Novel biodegradable polyesters based on lignin-derived 3-carboxymuconolactone

• (4 S )-3-Carboxymuconolactone (3CML) was polycondensed with various α,ω-alkylene diols via dehydration polymerization to afford a series of 3CML polyesters, P(3CMLm). • DFT calculations revealed that 3CML adopts a nonplanar structure due to the presence of a stereogenic center, leading to flexible polymer chains. • The thermal decomposition temperature (T d,5% ) of P(3CMLm) increased with increasing alkylene spacer length. • In BOD tests using surface and deep seawater, P(3CMLm) showed over 40% biodegradation after 54 days, attributable to hydrolysis under mildly alkaline conditions. Lignin has attracted considerable attention as an abundant natural carbon feedstock capable of replacing petroleum-based resources. Recent development in microbial funneling techniques has enabled the stable production of dibasic compounds as biometabolic intermediates such as 2-pyron-4,6-dicarboxylic acid ( PDC ) and (4 S )-3-carboxymuconolactone ( 3CML ) from lignin-derived aromatic molecules under controlled metabolic processes. Our group has demonstrated that PDC -incorporated polymers exhibit excellent heat resistance, mechanical performance, adhesive nature to metal and wood substrates, and biodegradability in simulated natural environments. In this study, a series of 3CML -based polyesters was synthesized by dehydrated polycondensation with diol compounds containing various alkyl spacer lengths. The resulting polyesters displayed distinct macroscopic behavior and thermal properties compared with PDC -based analogues due to the nonplanar molecular structure arising from the asymmetric center in 3CML . Biodegradation tests of 3CML -based polyesters in both surface and deep seawater revealed biodegradation rates exceeding ca. 40% after 54 days, comparable to those of polyhydroxyalkanoates and polycaprolactone.

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Publication Details

Journal
Polymer Degradation and Stability
Published
2026-04-22
DOI
https://doi.org/10.1016/j.polymdegradstab.2026.112159
Primary Topic
Lignin and Wood Chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

Novel biodegradable polyesters based on lignin-derived 3-carboxymuconolactone

Tsuyoshi Michinobu, E. Masai, M. Joshi, Y. Suzuki et al.
Polymer Degradation and Stability
Lignin and Wood Chemistry
article

Novel biodegradable polyesters based on lignin-derived 3-carboxymuconolactone

Tsuyoshi Michinobu, E. Masai, M. Joshi, Y. Suzuki, Y. Otsuka, N. Kamimura, M. Fujita, A. Isobe, T. Araki, Y. Jin, K. Jimbo
article en

Abstract

• (4 S )-3-Carboxymuconolactone (3CML) was polycondensed with various α,ω-alkylene diols via dehydration polymerization to afford a series of 3CML polyesters, P(3CMLm). • DFT calculations revealed that 3CML adopts a nonplanar structure due to the presence of a stereogenic center, leading to flexible polymer chains. • The thermal decomposition temperature (T d,5% ) of P(3CMLm) increased with increasing alkylene spacer length. • In BOD tests using surface and deep seawater, P(3CMLm) showed over 40% biodegradation after 54 days, attributable to hydrolysis under mildly alkaline conditions. Lignin has attracted considerable attention as an abundant natural carbon feedstock capable of replacing petroleum-based resources. Recent development in microbial funneling techniques has enabled the stable production of dibasic compounds as biometabolic intermediates such as 2-pyron-4,6-dicarboxylic acid ( PDC ) and (4 S )-3-carboxymuconolactone ( 3CML ) from lignin-derived aromatic molecules under controlled metabolic processes. Our group has demonstrated that PDC -incorporated polymers exhibit excellent heat resistance, mechanical performance, adhesive nature to metal and wood substrates, and biodegradability in simulated natural environments. In this study, a series of 3CML -based polyesters was synthesized by dehydrated polycondensation with diol compounds containing various alkyl spacer lengths. The resulting polyesters displayed distinct macroscopic behavior and thermal properties compared with PDC -based analogues due to the nonplanar molecular structure arising from the asymmetric center in 3CML . Biodegradation tests of 3CML -based polyesters in both surface and deep seawater revealed biodegradation rates exceeding ca. 40% after 54 days, comparable to those of polyhydroxyalkanoates and polycaprolactone.

Polymer Degradation and StabilityVol. 250
Tokyo Institute of Technology (JP), Nagaoka University (JP), Forestry and Forest Products Research Institute (JP), Nagaoka University of Technology (JP)
Fuji Seal Foundation, Japan Society for the Promotion of Science, Japan Science and Technology Agency
Life below water
Openalex Percentile: Top 19%
Lignin and Wood Chemistry
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