93598
Itaconic acid
analytical standard
Synonym(s):
Methylenesuccinic acid
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About This Item
Linear Formula:
HO2CCH2C(=CH2)CO2H
CAS Number:
Molecular Weight:
130.10
Beilstein:
1759501
EC Number:
MDL number:
UNSPSC Code:
85151701
PubChem Substance ID:
NACRES:
NA.24
Recommended Products
grade
analytical standard
Quality Level
Assay
≥96.0% (GC)
autoignition temp.
1472 °F
shelf life
limited shelf life, expiry date on the label
technique(s)
HPLC: suitable
gas chromatography (GC): suitable
impurities
≤0.5% water
mp
165-168 °C (lit.)
density
1.573 g/mL at 25 °C (lit.)
format
neat
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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General description
Itaconic acid, an unsaturated dicarbonic organic acid, is a metabolic product of Aspergillus itaconicus.
This substance is listed on the positive list of the EU regulation 10/2011 for plastics intended to come into contact with food.
Application
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Dam. 1
Storage Class Code
13 - Non Combustible Solids
WGK
WGK 1
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Pharmaceutical Biotechnology, 56(3-4), 289-295 (2006)
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
Metabolism: pathogens love the poison.
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Nature chemical biology, 10(5), 326-327 (2014-04-20)
T Willke et al.
Applied microbiology and biotechnology, 56(3-4), 289-295 (2001-09-11)
Itaconic acid (IA) is an unsaturated dicarbonic organic acid. It can easily be incorporated into polymers and may serve as a substitute for petrochemical-based acrylic or methacrylic acid. It is used at 1-5% as a co-monomer in resins and also
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