This section is from the book "The Volatile Oils Vol1", by E. Gildemeister. Also available from Amazon: The Volatile Oils.
Isopulegol, C10H18O, has not yet been found in volatile oils. It results from citronellal when this is treated with acids. The observation made by Schimmel & Co.3) viz., when the oil of Barosma pulchellum is distilled the odor of isopulegol is notice-able, is possibly referrable to this circumstance.
Isopulegol boils at 91° (13 mm.); d17.5o 0,9154; aD - 2°40'; nDl,47292.4)
The acetate boils at 104 to 105° (10 mm.).5)
1) Wallach, Liebig's Annalen 275 (1893), 115.
2) Wallach, ibidem 112.
3) Report of Schimmel & Co. April 1909, 96.
4) Tiemann and Schmidt, Berl. Berichte 29 (1896), 914.
5) Barbier and Leser, Compt. rend. 124 (1897), 1309.
6) Wallach, Liebig's Annalen 365 (1909), 251.
For purposes of identification, the alcohol is oxidized to pulegone6) and this characterized by means of its oxime (m. p. of the active modification abt. 121°, of the inactive abt. 140°), or its semicarbazone (m. p. of the active modifications 172 to 173°, of the inactive 182 to 183°).
 
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