3,6,9,12-Tetraoxatetradecane-1,14-dioic acid - CAS 32775-08-9

3,6,9,12-Tetraoxatetradecane-1,14-dioic acid is a polyethylene glycol (PEG)-based PROTAC linker that can be used in the synthesis of a series of PROTACs.

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Molecular Formula
C10H18O8
Molecular Weight
266.25

3,6,9,12-Tetraoxatetradecane-1,14-dioic acid

    • Specification
      • Purity
        ≥95%
        Appearance
        Liquid
        Storage
        Store at 2-8°C
        Shipping
        Room temperature in continental US; may vary elsewhere.
        IUPAC Name
        2-[2-[2-[2-(carboxymethoxy)ethoxy]ethoxy]ethoxy]acetic acid
        Synonyms
        CH2COOH-PEG3-CH2COOH; 3,6,9,12-Tetraoxatetradecanedioic acid; COOH-CH2-PEG4-CH2-COOH; COOH-CH2-PEG3-CH2-COOH
    • Properties
      • Boiling Point
        468.0±35.0 °C at 760 mmHg
        Density
        1.278±0.06 g/cm3 (Predicted)
        InChI Key
        BEAPHLNTCMLNPR-UHFFFAOYSA-N
        InChI
        InChI=1S/C10H18O8/c11-9(12)7-17-5-3-15-1-2-16-4-6-18-8-10(13)14/h1-8H2,(H,11,12)(H,13,14)
        Canonical SMILES
        C(COCCOCC(=O)O)OCCOCC(=O)O
    • Reference Reading
      • 1. Extracellular application of the N-methyl-D-aspartate receptor allosteric modulator rapastinel acts remotely to regulate Ca2+ inactivation at an intracellular locus
        Xiao-Lei Zhang, Nils A Berglund, Jeffrey S Burgdorf, John E Donello, Joseph R Moskal, Patric K Stanton Neuroreport. 2022 May 4;33(7):312-319.doi: 10.1097/WNR.0000000000001787.Epub 2022 Apr 8.
        Background:A novel N-methyl-D-aspartate receptor (NMDAR) allosteric modulator, rapastinel (RAP, formerly GLYX-13), elicits long-lasting antidepressant-like effects by enhancing long-term potentiation (LTP) of synaptic transmission. RAP elicits these effects by binding to a unique site in the extracellular region of the NMDAR complex, transiently enhancing NMDAR-gated current in pyramidal neurons of both hippocampus and medial prefrontal cortex.
        2. Phytochemical investigation and cytotoxic evaluation of the components of the medicinal plant Ligularia atroviolacea
        Xiaoyu Wang, Lianli Sun, Kexin Huang, Shuyun Shi, Lijuan Zhang, Juanhua Xu, Hua Peng, Xianfeng Sun, Liwei Wang, Xiumei Wu, Yu Zhao, Xiaokun Li, Joachim Stöckigt, Jia Qu Chem Biodivers. 2009 Jul;6(7):1053-65.doi: 10.1002/cbdv.200800128.
        A phytochemical investigation of the roots of Ligularia atroviolacea resulted in the isolation of 24 compounds including seven new eremophilanoids named eremophila-3,7(11),8-triene-12,8;14,6alpha-diolide (1), 3beta-(angeloyloxy)eremophil-7(11)-en-12,8beta-olid-14-oic acid (2), 1alpha-chloro-10beta-hydroxy-6beta-(2-methylpropanoyloxy)-9-oxo-7,8-furoeremophilane (3), (10betaH)-8-oxoeremophila-3(4),6(7)-diene-12,14-dioic acid (4), (10alphaH)-8-oxoeremophila-3(4),6(7)-diene-12,14-dioic acid (5), 8beta-[eremophila-3',7'(11')-diene-12',8'alpha;14',6'alpha-diolide]eremophila-3,7(11)-diene-12,8alpha;14,6alpha-diolide (6), and ligulatrovine A (7), eleven known eremophilanoids, 8-18, four steroids, one glucose derivative, and one fatty acid. The structures of these compounds were elucidated by spectroscopic methods including 2D-NMR experiments. The structure of 3 was also established by an X-ray diffraction study. The in vitro cytotoxicity evaluation of selected compounds was performed on seven cultured tumor cell lines, i.e., KB, BEL-7404, A549, HL-60, HeLa, CNE, and P-388D1. The preliminary taxonomy of this species was also discussed, and the possible biogenesis of a dimer possessing a new noreremophilanoid type skeleton, 7, is presented in a preliminary form.
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