Picrolichenic Acid
Title: Picrolichenic Acid
CAS Registry Number: 466-34-2
CAS Name: 6-Hydroxy-2¢-methoxy-2,4¢-dioxo-4,6¢-dipentylspiro[benzofuran-3(2H),1¢-[2,5]cyclohexadiene]-5-carboxylic acid
Additional Names: picrolichenin
Molecular Formula: C25H30O7
Molecular Weight: 442.50
Percent Composition: C 67.86%, H 6.83%, O 25.31%
Literature References: Bitter acidic principle of crustose lichen, Pertusaria amara (Ach.) Nyl., Pertusariaceae. Isoln: Alms, Ann. Pharm. 1, 61 (1832). Identity of picrolichenin and picrolichenic acid: Zopf, Ann. 321, 38 (1902). Isoln and structure: Wachmeister, Acta Chem. Scand. 12, 147 (1958). Synthesis: Davidson, Scott, J. Chem. Soc. 1961, 4075.
Properties: Prisms from benzene, dec 184-187°; prisms from aqueous acetic acid, decomp 187-190°. Intense bitter taste similar to that of quinine. Optically inactive. uv max: 245, 270-277 nm (e 24,000, 7800). Readily sol in most organic solvents except benzene and light petroleum.
Absorption maximum: uv max: 245, 270-277 nm (e 24,000, 7800)
 
Derivative Type: Methyl picrolichenate
Molecular Formula: C26H32O7
Molecular Weight: 456.53
Percent Composition: C 68.40%, H 7.07%, O 24.53%
Properties: Needles from methanol, mp 102-103.5°. Soluble in cold 0.5N NaOH.
Melting point: mp 102-103.5°
 
Derivative Type: Methyl O-methylpicrolichenate
Molecular Formula: C27H34O7
Molecular Weight: 470.55
Percent Composition: C 68.92%, H 7.28%, O 23.80%
Properties: Needles from hexane, mp 80-82°. Practically insol in cold 0.1N NaOH.
Melting point: mp 80-82°
 
 
Status: This monograph has been retired and is no longer subject to revision or update.

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