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
UNSPSC Code:
85151701
NACRES:
NA.24
PubChem Substance ID:
EC Number:
202-599-6
Beilstein/REAXYS Number:
1759501
MDL number:
InChI key
LVHBHZANLOWSRM-UHFFFAOYSA-N
InChI
1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h1-2H2,(H,6,7)(H,8,9)
SMILES string
OC(=O)CC(=C)C(O)=O
grade
analytical standard
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
Quality Level
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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.
signalword
Danger
hcodes
Hazard Classifications
Eye Dam. 1
Storage Class
13 - Non Combustible Solids
wgk
WGK 1
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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
Sambamurthy K.
Pharmaceutical Biotechnology, 56(3-4), 289-295 (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
Mitsuyasu Okabe et al.
Applied microbiology and biotechnology, 84(4), 597-606 (2009-07-25)
More than 80,000 tons of itaconic acid (IA) is produced worldwide each year and is sold at a price of around US$ 2/kg. The IA production yield from sugar is higher than 80 g/l. The widespread use of IA in
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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