53956-04-0 , Glycyrrhizin monoammonium salt
Cas:53956-04-0
C42H65NO16 / 839.96
MFCD00167400
Glycyrrhizic acid is a natural triterpenoid saponin that can be isolated from the root of licorice. It is an agonist of the human sweet taste receptor and is used as a flavorant. Glycyrrhizic acid has diverse cellular effects at low doses, including antioxidant, anti-inflammatory, antimicrobial, and antiviral actions. Presumably through its role as an antioxidant, glycyrrhizic acid alters signaling through a variety of signaling pathways, impacting pathologies such as metabolic syndrome, fibrosis, and ultraviolet-B-induced skin damage in cellular and animal models.
Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards. Ammonium Glycyrrhizate is the ammonium salt of glycyrrhizic acid (GA), an important ingredient in the liquorice root with a broad-spectrum of biological and pharmacological properties.
Glycyrrhizic acid (GA) is a non-selective inhibitor of 11β-hydroxysteroid dehydrogenase (11β-HSD), which mediates the inter-conversion of active and inactive glucocorticoids. GA also shows inhibitory effect on the cytokine activity of high-mobility group box 1 protein (HMGB1).
Ammonium glycyrrhizate is a commercial flavorant and emulsifer found in Glycyrrhiza. It inhibits 11β-HSD and is used to treat herpes virus infection. It inhibits viral entry to host cells, prevents glial inflammation and kaninic acid-induced neuronal death, and suppresses DMH-induced carcinogenesis.
Glycyrrhizin is a natural triterpenoid and the main active ingredient of licorice. In humans, the main side effects are increasing blood pressure (hypertension) and of enhancing the risk of hypokalemia-induced disorders, i.e. caused by low potassium levels in blood (Omar, 2012). Used as a flavouring agent, glycyrrhizin is the triterpenoid compound behind the sweet taste of licorice. Glycyrrhizin is naturally present at concentrations up to 25% in the roots of the Glycyrrhiza glabra. In mice, rats, and human cancer cell lines, glycyrrhizin is an antioxidant and a DNA-protective agent with additional, multiple anticancer activities.
CAS Number | 53956-04-0 |
Product Name | Ammonium glycyrrhizate |
IUPAC Name | (2S,3S,4S,5R,6R)-6-[(2S,3R,4S,5S,6S)-2-[[(3S,4aR,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;azane |
Molecular Formula | C42H65NO16 |
Molecular Weight | 839.96 g/mol |
InChI | InChI=1S/C42H62O16.H3N/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);1H3/t19-,21-,22-,23-,24-,25-,26-,27+,28-,29-,30+,31+,34-,35-,38+,39-,40-,41+,42+;/m0./s1 |
InChI Key | ILRKKHJEINIICQ-YLBMWBJISA-N |
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.N |
Solubility | Soluble in DMSO |
Synonyms | (+)-Glycyram; 18β-Glycyrrhizic acid monoammonium salt; Ammonium glycyrrhizate; Ammonium glycyrrhizinate; Glycamil; Glycymin; Glycyron ammonium salt; Glycyron monoammonium salt; Glycyrram; Glycyrrhizic acid ammonium salt; Glycyrrhizic acid monoammonium salt; Glycyrrhizin ammonium salt; Glycyrrhizin monoammonium salt; Magnasweet; Monoammonium 18β-glycyrrhizinate; Monoammonium glycyrrhizate; Monoammonium glycyrrhizinate; NSC 2800; NSC 35348. |
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.[NH4+].[NH4+].[NH4+] |
Isomeric 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-].[NH4+].[NH4+].[NH4+] |
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