o-Orsellinic Acid
Title: o-Orsellinic Acid
CAS Registry Number: 480-64-8
CAS Name: 2,4-Dihydroxy-6-methylbenzoic acid
Additional Names: 6-methyl-b-resorcylic acid; 4,6-dihydroxy-o-toluic acid; 2,4-dihydroxy-6-methylbenzenecarboxylic acid; orcinolcarboxylic acid
Molecular Formula: C8H8O4
Molecular Weight: 168.15
Percent Composition: C 57.14%, H 4.80%, O 38.06%
Literature References: Found in conjugated form or in depside form in Roccella and Lecanora lichens, postulated to arise by autocondensation of acetoacetic acid. Isoln from the fungus Chaetomium cochliodes: Mosback, Z. Naturforsch. 14B, 69 (1959). Synthesis: Sonn, Ber. 61, 926 (1928); Kloss, Clayton, J. Org. Chem. 30, 3566 (1965).
Properties: Needles from acetone, mp 176° (effervescence). pK (25°) 3.90. uv max (0.1N HCl): 214, 260, 296 nm; in 0.1N NaOH: 272 nm. Sol in water, alcohol, glycerol. Soly in ether at 20° = 15.7%. Slightly sol in benzene.
Melting point: mp 176° (effervescence)
pKa: pK (25°) 3.90
Absorption maximum: uv max (0.1N HCl): 214, 260, 296 nm; in 0.1N NaOH: 272 nm
 
Derivative Type: Monohydrate
Properties: Needles from water, mp 186-189°.
Melting point: mp 186-189°
 
Derivative Type: Methyl ester
Molecular Formula: C9H10O4
Molecular Weight: 182.17
Percent Composition: C 59.34%, H 5.53%, O 35.13%
Properties: Crystals, mp 140°.
Melting point: mp 140°
 
Derivative Type: Ethyl ester
Molecular Formula: C10H12O4
Molecular Weight: 196.20
Percent Composition: C 61.22%, H 6.16%, O 32.62%
Properties: Crystals, mp 132°.
Melting point: mp 132°

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