infl ammatory drugs with which Ammonium Glycyrrhizinate is associated.
UsesGlycyrrhizic acid ammonium salt is a flavoring and sweetening agent obtained from licorice flavonoids. It has a slight licorice flavor and an intense and rounded sweetness. It is soluble in water, glycerin, and propylene glycol and has good thermal stability but can degrade under prolonged heating. It is stable over a ph of 3.5–9 but could precipitate below ph of 3.5. It can be used in beverages, desserts, confectionary products, soups, and dressings.
DefinitionChEBI: Monoammonium glycyrrhizinate is an organic molecular entity.
General DescriptionProduced and qualified by HWI pharma services GmbH.
Exact content by quantitative NMR can be found on the certificate.
Biochem/physiol ActionsBiologically active constituent in the sweet root of Glycyrrhiza species (licorice). Antiviral.
Anticancer ResearchGlycyrrhizin (GL) is a saponin-like compound that provides the main sweet flavourfor G. glabra (licorice), and it is commonly used in clinical treatment for itsoutstanding pharmacological action such as antitumour, anti-inflammatory andanti-oxidativeactions (Rebhun et al. 2015; Wu et al. 2015). Cai et al. (2017) triedto evaluate the anticancer properties of GA and GL against TNBC in combinationwith etoposide.
Safety ProfileModerately toxic by intravenous route. An experimental teratogen. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NH3.
targetROS
Purification MethodsCrystallise the ammonium salt from glacial acetic acid, then dissolve it in ethanolic ammonia and evaporate. The pentahydrate forms needles from 75% aqueous EtOH, m 212-217o. The free acid crystallises from glacial acetic acid. [Karrer et al. Helv Chim Acta 4 100 1921, Lithgoe & Tripett J Chem Soc 1983, 1987 1950, Beilstein 18 IV 5156.]
Glycyrrhizic acid ammonium salt Preparation Products And Raw materials
Raw materialsAmmonium hydroxide-->LACQUER THINNER-->Glycyrrhizic acid-->DGL
Preparation ProductsAmmonium Glycyrrhizinate
Glycyrrhizic acid 5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione Sodium hyaluronate DGL GLYCYRRHIZIC ACID AMMONIUM SALT TRIHYDRATE Glycyrrhizic acid ammonium salt Ammonium hydroxide AMMONIUM GLYCYRRHIZIC ACID, MONOAMMONIUM SALT HYDRATE, CA. 75 Diammonium glycyrrhizinate Ammonium nitrate Ammonium chloride GLYCYRRHIZIC ACID, AMMONIUM SALT, TRIHYDRATE(RG) BETA MAX? Ammonium acetate Ammonium Glycyrrhizinate Ammonium sulfate

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