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]
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.
Toxicityedit
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 discoveryedit
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.
^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.
^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.
^Lloyd, J. U. (1898). "Croton tiglium 2003-08-01 at the Wayback Machine". Lloyd Brothers plant drug pamphlets, Lloyd Brothers Pharmacy: Cincinnati.
^G. Barger, W.F. Martin, and W. Mitchell, "The minor alkaloids of Duboisia myoporoides", Journal of the Chemical Society, 1937, p. 1820-23.
March 17, 2024
tiglic, acid, monocarboxylic, unsaturated, organic, acid, found, croton, several, other, natural, products, also, been, also, isolated, from, defensive, secretion, certain, beetles, namespreferred, iupac, name, methylbut, enoic, acidother, names, methylbut, en. 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 Tiglic acid NamesPreferred IUPAC name 2E 2 Methylbut 2 enoic acidOther names E 2 Methylbut 2 enoic acidCevadic acidSabadillic acidTiglinic acidIdentifiersCAS Number 80 59 1 Y3D model JSmol Interactive imageChEBI CHEBI 9592 NChemSpider 111629 NECHA InfoCard 100 001 178IUPHAR BPS 6499PubChem CID 125468UNII I5792N03HC YCompTox Dashboard EPA DTXSID80883257InChI InChI 1S C5H8O2 c1 3 4 2 5 6 7 h3H 1 2H3 H 6 7 b4 3 NKey UIERETOOQGIECD ONEGZZNKSA N NInChI 1 C5H8O2 c1 3 4 2 5 6 7 h3H 1 2H3 H 6 7 b4 3 Key UIERETOOQGIECD ONEGZZNKBLSMILES O C O C C C CPropertiesChemical formula C5H8O2Molar mass 100 116 g molDensity 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 96Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Properties and uses 2 Toxicity 3 Names and discovery 4 See also 5 ReferencesProperties and uses editTiglic 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 editTiglic 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 editIn 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 Frohlich 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 editTiglyl CoA a thioester with coenzyme A Duboisia myoporoides produces an alkaloid known as tigloidine 4 References edit 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 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 Lloyd J U 1898 Croton tiglium Archived 2003 08 01 at the Wayback Machine Lloyd Brothers plant drug pamphlets Lloyd Brothers Pharmacy Cincinnati G Barger W F Martin and W Mitchell The minor alkaloids of Duboisia myoporoides Journal of the Chemical Society 1937 p 1820 23 Retrieved from https en wikipedia org w index php title Tiglic acid amp oldid 1134887549, wikipedia, wiki, book, books, library,
