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Journal articles on the topic 'Triacetic acid lactone'

Author: Grafiati
Published: 5 June 2025
Last updated: 1 August 2025

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1

Xie, Dongming, Zengyi Shao, Jihane Achkar, Wenjuan Zha, John W. Frost, and Huimin Zhao. "Microbial synthesis of triacetic acid lactone." Biotechnology and Bioengineering 93, no. 4 (2006): 727–36. http://dx.doi.org/10.1002/bit.20759.

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2

Tang, Shuang-Yan, Shuai Qian, Olubolaji Akinterinwa, Christopher S. Frei, Joseph A. Gredell, and Patrick C. Cirino. "Screening for Enhanced Triacetic Acid Lactone Production by Recombinant Escherichia coli Expressing a Designed Triacetic Acid Lactone Reporter." Journal of the American Chemical Society 135, no. 27 (2013): 10099–103. http://dx.doi.org/10.1021/ja402654z.

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3

Sajjad, Hussnain, Emily A. Prebihalo, William B. Tolman та Theresa M. Reineke. "Ring opening polymerization of β-acetoxy-δ-methylvalerolactone, a triacetic acid lactone derivative". Polymer Chemistry 12, № 46 (2021): 6724–30. http://dx.doi.org/10.1039/d1py00561h.

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4

MORENO-MANAS, M., and R. PLEIXATS. "ChemInform Abstract: Dehydroacetic Acid, Triacetic Acid Lactone, and Related Pyrones." ChemInform 24, no. 9 (2010): no. http://dx.doi.org/10.1002/chin.199309306.

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5

Obydennov, Dmitrii L., Asmaa I. El-Tantawy, and Vyacheslav Ya Sosnovskikh. "Bio-based triacetic acid lactone in the synthesis of azaheterocyclesviaa ring-opening transformation." New Journal of Chemistry 42, no. 11 (2018): 8943–52. http://dx.doi.org/10.1039/c8nj01044g.

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In the present article a new way of converting biobased triacetic acid lactone (TAL) into azaheterocyclic compounds, such as 4-pyridones, pyrazoles, isoxazolines and isoxazoles, has been found through reactive and multifunctional polycarbonyl intermediates.
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6

Chia, Mei, Thomas J. Schwartz, Brent H. Shanks, and James A. Dumesic. "Triacetic acid lactone as a potential biorenewable platform chemical." Green Chemistry 14, no. 7 (2012): 1850. http://dx.doi.org/10.1039/c2gc35343a.

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7

Kraus, George A., Kevin Basemann, and Tezcan Guney. "Selective pyrone functionalization: reductive alkylation of triacetic acid lactone." Tetrahedron Letters 56, no. 23 (2015): 3494–96. http://dx.doi.org/10.1016/j.tetlet.2015.01.141.

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8

Kornev, Mikhail Yu, Denis S. Tishin, Dmitrii L. Obydennov, and Vyacheslav Ya Sosnovskikh. "Reactions of 3-functionalized chromones with triacetic acid lactone." Mendeleev Communications 30, no. 2 (2020): 233–35. http://dx.doi.org/10.1016/j.mencom.2020.03.035.

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9

Yu, James, Jenny Landberg, Farbod Shavarebi, et al. "Bioengineering triacetic acid lactone production inYarrowia lipolyticafor pogostone synthesis." Biotechnology and Bioengineering 115, no. 9 (2018): 2383–88. http://dx.doi.org/10.1002/bit.26733.

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10

Moreno-Ma紡s, Marcial, and Roser Pleixats. "Bicyclic Compounds Structurally Relted to Dehydroacetic Acid and Triacetic Acid Lactone." HETEROCYCLES 37, no. 1 (1994): 585. http://dx.doi.org/10.3987/rev-93-sr2.

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11

Spencer, J. B., and P. M. Jordan. "Purification and properties of 6-methylsalicylic acid synthase from Penicillium patulum." Biochemical Journal 288, no. 3 (1992): 839–46. http://dx.doi.org/10.1042/bj2880839.

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6-Methylsalicylic acid synthase has been isolated in homogeneous form from Penicillium patulum grown in liquid culture from a spore inoculum. The enzyme is highly susceptible to proteolytic degradation in vivo and in vitro, but may be stabilized during purification by incorporating proteinase inhibitors in the buffers. The enzyme exists as a homotetramer of M(r) 750,000, with a subunit M(r) of 180,000. 6-Methylsalicyclic acid synthase also accepts acetoacetyl-CoA as an alternative starter molecule to acetyl-CoA. The enzyme also catalyses the formation of small amounts of triacetic acid lactone
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12

Fedin, Vladislav V., Sergey A. Usachev, Dmitrii L. Obydennov, and Vyacheslav Y. Sosnovskikh. "Reactions of Trifluorotriacetic Acid Lactone and Hexafluorodehydroacetic Acid with Amines: Synthesis of Trifluoromethylated 4-Pyridones and Aminoenones." Molecules 27, no. 20 (2022): 7098. http://dx.doi.org/10.3390/molecules27207098.

