Crotonic acid

Crotonic acid
Names
	Preferred IUPAC name (2E)-But-2-enoic acid
	Other names (E)-But-2-enoic acid; (E)-2-Butenoic acid; Crotonic acid; trans-2-Butenoic acid; β-Methylacrylic acid; 3-Methylacrylic acid
Identifiers
CAS Number	107-93-7 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:41131 ;
ChEMBL	ChEMBL1213528 ;
ChemSpider	552744 ;
DrugBank	DB02074 ;
ECHA InfoCard	100.003.213
PubChem CID	637090;
UNII	YW5WZZ4O5Q ;
CompTox Dashboard (EPA)	DTXSID30880973 ;
	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	86.090 g·mol−1
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
Hazards
Safety data sheet (SDS)	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; tetrolic 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 ((2E)-but-2-enoic acid) is a short-chain unsaturated carboxylic acid described by the formula CH₃CH=CHCO₂H. The name crotonic acid was given because it was erroneously thought to be a saponification product of croton oil.^[2] It crystallizes as colorless needles from hot water. With a cis-alkene, Isocrotonic acid is an isomer of crotonic acid. Crotonic acid is soluble in water and many organic solvents. Its odor is similar to that of butyric acid.

^ Dawson, R. M. C.; et al. (1959). Data for Biochemical Research. Oxford: Clarendon Press.
^ Chisholm, Hugh, ed. (1911). "Crotonic Acid" . Encyclopædia Britannica. Vol. 7 (11th ed.). Cambridge University Press. p. 511.

[1] Dawson, R. M. C.; et al. (1959). Data for Biochemical Research. Oxford: Clarendon Press.

[2] Chisholm, Hugh, ed. (1911). "Crotonic Acid" . Encyclopædia Britannica. Vol. 7 (11th ed.). Cambridge University Press. p. 511.

[1]

[2]

Names


Preferred IUPAC name (2E)-But-2-enoic acid
Other names (E)-But-2-enoic acid (E)-2-Butenoic acid Crotonic acid trans-2-Butenoic acid β-Methylacrylic acid 3-Methylacrylic acid
Identifiers
CAS Number	107-93-7^N
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:41131^Y
ChEMBL	ChEMBL1213528^Y
ChemSpider	552744^Y
DrugBank	DB02074^Y
ECHA InfoCard	100.003.213
PubChem CID	637090
UNII	YW5WZZ4O5Q^N
CompTox Dashboard (EPA)	DTXSID30880973
InChI InChI=1S/C4H6O2/c1-2-3-4(5)6/h2-3H,1H3,(H,5,6)/b3-2+^Y Key: LDHQCZJRKDOVOX-NSCUHMNNSA-N^Y 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	86.090 g·mol⁻¹
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 (pK_a)	4.69 ^[1]
Hazards
Safety data sheet (SDS)	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 tetrolic 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). N verify (what is ^YN ?) Infobox references