Glycyrrhizic Acid
Title: Glycyrrhizic Acid
CAS Registry Number: 1405-86-3
CAS Name: (3b,20b)-20-Carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-b-D-glucopyranuronosyl-a-D-glucopyranosiduronic acid
Additional Names: glycyrrhizin; glycyrrhizinic acid; glycyrrhetinic acid glycoside
Molecular Formula: C42H62O16
Molecular Weight: 822.93
Percent Composition: C 61.30%, H 7.59%, O 31.11%
Literature References: Triterpene saponin used in traditional Chinese medicinal preparations for its anti-inflammatory, antiulcerous and antiallergic effects. 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 (1956). Structure: Lythgoe, Trippett, J. Chem. Soc. 1950, 1983. Revised structure: Marsh, Levvy, Biochem. J. 63, 9 (1956). See also: I. Kitagawa et al., Chem. Pharm. Bull. 36, 3710 (1988); T. Hatano et al., ibid. 39, 1238 (1991). Synthesis of derivatives: Brieskorn, Sax, Arch. Pharm. 303, 905 (1970). LC-MS/MS determn in plasma: Z. J. Lin et al., J. Chromatogr. B 814, 201 (2005). Review: Nieman, Chem. Weekbl. 48, 213 (1952).
Properties: Crystals from glacial acetic acid. Intensely sweet taste. [a]D17 +46.2° (c = 1.5 in alc). Freely sol in hot water, alcohol; practically insol in ether.
Optical Rotation: [a]D17 +46.2° (c = 1.5 in alc)
 
Derivative Type: Ammonium glycyrrhizinate pentahydrate
Molecular Formula: C42H65NO16.5H2O
Molecular Weight: 930.04
Percent Composition: C 54.24%, H 8.13%, N 1.51%, O 36.13%
Properties: Needles from 75% aqueous ethanol, decomp 212-217°. [a]D20 +46.9° (c = 1.5 in 40% ethanol). uv max: 248 nm (e 11400). Sol in ammonia water, glacial acetic acid.
Optical Rotation: [a]D20 +46.9° (c = 1.5 in 40% ethanol)
Absorption maximum: uv max: 248 nm (e 11400)
 
Derivative Type: Dipotassium salt
Trademarks: Rizinsan K2 A2
Molecular Formula: C42H60K2O16
Molecular Weight: 899.11
Percent Composition: C 56.11%, H 6.73%, K 8.70%, O 28.47%

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