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Dehydroacetic acid and triacetic acid lactone are known to be versatile substrates for the synthesis of a variety of azaheterocycles. However, their fluorinated analogs were poorly described in the literature. In the present work, we have investigated reactions of trifluorotriacetic acid lactone and hexafluorodehydroacetic acid with primary amines, phenylenediamine, and phenylhydrazine. While hexafluorodehydroacetic acid reacted the same way as non-fluorinated analog giving 2,6-bis(trifluoromethyl)-4-pyridones, trifluorotriacetic acid lactone had different regioselectivity of nucleophilic atta
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13

Markham, Kelly A., Claire M. Palmer, Malgorzata Chwatko, et al. "Rewiring Yarrowia lipolytica toward triacetic acid lactone for materials generation." Proceedings of the National Academy of Sciences 115, no. 9 (2018): 2096–101. http://dx.doi.org/10.1073/pnas.1721203115.

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Polyketides represent an extremely diverse class of secondary metabolites often explored for their bioactive traits. These molecules are also attractive building blocks for chemical catalysis and polymerization. However, the use of polyketides in larger scale chemistry applications is stymied by limited titers and yields from both microbial and chemical production. Here, we demonstrate that an oleaginous organism (specifically, Yarrowia lipolytica) can overcome such production limitations owing to a natural propensity for high flux through acetyl–CoA. By exploring three distinct metabolic engi
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14

Obydennov, Dmitrii L., Asmaa I. El-Tantawy, and Vyacheslav Ya Sosnovskikh. "Triacetic acid lactone as a bioprivileged molecule in organic synthesis." Mendeleev Communications 29, no. 1 (2019): 1–10. http://dx.doi.org/10.1016/j.mencom.2019.01.001.

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15

Kraus, George A., Kevin Basemann, and Tezcan Guney. "ChemInform Abstract: Selective Pyrone Functionalization: Reductive Alkylation of Triacetic Acid Lactone." ChemInform 46, no. 38 (2015): no. http://dx.doi.org/10.1002/chin.201538155.

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16

MORENO-MANAS, M., and R. PLEIXATS. "ChemInform Abstract: Bicyclic Compounds Structurally Related to Dehydroacetic Acid and Triacetic Acid Lactone." ChemInform 25, no. 19 (2010): no. http://dx.doi.org/10.1002/chin.199419312.

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17

Sajjad, Hussnain, William B. Tolman, and Theresa M. Reineke. "Block Copolymer Pressure-Sensitive Adhesives Derived from Fatty Acids and Triacetic Acid Lactone." ACS Applied Polymer Materials 2, no. 7 (2020): 2719–28. http://dx.doi.org/10.1021/acsapm.0c00317.

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18

Frei, Christopher S., Zhiqing Wang, Shuai Qian, Samuel Deutsch, Markus Sutter, and Patrick C. Cirino. "Analysis of amino acid substitutions in AraC variants that respond to triacetic acid lactone." Protein Science 25, no. 4 (2016): 804–14. http://dx.doi.org/10.1002/pro.2873.

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19

Cardenas, Javier, and Nancy A. Da Silva. "Metabolic engineering of Saccharomyces cerevisiae for the production of triacetic acid lactone." Metabolic Engineering 25 (September 2014): 194–203. http://dx.doi.org/10.1016/j.ymben.2014.07.008.

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20

Feng, Linjuan, Junhao Xu, Cuifang Ye, et al. "Metabolic Engineering of Pichia pastoris for the Production of Triacetic Acid Lactone." Journal of Fungi 9, no. 4 (2023): 494. http://dx.doi.org/10.3390/jof9040494.

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Triacetic acid lactone (TAL) is a promising renewable platform polyketide with broad biotechnological applications. In this study, we constructed an engineered Pichia pastoris strain for the production of TAL. We first introduced a heterologous TAL biosynthetic pathway by integrating the 2-pyrone synthase encoding gene from Gerbera hybrida (Gh2PS). We then removed the rate-limiting step of TAL synthesis by introducing the posttranslational regulation-free acetyl-CoA carboxylase mutant encoding gene from S. cerevisiae (ScACC1*) and increasing the copy number of Gh2PS. Finally, to enhance intrac
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21

Chen, Bingfeng, Zhenbing Xie, Fangfang Peng та ін. "Production of Piperidine and δ‐Lactam Chemicals from Biomass‐Derived Triacetic Acid Lactone". Angewandte Chemie International Edition 60, № 26 (2021): 14405–9. http://dx.doi.org/10.1002/anie.202102353.

