Itaconic acid (IA, 2-methylidenebutanedioic acid) is a dicarboxylic acid in which one of the methyl hydrogens is substituted by a carboxylic acid group, as shown in figure 1. Itaconic acid is mainly produced by fungi and it is widely used for production of polymers including poly(itaconic acid) and acrylic-replacement fibers, and chemical intermediates such as styrene, 2-methyl-1,4-butanediol, and 3-methytetrahydrofuran. On the other hand, some fungi and lichens produce itaconic acid derivatives possessing itaconic acid skeleton, and the number of the derivatives is currently more than seventy[1].
Fig. 1 Chemical structure of itaconic acid
Synthesis of Itaconic Acid
In the production of itaconic acid, the yield and purification of the product are closely related to the strain. There are many kinds of microorganisms that can produce itaconic acid, such as A. terrus, A. itaconicus, Candida species, Rhodotrorula, Ustilago jeae, Helicobasidium mompa, Penicillum charlesii and A. niger. Among them, A. terreus has served as the most popular model system for investigating itaconic acid biosynthetic pathways. Sugars, such as glucose, xylose, or arabinose, can be used as biomass in the formation of itaconic acid. The biosynthesis pathway is showed in figure 2[2].
Fig. 2 Simplified illustration of the pathway of itaconic acid in A. terreus and equilibrium of weak acids in the medium and cytoplasm (1-Citrate synthase, 2-Isocitrate dehydrogenase, 3-Citrate malate antiporter, mitochondrial tricarboxylate transporter (mtt), 4-Cisaconitate decarboxylase (CAD), 5-Major facilitator superfamily protein (mfs), 6-H+-ATPase. EMP Embden-Meyerhof-Parnas, PPP pentose phosphate pathway)
Our Itaconic Acid and Derivatives
Our itaconic acid is produced via fermentation and its basic properties are listed in the following table.
| Product Name | Itaconic acid, 2-methylidenebutanedioic acid, IA |
| Catalog | BIOS97654 |
| Appearance | White crystal or powder |
| CAS No. | 97-65-4 |
| Molecular formula | C5H6O4 |
| Molecular weight | 130.1 |
| Content | ≥ 99.6% |
| Melting point | 165-168 ℃ |
| Loss on drying | 0.2% max |
| Ignition residue | 0.03% max |
| Iron(Fe) | 0.0002% max |
| Heavy metal(Pb) | 0.001% max |
| Chloride(Cl-) | 0.0005% max |
| Sulfate(SO42-) | 0.002% max |
| Applications | Itaconic acid and its polymers can be made into effective deodorant by adding a little natural substance. For instance, they can be utilized in paper and plastic thin film with deodorizing function.
Itaconic acid can copolymerize with styrene and butadiene to prepare SBR latex which is widely used in paper coatings, metal and concrete paint.
Itaconic acid can react with acrylic and methacrylic acid or their esters to prepare resins which can be widely used in emulsion coating, leather coating, coatings for car, refrigerator and other electrical appliances to improve adhesion, color and weather resistance. |
In addition to itaconic acid, we also supply high quality itaconic acid derivatives:
Alfa Chemistry is a professional supplier of biosynthetic itaconic acid and its derivatives. For high quality products, professional technical service, use suggestion and latest industry news, please feel free to contact us.
References
- Sano, M., Tanaka, T., Ohara, H., & Aso, Y. Itaconic acid derivatives: structure, function, biosynthesis, and perspectives. Applied Microbiology and Biotechnology, 2020, 104(21), 9041–9051./li>
- Kuenz, A., & Krull, S. Biotechnological production of itaconic acid-things you have to know. Applied Microbiology and Biotechnology, 2018, 102(9), 3901–3914./li>
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