Yangonin
Title: Yangonin
CAS Registry Number: 500-62-9
CAS Name: (E)-4-Methoxy-6-[2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one
Additional Names: 4-methoxy-6-(p-methoxystyryl)-2H-pyran-2-one; 5-hydroxy-3-methoxy-7-(p-methoxyphenyl)-2,4,6-heptatrienoic acid d-lactone; 4-methoxy-6-[b-(p-anisyl)vinyl]-a-pyrone; 6-(p-methoxystyryl)-4-methoxy-a-pyrone
Molecular Formula: C15H14O4
Molecular Weight: 258.27
Percent Composition: C 69.76%, H 5.46%, O 24.78%
Literature 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 e 4.33). Practically insol in water; sol in hot alcohol, glacial acetic acid, ethyl acetate, acetone; slightly sol in benzene, ether.
Melting point: mp 155-157°
Absorption maximum: uv max (ethanol): 360 nm (log e 4.33)
 
Derivative Type: Dihydroyangonin
Molecular Formula: C15H16O4
Molecular Weight: 260.29
Percent Composition: C 69.22%, H 6.20%, O 24.59%
Properties: Needles from alc, mp 106-107°. uv max (methanol): 274, 228 nm (log e 3.82, 3.71).
Melting point: mp 106-107°
Absorption maximum: uv max (methanol): 274, 228 nm (log e 3.82, 3.71)

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