Tiglic acid

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.[1]

Tiglic acid
Names
Preferred IUPAC name
(2E)-2-Methylbut-2-enoic acid
Other names
(E)-2-Methylbut-2-enoic acid
Cevadic acid
Sabadillic acid
Tiglinic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.178
UNII
Properties
C5H8O2
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).
N verify (what is YN ?)
Infobox references

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.

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

gollark: Solution: Infiltrate the standards committees. While they're distracted bikeshedding function names and cylindrical Bessel functions and such, swap out some of the pages of the new standard for ones from Boost docs.
gollark: Also, potatOS would inevitably stop it.
gollark: Might it not delete itself, then?
gollark: It's much more maintainable due to not doing accursed things with unsafe raw memory access.
gollark: This is why you should use osmarkspythonbuildsystem™ instead.

See also

References
  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. Lloyd, J. U. (1898). "Croton tiglium Archived 2003-08-01 at the Wayback Machine". Lloyd Brothers plant drug pamphlets, Lloyd Brothers Pharmacy: Cincinnati.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.