Title: Curvularin
CAS Registry Number: 10140-70-2
CAS Name: 4,5,6,7,8,9-Hexahydro-11,13-dihydroxy-4-methyl-2H-3-benzoxacyclododecin-2,10(1H)-dione
Molecular Formula: C16H20O5
Molecular Weight: 292.33
Percent Composition: C 65.74%, H 6.90%, O 27.37%
Literature References: Mold metabolite from a species of Convalaria: Musgrave, J. Chem. Soc. 1956, 4301; from Penicillium steckii: Fennell et al., Chem. Ind. (London) 1959, 1382. Structure: Birch et al., J. Chem. Soc. 1959, 3146. Synthesis: H. Gerlach, Helv. Chim. Acta 60, 3039 (1977); of dl-O,O-dimethyl ether: Baker et al., J. Chem. Soc. C 1967, 1913; T. Takahashi et al., Tetrahedron Lett. 21, 3885 (1980); H. H. Wasserman, R. J. Gambale, ibid. 22, 4849 (1981).
Properties: Plates from hot benzene + methanol, mp 206-206.5°. [a]D18 -36.3° (c = 3.8 in ethanol). uv max (ethanol): 223, 272, 304.5 nm (e 11300; 6350; 5100). Sol in ethanol, methanol, dioxane, acetone, pyridine, concd H2SO4; moderately sol in acetic acid, ether; sparingly sol in benzene, petr ether, chloroform, water. Gives yellow solns with aq ammonia, sodium carbonate, and sodium hydroxide. Alkaline solns darken rapidly in air, eventually becoming purple.
Melting point: mp 206-206.5°
Optical Rotation: [a]D18 -36.3° (c = 3.8 in ethanol)
Absorption maximum: uv max (ethanol): 223, 272, 304.5 nm (e 11300; 6350; 5100)
Derivative Type: Dibenzoate
Molecular Formula: C30H28O7
Molecular Weight: 500.54
Percent Composition: C 71.99%, H 5.64%, O 22.37%
Properties: Needles from benzene + petr ether, mp 133-134°. [a]D18 -10.8° (c = 1.9 in chloroform). uv max (ethanol): 236 nm (e 36700).
Melting point: mp 133-134°
Optical Rotation: [a]D18 -10.8° (c = 1.9 in chloroform)
Absorption maximum: uv max (ethanol): 236 nm (e 36700)
Derivative Type: O,O-Dimethyl ether
Molecular Formula: C18H24O5
Molecular Weight: 320.38
Percent Composition: C 67.48%, H 7.55%, O 24.97%
Properties: Short rods from aq ethanol, mp 72°. [a]D18 -2.9° (c = 2.7 in chloroform). uv max (ethanol): 223, 267.5 nm (e 10500; 5100).
Melting point: mp 72°
Optical Rotation: [a]D18 -2.9° (c = 2.7 in chloroform)
Absorption maximum: uv max (ethanol): 223, 267.5 nm (e 10500; 5100)
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