Dillapiol 195

Dillapiol occurs in matico oil, in East Indian, Japanese, and Spanish dill oils, also in the oil of Crithmum maritimum. It is a viscid, oily liquid, which boils at 285° under ordinary pressure and at 162° under a pressure of 11 mm.1) Its constitution finds expression in the formula given above, the correctness of which has been established by Thorns.2)

1) Ciamician and Silber, Berl. Berichte 21 (1888), 1622.

2) Eykman, ibidem 23 (1890), 862.

3) Observations made in the laboratory of Schimmel & Co.

When acted upon with an excess of bromine, dillapiol yields a substance C12H13Br304, which crystallizes in colorless prisms, melts at 110°, and which is the dibromide of monobromapiol.3)

Dill/'soapiol, which is obtained by inversion, is solid, and can be obtained in monoclinic crystals that melt at 44°. Its boiling point is 296°. The melting point of the tribromide is 115°. When oxidized with alkaline permanganate solution, it yields dill-apiol aldehyde, C10H10O5, m. p. 75°, and dillapiolic acid, C10H10Ott, m. p. 151 to 152°. Whether dillisoapiol occurs in nature or not has not yet been ascertained.