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Acetyl compound of methyl ester of anthranilic acid. 
Methyl ester of anthranilic acid 
/NH, (i) 
' ' ' ' '\cOO.CH3 (2) 
was discovered in the year 1894, in the laboratory of Messrs. 
Schimmel & Co., as a constituent of oil of orange flowers (neroli oil). 
It plays an important part in the formation of the aroma of the 
orange-flower. The proportion of methyl anthranilate in oil of orange- 
flowers is about 0,6 per cent. The melting point of this compound 
lies at 25,5°. The solutions show a beautiful blue fluorescence. In 
the undiluted state the full odour is disagreeable, and only when it 
has been diluted in due proportion, it reminds of the odour of orange 
flowers. When a solution of methyl ester of anthranilic acid in water 
is submitted to destination, the ester passes over into the receiver. 
The ester has basic properties. 
The acetyl compound of methyl ester of anthranilic acid: 
/NH.COCHo (i) 
^COO.CHg (2) 
represents a loose flocculent white powder free from odour and taste, 
which can be sublimed. In cold or hot water it dissolves with dif- 
ficulty; in alcohol, ether, and concentrated hydrochloric acid it is 
readily soluble. Its solutions show no fluorescence. From water 
the acetyl compound crystallises in delicate needles. It does not 
reduce solutions of salts of copper, silver, gold or platinum, or of 
potassium chromate and permanganate. With platinum chloride it 
forms a double salt, which crystallises out in beautiful, long needles. 
When boiled for several hours in concentrated hydrochloric acid, it 
splits up into methyl anthranilate and acetic acid. 
The ph3^siological action of the acetyl compound of methyl ester 
of anthranilic acid on the animal organism is also slight. 
Experiment No. I. A frog weighing 52 g received 0,1 g methyl ester 
of acetyl anthranilic acid in emulsion with olive oil. After 45 minutes the 
animal in dorsal position (without being able to turn over on its abdomen) 
still made fairly strong movements as if swimming, but subsequently only 
a few inco- ordinate movements. After 1Y2 hours the frog lay quietly; the 
reflex-action was much reduced, and after 4 hours only indicated. The heart 
continued its normal action for several hours longer. After 18 hours the frog 
was found dead. 
Section: The cavity of the mouth slightly injected. The stomach was 
filled with a glutinous gi^een mucus; the intestine also contained some greenish 
mucus. The stomach and mesentery were strongly injected; the intestine had a 
dark-red appearance, in consequence of hypersemia. No blood extravasation was 
present in the alimentary tract. When stimulated electrically, the muscles and 
nerves reacted normally. 
