187. Agaritine

Nomenclature

CAS number: 2757-90-6
l-Glutamic acid 5-[2-[4-(hydroxymethyl)phenyl]hydrazide]; β-N-[γ-l(+)-glutamyl]-4-hydroxymethylphenylhydrazine.
C12H17N3O4; mol wt 267.28.
C 53.92%, H 6.41%, N 15.72%, O 23.94%.

Description and references

Constituent of the commercial, edible mushroom Agaricus bisporus (Lange) Sing. [Psalliota hortensis Cooke var. bispora], Agaricaceae (Agaricales). Isoln and structure: Levenberg, Fed. Proc. 19, 6 (1960); J. Am. Chem. Soc. 83, 503 (1961); Daniels et al., ibid. 3333; see also Levenberg in Methods Enzymol. 17 (Part A), 877 (1970). Synthesis: Kelly et al., J. Org. Chem. 27, 3229 (1962); Hinman, Kelly, US 3274232; US 3288848 (both 1966 to Upjohn).

Chemical structure

Properties

Glistening crystals from dil alcohol, dec 205-209°. [α]D25 +7° (c = 0.8). uv max (water): 237.5, 280 nm (ε 12,000, 1,400). Very freely sol in water, practically insol in the usual anhydr organic solvents. pKa in water: 3.4 and 8.86.