Tiglic acid

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Tiglic acid
Tiglic acid.png
Preferred IUPAC name
(2E)-2-Methylbut-2-enoic acid
Other names
(E)-2-Methylbut-2-enoic acid
Cevadic acid
Sabadillic acid
Tiglinic acid
3D model (JSmol)
ECHA InfoCard 100.001.178 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
  • InChI=1S/C5H8O2/c1-3-4(2)5(6)7/h3H,1-2H3,(H,6,7)/b4-3+ X mark.svgN
  • InChI=1/C5H8O2/c1-3-4(2)5(6)7/h3H,1-2H3,(H,6,7)/b4-3+
  • O=C(O)/C(=C/C)C
Molar mass 100.116 g/mol
Density 0.9641 g/cm3 (76 °C)
Melting point 63.5 to 64 °C (146.3 to 147.2 °F; 336.6 to 337.1 K)
Boiling point 198.5 °C (389.3 °F; 471.6 K)
Acidity (pKa)4.96
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 beetles. [1]


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 perfumes and flavoring agents. The salts and esters of tiglic acid are called tiglates.


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. [2] In 1870 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. [3] The compound was shown to be identical with the previously described methyl-crotonic acid.

See also

Related Research Articles

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<span class="mw-page-title-main">Anethole</span> Chemical compound

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Crotonic acid ((2E)-but-2-enoic acid) is a short-chain unsaturated carboxylic acid, described by the formula CH3CH=CHCO2H. It is called crotonic acid because it was erroneously thought to be a saponification product of croton oil. It crystallizes as colorless needles from hot water. The cis-isomer of crotonic acid is called isocrotonic acid. Crotonic acid is soluble in water and many organic solvents. Its odor is similar to butyric acid.

<span class="mw-page-title-main">Methacrylic acid</span> Chemical compound

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Ivan Addae-Mensah, is a Ghanaian chemist and university administrator who served as the Vice-Chancellor of the University of Ghana, Legon from 1996 to 2002. He is an Emeritus Professor of Chemistry at the same institution. He is a Life Fellow of the Royal Society of Chemistry, Fellow of the Ghana Academy of Arts and Sciences and a Fellow of the Ghana Chemical Society.


  1. 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. PMID   17404818.
  2. Frankland, E.; Duppa, B. F. (1865). "XXV.—Researches on acids of the acrylic series.—No. 1. Transformation of the lactic into the acrylic series of acids". J. Chem. Soc. 18: 133–156. doi:10.1039/js8651800133. ISSN   0368-1769.
  3. Lloyd, J. U. (1898). "Croton tiglium Archived 2003-08-01 at the Wayback Machine ". Lloyd Brothers plant drug pamphlets, Lloyd Brothers Pharmacy: Cincinnati.
  4. G. Barger, W.F. Martin, and W. Mitchell, "The minor alkaloids of Duboisia myoporoides", Journal of the Chemical Society, 1937, p. 1820-23.