Crotonic acid


Crotonic acid
Crotonic acid
Identifiers
CAS number 107-93-7 N
PubChem 637090
ChemSpider 552744 YesY
DrugBank DB02074
ChEBI CHEBI:41131 YesY
ChEMBL CHEMBL1213528 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C4H6O2
Molar mass 86.09 g/mol
Density 1.02 g/cm3
Melting point

70–73 °C

Boiling point

185–189 °C

Acidity (pKa) 4.69 [1]
Hazards
MSDS SIRI.org
Related compounds
Other anions crotonate
Related carboxylic acids propionic acid
acrylic acid
butyric acid
succinic acid
malic acid
tartaric acid
fumaric acid
pentanoic acid
Related compounds butanol
butyraldehyde
crotonaldehyde
2-butanone
 N acid (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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. 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

References

  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., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv3p0813 ; Coll. Vol. 3: 813 

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


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  • Crotonic acid — Crotonic Cro*ton ic (kr? t?n ?k), a. Of or pertaining to, or derived from, a plant of the genus {Croton}, or from croton oil. [1913 Webster] {Crotonic acid} (Chem.), a white crystalline organic acid, {C3H5.CO2H}, of the ethylene, or acrylic acid… …   The Collaborative International Dictionary of English

  • crotonic acid — [krō tän′ik] n. [ CROTON + IC] a colorless crystalline compound, CH3CH:CHCOOH, existing in two isomeric forms: used in organic synthesis, the manufacture of resins, etc …   English World dictionary

  • crotonic acid — krotono rūgštis statusas T sritis chemija formulė CH₃CH=CHCOOH atitikmenys: angl. crotonic acid rus. кротоновая кислота ryšiai: sinonimas – (E) 2 buteno rūgštis …   Chemijos terminų aiškinamasis žodynas

  • crotonic acid — noun An unsaturated organic acid, CH CH=CH COOH, found in croton oil and having many industrial uses; the cis form is isocrotonic acid. Syn: trans 2 butenoic acid, beta methylacrylic acid …   Wiktionary

  • crotonic acid — cro·ton·ic acid (.)krō .tän ik n an unsaturated aliphatic acid C4H6O2 that occurs in croton oil * * * cro·ton·ic ac·id (kro tonґik) an unsaturated fatty acid, CH3CH CHCOOH, found in croton oil …   Medical dictionary

  • crotonic acid — (ˈ)krō|tänik noun Etymology: French crotonique, from New Latin Croton + French ique ic : an unsaturated aliphatic acid CH3CH . CHCOOH existing in cis and trans forms; β methyl acrylic acid; especially : the colorless crystalline trans form… …   Useful english dictionary

  • crotonic acid — C3H5COOH, water soluble acid used primarily in organic synthesis (Chemistry) …   English contemporary dictionary

  • crotonic acid — /kroʊˌtɒnɪk ˈæsəd/ (say kroh.tonik asuhd) noun an unsaturated, aliphatic acid, CH3CH=CHCOOH, used in organic synthesis …   Australian English dictionary

  • crotonic acid — /kroh ton ik, toh nik/, Chem. a colorless, crystalline, water soluble solid, C4H6O2, used chiefly in organic synthesis. [1830 40; CROTON + IC] * * * …   Universalium

  • Crotonic — Cro*ton ic (kr? t?n ?k), a. Of or pertaining to, or derived from, a plant of the genus {Croton}, or from croton oil. [1913 Webster] {Crotonic acid} (Chem.), a white crystalline organic acid, {C3H5.CO2H}, of the ethylene, or acrylic acid series.… …   The Collaborative International Dictionary of English