UMBELLIFEE^] 315
ous constituent of the oil. Sedanonic acid C 12 H 20 O 3 is a crystalline
body melting at 88° to 89°, and is easily converted into its laetone
sedanolide C 12 H 18 O 2. Sedanonic acid C 12 H, 8 O 3 melts at 113°, and
possibly occurs as an anhydride in the oil. These two acids are nearly
related, and Ciamician and Silber consider that sedanolic acid is ortho-
oxyamyl-tetrahydrobenzoic acid, and that sedanonic acid is a related
ketonic acid. The following formulae thus express the relations of
these bodies:—
CH 2 CH
/ \ / \
H 2 C CH.CO.C4H 9 H 2 C C.CH(OH)C 4 HCH 2 C C.COOH , H 2 C CH.COOH
\ ^ \ /
CH CH 2
Sedanonic Acid. Sedanolic Acid.
Sedanolide, the chief odorous constituent, would thus be tetra-
hydrobutyl-phthalide of the formula—
CH
/ \
H2C C. CH. C4H90
/
H 2 C CH. COCH 2
A closely-related body, phthalylisopropylidene, and its reduction
products, were prepared artificially and found to have an odour much
resembling celery.
Schimmel & Co.
1
have also examined the oil and isolated from it a
new sesquiterpene, to which they have given the name selinene. It is-
probably identical with the sesquiterpene discovered by Ciamician and
Silber, but not further investigated by them.
The sesquiterpene fraction was separated into the following two
portions:—
First fraction. Boiling-point 120° to 121° (6 mm.); di7.5o 0'9197;
aD + 35° 11'; m^ 1*49863.
Second fraction. Boiling-point 121° to 122° (6 mm.); di8° 0-9170;
aD + 38° 12' WDSSIO 1-4956.
The sesquiterpene, or rather mixture of sesquiterpenes, was a yellow
liquid of an agreeable odour, which did not solidify even when cooled
considerably.
By passing hydrochloric acid into the ethereal solution of the hydro-
carbon a solid chloride was obtained, which, after evaporation of the
ether, crystallised out in needles from the reddish-blue residue. The
crystallising process of the chloride was materially facilitated by a
slight addition of alcohol and the application of a freezing mixture.
The product, after being crystallised once, melted at 68° to 70°. The
melting-point of a sample which had been repeatedly recrystallised
from methyl alcohol was found to be 72° to 74°.
1
Report, April, 1910, 33.