Skip to Content
Merck
CN

I29204

Itaconic acid

≥99%

Synonym(s):

Methylenesuccinic acid

Sign In to View Organizational & Contract Pricing

Select a Size

About This Item

Linear Formula:
HO2CCH2C(=CH2)CO2H
CAS Number:
97-65-4
Molecular Weight:
130.10
Beilstein:
1759501
EC Number:
202-599-6
MDL number:
MFCD00004260
UNSPSC Code:
12352100
PubChem Substance ID:
24896018
NACRES:
NA.22

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Assay

≥99%

autoignition temp.

1472 °F

mp

165-168 °C (lit.)

density

1.573 g/mL at 25 °C (lit.)

SMILES string

OC(=O)CC(=C)C(O)=O

InChI

1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h1-2H2,(H,6,7)(H,8,9)

InChI key

LVHBHZANLOWSRM-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

Application

Itaconic acid (IA) can be used:
  • As a comonomer in the polymerization of polyacrylonitrile (PAN) to promote the thermo-oxidative stabilization of polymer.
  • In combination with acrylamide to form (poly[acrylamide-co-(itaconicacid)]) to synthesize biodegradable superabsorbent polymers.
  • To synthesize biobased polyester composite in fabric industry.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H318

Precautionary Statements

P280 - P305 + P351 + P338

Hazard Classifications

Eye Dam. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
SDBB6001
SDBB4146
SDBB3434
SDBB2122
STBL4560

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Graft copolymerization, characterization, and degradation of cassava starch-g-acrylamide itaconic acid superabsorbents
Lanthong P, et al.
Carbohydrate Polymers, 66(2), 229-245 (2006)
Mechanism and kinetics of the stabilization reactions of itaconic acid-modified polyacrylonitrile
Ouyang Q, et al.
Polymer Degradation and Stability, 93(8), 1415-1421 (2008)
Fully Biobased Composites of an Itaconic Acid Derived Unsaturated Polyester Reinforced with Cotton Fabrics
Dai Z, et al.
ACS sustainable chemistry & engineering, 6(11), 15056-15063 (2018)
Tobias Klement et al.
Bioresource technology, 135, 422-431 (2013-01-10)
In the last years, itaconic acid has gained increasing interest as future bio-based platform chemical. To replace petrol-based compounds such as methacrylic acid in industry, the economic efficiency of the current biotechnological production processes with the fungus Aspergillus terreus has
Jahminy Sasikaran et al.
Nature chemical biology, 10(5), 371-377 (2014-03-25)
Itaconate (methylenesuccinate) was recently identified as a mammalian metabolite whose production is substantially induced during macrophage activation. This compound is a potent inhibitor of isocitrate lyase, a key enzyme of the glyoxylate cycle, which is a pathway required for the
View All Related Papers

Articles

Starbons: Cooking up Nanostructured Mesoporous Materials

Our strategy is to synthesize mesoporous carbonaceous materials (“Starbons”) using mesoporous expanded starch as the precursor without the need for a templating agent.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service