Tiglic acid

Tiglic acid
Chemical structure of tiglic acid
Ball-and-stick model of 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 Edit this at Wikidata
UNII
  • InChI=1S/C5H8O2/c1-3-4(2)5(6)7/h3H,1-2H3,(H,6,7)/b4-3+ ☒N
    Key: UIERETOOQGIECD-ONEGZZNKSA-N ☒N
  • InChI=1/C5H8O2/c1-3-4(2)5(6)7/h3H,1-2H3,(H,6,7)/b4-3+
    Key: UIERETOOQGIECD-ONEGZZNKBL
  • O=C(O)/C(=C/C)C
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 checkY☒N ?)

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.

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. 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

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. ^ 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.