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Encyclopedia Britannica



EUGENOL (allyl guaiacol, eugenic acid), C10H1202

This article appears in Volume V09, Page 886 of the Encyclopedia Britannica.

Encyclopedia Britannica - Main :: EUD-FAT
EUGENOL (allyl guaiacol, eugenic acid), C10H1202 , an odoriferous principle; it is the
chief
  constituent of oil of
cloves
 , and occurs in many other essential
oils
 . It can be synthetically prepared by the reduction of con iferyl
alcohol
 , (HO) (CH3O) C 6H3 CH :CH CH2OH, which occurs in combination with
glucose
  in the
glucoside
  coniferin, C16H2208. It is a colourless oil boiling at 247 C., and having a spicy odour; On oxidation with potassium permanganate it gives homovanillin, vanillin, &c.; with chromic acid in acetic acid solution it is converted into carbon dioxide and acetic acid, whilst nitric acid oxidizes it to oxalic acid. By the action of alkalis it is converted into iso-eugenol, which on oxidation yields vanillin, the odorous principle of vanilla (q.v.). This transformation of allyl phenols into propenyl phenols is very general (see Ber., 1889, 22, p. 2747; 1890, 23, p. 862).
Alkali
  fusion of eugenol gives protocatechuic acid. The amount of eugenol in oil of
cloves
  can be estimated by acetylation, in presence of
pyridine
  (A. Verley and Fr. Baelsing, Bee., 1901, 34, p. 3359). Chavibetol, an isomer of eugenol, occurs in the ethereal oil obtained from Piper belle.
The structural relations are:
OH oil
/iocu3 /\ocH, /OHOClis
CHO


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