Tiglic acid is a monocarboxylic unsaturated organic acid. It is found in croton oil

Croton oil

Croton oil is an oil prepared from the seeds of Croton tiglium, a tree belonging to the natural order Euphorbiales and family Euphorbiaceae, and native or cultivated in India and the Malay Archipelago. Small doses taken internally cause diarrhea. Externally, the oil can cause irritation and swelling...

 and in several other natural products. It was also isolated from the defensive secretion of certain beetle

Beetle

Coleoptera is an order of insects commonly called beetles. The word "coleoptera" is from the Greek , koleos, "sheath"; and , pteron, "wing", thus "sheathed wing". Coleoptera contains more species than any other order, constituting almost 25% of all known life-forms...

s.

Properties and uses

Tiglic acid has a double bond

Double bond

A double bond in chemistry is a chemical bond between two chemical elements involving four bonding electrons instead of the usual two. The most common double bond, that between two carbon atoms, can be found in alkenes. Many types of double bonds between two different elements exist, for example in...

 between the second and third carbons of the chain. Together with angelic acid

Angelic acid

Angelic acid is a monocarboxylic unsaturated organic acid. It is mostly found in the plants of the family Apiaceae. German pharmacist Ludwig Andreas Buchner isolated angelic acid in 1842 from the roots of garden angelica which gave the acid its name. Angelic acid is a volatile solid with a biting...

 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 perfume

Perfume

Perfume is a mixture of fragrant essential oils and/or aroma compounds, fixatives, and solvents used to give the human body, animals, objects, and living spaces "a pleasant scent"...

s and flavoring agents. 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

Toxic Substances Control Act

The Toxic Substances Control Act is a United States law, passed by the United States Congress in 1976, that regulates the introduction of new or already existing chemicals. It grandfathered most existing chemicals, in contrast to the Registration, Evaluation and Authorization of Chemicals ...

 (TSCA).

Names and discovery

In 1819 Pelletier and Caventou isolated a peculiar volatile and crystallizable acid from the seeds of Schoenocaulon

Schoenocaulon

Schoenocaulon is a North American genus of 26 species of perennial herbaceous flowering plants, ranging from the southern United States to Peru. It is a member of the Melanthiaceae, according to the AGP II...

 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

Croton (genus)

Croton is an extensive flowering plant genus in the spurge family, Euphorbiaceae, established by Carl Linnaeus in 1737. The plants of this genus were described and introduced to Europeans by Georg Eberhard Rumphius. The common names for this genus are rushfoil and croton, but the latter also...

(Linn.), specific name of the croton oil plant. The compound was shown to be identical with the previously described methyl-crotonic acid.