Mono-methyl terephthalate
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Mono-methyl terephthalate

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Mono-methyl terephthalate is used in the synthesis of Hepatits C antiviral activity. Also used in the design and preparation of benzamide derivatives as BRAFV600E inhibitors, which if mutated, can influence malignancies and melanomas.

Category
Peptide Synthesis Reagents
Catalog number
BAT-006428
CAS number
1679-64-7
Molecular Formula
C9H8O4
Molecular Weight
180.16
Mono-methyl terephthalate
IUPAC Name
4-methoxycarbonylbenzoic acid
Synonyms
MMT; 1,4-Benzenedicarboxylic Acid Monomethyl Ester; Terephthalic Acid Monomethyl Ester; 4-(Carbomethoxy)benzoic Acid; 4-(Methoxycarbonyl)benzoic Acid; 4-[(Methyloxy)carbonyl]benzoic Acid; Hydrogen Methyl Terephthalate; Methyl 4-Carboxybenzoate; Methyl Hydrogen Terephthalate; Methyl p-Carboxybenzoate; Methyl p-Phthalate; Monomethyl terephthalate; NSC 210838; p-(Methoxycarbonyl)benzoic Acid; p-Carbomethoxybenzoic Acid
Appearance
White crystal
Purity
99 % (HPLC)
Density
1.199 g/cm3 (Predicted)
Melting Point
220-223 °C
Boiling Point
232.96 °C (Predicted)
Storage
-20 °C
Solubility
Soluble in DMSO; Slightly soluble in Methanol
InChI
InChI=1S/C9H8O4/c1-13-9(12)7-4-2-6(3-5-7)8(10)11/h2-5H,1H3,(H,10,11)
InChI Key
REIDAMBAPLIATC-UHFFFAOYSA-N
Canonical SMILES
COC(=O)C1=CC=C(C=C1)C(=O)O
1. Catalytic Degradation of Polyethylene Terephthalate Using a Phase-Transitional Zirconium-Based Metal-Organic Framework
Yufang Wu, et al. Angew Chem Int Ed Engl. 2022 Jun 13;61(24):e202117528. doi: 10.1002/anie.202117528. Epub 2022 Apr 20.
Polyethylene terephthalate (PET) is utilized as one of the most popular consumer plastics worldwide, but difficulties associated with recycling PET have generated a severe environmental crisis with most PET ending its lifecycle in landfills. We report that zirconium-based metal-organic framework (Zr-MOF) UiO-66 deconstructs waste PET into the building blocks terephthalic acid (TA) and mono-methyl terephthalate (MMT) within 24 hours at 260 °C (total yield of 98 % under 1 atm H2 and 81 % under 1 atm Ar). Extensive structural characterization studies reveal that during the degradation process, UiO-66 undergoes an intriguing transformation into MIL-140A, which is another Zr-MOF that shows good catalytic activity toward PET degradation under similar reaction conditions. These results illustrate the diversity of applications for Zr-MOFs and establish MOFs as a new class of polymer degradation catalysts with the potential to address long-standing challenges associated with plastic waste.
2. Potential of esterase DmtH in transforming plastic additive dimethyl terephthalate to less toxic mono-methyl terephthalate
Xiaokun Cheng, Shuangshuang Dong, Dian Chen, Qi Rui, Jingjing Guo, Dayong Wang, Jiandong Jiang Ecotoxicol Environ Saf. 2020 Jan 15;187:109848. doi: 10.1016/j.ecoenv.2019.109848. Epub 2019 Oct 25.
Dimethyl terephthalate (DMT) is a primary ingredient widely used in the manufacture of polyesters and industrial plastics; its environmental fate is of concern due to its global use. Microorganisms play key roles in the dissipation of DMT from the environment; however, the enzymes responsible for the initial transformation of DMT and the possible altered toxicity due to this biotransformation have not been extensively studied. To reduce DMT toxicity, we identified the esterase gene dmtH involved in the initial transformation of DMT from the AOPP herbicide-transforming strain Sphingobium sp. C3. DmtH shows 24-41% identity with α/β-hydrolases and belongs to subfamily V of bacterial esterases. The purified recombinant DmtH was capable of transforming DMT to mono-methyl terephthalate (MMT) and potentially transforming other p-phthalic acid esters, including diallyl terephthalate (DAT) and diethyl terephthalate (DET). Using C. elegans as an assay model, we observed the severe toxicity of DMT in inducing reactive oxygen species (ROS) production, decreasing locomotion behavior, reducing lifespan, altering molecular basis for oxidative stress, and inducing mitochondrial stress. In contrast, exposure to MMT did not cause obvious toxicity, induce oxidative stress, and activate mitochondrial stress in nematodes. Our study highlights the usefulness of Sphingobium sp. C3 and its esterase DmtH in transforming p-phthalic acid esters and reducing the toxicity of DMT to organisms.
3. Biodegradation of dimethyl terephthalate by Pasteurella multocida Sa follows an alternative biochemical pathway
Jiaxi Li, Ji-Dong Gu Ecotoxicology. 2006 May;15(4):391-7. doi: 10.1007/s10646-006-0070-8. Epub 2006 May 5.
Pasteurella multocida Sa, a bacterial strain isolated from mangrove sediment by enrichment technique, was capable of transforming dimethyl terephthalate (DMT). Biodegradation of DMT was shown to take place as a series of sequential steps involving the hydrolysis of two ester linkages between the carboxyl groups of the terephthalate and the methyl side-chain initially to produce mono-methyl terephthalate (MMT) and then terephthalic acid (TA), respectively. However, with ethanol as the carrying solvent, there was a formation of one metabolite previously not observed. The two metabolites were characterized by high performance-liquid chromatography-electron ionization mass spectrometry as MMT and mono-ethyl terephthalate (MET), suggesting the existence of an alternative biochemical pathway in the degradation of DMT by P. multocida Sa. Since the presence of MMT and ethanol in culture inoculated with P. multocida Sa was prerequisites for the formation of MET, biologically mediated trans-esterification was proposed as a mechanism for the novel biochemical process observed.
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