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22

Chen, Bingfeng, Zhenbing Xie, Fangfang Peng та ін. "Production of Piperidine and δ‐Lactam Chemicals from Biomass‐Derived Triacetic Acid Lactone". Angewandte Chemie 133, № 26 (2021): 14526–30. http://dx.doi.org/10.1002/ange.202102353.

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23

Bowman, Emily K., James M. Wagner, Shuo-Fu Yuan, et al. "Sorting for secreted molecule production using a biosensor-in-microdroplet approach." Proceedings of the National Academy of Sciences 118, no. 36 (2021): e2106818118. http://dx.doi.org/10.1073/pnas.2106818118.

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Sorting large libraries of cells for improved small molecule secretion is throughput limited. Here, we combine producer/secretor cell libraries with whole-cell biosensors using a microfluidic-based screening workflow. This approach enables a mix-and-match capability using off-the-shelf biosensors through either coencapsulation or pico-injection. We demonstrate the cell type and library agnostic nature of this workflow by utilizing single-guide RNA, transposon, and ethyl-methyl sulfonate mutagenesis libraries across three distinct microbes (Escherichia coli, Saccharomyces cerevisiae, and Yarrow
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24

Zeba, N. Siddiqui, and Asad Mohammad. "Synthesis and biological significance of pyrano pyrazoles from 8,9-dimethyl-3- acetoacetyl pyrano[3,2-c ][1 ]benzopyran-2,5-dione." Journal of Indian Chemical Society Vol. 87, Apr 2010 (2010): 501–6. https://doi.org/10.5281/zenodo.5785692.

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Department of Chemistry, Aligarh Muslim University, Aligarh-202 002, Uttar Pradesh, India <em>E-mail:</em> siddiqui_zeba@yahoo.co.in <em>Manuscript received 6 August 2008, revised 13 April 2009, accepted 4 September 2009</em> 6,7-Dimethyl-3-formyl-4-hydroxycoumarln 1 was treated with triacetic acid lactone 2 in heating methanol to afford 8,9-dlmethyl-3-acetoacetyl pyrano[3,2-c][l]benzopyran-2,5-dione 3. The compound 3 was transformed to pyrano pyrazole derivatives 4a-c by treatment with nitrogen bases such as hydrazine hydrate, phenylhydrazine and hydrazinobenzothiazole. The structure of all c
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25

Moreno-Mañas, Marcial, Maria Prat, Jordi Ribas, and Albert Virgili. "Palladium catalyzed allylic C-alkylation of highly acidic and enolic heterocyclic substrates: tetronic acid and triacetic acid lactone." Tetrahedron Letters 29, no. 5 (1988): 581–84. http://dx.doi.org/10.1016/s0040-4039(00)80156-2.

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26

Moreno-Manas, Marcial, Jordi Ribas, and Albert Virgili. "Palladium-catalyzed C-alkylations of the highly acidic and enolic triacetic acid lactone. Mechanism and stereochemistry." Journal of Organic Chemistry 53, no. 22 (1988): 5328–35. http://dx.doi.org/10.1021/jo00257a023.

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27

Cervello, Jordi, Jorge Marquet, and Marcial Moreno-Mañas. "Copper and cobalt mediated regioselective alkylation of polyketide models: methyl 3,5-dioxohexanoate and triacetic acid lactone." Tetrahedron 46, no. 6 (1990): 2035–46. http://dx.doi.org/10.1016/s0040-4020(01)89770-2.

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28

Jonassohn, Mikaei, Olov Sterner, and Heidrun Anke. "Structure-activity relationships for unsaturated dialdehydes 12. The reactivity of unsaturated dialdehydes towards triacetic acid lactone." Tetrahedron 52, no. 4 (1996): 1473–78. http://dx.doi.org/10.1016/0040-4020(95)00973-6.

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29

March, Pedro De, Marcial Moreno-Mañas, and Isabel Ripoll. "Alkylation of Position C-5 of Triacetic Acid Lactone by [2,3] Sigmatropic Rearrangement of Sulphonium Ylides." Chemische Berichte 120, no. 8 (1987): 1413–19. http://dx.doi.org/10.1002/cber.19871200819.

