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Fumaric acid

Athanor · official

C4H4O4 · 116.07 g/mol

IUPAC name: (E)-but-2-enedioic acid

Also called fumarate, trans-butenedioic acid, E297

Metabolites
Open in Athanor
The structure of Fumaric acid
Drawn from its SMILES with RDKit
Harmful or irritantWarningCauses serious eye irritation

Names and identifiers

IUPAC name
(E)-but-2-enedioic acid
Synonyms
fumarate, trans-butenedioic acid, E297
+ 37 more

trans-Butenedioic acid, Allomaleic acid, Lichenic acid, Boletic acid, (2E)-but-2-enedioic acid, Tumaric acid, trans-1,2-Ethylenedicarboxylic acid, (E)-2-Butenedioic acid, Allomalenic acid, trans-2-Butenedioic acid, (2E)-2-butenedioic acid, Fumaricum acidum, 2-Butenedioic acid, (E)-, Kyselina fumarova, (E)-but-2-enedioic acid, USAF EK-P-583, Butenedioic acid, (E)-, FEMA No. 2488, 2-Butenedioic acid (2E)-, NSC-2752, Allomaleic-acid, Boletic-acid, trans-but-2-enedioic acid, U-1149, (E)-Butenedioic acid, DTXSID3021518, INS NO.297, INS-297, NSC2752, FC 33, 88XHZ13131, DTXCID601518, E-297, CHEBI:18012, (E)-but-2-enedioate;hydron, (E)-1,2-Ethylenedicarboxylic acid, RefChem:5844

Molecular formula
C4H4O4
Empirical formula
CHO
Molecular weight
116.07 g/mol
Exact mass
116.01096
CAS number
110-17-8
PubChem CID
444972
Canonical SMILES
C(=CC(=O)O)C(=O)O
Isomeric SMILES
C(=C/C(=O)O)\C(=O)O
InChI
InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+
InChIKey
VZCYOOQTPOCHFL-OWOJBTEDSA-N
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Physical properties

TemperaturePressureDensity
Appearance
Colorless crystals[4]
5 values

From Hazardous Substances Data Bank (HSDB), the most authoritative source here.

ValueAs writtenSource
–Fumaric acid appears as a colorless crystalline solid. The primary hazard is the threat to the environment. Immediate steps should be taken to limit spread to the environment. Combustible, though may be difficult to ignite. Used to make paints and plastics, in food processing and preservation, and for other uses.[1] CAMEO Chemicals
–Liquid; Other Solid; Dry Powder; CBI; Large Crystals[2] EPA Chemical Data Reporting (CDR)
–ODOURLESS COLOURLESS CRYSTALLINE POWDER.[3] ILO-WHO International Chemical Safety Cards (ICSCs)
–shownColorless crystals[4] Hazardous Substances Data Bank (HSDB)cites Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 586
–WHITE CRYSTALLINE POWDER[4] Hazardous Substances Data Bank (HSDB)cites Merory, J. Food Flavorings: Composition, Manufacture, and Use. 2nd ed. Westport, Conn.: Avi Publishing Co., 1968., p. 343
Odor
Odorless[4]
Melting point
287 °C decomposes[4]
Boiling point
165 °C (329 °F) at 1.7 mmHg[1]
Density
1.635 at 20 °C (68 °F) (USCG, 1999) - Denser than water[1]
Solubility in water
Solubility in water, g/100ml at 25 °C: 0.63 (poor)[3]
4 values

From ILO-WHO International Chemical Safety Cards (ICSCs), the most authoritative source here.

ValueAs writtenSource
–less than 1 mg/mL at 72 °F (NTP, 1992)[1] CAMEO Chemicalscites National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
–Soluble in alcohol 5.76 g/100 g at 30 °C. Insoluble in chloroform and benzene[4] Hazardous Substances Data Bank (HSDB)cites Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 586
–In water, 7X10-3 mg/L at 25 °C[4] Hazardous Substances Data Bank (HSDB)cites Yalkowsky, S.H., He, Yan., Handbook of Aqueous Solubility Data: An Extensive Compilation of Aqueous Solubility Data for Organic Compounds Extracted from the AQUASOL dATAbASE. CRC Press LLC, Boca Raton, FL. 2003., p. 86
–shownSolubility in water, g/100ml at 25 °C: 0.63 (poor)[3] ILO-WHO International Chemical Safety Cards (ICSCs)
log P
0.46 (estimated)[3]
2 values

2 of 2 sources agree on it (most common value).

ValueAs writtenSource
–log Kow = 0.46[4] Hazardous Substances Data Bank (HSDB)cites Hansch, C., Leo, A., D. Hoekman. Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society., 1995., p. 8
–shown0.46 (estimated)[3] ILO-WHO International Chemical Safety Cards (ICSCs)
Flash point
273 °C[3]
3 values

2 of 2 sources agree on it (most common value).

