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Key Documents

I29204

Sigma-Aldrich

Itaconic acid

≥99%

Synonym(s):

Methylenesuccinic acid

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$63.30
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Estimated to ship on31 March 2025


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100 G
$63.30
1 KG
$89.90

About This Item

Linear Formula:
HO2CCH2C(=CH2)CO2H
CAS Number:
Molecular Weight:
130.10
Beilstein:
1759501
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Assay:
≥99%

$63.30


Estimated to ship on31 March 2025


Request a Bulk Order

Quality Level

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.[1]
  • In combination with acrylamide to form (poly[acrylamide-co-(itaconicacid)]) to synthesize biodegradable superabsorbent polymers.[2]
  • To synthesize biobased polyester composite in fabric industry.[3]

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Precautionary Statements

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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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)
Graft copolymerization, characterization, and degradation of cassava starch-g-acrylamide itaconic acid superabsorbents
Lanthong P, et al.
Carbohydrate Polymers, 66(2), 229-245 (2006)
Selective and flexible transformation of biomass-derived platform chemicals by a multifunctional catalytic system.
Frank M A Geilen et al.
Angewandte Chemie (International ed. in English), 49(32), 5510-5514 (2010-06-30)
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
E Karadağ et al.
Biomaterials, 17(1), 67-70 (1996-01-01)
In this in vitro study, the biocompatibility of acrylamide-based hydrogels such as acrylamide/crotonic and acrylamide/itaconic acid, prepared by using gamma-rays, has been investigated against some biochemical parameters of human serum. The swelling kinetics of acrylamide/crotonic and acrylamide/itaconic acid hydrogels are

Articles

Our strategy is to synthesize mesoporous carbonaceous materials (“Starbons”) using mesoporous expanded starch as the precursor without the need for a templating agent.

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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