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Glycyrrhizic acid(CAS No. 1405-86-3)

Glycyrrhizic acid C42H62O16 (cas 1405-86-3) Molecular Structure

1405-86-3 Structure

Identification and Related Records

【Name】
Glycyrrhizic acid
【CAS Registry number】
1405-86-3
【Synonyms】
6-[(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-(6-carboxy-3,4,5-trihydroxy-oxan-2-yl)oxy-3,4-dihydroxy-oxane-2-carboxylic acid
See R-D-Glucopyranosiduronic acid,(3a,20a)-20-carboxy-11-oxo-30- norolean-12-en-3-yl 2-O-a-D-glucopyranuronosyl-
Glycyrrhizinic acid
Glycyrrhizinate
Rizinsan K2 A2 (free acid)
Glycyrrizin
Glycyrrhizin (JAN)
Glycrrhizin
Glycyron (TN)
Glycyrrhetinic acid glycoside
Liquorice
【EINECS(EC#)】
215-785-7
【Molecular Formula】
C42H62O16 (Products with the same molecular formula)
【Molecular Weight】
822.94
【Inchi】
InChI=1/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
【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
【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
【MOL File】
1405-86-3.mol

Chemical and Physical Properties

【Appearance】
Crystals from glacial acetic acid. Obtained from licorice.
【Density】
1.43g/cm3
【Melting Point】
220 deg C decomposes
【Boiling Point】
971.4°Cat760mmHg
【Vapour】
0mmHg at 25°C
【Refractive Index】
61 ° (C=1.5, EtOH)
【Flash Point】
288.1°C
【Solubilities】
Insoluble
【Color/Form】
Crystals from glacial acetic acid
PLATES OR PRISMS FROM ACETIC ACID
【Spectral properties】
Specific optical rotation: +46.2 deg @ 17 deg C/D (alcohol, 1.5%)
【Computed Properties】
Molecular Weight:822.93208 [g/mol]
Molecular Formula:C42H62O16
XLogP3-AA:3.7
H-Bond Donor:8
H-Bond Acceptor:16
Rotatable Bond Count:7
Tautomer Count:5
Exact Mass:822.403786
MonoIsotopic Mass:822.403786
Topological Polar Surface Area:267
Heavy Atom Count:58
Formal Charge:0
Complexity:1730
Isotope Atom Count:0
Defined Atom Stereocenter Count:19
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1

Safety and Handling

【Safety Statements 】
S22;S24/25
【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.
【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.
【Exposure Standards and Regulations】
Substance added directly to human food affirmed as generally recognized as safe (GRAS). /Licorice and licorice derivatives/
【Octanol/Water Partition Coefficient】
log Kow = 2.80
【Disposal Methods】
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.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Extraction from Glycyrrhiza glabra L., Leguminosae: Karrer, Chao, Helv Chim Acta 4,100 (1921); Ruzicka, Louenberger, ibid 19, 1402 (1936).
From commercial glycyrrhizinum ammoniacale: Tschirch, Cederberg, Arch Pharm 245, 97 (1907); Voss et al, Ber 70, 122 (1937).
Revised method of isoln: Conn, Conn, J Lab Clin Med 47, 20 (1965).
【Usage】

Antiviral, hepatoprotective.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Substances that reduce or suppress INFLAMMATION.
【Therapeutic Uses】
DEMULCENT, MILD LAXATIVE; EXPECTORANT; USED TO DISGUISE TASTE OF MEDICATIONS
SNMC (stronger Neominophagen C), whose active component is glycyrrhizin (a saponin extracted from licorice) has been utilized to improve the liver function in Japan. To assess the effectiveness of interferon (IFN), stronger Neominophagen C combination therapy in patients, who did not respond to interferon therapy alone, we investigate 28 patients with histology of CAH 2B at 12 weeks after interferon administration. 15 patients received interferon alone continuously (group A), and 13 patients received interferon with stronger Neominophagen C (group B) for 12 weeks thereafter. Normalization of serum ALT level was observed in 33.3% of group A and in 64.3% of group B. Disappearance of serum HVC RNA was 13.3% in group A and 38.5% in group B. But these data were not significant statistically. Histological improvement was not significant, between group A and B by Knodel's HAI score, but reversal of histological grade (Europe classification) was noted more frequently in group B. A case of post transfusion hepatitis type C, exacerbated by interferon therapy is reported. HLA class I antigen was strongly expressed in the liver tissue after administration of interferon. In this case, potentiation of cellular immunity was thought to be the cause of the exacerbation and interferon, stronger Neominophagen C combination therapy was useful in improving liver function. [Abe Y et al; Nippon Rinsho 52 (7): 1817-22 (1994)]

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