10067. Xanthoxylin

Nomenclature

CAS number: 90-24-4
1-(2-Hydroxy-4,6-dimethoxyphenyl)ethanone; 2′-hydroxy-4′,6′-dimethoxyacetophenone; phloracetophenone 4,6-dimethyl ether; 2,4-dimethoxy-6-hydroxyacetophenone; brevifolin.
C10H12O4; mol wt 196.20.
C 61.22%, H 6.16%, O 32.62%.

Description and references

Found in Xanthoxylum piperitum DC., X. alatum Roxb., Rutaceae, Artemisia brevifolia Wallich, Compositae, Hippomane mancinella L., Sapium sebiferum Roxb., Euphorbiaceae. Isoln: Stenhouse, Ann. 89, 251 (1854); 104, 236 (1857); Semmler, Schossberger, Ber. 44, 2885 (1911); Smith, Smith, Pharm. J. 119, 688 (1927); 123, 604, 611 (1929); Schaeffer et al., J. Am. Pharm. Assoc. 43, 43 (1954); Chu et al., C.A. 53, 10532g (1959). Synthesis: Kostanecki, Lambor, Ber. 32, 2260 (1899); Canter et al., J. Chem. Soc. 1931, 1245; Belton et al., Sci. Proc. R. Dublin Soc. 25, 19 (1949); Schmid, Bolleter, Helv. Chim. Acta 33, 917 (1950); MacKenzie et al., J. Chem. Soc. 1950, 2965; Dean, Robertson, ibid. 1953, 1244; Kawano, Chem. Ind. (London) 1959, 368.

Chemical structure

Properties

Crystals from ethanol, mp 81-83°. Practically insol in water. Sol in alcohol, ether.