Athamantin

Title: Athamantin
CAS Registry Number: 1892-56-4
CAS Name: (8S-cis)-3-Methylbutanoic acid 8,9-dihydro-8-[1-methyl-1-(3-methyl-1-oxobutoxy)ethyl]-2-oxo-2H-furo[2,3-h]-1-benzopyran-9-yl ester
Additional Names: isovaleric acid diester with 8,9-dihydro-9-hydroxy-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]-1-benzopyran-2-one; 2,3-dihydro-3,4-dihydroxy-2-(1-hydroxy-1-methylethyl)-5-benzofuranacrylic acid d-lactone diisovalerate
Molecular Formula: C24H30O7
Molecular Weight: 430.49
Percent Composition: C 66.96%, H 7.02%, O 26.02%
Literature References: From Peucedanum oreoselinum (L.) Moench (Athamanta oreoselinum L.), Ammi visnaga Lam., Umbelliferae. Isoln: Schnedermann, Winckler, Ann. 51, 315 (1844). Structure: Halpern et al., Helv. Chim. Acta 40, 758 (1957). Absolute configuration: Nakazaki et al., Tetrahedron Lett. 1966, 4735.
Properties: Fine needles from petr ether, mp 58-60°; sublimes in high vacuum at 180-200°. [a]D20 +88° (c = 1.145 in glacial acetic acid); [a]22546 +129° (c = 0.5575 in methanol); [a]21546 +73.9° (c = 1.024 in chloroform). [M]D +440° (methanol); +258° (chloroform). uv max (96% ethanol): 217, 322 nm (log e 4.18, 4.17). Practically insol in water; sol in alc, ether, chloroform.
Melting point: mp 58-60°
Optical Rotation: [a]D20 +88° (c = 1.145 in glacial acetic acid); [a]22546 +129° (c = 0.5575 in methanol); [a]21546 +73.9° (c = 1.024 in chloroform)
Absorption maximum: uv max (96% ethanol): 217, 322 nm (log e 4.18, 4.17)
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