Chemistry of Essential Oils

CHENOPODIACE^ 121

Distilled at

748 mm.

Pressure.

158° to 159° 6 per cent.

159° 1

160° 1

161° 1

161-5 1

163° 1

165° 1

168° 1

174° 1

, 160°

, 161°

, 161-5°

, 163°

, 165°

, 168°

, 174°

, 194°

Residue

35 ,

10 ,

10 ,

10 ,

10 ,

7

2

8!

2 ,

The oil contains a-pinene and sabinene.

CHENOPODIACE/E.

OLL OF WORMSEED.

This oil, known as American wormseed oil, is distilled from the

herb Ghenopodium ambrosioides, var. anthelminticum, in the United

States, principally in Maryland. A certain amount of oil is distilled

from the fruit only. Normal oils have the following characters :—

Specific gravity

Optical rotation

0-958 to 0-990

• 4° „ - 12°
  The oil is soluble in 3 to 10 volumes of 70 per cent, alcohol.
  No portion of the oil distils below 170°, and any distillate obtained
  below that temperature indicates adulteration with turpentine.
  The oil has been very exhaustively examined recently by Nelson, to
  whom our knowledge of the chemistry of this oil is in the main due.
  The lowest boiling fraction consists of _p-cymene; Z-limonen,
  sylvestrene and camphor are also present, but the principal con-
  stituent of the oil is the body ascaridol. Nelson has fully investigated
  this body, CJOH 16 O 2 , which was originally isolated by Schimmel & Co.
  He examined four samples of the oil which had the following charac-
  ters: d 25 o0-955to0-9691; aDi - 5-4 to 8-8°; NOW 1'4723to 1-4726; soluble
  in from 3 to 7 volumes 70 per cent, alcohol. A fifth sample, at least
  one year old, which was used for the purposes of the examination, had
  the following characters : d 25 ° 0-9694 ; aD - 0'35°; nDi0° 14780; soluble
  in 3 volumes 70 per cent, alcohol; acid value 0; ester value 5*0. As-
  oaridol has the following characters :—
  Specific gravity
  Optical rotation
  Refractive index
  Boiling-point at 5 mm.

1-008

- 4° 14'

1-4731

83°

The results obtained by shaking ascaridol with saturated solution of
ferrous sulphate are, however, of particular interest. At ordinary tem-
perature this peculiar reaction proceeds with such violence as to decom-
pose the ascaridol, the temperature rising considerably with evolution
•of a combustible gas. Jsopropyl alcohol is also formed as a product of
reaction and was isolated from the syrupy product of conversion by
steam-distillation and identified as acetone by oxidising it with chromic
acid. Below 35° the reaction proceeds normally and without decom-
position. In these conditions ascaridol adds the elements of the water and

Jour. Amer. Cliem. Soc., 33 (1911), 1405.