Ethylene Terephthalate Cyclic Dimer

  • CAT Number: R090010
  • CAS Number: 24388-68-9
  • Molecular Formula: C₂₀H₁₆O₈
  • Molecular Weight: 384.34
  • Purity: 95%
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Ethylene Terephthalate Cyclic Dimer(CAS: 24388-68-9) is an impurity in the synthesis of Ethylene Terephthalate Cyclic Trimer. Ethylene Terephthalate Cyclic Trimer can be used as migration indicators into foods and simulants, for microwave-active materials.

Catalog Number R090010
CAS Number 24388-68-9
Molecular Formula

C₂₀H₁₆O₈

Purity 95
IUPAC Name 3,6,13,16-tetraoxatricyclo[16.2.2.28,11]tetracosa-1(21),8,10,18(22),19,23-hexaene-2,7,12,17-tetrone
InChI InChI=1S/C20H16O8/c21-17-13-1-2-14(4-3-13)18(22)26-11-12-28-20(24)16-7-5-15(6-8-16)19(23)27-10-9-25-17/h1-8H,9-12H2
InChIKey NFFNGYZBZAPKKE-UHFFFAOYSA-N
SMILES C1COC(=O)C2=CC=C(C=C2)C(=O)OCCOC(=O)C3=CC=C(C=C3)C(=O)O1
Reference

