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Tiglic acid



Tiglic acid
Systematic name (E)-2-methylbut-2-enoic acid
Other names cevadic acid, sabadillic acid, tiglinic acid
Chemical formula C5H8O2
Molecular mass 100.116 g/mol
Density 0.9641 g/cm3 (76 °C)
Melting point 63.5-64 °C
Boiling point 198.5 °C
CAS number 80-59-1
SMILES CC=C(C)C(=O)O
Disclaimer and references

Tiglic acid is a monocarboxylic unsaturated organic acid. It is found in croton oil and in several other natural products. It was also isolated from the defensive secretion of certain beetles.

Additional recommended knowledge

Properties and uses

Tiglic acid has a double bond between the second and third carbons of the chain. Together with 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.

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. It was later found to be identical with Frankland and Duppa's methylcrotonic acid (1865). 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. The compound was shown to be identical with the previously described methyl-crotonic acid.

 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Tiglic_acid". A list of authors is available in Wikipedia.
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