LICHEN ACIDS
Lichens are a unique life form that depends upon the symbiotic relationship between algae and fungi. Together this association produces some of the most hardy organisms on earth. Lichens have another unique characteristic: they are veritable chemical factories. The chemistry of lichen constituents has been studied extensively for more than a century. Hundreds of compounds have been identified, yet most fall under the generic classification of “lichen acids”, which encompasses two chemical classes: the depsides (e.g., atranorin, lecanoric acid, gyrophoric acid) and depsidones (e.g., psoromic acid, stictic acid). Other groups, while less common as structural classes, are noteworthy in their individual abundance (e.g., usnic acid).
Lichen acids have been reported to have antibiotic and antiinflammatory activities, however most have seen little attention in today’s broad screens. Their structural novelty holds a wealth of discovery potential.
D1000: ATRANORIN
3-Hydroxy-4-(methoxycarbonyl)-2,5-dimethylphenyl 3-formyl-2,4-dihydroxy-6-methylbenzoate. Parmelin
CAS #: 479-20-9; C19H18O8; mol wt. 374.35.
Occurrence: common constituent of Parmelia, Lecanora and numerous other genera.
Appearance: colorless crystals, mp: 196-197°C.
Solubility: insoluble in water; soluble in DMSO, ethanol, and most nonpolar solvents.
Stability: unstable to alkali; store at room temperature.
References: Helv Chim Acta 17: 1319 (1934); Tetrahedron 21: 3531 (1965)Availability: 100 mg, 1 gram
D3000: LECANORIC ACID
4-Carboxy-3-hydroxy-5-methylphenyl 2,4-dihydroxy-6-methylbenzoate. Glabratic acid
CAS #: 480-56-8; C16H14O7; mol wt. 318.28.
Occurrence: Evernia, Parmelia and Umbilicaria species.
Appearance: colorless crystals, mp: 175-176°C.
Solubility: insoluble in water and hexane; soluble in DMSO, ethanol, and ethyl acetate.
Stability: unstable to alkali; store at room temperature.
References: Monatsh Chem 61: 147 (1932); Tetrahedron 21: 3531 (1965)Availability: 100 mg, 1 gram
D3200: DIFFRACTAIC ACID
4-Carboxy-3-hydroxy-2,5-dimethylphenyl 2,4-dimethoxy-3,6-dimethylbenzoate. Dirhizonic acid
CAS #: 436-32-8; C20H22O7; mol wt. 374.39.
Occurrence: Usnea species.
Appearance: colorless crystals, mp: 189°C dec.
Solubility: insoluble in water and hexane; soluble in DMSO, ethanol, and ethyl acetate.
Stability: unstable to alkali; store at room temperature.
References: Helv Chim Acta 11: 864 (1928); J Chem Soc 1932: 1675Availability: 100 mg, 1 gram
D4100: GANGLEOIDIN
Methyl 2,4-dichloro-3-hydroxy-8-methoxy-1,6-dimethyl-11-oxo-11H-dibenzo[b,e][1,4]dioxepin-7-carboxylate
CAS #:55365-63-4; C18H14Cl2O7; mol wt. 413.21.
Occurrence: Lecanora species.
Appearance: colorless crystals, mp: 214-215°C.
Solubility: insoluble in water and hexane; soluble in DMSO, ethanol, and ethyl acetate.
Stability: stable; store at room temperature.
References: J Chem Soc 1986: 1491Availability: 100 mg, 1 gram
D4200: LEOIDIN
2,4-Dichloro-3,8-dihydroxy-1,6,9-trimethyl-11-oxo-11H-dibenzo[b,e][1,4]dioxepin-7-carboxylic acid
CAS #:105350-54-7; C18H14Cl2O7; mol wt. 413.21.
Occurrence: Lecanora gangaleoides.
Appearance: colorless crystals, mp: 232-233°C.
Solubility: insoluble in water and hexane; soluble in DMSO, ethanol, and ethyl acetate.
Stability: stable; store at room temperature.
References: J Chem Soc 1986: 1491Availability: 100 mg, 1 gram
D4850: PROTOCETRARIC ACID
D4900: FUMARPROTOCETRARIC ACID
D5000: LOBARIC ACID
Usnetic acid
CAS #: 522-53-2; C25H28O8; mol wt. 459.49.
Occurrence: Stereocaulon and Parmelia species.
Appearance: colorless crystals, mp: 192°C.
Solubility: insoluble in water and hexane; soluble in DMSO, ethanol, and ethyl acetate.
Stability: stable; store at room temperature.
References: Ber 69: 643 (1936); Phytochemistry 13: 2315 (1974)Availability: 100 mg, 1 gram
D7000: STICTIC ACID
1,3-dihydro-1,4-dihydroxy-10-methoxy-5,8-dimethyl-3,7-dioxo07H-isobenzofuro[4,5-b][1,4]benzodioxepin-11-carboxaldehyde; Stereocaulonic acid
CAS #:549-06-4; C19H14O9; mol wt. 386.31.
Occurrence: Lecanora, Sterocaulon, and other genera.
Appearance: colorless crystals, mp: 268°C dec.
Solubility: insoluble in water and nonpolar solvents; soluble in DMSO; slightly soluble in ethanol.
Stability: stable; store at room temperature.
References: Ber 66, 943 (1933); Tetrahedron 24, 2707 (1966)Availability: 100 mg, 1 gram
D9000:VULPINIC ACID
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