Fumaric acid

Fumaric acid
Skeletal formula of fumaric acid
Ball-and-stick model of the fumaric acid molecule
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
3D model (JSmol)
605763
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.404 Edit this at Wikidata
EC Number
  • 203-743-0
E number E297 (preservatives)
49855
KEGG
RTECS number
  • LS9625000
UNII
UN number 9126
  • InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+ checkY
    Key: VZCYOOQTPOCHFL-OWOJBTEDSA-N checkY
  • InChI=1/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+
    Key: VZCYOOQTPOCHFL-OWOJBTEDBF
  • C(=C/C(=O)O)\C(=O)O
Properties
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)[2]
6.3 g/L at 25 °C[1]
Acidity (pKa) pka1 = 3.03, pka2 = 4.44 (15 °C, cis isomer)
−49.11·10−6 cm3/mol
non zero
Pharmacology
D05AX01 (WHO)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H319
P264, P280, P305+P351+P338, P313
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
375 °C (707 °F; 648 K)
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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.[3] 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.

  1. ^ Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. ^ Pubchem. "Fumaric acid". pubchem.ncbi.nlm.nih.gov.
  3. ^ Lohbeck, Kurt; Haferkorn, Herbert; Fuhrmann, Werner; Fedtke, Norbert (2000). "Maleic and Fumaric Acids". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a16_053. ISBN 3-527-30673-0.