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I29204

Sigma-Aldrich

Itaconic acid

≥99%

Synonym(s):

Methylenesuccinic acid

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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

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

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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

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Certificates of Analysis (COA)

Lot/Batch Number
STBL4560
STBL0316
STBL2322
STBK7331
STBK9554

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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)
Tobias Klement et al.
Microbial cell factories, 11, 43-43 (2012-04-07)
In the last years, the biotechnological production of platform chemicals for fuel components has become a major focus of interest. Although ligno-cellulosic material is considered as suitable feedstock, the almost inevitable pretreatment of this recalcitrant material may interfere with the
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
Graft copolymerization, characterization, and degradation of cassava starch-g-acrylamide itaconic acid superabsorbents
Lanthong P, et al.
Carbohydrate Polymers, 66(2), 229-245 (2006)
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
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