10093. Yangonin
Nomenclature
CAS number: 500-62-9
(E)-4-Methoxy-6-[2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one; 4-methoxy-6-(p-methoxystyryl)-2H-pyran-2-one; 5-hydroxy-3-methoxy-7-(p-methoxyphenyl)-2,4,6-heptatrienoic
acid δ-lactone; 4-methoxy-6-[β-(p-anisyl)vinyl]-α-pyrone; 6-(p-methoxystyryl)-4-methoxy-α-pyrone. C15H14O4; mol wt 258.27.
C 69.76%, H 5.46%, O 24.78%.
Description and references
From root of Piper methysticum Forst., Piperaceae (kava): Winzhermer, Arch. Pharm. 246, 338 (1908); Borsche, Gerhardt, Ber. 47, 2902 (1914). From Ranunculus quelpaertensis Nakai, Ranunculaceae: Shibata et al., Bull. Chem. Soc. Jpn. 45, 930 (1972). Structure: Chmielewska et al., Tetrahedron 4, 36 (1958); Bu'Lock, Smith, J. Chem. Soc. 1960, 502. Synthesis: Harris, Combs, J. Org. Chem. 33, 2399 (1968); R. Bacardit, J. Heterocycl. Chem. 19, 157 (1982). Molecular and crystal structure: Engel, Nowacki, Z. Kristallogr. Kristallgeom. Kristallphys. Kristallchem. 134, 180 (1971). Activity studies: Kretzschmar et al., Arch. Int. Pharmacodyn. Ther. 180, 471 (1969).
Properties
Crystals from methanol, mp 155-157°. uv max (ethanol): 360 nm (log ε 4.33). Practically insol in water; sol in hot alcohol, glacial acetic acid, ethyl acetate, acetone; slightly sol in benzene, ether.Derivative
Dihydroyangonin.C15H16O4; mol wt 260.29.
C 69.22%, H 6.20%, O 24.59%.