Tiglic acid is a monocarboxylic unsaturated organic acid. It is found in croton oil and in several other natural products. It has also been also isolated from the defensive secretion of certain .[Attygalle, A. B.; Wu, X.; Will, K. W. (2007). "Biosynthesis of tiglic, ethacrylic, and 2-methylbutyric acids in a carabid beetle, Pterostichus (Hypherpes) californicus". J Chem Ecol. 33: 963–970. .]
Properties and uses
Tiglic acid has a
double bond between the second and third carbons of the chain. Tiglic acid and
angelic acid form a pair of
cis-trans isomers. Tiglic acid is a volatile and crystallizable substance with a sweet, warm, spicy odour. It is used in making
and
. The salts and esters of tiglic acid are called
tiglates.
Toxicity
Tiglic acid is a skin and eye irritant. The inhalation of the substance causes respiratory tract irritation. It is listed on the Toxic Substances Control Act (TSCA).
Names and discovery
In 1819 Pelletier and Caventou isolated a peculiar volatile and crystallizable acid from the seeds of
Schoenocaulon officinalis, a Mexican plant of family
Melanthaceae (also called
cevadilla or
sabadilla). Consequently, the substance was named
sabadillic or
cevadic acid. In 1865 it was found to be identical with B. F. Duppa and
Edward Frankland's methyl-
crotonic acid.
In 1870
Anton Geuther and Fröhlich prepared an acid from croton oil to which they gave the name
tiglic acid (or
tiglinic acid) after
Croton tiglium (Linn.), specific name of the croton oil plant.
[Lloyd, J. U. (1898). " Croton tiglium ". Lloyd Brothers plant drug pamphlets, Lloyd Brothers Pharmacy: Cincinnati.] The compound was shown to be identical with the previously described methyl-crotonic acid.
See also
-
Tiglyl-CoA, a thioester with coenzyme A
-
Duboisia myoporoides produces an alkaloid known as tigloidine.
[G. Barger, W.F. Martin, and W. Mitchell, "The minor alkaloids of Duboisia myoporoides", Journal of the Chemical Society, 1937, p. 1820-23.]
