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

beetle Beetles are insects that form the order Coleoptera (), in the superorder Endopterygota. Their front pair of wings are hardened into wing-cases, elytra, distinguishing them from most other insects. The Coleoptera, with about 400,000 describ ...

Properties and uses

Tiglic acid has a

double bond In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist betw ...

between the second and third carbons of the chain. Tiglic acid and

angelic acid Angelic acid is a monocarboxylic unsaturated organic acid, mostly found in the plants of the family Apiaceae. It is a volatile solid with a biting taste and pungent sour odor. It is the ''cis'' isomer of 2-methyl-2-butenoic acid, which easily c ...

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 (, ; french: parfum) is a mixture of fragrant essential oils or aroma compounds (fragrances), fixatives and solvents, usually in liquid form, used to give the human body, animals, food, objects, and living-spaces an agreeable scent. Th ...

s and

flavoring agent A flavoring (or flavouring), also known as flavor (or flavour) or flavorant, is a food additive used to improve the taste or smell of food. It changes the perceptual impression of food as determined primarily by the chemoreceptors of the gustat ...

s. 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 The Toxic Substances Control Act (TSCA) is a United States law, passed by the 94th United States Congress in 1976 and administered by the United States Environmental Protection Agency (EPA), that regulates chemicals not regulated by other U. ...

(TSCA).

Names and discovery

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

Schoenocaulon ''Schoenocaulon'' is a North American genus of perennial herbaceous flowering plants, ranging from the southern United States to Peru. It is a member of the Melanthiaceae, according to the APG III classification system, and is placed in the trib ...

officinalis'', a Mexican plant of family

Melanthaceae Melanthiaceae, also called the bunchflower family, is a family of flowering herbaceous perennial plants native to the Northern Hemisphere. Along with many other lilioid monocots, early authors considered members of this family to belong to th ...

(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 Sir Edward Frankland, (18 January 18259 August 1899) was an English chemist. He was one of the originators of organometallic chemistry and introduced the concept of combining power or valence. An expert in water quality and analysis, he was a ...

's methyl-

crotonic acid Crotonic acid ((2''E'')-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 crysta ...

. 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.

References

{{reflist Enoic acids Hemiterpenes

Properties and uses

Toxicity

Names and discovery

See also

References