9735. Trioxsalen

Nomenclature

CAS number: 3902-71-4
2,5,9-Trimethyl-7H-furo[3,2-g][1]benzopyran-7-one; 6-hydroxy-β,2,7-trimethyl-5-benzofuranacrylic acid δ-lactone; 4,5′,8-trimethylpsoralen; NSC-71047; Trisoralen (Valeant).
C14H12O3; mol wt 228.24.
C 73.67%, H 5.30%, O 21.03%.

Description and references

Synthetic trimethyl psoralen deriv. Prepn: K. D. Kaufman, J. Org. Chem. 26, 117 (1961); US 3201421 (1965). Protective effect vs UV-B erythema: P. G. Agache, L. Coupez, Arch. Dermatol. Res. 268, 85 (1980). Clinical study: N. Vaatainen et al., Clin. Exp. Dermatol. 6, 133 (1981). Comprehensive description: M. M. A. Hassan, M. A. Loutfy, Anal. Profiles Drug Subs. 10, 705-727 (1981). See also Psoralen, Methoxsalen.

Chemical structure

Properties

Prisms from chloroform, mp 234.5-235°. uv max (methanol): 250, 295, 335 nm (log ε 4.35, 3.99, 3.80). Sol in methylene chloride. Slightly sol in alc, chloroform. Practically insol in water.

Therapeutic Category

Pigmentation agent (photosensitizer).

Keywords

Pigmentation Agent