8093. Radicinin
Nomenclature
CAS number: 10088-95-6
[2S-[2α,3β,7(E)]]-2,3-Dihydro-3-hydroxy-2-methyl-7-(1-propenyl)-4H,5H-pyrano[4,3-b]pyran-4,5-dione; stemphylone. C12H12O5; mol wt 236.22.
C 61.01%, H 5.12%, O 33.87%.
Description and 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°. [α]D27 -217.4° (c = 2.37 in pyridine); [α]D27 -175.7° (c = 0.2 in ethanol); [α]D27 -208° (c = 1.25 in chloroform). uv max: 343, 280, 270 nm (log ε 4.27, 3.62, 3.79). Soluble in alkali. Practically insol in dil acids, sodium bicarbonate, sodium carbonate.Derivative
Monoacetate.C14H14O6; mol wt 278.26.
C 60.43%, H 5.07%, O 34.50%.