PubMed · 85892
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L G Millard. 1979-03-24. Dithranol for psoriasis.. https://pubmed.ncbi.nlm.nih.gov/85892/
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The central ring of the anthrone system in 1,8-diiodo-10-hydroxy-10-(3-methylbut-3-en-1-ynyl)anthrac en-9(10H)-one, C19H12I2O2, has a boat conformation and the two outer rings form a dihedral angle of 41.1 (2) degrees. The I-C bond lengths are 2.094 (4) and 2.083 (4) A. The hydroxyl and carbonyl groups form an intermolecular hydrogen bond having an O...O distance of 2.853 (4) A.
The title compound, C15H10O2, was found to crystallize in the centrosymmetric space group P2(1)/n. The hydrogen bonding is of the cyclic dimer type about a center of symmetry. The carboxyl O atoms are ordered as is the carboxyl H atom. The anthracene core, while less nearly planar, shows good agreement with the anthracene cores of anthracene-9-carboxylic acid and anthracene-1,6-dicarboxylic acid. The carboxyl group plane makes a dihedral angle of 12.4 (2) degrees with the best-fit anthracene core plane.
Sphingomonas yanoikuyae B1 is extremely versatile in its catabolic ability. An insertional mutant strain, S. yamoikuyae EK504, which is unable to grow on naphthalene due to the loss of 2-hydroxychromene-2-carboxylate isomerase activity, was utilized to investigate the role of this enzyme in the degradation of anthracene by S. yanoikuyae B1. Although EK504 is unable to grow on anthracene, this strain could transform anthracene to some extent. A metabolite in the degradation of anthracene by EK504 was isolated by high-pressure liquid chromatography (HPLC) and was identified as 6,7-benzocoumarin by UV-visible, gas-chromatographic, HPLC/mass-spectrometric, and 1H nuclear magnetic resonance spectral techniques. The identification of 6,7-benzocoumarin provides direct chemical and genetic evidence for the involvement of nahD in the degradation of anthracene by S. yanoikuyae B1.