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Tiglic acid information


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
CAS Number
  • 80-59-1 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:9592 ☒N
ChemSpider
  • 111629 ☒N
ECHA InfoCard 100.001.178 Edit this at Wikidata
IUPHAR/BPS
  • 6499
PubChem CID
  • 125468
UNII
  • I5792N03HC checkY
CompTox Dashboard (EPA)
  • DTXSID80883257 Edit this at Wikidata
InChI
  • 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
SMILES
  • O=C(O)/C(=C/C)C
Properties
Chemical formula
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 ?)
Infobox references

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]

  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.

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