Crotonic acid

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Crotonic acid
Skeletal formula of crotonic acid
Ball-and-stick model of the crotonic acid molecule
IUPAC name
(E)-2-butenoic acid
Other names
trans-2-butenoic acid
beta-methylacrylic acid
3-methylacrylic acid
(E)-2-butenoic acid
107-93-7 N
ChEBI CHEBI:41131 YesY
ChEMBL ChEMBL1213528 YesY
ChemSpider 552744 YesY
DrugBank DB02074 YesY
Jmol interactive 3D Image
PubChem 637090
Molar mass 86.09 g/mol
Density 1.02 g/cm3
Melting point 70 to 73 °C (158 to 163 °F; 343 to 346 K)
Boiling point 185 to 189 °C (365 to 372 °F; 458 to 462 K)
Acidity (pKa) 4.69 [1]
Safety data sheet
Related compounds
Other anions
propionic acid
acrylic acid
butyric acid
succinic acid
malic acid
tartaric acid
fumaric acid
pentanoic acid
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Crotonic acid, or trans-2-butenoic acid, is a short-chain unsaturated carboxylic acid, described by the formula CH3CH=CHCO2H. Crotonic acid is so named because it was erroneously thought to be a saponification product of croton oil.[citation needed] It crystallizes as needles from hot water.

Racemic threonine can be prepared from crotonic acid by alpha-functionalization using mercury(II) acetate.[2]

See also[edit]


  1. ^ Dawson, R. M. C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
  2. ^ Carter, H. E.; West, H. D. (1955). "dl-Threonine". Org. Synth. ; Coll. Vol. 3, p. 813 

Public Domain This article incorporates text from a publication now in the public domainChisholm, Hugh, ed. (1911). Encyclopædia Britannica (11th ed.). Cambridge University Press.