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	6.3 g/L at 25 °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 or trans-butenedioic 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.

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^Y
3D model (JSmol)	Interactive image
Beilstein Reference	605763
ChEBI	CHEBI:18012^Y
ChEMBL	ChEMBL503160^Y
ChemSpider	10197150^Y
DrugBank	DB04299^Y
ECHA InfoCard	100.003.404
EC Number	203-743-0
E number	E297 (preservatives)
Gmelin Reference	49855
KEGG	C00122^Y
PubChem CID	444972
RTECS number	LS9625000
UNII	88XHZ13131^Y
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+^Y Key: VZCYOOQTPOCHFL-OWOJBTEDSA-N^Y 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	6.3 g/L at 25 °C
Acidity (pK_a)	pk_a1 = 3.03, pk_a2 = 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). Y verify (what is ^YN ?) Infobox references