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Merck
CN

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:
Technical Service
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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

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.


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pictograms

Corrosion

signalword

Danger

hcodes

Hazard Classifications

Eye Dam. 1

Storage Class

13 - Non Combustible Solids

wgk

WGK 1



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Sambamurthy K.
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



Global Trade Item Number

SKUGTIN
93598-100MG04061833282946