CAS 123-76-2: Levulinic acid

Levulinic acid (4-Oxovaleric acid), derived from the degradation of cellulose, is a precursor for the synthesis of biofuels, such as ethyl levulinate.

Mainly used as an intermediate for medicines, agricultural chemical and organic synthesis. Used as raw material of perfume, modifier and solvent of plastics. It is also employed as an additive of polymer, paints and lubricating oil. Also used as a surfactant and auxiliary for making printing ink, rubber flux and cosmetics(including shampoo). This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Levulinic acid is a dicarboxylic acid that is resistant to the formation of the levulinate ester. In vitro, it has been shown to have a synergistic effect with other antibiotics such as erythromycin and cefazolin against bacteria in experimental models. The mechanism of this synergistic effect is not known, but may be due to inhibition of bacterial cell wall synthesis. Levulinic acid can also be used as an injection solution or magnesium salt for surface methodology experiments. The rate of reaction with magnesium is slow, and the reactivity is similar to that of levulinate. Kinetic studies have shown that the rate-determining step in the reaction between levulinic acid and magnesium chloride is the binding of MgCl2 to LHA (levulinic acid). This binding also reacts slowly with water and formaldehyde.

This Thermo Scientific Chemicals brand product was originally part of the Acros Organics product portfolio. Some documentation and label information may refer to the legacy brand. The original Acros Organics product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Levulinic acid is an organic compound, which is derived from the acid hydrolysis of biomass, such as lignocellulosic materials. Its chemical structure makes it a pivotal platform chemical with potential for diverse transformations. Levulinic acid functions as a building block for various chemical synthesis processes, facilitating the production of numerous derivatives including pharmaceuticals, agrochemicals, plasticizers, and biofuels. In terms of its mechanisms, levulinic acid serves as a precursor in chemical reactions due to its keto-acid functionality, allowing for conversions via reduction, esterification, and condensation reactions. These transformations enable the production of value-added compounds such as gamma-valerolactone and 5-aminolevulinic acid. Levulinic acid's applications are wide-ranging. It is utilized in the synthesis of resins and coatings, offering sustainable alternatives to petrochemical-derived products. Additionally, it plays a role in the agricultural sector as an ingredient in herbicides and plant growth regulators. It is also explored in pharmaceutical formulations for its potential contributions to drug design, highlighting its significance across multiple scientific and industrial domains.

Applications Levulinic Acid is derived from the degredation of cellulose and is a potential precursor to biofuels. Levulinic acid is also a photosensitizer for photodynamic therapy. References Serrano-Ruiz, J.C., et al.: Catalysis., 195, 162 (2012); Liedtke, A.J. et al.: Tetrahedron., 68, 10049 (2012);