Title: Radicinin
CAS Registry Number: 10088-95-6
CAS Name: [2S-[2a,3b,7(E)]]-2,3-Dihydro-3-hydroxy-2-methyl-7-(1-propenyl)-4H,5H-pyrano[4,3-b]pyran-4,5-dione
Additional Names: stemphylone
Molecular Formula: C12H12O5
Molecular Weight: 236.22
Percent Composition: C 61.01%, H 5.12%, O 33.87%
Literature References: A mold metabolite from the plant pathogen Stemphylium radicinum: Clark, Nord, Arch. Biochem. Biophys. 45, 469 (1953); 59, 269 (1955). Structure and identity with stemphylone: Grove, J. Chem. Soc. 1964, 3234. Absolute configuration: M. Nukina, S. Marumo, Tetrahedron Lett. 1977, 3271. Synthesis of dl-form: Kato et al., Chem. Commun. 1969, 95.
Properties: Needles from ethanol, dec 238-240°. [a]D27 -217.4° (c = 2.37 in pyridine); [a]D27 -175.7° (c = 0.2 in ethanol); [a]D27 -208° (c = 1.25 in chloroform). uv max: 343, 280, 270 nm (log e 4.27, 3.62, 3.79). Soluble in alkali. Practically insol in dil acids, sodium bicarbonate, sodium carbonate.
Optical Rotation: [a]D27 -217.4° (c = 2.37 in pyridine); [a]D27 -175.7° (c = 0.2 in ethanol); [a]D27 -208° (c = 1.25 in chloroform)
Absorption maximum: uv max: 343, 280, 270 nm (log e 4.27, 3.62, 3.79)
Derivative Type: Monoacetate
Molecular Formula: C14H14O6
Molecular Weight: 278.26
Percent Composition: C 60.43%, H 5.07%, O 34.50%
Properties: Crystals from methanol, mp 197°. [a]D27 -267° (c = 0.69 in pyridine).
Melting point: mp 197°
Optical Rotation: [a]D27 -267° (c = 0.69 in pyridine)
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