Title: Xanthoxyletin
CAS Registry Number: 84-99-1
CAS Name: 5-Methoxy-8,8-dimethyl-2H,8H-benzo[1,2-b:5,4-b¢]dipyran-2-one
Additional Names: 7-hydroxy-5-methoxy-2,2-dimethyl-2H-1-benzopyran-6-acrylic acid d-lactone; xanthoxylin N; xanthoxyloin
Molecular Formula: C15H14O4
Molecular Weight: 258.27
Percent Composition: C 69.76%, H 5.46%, O 24.78%
Literature References: Found in Xanthoxylum americanum Mill., Melicope ternata Forst., M. mantelli Buch., Halifordia scleroxyla F. Muell., Rutaceae; Chloroxylon swietenia DC., Meliaceae. Isoln: Staples, Am. J. Pharm. 1829, 123; Witte, Arch. Pharm. 212, 283 (1878); Lloyd, Am. J. Pharm. 1890, 229; Gordin, J. Am. Chem. Soc. 28, 1649 (1906); Bell et al., J. Chem. Soc. 1936, 627; Robertson, Subramaniam, ibid. 1937, 286; Dieterle, Kruta, Arch. Pharm. 275, 45 (1937); Briggs, Locker, J. Chem. Soc. 1951, 3131; King et al., ibid. 1954, 1392; Hegarty, Lahey, Aust. J. Chem. 9, 120 (1956); Cambie, J. Chem. Soc. 1960, 2376. Synthesis: Joshi, Kamat, Tetrahedron Lett. 1966, 5767.
Properties: Elongated prisms from methanol, mp 132-133°. uv max: 277, 269, 322, 347 nm (log e 4.28, 4.32, 3.99, 4.05 in ethanol). Very easily sol in benzene, chloroform, hot alcohol; sol in acetone; sparingly sol in ether. Sol in 49 parts cold acetone and 25,000 parts cold water.
Melting point: mp 132-133°
Absorption maximum: uv max: 277, 269, 322, 347 nm (log e 4.28, 4.32, 3.99, 4.05 in ethanol) |