[1]. Int J Syst Evol Microbiol. 2016 Aug;66(8):2813-2818. doi: 10.1099/ijsem.0.001058. Epub 2016 Apr 5.<br />
Ideonella sakaiensis sp. nov., isolated from a microbial consortium that degrades poly(ethylene terephthalate).<br />
Tanasupawat S(1), Takehana T(2), Yoshida S(3), Hiraga K(3), Oda K(3).<br />
Author information: (1)Department of Biochemistry and Microbiology, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Bangkok 10330, Thailand. (2)Life Science Materials Laboratory, ADEKA Corporation, 7-2-34 Higashiogu, Arakawa-ku, Tokyo 116-8553, Japan. (3)Department of Applied Biology, Graduate School of Science and Technology, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan.<br />
A Gram-stain-negative, aerobic, non-spore-forming, rod-shaped bacterium, designed strain 201-F6T, was isolated from a microbial consortium that degrades poly(ethylene terephthalate) (PET) collected in Sakai city, Japan, and was characterized on the basis of a polyphasic taxonomic study. The cells were motile with a polar flagellum. The strain contained cytochrome oxidase and catalase. It grew within the pH range 5.5-9.0 (optimally at pH 7-7.5) and at 15-42&thinsp;&ordm;C (optimally at 30-37&thinsp;&ordm;C). The major isoprenoid quinone was ubiquinone with eight isoprene units (Q-8). C16&thinsp;:&thinsp;0, C17&thinsp;:&thinsp;0 cyclo, C18&thinsp;:1&omega;7c and C12&thinsp;:&thinsp;0 2-OH were the predominant cellular fatty acids. The major polar lipids were phosphatidylethanolamine, lyso-phosphatidylethanolamine, phosphatidylglycerol and diphosphatidylglycerol. The G+C content of genomic DNA was 70.4 mol%. Phylogenetic analysis using the 16S rRNA gene sequences showed that strain 201-F6T was affiliated to the genus Ideonella, and was closely related to Ideonella dechloratans LMG 28178T (97.7&thinsp;%) and Ideonella azotifigens JCM 15503T (96.6&thinsp;%). Strain 201-F6T could be clearly distinguished from the related species of the genus Ideonella by its physiological and biochemical characteristics as well as by its phylogenetic position and DNA-DNA relatedness. Therefore, the strain represents a novel species of the genus Ideonella, for which the name Ideonella sakaiensis sp. nov. (type strain 201-F6T=NBRC 110686T=TISTR 2288T) is proposed.<br />
DOI: 10.1099/ijsem.0.001058 PMID: 27045688<br />
<br />
[2]. Sci Total Environ. 2020 Dec 20;749:141608. doi: 10.1016/j.scitotenv.2020.141608. Epub 2020 Aug 10.<br />
Marine hydrocarbon-degrading bacteria breakdown poly(ethylene terephthalate) (PET).<br />
Denaro R(1), Aulenta F(2), Crisafi F(3), Di Pippo F(2), Cruz Viggi C(2), Matturro B(2), Tomei P(2), Smedile F(3), Martinelli A(4), Di Lisio V(4), Venezia C(2), Rossetti S(2).<br />
Author information: (1)Water Research Institute (IRSA) (CNR), Via Salaria km 29, 300, 00015 Monterotondo, Rome, Italy. Electronic address: [email protected]. (2)Water Research Institute (IRSA) (CNR), Via Salaria km 29, 300, 00015 Monterotondo, Rome, Italy. (3)Institute for Biological Resources and Marine Biotechnology (IRBIM) (CNR), Spianata San Raineri, 86, 98121 Messina, Italy. (4)Department of Chemistry, Sapienza University of Rome, Piazzale Aldo Moro, 5, 00185 Rome, Italy.<br />
Pollution of aquatic ecosystems by plastic wastes poses severe environmental and health problems and has prompted scientific investigations on the fate and factors contributing to the modification of plastics in the marine environment. Here, we investigated, by means of microcosm studies, the role of hydrocarbon-degrading bacteria in the degradation of poly(ethylene terephthalate) (PET), the main constituents of plastic bottles, in the marine environment. To this aim, different bacterial consortia, previously acclimated to representative hydrocarbons fractions namely, tetradecane (aliphatic fraction), diesel (mixture of hydrocarbons), and naphthalene/phenantrene (aromatic fraction), were used as inocula of microcosm experiments, in order to identify peculiar specialization in poly(ethylene terephthalate) degradation. Upon formation of a mature biofilm on the surface of poly(ethylene terephthalate) films, the bacterial biodiversity and degradation efficiency of each selected consortium was analyzed. Notably, significant differences on biofilm biodiversity were observed with distinctive hydrocarbons-degraders being enriched on poly(ethylene terephthalate) surface, such as Alcanivorax, Hyphomonas, and Cycloclasticus species. Interestingly, ATR-FTIR analyses, supported by SEM and water contact angle measurements, revealed major alterations of the surface chemistry and morphology of PET films, mainly driven by the bacterial consortia enriched on tetradecane and diesel. Distinctive signatures of microbial activity were the alteration of the FTIR spectra as a consequence of PET chain scission through the hydrolysis of the ester bond, the increased sample hydrophobicity as well as the formation of small cracks and cavities on the surface of the film. In conclusion, our study demonstrates for the first time that hydrocarbons-degrading marine bacteria have the potential to degrade poly(ethylene terephthalate), although their degradative activity could potentially trigger the formation of harmful microplastics in the marine environment.<br />
<br />
DOI: 10.1016/j.scitotenv.2020.141608 PMID: 32836129<br />
<br />
[3]. Nat Commun. 2018 Jan 26;9(1):382. doi: 10.1038/s41467-018-02881-1.<br />
Structural insight into molecular mechanism of poly(ethylene terephthalate) degradation.<br />
Joo S(1), Cho IJ(2), Seo H(1), Son HF(1), Sagong HY(1), Shin TJ(3), Choi SY(2), Lee SY(4), Kim KJ(5).<br />
Author information: (1)School of Life Sciences (KNU Creative BioResearch Group), KNU Institute for Microorganisms, Kyungpook National University, Daehak-ro 80, Buk-gu, Daegu, 41566, Republic of Korea. (2)Metabolic and Biomolecular Engineering National Research Laboratory, Department of Chemical and Biomolecular Engineering (BK21 Plus Program), BioProcess Engineering Research Center, and KAIST Institute (KI) for the BioCentury, Korea Advanced Institute of Science and Technology (KAIST), 291 Daehak-ro, Yuseong-gu, Daejeon, 34141, Republic of Korea. (3)UNIST Central Research Facilities &amp; School of Natural Science, Ulsan National Institute of Science and Technology, 50 UNIST-gil, Eonyang-eup, Ulju-gun, Ulsan, 44919, Republic of Korea. (4)Metabolic and Biomolecular Engineering National Research Laboratory, Department of Chemical and Biomolecular Engineering (BK21 Plus Program), BioProcess Engineering Research Center, and KAIST Institute (KI) for the BioCentury, Korea Advanced Institute of Science and Technology (KAIST), 291 Daehak-ro, Yuseong-gu, Daejeon, 34141, Republic of Korea. [email protected]. (5)School of Life Sciences (KNU Creative BioResearch Group), KNU Institute for Microorganisms, Kyungpook National University, Daehak-ro 80, Buk-gu, Daegu, 41566, Republic of Korea. [email protected].<br />
Comment in Nat Commun. 2019 Dec 6;10(1):5581. Nat Commun. 2019 Dec 6;10(1):5582.<br />
Plastics, including poly(ethylene terephthalate) (PET), possess many desirable characteristics and thus are widely used in daily life. However, non-biodegradability, once thought to be an advantage offered by plastics, is causing major environmental problem. Recently, a PET-degrading bacterium, Ideonella sakaiensis, was identified and suggested for possible use in degradation and/or recycling of PET. However, the molecular mechanism of PET degradation is not known. Here we report the crystal structure of I. sakaiensis PETase (IsPETase) at 1.5&thinsp;&Aring; resolution. IsPETase has a Ser-His-Asp catalytic triad at its active site and contains an optimal substrate binding site to accommodate four monohydroxyethyl terephthalate (MHET) moieties of PET. Based on structural and site-directed mutagenesis experiments, the detailed process of PET degradation into MHET, terephthalic acid, and ethylene glycol is suggested. Moreover, other PETase candidates potentially having high PET-degrading activities are suggested based on phylogenetic tree analysis of 69 PETase-like proteins.<br />
DOI: 10.1038/s41467-018-02881-1 PMCID: PMC5785972 PMID: 29374183<br />
<br />
[4]. Peebles, L.H., Jr., Huffman, M.W. and Ablett, C.T. (1969), Isolation and identification of the linear and cyclic oligomers of poly(ethylene terephthalate) and the mechanism of cyclic oligomer formation. J. Polym. Sci. A-1 Polym. Chem., 7: 479-496. https://doi.org/10.1002/pol.1969.150070207

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