Santonin

• (3S, 5as, 9bS ) -3a, 5,5 a, 9b -tetrahydro- 3, 5, 9 - trimethylnaphtho [1,2 -b] furan- 2, 8 (3H, 4H )-dione
• Santoninsäureanhydrid

Colorless crystals, which turn yellow in light; bitter taste

Fixed

1.19 g · cm -3

174 ° C.

( sublimates at 120 ° C)

Slightly soluble in hot water, readily soluble in hot ethanol and hot diethyl ether

Risk

900 mg · kg -1 ( LD50, mouse, oral)

Template: Infobox chemical / molecular formula search available

Santonin ( Santoninsäureanhydrid ) is the active ingredient of the so-called worm seed, from which it is shown factory default. Santonin forms of shiny, white, tabular crystals that are odorless and tasteless, but taste strongly bitter in alcoholic solution.

History

The substance was in 1830 simultaneously by Kahler in Dusseldorf and Joachim August Alms ( 1803-1847 ) discovered in Penzlin. In the U.S., santonin was the first commercially successful medical substance Pfizer.

Production and representation

To obtain Santonin to cook the worm seeds ( Artemisia cina, Zitwerblüte ) with dilute milk of lime from, mixed the resulting solution of santoninsauren lime with dilute hydrochloric acid, whereby the santonin is precipitated, removed at the same time and with deposited resin by treatment with hot ammoniacal water crystallized before dyeing santonin to after treatment of his alcoholic solution with animal charcoal, from alcohol. The yield is 1.8 to 2.3 percent.

Properties

The melting point is 174 ° C. In water, the santonin is sparingly soluble, to litmus, it has no effect. In chemical terms, it is the lactone of monoprotic santoninic ( C15H20O4 ) and formula C15H18O3 accordingly.

By boiling with barium hydroxide barium santoninsaurem is a new, but isomeric acid, the acid Santo. In the scattered sunlight, the faster in direct sunlight, the colors yellow santonin and therefore must be kept in black glasses in the dark. His acid santoninic, on the other hand suffers no change in color in the sunlight.

Use

The santonin as well as the santoninsaure sodium was formerly used against roundworms, but is no longer used because of its toxicity. Already 2 to 3 times the daily dose (100 mg for adults) can cause poisoning symptoms that manifest themselves first in violet then yellow vision; continue cramps and diarrhea may occur. Damage to the optic nerve were also observed after prolonged administration of therapeutic doses.