4505. Glycyrrhizic Acid

Nomenclature

CAS number: 1405-86-3
(3β,20β)-20-Carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-β-d-glucopyranuronosyl-α-d-glucopyranosiduronic acid; glycyrrhizin; glycyrrhizinic acid; glycyrrhetinic acid glycoside.
C42H62O16; mol wt 822.93.
C 61.30%, H 7.59%, O 31.11%.

Description and 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).

Chemical structure

Properties

Crystals from glacial acetic acid. Intensely sweet taste. [α]D17 +46.2° (c = 1.5 in alc). Freely sol in hot water, alcohol; practically insol in ether.

Derivative

Ammonium glycyrrhizinate pentahydrate.
C42H65NO16.5H2O; mol wt 930.04.
C 54.24%, H 8.13%, N 1.51%, O 36.13%.

Properties

Needles from 75% aqueous ethanol, decomp 212-217°. [α]D20 +46.9° (c = 1.5 in 40% ethanol). uv max: 248 nm (ε 11400). Sol in ammonia water, glacial acetic acid.

Derivative

Dipotassium salt.

Nomenclature

Rizinsan K2 A2.
C42H60K2O16; mol wt 899.11.
C 56.11%, H 6.73%, K 8.70%, O 28.47%.