Glycyrrhizic acid ammonium salt - analytical standard , CAS No.53956-04-0

CAS: 53956-04-0 Cat. No.: G109354 Molecular Weight: 839.96 Beilstein Registry Number: 3897076 EC Number: 258-887-7

GRADE & PURITY Analytical standard

Synonyms

AMMONIUM GLYCYRRHIZATE [INCI] | Ammonium glycyrrhizate, European Pharmacopoeia (EP) Reference Standard | Glycyrrhizin Acid Ammonium Salt | Glycyrrhizin ammoniacal | C18610 | Glycyrrhizin, ammoniated (Glycyrrhiza spp.) | Ammonium Glycyrrhizate, Pharmaceuti

Storage

Store at 2-8°C

Shipped In

Wet ice

Specifications

Synonyms

AMMONIUM GLYCYRRHIZATE [INCI] | Ammonium glycyrrhizate, European Pharmacopoeia (EP) Reference Standard | Glycyrrhizin Acid Ammonium Salt | Glycyrrhizin ammoniacal | C18610 | Glycyrrhizin, ammoniated (Glycyrrhiza spp.) | Ammonium Glycyrrhizate, Pharmaceuti

Specifications & Purity

analytical standard

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Analytical standard

Names and Identifiers

• 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.N
• 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
• InChIKey: ILRKKHJEINIICQ-OOFFSTKBSA-N
• 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
• 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.N
• WGK Germany: 2
• RTECS: LZ6500000
• Molecular Weight: 839.96
• Beilstein: 3897076
• Reaxy-Rn: 30023600
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=30023600&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Terpene glycosides
        • Level5 Triterpene glycosides
          • Level6 Triterpene saponins

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Terpene glycosides
• Intermediate Tree Nodes: Triterpene glycosides
• Direct Parent: Triterpene saponins
• Alternative Parents: Triterpenoids O-glucuronides Disaccharides O-glycosyl compounds Tricarboxylic acids and derivatives Beta hydroxy acids and derivatives Cyclohexenones Pyrans Oxanes Secondary alcohols Acetals Polyols Carboxylic acids Oxacyclic compounds Organic oxides Hydrocarbon derivatives Organic nitrogen compounds
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Triterpene saponin - Triterpenoid - 1-o-glucuronide - O-glucuronide - Glucuronic acid or derivatives - Disaccharide - Glycosyl compound - O-glycosyl compound - Tricarboxylic acid or derivatives - Cyclohexenone - Beta-hydroxy acid - Pyran - Hydroxy acid - Oxane - Secondary alcohol - Ketone - Organoheterocyclic compound - Polyol - Acetal - Carboxylic acid - Carboxylic acid derivative - Oxacycle - Organic oxide - Organic oxygen compound - Alcohol - Organic nitrogen compound - Carbonyl group - Hydrocarbon derivative - Organooxygen compound - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.
• External Descriptors: organic molecular entity

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Specific Rotation[α]: 49 ° (C=1.5, EtOH)
• Melt Point(°C): 209°C
• Molecular Weight: 840.000 g/mol
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 17
• Rotatable Bond Count: 7
• Exact Mass: 839.43 Da
• Monoisotopic Mass: 839.43 Da
• Topological Polar Surface Area: 268.000 Ų
• Heavy Atom Count: 59
• Formal Charge: 0
• Complexity: 1730.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 19
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 2

XLogP3

References

1. Jiajia Jin, Jun chen, Xin Shou, Keqing Shi, Xingjie Zan, Yan Zu, Xiaoying Huang.  (2023)  MAG-encapsulated PLGA microspheres for Lipopolysaccharide-induced acute lung injury.  JOURNAL OF DRUG DELIVERY SCIENCE AND TECHNOLOGY,      [PMID:] [10.1016/j.jddst.2023.104632]

2. Shaowei Tan, Qiyuan Li, Liwei Guo, Yongxiang Wang, Wenwei Zhong.  (2022)  Investigation of foaming behavior in herbal extracts via the characterization of solution environment for reverse osmosis concentration.  FOOD AND BIOPRODUCTS PROCESSING,      [PMID:] [10.1016/j.fbp.2022.10.011]

3. Hao Zhang, Nan Tang, Xia Yu, Zhongkai Guo, Zhen Liu, Xiaoming Sun, Min-Hui Li, Jun Hu.  (2021)  Natural glycyrrhizic acid-tailored hydrogel with in-situ gradient reduction of AgNPs layer as high-performance, multi-functional, sustainable flexible sensors.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2021.132779]