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93598

Supelco

Itaconic acid

analytical standard

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/REAXYS Number:
1759501
EC Number:
202-599-6
MDL number:
MFCD00004260
UNSPSC Code:
85151701
PubChem Substance ID:
329770255
NACRES:
NA.24

grade

analytical standard

Quality Level

100

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.

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H318

Hazard Classifications

Eye Dam. 1

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 1

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Certificates of Analysis (COA)

Lot/Batch Number
BCCF4378
BCBZ8506
BCBS8239V
BCBM5222V

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Sambamurthy K.
Pharmaceutical Biotechnology, 56(3-4), 289-295 (2006)
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
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
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.
Stéphane Ménage et al.
Nature chemical biology, 10(5), 326-327 (2014-04-20)
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