2613. Cubebin

Nomenclature

CAS number: 18423-69-3
3,4-Bis(1,3-benzodioxol-5-ylmethyl)tetrahydro-2-furanol; tetrahydro-3,4-dipiperonyl-2-furanol; 5-hydroxy-3,4-bis(3,4-methylenedioxybenzyl)tetrahydrofuran.
C20H20O6; mol wt 356.37.
C 67.41%, H 5.66%, O 26.94%.

Description and references

From cubeb. Isoln: Capitaine, Soubeiran, Ann. 31, 190 (1839). Structure: Haworth, Kelly, Chem. Ind. (London) 1936, 901; Haensel et al., Arch. Pharm. 300, 559 (1967). Synthesis: Batterbee et al., J. Chem. Soc. C 1969, 2470.

Chemical structure

Properties

Slender prisms from methanol, mp 131-132°. [α]D14 -17° (acetone). Practically insol in water. Sol in alcohol, chloroform, ether.

Note

“Cubebine” is the French designation for ethereal extract of cubeb.