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Itaconic acid

Athanor · official

C5H6O4 · 130.1 g/mol

IUPAC name: 2-methylidenebutanedioic acid

Also called itaconate, methylenesuccinic acid, immunometabolite

Reagents
Open in Athanor
The structure of Itaconic acid
Drawn from its SMILES with RDKit
CorrosiveHarmful or irritantDangerCauses skin irritation · Causes serious eye damage · Causes serious eye irritation · May cause respiratory irritation

Names and identifiers

IUPAC name
2-methylidenebutanedioic acid
Synonyms
itaconate, methylenesuccinic acid, immunometabolite
+ 36 more

2-Methylenesuccinic acid, 2-methylidenebutanedioic acid, METHYLENESUCCINIC ACID, Methylenebutanedioic acid, Propylenedicarboxylic acid, Butanedioic acid, methylene-, 2-Propene-1,2-dicarboxylic acid, Succinic acid, methylene-, 2-methylenebutanedioic acid, DTXSID2026608, NSC-3357, Q4516562YH, DTXCID006608, CHEBI:30838, methylidenebutanedioate, RefChem:792464, hydron;2-methylidenebutanedioate, 202-599-6, Itaconicacid, MFCD00004260, butanedioic acid, 2-methylene-, 3-Carboxy-3-butenoic acid, 2-methylenebutanedioate, AI3-16901, CHEMBL359159, NSC3357, CAS-97-65-4, HSDB 5308, NSC 3357, EINECS 202-599-6, Methylenesuccinate, UNII-Q4516562YH, ITN, Methylenebutanedioate, 2-Methylenesuccinate, Propylenedicarboxylate

Molecular formula
C5H6O4
Empirical formula
C5H6O4
Molecular weight
130.1 g/mol
Exact mass
130.02661
CAS number
97-65-4
PubChem CID
811
Canonical SMILES
C=C(CC(=O)O)C(=O)O
Isomeric SMILES
C=C(CC(=O)O)C(=O)O
InChI
InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h1-2H2,(H,6,7)(H,8,9)
InChIKey
LVHBHZANLOWSRM-UHFFFAOYSA-N
Molfile

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

Physical properties

TemperaturePressureDensity
Appearance
Liquid; Large Crystals; Dry Powder; Other Solid[1]
2 values

From EPA Chemical Data Reporting (CDR), the most authoritative source here.

ValueAs writtenSource
–shownLiquid; Large Crystals; Dry Powder; Other Solid[1] EPA Chemical Data Reporting (CDR)
–WHITE CRYSTALS[2] Hazardous Substances Data Bank (HSDB)cites Hawley, G.G. The Condensed Chemical Dictionary. 9th ed. New York: Van Nostrand Reinhold Co., 1977., p. 486
Boiling point
268 °C, SUBLIMES[2]
Solubility in water
SOL IN ACETONE[2]
pKa
Reported, but no value passed the checks.
The value and why
  • ACID DISSOCIATION CONSTANTS: 3.84 & 5.55 (could not be read; source [2])

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
9
Rings
0
Aromatic rings
0
Fraction sp³ carbons (Fsp3)
0.2
H-bond donors
2
H-bond acceptors
2 computed here · PubChem 4
Rotatable bonds
3
TPSA (Ų)
74.6
Formal charge
0
XLogP3
-0.1 PubChem
Complexity
158 PubChem
Stereocenters
None
Double-bond geometry
None specified
Point group
C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

  • C46.16%
  • H4.65%
  • O49.19%

Isotope pattern

100%130.0275.6%131.030132.031

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
0.1 Crippen (Wildman and Crippen 1999)
log S (water solubility)
-0.51 ESOL (Delaney 2004), log mol/L
Synthetic accessibility
2.55 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

  • Molecular weight ≤ 500: 130.1
  • log P ≤ 5 (Crippen): 0.1
  • 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

Danger

Most widely reported: 555 company reports to ECHA. Source [3].

  • Corrosive
  • Harmful or irritant
  • H315Causes skin irritation (14.8% of reports)
  • H318Causes serious eye damage (77.7% of reports)
  • H319Causes serious eye irritation (14.1% of reports)
  • H335May cause respiratory irritation (16% of reports)

Precautionary statements: P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501

View all classifications (2)
  • [3] European Chemicals Agency (ECHA)This chemical does not meet GHS hazard criteria for 5.9% (33 of 555) of reports.
  • [3] European Chemicals Agency (ECHA) · 555 reports · DangerH315, H318, H319, H335

Safety data sheets on the supplier’s page: CymitQuimica, Smolecule, eNovation Chemicals.

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]EPA Chemical Data Reporting (CDR) · Public domain (US EPA) · via PubChem · retrieved 2026-10-14
  2. [2]Hazardous Substances Data Bank (HSDB) · Public domain (US NLM) · via PubChem · retrieved 2026-10-14
  3. [3]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
  4. [4]NMRShiftDB · Linked only · via PubChem · retrieved 2026-10-14
  5. [5]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
  6. [6]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
  7. [7]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
  8. [8]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
  9. [9]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
  10. ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
  11. ·Literature on PubChem

Data last updated 2026-10-14.