733. Apiole (Dill)

Nomenclature

CAS number: 484-31-1
4,5-Dimethoxy-6-(2-propen-1-yl)-1,3-benzodioxole; 1-allyl-2,3-dimethoxy-4,5-(methylenedioxy)benzene; dill apiole.
C12H14O4; mol wt 222.24.
C 64.85%, H 6.35%, O 28.80%.

Description and references

Occurs in dill oil, Anethum graveolus L., Umbelliferae. Isoln: G. Ciamician, P. Silber, Ber. 29, 1799 (1896); D. B. Spoelstra, Rec. Trav. Chim. 48, 372 (1929). Structure: H. Thoms, Arch. Pharm. 242, 344 (1904). Synthesis: W. Baker et al., J. Chem. Soc. 1934, 1681; F. Dallacker, Ber. 102, 2663 (1969); J. R. Cannon et al., J. Sci. Soc. Thailand 6, 59 (1980). Synergistic activity with insecticides: E. P. Lichtenstein et al., J. Agric. Food Chem. 22, 658 (1974); S.S. Tomar et al., Agric. Biol. Chem. 43, 1479 (1979).

Chemical structure

Properties

Oil, mp 29.5°. bp 285°. nD17 1.5305; d1515 1.1598.