Hypericin
Title: Hypericin
CAS Registry Number: 548-04-9
CAS Name: 1,3,4,6,8,13-Hexahydroxy-10,11-dimethylphenanthro[1,10,9,8-opqra]perylene-7,14-dione
Additional Names: 4,5,7,4¢,5¢,7¢-hexahydroxy-2,2¢-dimethylnaphthodianthrone; hypericum red
Molecular Formula: C30H16O8
Molecular Weight: 504.44
Percent Composition: C 71.43%, H 3.20%, O 25.37%
Literature References: Characteristic principal of hypericum, q.v. (St. John's wort). Isoln from Hypericum perforatum L., Hypericaceae: Brockmann et al., Ann. 553, 1 (1942). Synthesis from bromoemodin trimethylether: Brockmann, Muxfeld, Naturwissenschaften 40, 411 (1953). Structure: Brockmann et al., ibid. 37, 540 (1950); Brockmann, Sanne, ibid. 40, 509 (1953). Total synthesis: Brockmann, Kluge, US 2707704 (1955 to Schenley); Brockmann et al., Ber. 90, 2302 (1957); Brockmann, Eggers, ibid. 91, 547 (1958). Clinical pharmacokinetics and evaluation of phototoxic potential: J. Brockmöller et al., Pharmacopsychiatry 30, Suppl 2, 94 (1997). HPLC determn in plasma: J. D. Chi, M. Franklin, J. Chromatogr. B 724, 195 (1999).
Properties: Solvated blue-black needles from pyridine + methanolic HCl, dec 320°. Freely sol in pyridine and other organic bases yielding cherry-red solns with red fluorescence. Almost insol in most other organic solvents. Sol in alkaline aq solns; below pH 11.5 solns are red, above pH 11.5 they are green with red fluorescence. Absorption and fluorescence spectra: Scheibe, Schöntag, Ber. 75, 2019 (1942); Brockmann, Neef, loc. cit.
Therap-Cat: Antidepressant.
Keywords: Antidepressant.

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