186. Agaricic Acid

Nomenclature

CAS number: 666-99-9
2-Hydroxy-1,2,3-nonadecanetricarboxylic acid; agaric acid; agaricin; agaricinic acid; laricic acid; n-hexadecylcitric acid; α-cetylcitric acid.
C22H40O7; mol wt 416.55.
C 63.43%, H 9.68%, O 26.89%.

Description and references

Active principle of Fomes laricis (Jacq.) Murrill (Polyporus officinalis Fries), Polyporaceae: Thoms, Vogelsang, Ann. 357, 145 (1907). Attempted syntheses: Evans, J. Chem. Soc. 1959, 1313; Graf, Liu, Arch. Pharm. 306, 366 (1973). Activity studies: Bacchi et al., J. Bacteriol. 98, 23 (1969).

Chemical structure

Properties

Sesquihydrate, odorless, almost tasteless, crystalline powder. Anhydrous, mp 142° (dec). [α]D19 9° (NaOH). Slightly sol in cold water, chloroform or ether; freely sol in boiling water, alkalies, hot glacial acetic acid. One gram dissolves in 180 ml cold, 10 ml boiling alcohol.

Note

The name agaric acid has also been used for a lanostane-like mixture [C.A. 68, 29894j (1968)].

Use

Has been used as antiperspirant.