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30

Liu, Huan, Monireh Marsafari, Fang Wang, Li Deng, and Peng Xu. "Engineering acetyl-CoA metabolic shortcut for eco-friendly production of polyketides triacetic acid lactone in Yarrowia lipolytica." Metabolic Engineering 56 (December 2019): 60–68. http://dx.doi.org/10.1016/j.ymben.2019.08.017.

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31

Li, Ye, Shuai Qian, Rachel Dunn, and Patrick C. Cirino. "Engineering Escherichia coli to increase triacetic acid lactone (TAL) production using an optimized TAL sensor-reporter system." Journal of Industrial Microbiology & Biotechnology 45, no. 9 (2018): 789–93. http://dx.doi.org/10.1007/s10295-018-2062-0.

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32

Zha, Wenjuan, Zengyi Shao, John W. Frost, and Huimin Zhao. "Rational Pathway Engineering of Type I Fatty Acid Synthase Allows the Biosynthesis of Triacetic Acid Lactone fromd-Glucose in Vivo." Journal of the American Chemical Society 126, no. 14 (2004): 4534–35. http://dx.doi.org/10.1021/ja0317271.

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33

Shao, Siyuan, Yanan Yang, Ziming Feng, Jianshuang Jiang, and Peicheng Zhang. "New triacetic acid lactone glycosides from the fruits of Forsythia suspensa and their nitric oxide production inhibitory activity." Carbohydrate Research 488 (February 2020): 107908. http://dx.doi.org/10.1016/j.carres.2020.107908.

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34

JONASSOHN, M., O. STERNER, and H. ANKE. "ChemInform Abstract: Structure-Activity Relationships for Unsaturated Dialdehydes. Part 12. The Reactivity of Unsaturated Dialdehydes Towards Triacetic Acid Lactone." ChemInform 27, no. 19 (2010): no. http://dx.doi.org/10.1002/chin.199619267.

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35

Kraus, George A., Umayangani K. Wanninayake, and Jashaun Bottoms. "Triacetic acid lactone as a common intermediate for the synthesis of 4-hydroxy-2-pyridones and 4-amino-2-pyrones." Tetrahedron Letters 57, no. 11 (2016): 1293–95. http://dx.doi.org/10.1016/j.tetlet.2016.02.043.

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36

Wen, Ching-Mei, and Marianthi Ierapetritou. "Improving life cycle assessment consistency for biomass-derived processes: A case study on triacetic acid lactone production with CO2 recycling." Computers & Chemical Engineering 201 (October 2025): 109244. https://doi.org/10.1016/j.compchemeng.2025.109244.

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37

Anouar, El Hassane, Sanae Lahmidi, Insaf Filali, and El Mokhtar Essassi. "Synthesis, NMR spectroscopic characterization, DFT calculations, and molecular docking of new substituted phenolic and pyranopyran derivatives obtained from triacetic acid lactone." Journal of Molecular Structure 1331 (June 2025): 141538. https://doi.org/10.1016/j.molstruc.2025.141538.

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38

Moreno-Mañas, M., E. Papell, J. Ribas, A. Virgili, and R. Pleixats. "4-Hydroxy-6-methyl-2-pyrone (triacetic acid lactone) and its 3-phenylthiomethyl derivative towards aldehydes in the presence of piperidine." Journal of Heterocyclic Chemistry 23, no. 2 (1986): 413–16. http://dx.doi.org/10.1002/jhet.5570230220.

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39

Cervelló, Jordi, Jorge Marquet та Marcial Moreno-mañas. "An Improved Method for γ-Carboxylation of β-Diketones. Synthesis of 4-Alkyl-3,5-Dioxohexanoic Acids and 5-Alkyl Derivatives of Triacetic Acid Lactone". Synthetic Communications 20, № 13 (1990): 1931–41. http://dx.doi.org/10.1080/00397919008053123.

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40

Majumdar, K. C., U. K. Kundu, and S. Ghosh. "Studies on triacetic acid lactone-annulated heterocycles: synthesis of 3-aryloxyacetyl-6-methyl-2,3-dihydrothieno[3,2- c ]pyran-4-ones by tandem cyclization." Tetrahedron 58, no. 52 (2002): 10309–13. http://dx.doi.org/10.1016/s0040-4020(02)01418-7.

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41

CERVELLO, J., J. MARQUET та M. MORENO-MANAS. "ChemInform Abstract: An Improved Method for γ-Carboxylation of β-Diketones. Synthesis of 4-Alkyl-3,5-dioxohexanoic Acids and 5-Alkyl Derivatives of Triacetic Acid Lactone." ChemInform 22, № 9 (2010): no. http://dx.doi.org/10.1002/chin.199109124.

