Title: Otobain
CAS Registry Number: 3738-01-0
CAS Name: (7S,8R,9R)-9-(1,3-Benzodioxol-5-yl)-6,7,8,9-tetrahydro-7,8-dimethylnaphtho[1,2-d]-1,3-dioxole
Additional Names: 5,6-methylenedioxy-2,3-dimethyl-4-(3¢,4¢-methylenedioxyphenyl)-1,2,3,4-tetrahydronaphthalene; otobite
Molecular Formula: C20H20O4
Molecular Weight: 324.37
Percent Composition: C 74.06%, H 6.21%, O 19.73%
Literature References: Lignan isolated from otoba butter, the fat expressed from the fruit of Myristica otoba Humb. & Bonpl., Myristicaceae. Isoln: W. F. Baughman et al., J. Am. Chem. Soc. 43, 199 (1921). Structure: T. Gilchrist et al., J. Chem. Soc. 1962, 1780; N. S. Bhacca, R. Stevenson, J. Org. Chem. 28, 1638 (1963). Absolute configuration: W. Klyne et al., J. Chem. Soc. C 1966, 893. Synthesis of (±)-form: I. Maclean, R. Stevenson, ibid. 1717; T. B. H. McMurry, H. K. Kennedy-Skipton, Tetrahedron Lett. 1966, 975.
Properties: Needles from ethanol, mp 137-138°. [a]D -40.5° (c = 3.2 in chloroform). uv max (ethanol): 234, 287 nm (e 9300, 6700). Sol in ether, hot alcohol. Practically insol in water.
Melting point: mp 137-138°
Optical Rotation: [a]D -40.5° (c = 3.2 in chloroform)
Absorption maximum: uv max (ethanol): 234, 287 nm (e 9300, 6700) |