3555. Embelin

Nomenclature

CAS number: 550-24-3
2,5-Dihydroxy-3-undecyl-2,5-cyclohexadiene-1,4-dione; 2,5-dihydroxy-3-undecyl-p-benzoquinone; “Embelic acid”.
C17H26O4; mol wt 294.39.
C 69.36%, H 8.90%, O 21.74%.

Description and references

From fruit of Embelia ribes Burm., Myrsinaceae. Isoln: Heffter, Feuerstein, Arch. Pharm. 238, 15 (1900). Structure and synthesis: Fieser, Chamberlin, J. Am. Chem. Soc. 70, 71 (1948).

Chemical structure

Properties

Glistening orange plates from alcohol, benzene or acetic acid, mp 142-143°. Soluble in the usual hot organic solvents or in alkali hydroxide solns; very slightly sol in petr ether. Practically insol in water.

Derivative

Diammonium salt.

Nomenclature

Ammonium embelate.
C17H34N2O4; mol wt 330.46.
C 61.79%, H 10.37%, N 8.48%, O 19.37%.

Properties

Grayish-violet powder. Sol in water, dil alcohol.

Caution

Handle with care; irritates mucous membranes and may cause prolonged and violent sneezing!

Derivative

Disemicarbazone.
C19H32N6O4; mol wt 408.50.
C 55.86%, H 7.90%, N 20.57%, O 15.67%.

Properties

Pale-brown needles from dil alcohol, dec 236°.

Derivative

Dioxime.
C17H28N2O4; mol wt 324.42.
C 62.94%, H 8.70%, N 8.63%, O 19.73%.

Properties

Pale-yellow needles from acetic acid, mp 278°.

Therapeutic Category

Ammonium embelate as an anthelmintic (Cestodes).

Keywords

Anthelmintic (Cestodes)