Fumaric acid

Fumaric acid
Names
	Preferred IUPAC name (2E)-But-2-enedioic acid
	Other names Fumaric acid; trans-1,2-Ethylenedicarboxylic acid; 2-Butenedioic acid; trans-Butenedioic acid; Allomaleic acid; Boletic acid; Donitic acid; Lichenic acid;
Identifiers
CAS Number	110-17-8 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	605763
ChEBI	CHEBI:18012 ;
ChEMBL	ChEMBL503160 ;
ChemSpider	10197150 ;
DrugBank	DB04299 ;
ECHA InfoCard	100.003.404
EC Number	203-743-0;
E number	E297 (preservatives)
Gmelin Reference	49855
KEGG	C00122 ;
PubChem CID	444972;
RTECS number	LS9625000;
UNII	88XHZ13131 ;
UN number	9126
CompTox Dashboard (EPA)	DTXSID3021518 ;
	InChI InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+ Key: VZCYOOQTPOCHFL-OWOJBTEDSA-N ; InChI=1/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+ Key: VZCYOOQTPOCHFL-OWOJBTEDBF;
	SMILES C(=C/C(=O)O)\C(=O)O;
Properties
Chemical formula	C4H4O4
Molar mass	116.072 g·mol−1
Appearance	White solid
Density	1.635 g/cm3
Melting point	287 °C (549 °F; 560 K) (decomposes)
Solubility in water	4.9 g/L at 20 °C
Acidity (pKa)	pka1 = 3.03, pka2 = 4.44 (15 °C, cis isomer)
Magnetic susceptibility (χ)	−49.11·10−6 cm3/mol
Dipole moment	non zero
Pharmacology
ATC code	D05AX01 (WHO)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H319
Precautionary statements	P264, P280, P305+P351+P338, P313
NFPA 704 (fire diamond)	2 1 0
Autoignition; temperature	375 °C (707 °F; 648 K)
Related compounds
Related carboxylic acids	Maleic acid; Succinic acid; Crotonic acid;
Related compounds	Fumaryl chloride; Fumaronitrile; Dimethyl fumarate; Ammonium fumarate; Iron(II) fumarate;
	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

Fumaric acid is an organic compound with the formula HO₂CCH=CHCO₂H. A white solid, fumaric acid occurs widely in nature. It has a fruit-like taste and has been used as a food additive. Its E number is E297. The salts and esters are known as fumarates. Fumarate can also refer to the C
₄H
₂O²⁻
₄ ion (in solution). Fumaric acid is the trans isomer of butenedioic acid, while maleic acid is the cis isomer.

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