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42

Ewan, H. Samuel, Shruti A. Biyani, Jaycie DiDomenico, et al. "Aldol Reactions of Biorenewable Triacetic Acid Lactone Precursor Evaluated Using Desorption Electrospray Ionization Mass Spectrometry High-Throughput Experimentation and Validated by Continuous Flow Synthesis." ACS Combinatorial Science 22, no. 12 (2020): 796–803. http://dx.doi.org/10.1021/acscombsci.0c00119.

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43

De March, P., M. Moreno-Mañas, J. L. Roca, G. Germain, J. F. Piniella, and O. Dideberg. "Reactions of triacetic acid lactone with carbonyl compounds. X-Ray structure determination of 3-acetoacetyl-2-chromenone and 3,6,9,12-tetramethyl-1H,6H,7H,12H-6,12-methanodipyrano[4,3-b:4,3-f]-dioxocin-1,7-dione." Journal of Heterocyclic Chemistry 23, no. 5 (1986): 1511–13. http://dx.doi.org/10.1002/jhet.5570230550.

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44

Choi, Yejin, Sangjae Jeong, Young-Kwon Park, et al. "Chemical Feedstock Recovery via the Pyrolysis of Electronically Heated Tobacco Wastes." Sustainability 13, no. 22 (2021): 12856. http://dx.doi.org/10.3390/su132212856.

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The pyrolysis of waste electronically heated tobacco (EHT), consisting of tobacco leaves (TL), a poly-lactic acid (PLA) filter, and a cellulose acetate (CA) filter, was investigated using thermogravimetric (TG) and pyrolyzer–gas chromatography/mass spectrometry (Py-GC/MS) analysis. The pyrolytic properties of waste EHT obtained after smoking were comparable to those of fresh EHT. Although the maximum decomposition temperatures (TmaxS) of waste TL and CA were similar to those of fresh EHT components, the Tmax of waste PLA was slightly higher than that of fresh PLA due to smoldering. The Tmaxs o
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45

Duarte Ortin, Gilberto G., and Airton G. Salles. "Persulfate-promoted synthesis of biphenyl compounds in water from biomass-derived triacetic acid lactone." Organic & Biomolecular Chemistry, 2022. http://dx.doi.org/10.1039/d2ob01900k.

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46

Kim, Min Soo, Sarang Sunil Bhagwat, Leoncio Santiago-Martínez, et al. "Sustainable Potassium Sorbate Production from Triacetic Acid Lactone in Food-grade Solvents." Green Chemistry, 2025. https://doi.org/10.1039/d4gc04832f.

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This study advances the production of potassium sorbate (KS) from triacetic acid lactone (TAL) utilizing food-grade solvents, ethanol (EtOH) and isopropyl alcohol (IPA). Employing a catalytic approach in food-grade solvents...
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47

Siddiqui, Zeba, Shagufta Praveen, and Farheen Farooq. "Novel benzopyranopyridine derivatives of 2-amino-3-formylchromone." Chemical Papers 64, no. 6 (2010). http://dx.doi.org/10.2478/s11696-010-0072-0.

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AbstractEnol lactones such as 4-hydroxy-6-methyl-2H-pyran-2-one (triacetic acid lactone, TAL) and 4-hydroxycoumarin when treated with 2-amino-3-formylchromone under basic conditions afforded 3-acetoacetyl benzopyranopyridones and benzopyranopyridines, respectively. A series of pyrazole derivatives was prepared by the reaction of 3-acetoacetyl benzopyranopyridones with different hydrazines. All compounds were characterised on the basis of spectral data and their antibacterial activity evaluated.
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48

Saunders, Lauren P., Michael J. Bowman, Jeffrey A. Mertens, Nancy A. Da Silva, and Ronald E. Hector. "Triacetic acid lactone production in industrial Saccharomyces yeast strains." Journal of Industrial Microbiology & Biotechnology, February 15, 2015. http://dx.doi.org/10.1007/s10295-015-1596-7.

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49

Singh, Ramkrishna, Sarang S. Bhagwat, Mothi Bharath Viswanathan, et al. "Adsorptive separation and recovery of triacetic acid lactone from fermentation broth." Biofuels, Bioproducts and Biorefining, August 19, 2022. http://dx.doi.org/10.1002/bbb.2427.

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50

Singh, Ramkrishna, Sarang Bhagwat, Mothi Bharath Viswanathan, et al. "Adsorptive Separation and Recovery of Triacetic Acid Lactone from Fermentation Broth." SSRN Electronic Journal, 2022. http://dx.doi.org/10.2139/ssrn.4109741.

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