Methysticin
Title: Methysticin
CAS Registry Number: 495-85-2
CAS Name: (6R)-6-[(1E)-2-(1,3-Benzodioxol-5-yl)ethenyl]-5,6-dihydro-4-methoxy-2H-pyran-2-one
Additional Names: 5-hydroxy-3-methoxy-7-[3,4-(methylenedioxy)phenyl]-2,6-heptadienoic acid d-lactone; 4-methoxy-6-[b-(3¢,4¢-methylenedioxyphenyl)vinyl]-5,6-dihydro-a-pyrone; 6-(3¢,4¢-methylenedioxystyryl)-4-methoxy-5,6-dihydro-2H-pyran-2-one; kavahin; kavatin
Molecular Formula: C15H14O5
Molecular Weight: 274.27
Percent Composition: C 65.69%, H 5.14%, O 29.17%
Literature References: One of the active components of the intoxicating beverage Kava from the Pacific Islands. From root of Piper methysticum Forst., Piperaceae (kava): Pomeranz, Monatsh. Chem. 10, 783 (1889); Hänsel, Beiersdorff, Arzneim.-Forsch. 9, 581 (1955). Structure: Borsche et al., Ber. 60, 2113 (1927). Synthesis of racemate: Klohs et al., J. Org. Chem. 24, 1829 (1959). Absolute config: Snatzke, Hänsel, Tetrahedron Lett. 1968, 1797. Crystal structure: P. Engel, W. Nowacki, Z. Kristallogr. 136, 437 (1972). 13C NMR: A. Banerji et al., Org. Magn. Reson. 13, 345 (1980). HPLC determn: R. M. Smith et al., J. Chromatogr. 283, 303 (1984). Anticonvulsant effects: Kretzschmar, Meyer, Arch. Int. Pharmacodyn. Ther. 177, 261 (1969). Neuroprotective activity: C. Backhauss, J. Krieglstein, Eur. J. Pharmacol. 215, 265 (1992).
Properties: Crystals from methanol, mp 132-134°. uv max (alcohol): 226, 267, 306 nm (log e 4.40, 4.14, 3.93). Practically insol in water. Sol in alcohol, ether, acetone.
Melting point: mp 132-134°
Absorption maximum: uv max (alcohol): 226, 267, 306 nm (log e 4.40, 4.14, 3.93)
 
Derivative Type: (±)-Dihydromethysticin
CAS Registry Number: 3155-57-5
Molecular Formula: C15H16O5
Molecular Weight: 276.28
Percent Composition: C 65.21%, H 5.84%, O 28.96%
Properties: Prisms from methanol, mp 118°. uv max (methanol): 232, 288 nm (log e 4.18, 3.56).
Melting point: mp 118°
Absorption maximum: uv max (methanol): 232, 288 nm (log e 4.18, 3.56)

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