Crotonic acid

Crotonic acid
	Skeletal formula of crotonic acid
	Ball-and-stick model of the crotonic acid molecule
Names
	IUPAC name (E)-2-butenoic acid
	Other names trans-2-butenoic acid; beta-methylacrylic acid; 3-methylacrylic acid; (E)-2-butenoic acid
Identifiers
CAS Number	107-93-7
ChEBI	CHEBI:41131
ChEMBL	ChEMBL1213528
ChemSpider	552744
DrugBank	DB02074
Jmol 3D model	Interactive image; Interactive image
PubChem	637090
	InChI InChI=1S/C4H6O2/c1-2-3-4(5)6/h2-3H,1H3,(H,5,6)/b3-2+ Key: LDHQCZJRKDOVOX-NSCUHMNNSA-N ; InChI=1/C4H6O2/c1-2-3-4(5)6/h2-3H,1H3,(H,5,6)/b3-2+ Key: LDHQCZJRKDOVOX-NSCUHMNNBH ;
	SMILES C/C=C/C(O)=O ; O=C(O)/C=C/C ;
Properties
Chemical formula	C4H6O2
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
Vapor pressure	{{{value}}}
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
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	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]

References

↑ Dawson, R. M. C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
↑ Lua error in package.lua at line 80: module 'strict' not found.; Lua error in package.lua at line 80: module 'strict' not found.

This article incorporates text from a publication now in the public domain: Lua error in package.lua at line 80: module 'strict' not found.