ValueAs writtenSource
273 °C273 °C (open cup)[4] Hazardous Substances Data Bank (HSDB)cites European Commission, ESIS; IUCLID Dataset, Fumaric acid (110-17-8) p.15 (2000 CD-ROM edition). Available from, as of February 25, 2010: https://esis.jrc.ec.europa.eu/
230 °C230 °C (closed cup)[4] Hazardous Substances Data Bank (HSDB)cites Sigma-Aldrich Corp; Safety Data Sheet for Fumaric acid (Product Number: 47900) Version 3.2 (June 19, 2008). Available from, as of March 19, 2010: https://www.sigmaaldrich.com
273 °Cshown273 °C[3] ILO-WHO International Chemical Safety Cards (ICSCs)
Autoignition temperature
740 °C (1364 °F, powder)[4]
3 values

2 of 3 sources agree on it (most common value).

ValueAs writtenSource
740 °C1364 °F (USCG, 1999)[1] CAMEO Chemicalscites U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.
740 °Cshown1364 °F (powder)[4] Hazardous Substances Data Bank (HSDB)cites U.S. Coast Guard, Department of Transportation. CHRIS - Hazardous Chemical Data. Volume II. Washington, D.C.: U.S. Government Printing Office, 1984-5.
375 °C375 °C (powder)[3] ILO-WHO International Chemical Safety Cards (ICSCs)

Each value as its source reports it, with the source's number after it (listed under References). Where several sources report a property, the row shows the value most of them agree on, the rule the app uses; open the values to see every one.

Calculated

Heavy atoms
8
Rings
0
Aromatic rings
0
Fraction sp³ carbons (Fsp3)
0
H-bond donors
2
H-bond acceptors
2 computed here · PubChem 4
Rotatable bonds
2
TPSA (Ų)
74.6
Formal charge
0
XLogP3
-0.3 PubChem
Complexity
119 PubChem
Stereocenters
None
Double-bond geometry
C4=C5: E
Point group
Cs of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

  • C41.39%
  • H3.47%
  • O55.13%

Isotope pattern

100%116.0114.5%117.014118.015

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P
-0.29 Crippen (Wildman and Crippen 1999)
log S (water solubility)
-0.25 ESOL (Delaney 2004), log mol/L
Synthetic accessibility
2.11 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

  • Molecular weight ≤ 500: 116.07
  • log P ≤ 5 (Crippen): -0.29
  • H-bond donors ≤ 5: 2
  • H-bond acceptors ≤ 10: 2

Passes all four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

Warning

Harmonized EU classification (CLP Annex VI). Source [5].

  • Harmful or irritant
  • H319Causes serious eye irritation

Precautionary statements: P264+P265, P280, P305+P351+P338, P337+P317

View all classifications (3)
  • [5] Regulation (EC) No 1272/2008 of the European Parliament and of the Council · WarningH319
  • [6] European Chemicals Agency (ECHA)This chemical does not meet GHS hazard criteria for 0.4% (13 of 3331) of reports.
  • [6] European Chemicals Agency (ECHA) · 3,331 reports · WarningH319

First aid

  • Eyes: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. Immediately transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. Skin: Immediately flood affected skin with water while removing and isolating all contaminated clothing.[1]
  • Fresh air, rest.[3]
  • Rinse skin with plenty of water or shower.[3]
  • First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.[3]

Storage

  • Separated from oxidizing materials.[3]
  • The bulk material should be stored in a well-closed container in a cool, dry place.[4]
  • Store in cool place. Keep container tightly closed in a dry and well-ventilated place.[4]

Incompatibilities

  • Fumaric acid undergoes reactions typical of an organic acid.[4]
  • Materials to avoid: Oxidizing agents, amines, strong bases.[4]

Safety data sheets on the supplier’s page: LGC Standards, Aladdin Scientific, Alfa Chemistry.

Always read the supplier’s safety data sheet before working with it.

Spectra

Experimental spectra held by these sources; each link opens the source's own record.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

  1. [1]CAMEO Chemicals · Public domain (NOAA) · via PubChem · retrieved 2026-10-14
  2. [2]EPA Chemical Data Reporting (CDR) · Public domain (US EPA) · via PubChem · retrieved 2026-10-14
  3. [3]ILO-WHO International Chemical Safety Cards (ICSCs) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
  4. [4]Hazardous Substances Data Bank (HSDB) · Public domain (US NLM) · via PubChem · retrieved 2026-10-14
  5. [5]Regulation (EC) No 1272/2008 of the European Parliament and of the Council · EU reuse policy, CC BY 4.0 · via PubChem · retrieved 2026-10-14
  6. [6]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
  7. [7]NMRShiftDB · Linked only · via PubChem · retrieved 2026-10-14
  8. [8]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
  9. [9]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
  10. [10]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
  11. [11]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
  12. [12]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
  13. ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
  14. ·Literature on PubChem

Data last updated 2026-10-14.