3-(2-Carboxyethoxy)propanoic acid - CAS 5961-83-1

Bis-PEG1-acid is a polyethylene glycol (PEG)-based PROTAC linker. Bis-PEG1-acid can be used in the synthesis of a series of PROTACs.

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Molecular Formula
C6H10O5
Molecular Weight
162.14

3-(2-Carboxyethoxy)propanoic acid

    • Specification
      • Related CAS
        51178-68-8 (polymer)
        Purity
        95%
        Solubility
        Soluble in Aqueous Base (Slightly), Chloroform (Slightly), Methanol (Slightly), Water (Slightly)
        Appearance
        Pale Yellow to Light Yellow Low-melting Solid
        Storage
        Store at -20°C under inert atmosphere
        Shipping
        Room temperature in continental US; may vary elsewhere.
        IUPAC Name
        3-(2-carboxyethoxy)propanoic acid
        Synonyms
        Bis-PEG1-acid; 3,3'-Oxybis[propanoic Acid]; 3,3'-Oxydipropanoic Acid; 3,3'-Oxydipropionic Acid; Bis(2-carboxyethyl) Ether; NSC 361680; Propanoic acid, 3,3'-oxybis-
    • Properties
      • Boiling Point
        198-200°C at 1-2 Torr
        Melting Point
        60-61°C
        Density
        1.316±0.06 g/cm3 (Predicted)
        InChI Key
        FOSIWKADJDNVMJ-UHFFFAOYSA-N
        InChI
        InChI=1S/C6H10O5/c7-5(8)1-3-11-4-2-6(9)10/h1-4H2,(H,7,8)(H,9,10)
        Canonical SMILES
        C(COCCC(=O)O)C(=O)O
    • Reference Reading
      • 1. Synthesis of 3-Aryl-3-(Furan-2-yl)Propanoic Acid Derivatives, and Study of Their Antimicrobial Activity
        Mikhail V Kalyaev, Dmitry S Ryabukhin, Marina A Borisova, Alexander Yu Ivanov, Irina A Boyarskaya, Kristina E Borovkova, Lia R Nikiforova, Julia V Salmova, Nikolay V Ul'yanovskii, Dmitry S Kosyakov, Aleksander V Vasilyev Molecules. 2022 Jul 19;27(14):4612.doi: 10.3390/molecules27144612.
        Reactions of 3-(furan-2-yl)propenoic acids and their esters with arenes in Brønsted superacid TfOH affords products of hydroarylation of the carbon-carbon double bond, 3-aryl-3-(furan-2-yl)propenoic acid derivatives. According to NMR and DFT studies, the corresponding O,C-diprotonated forms of the starting furan acids and esters should be reactive electrophilic species in these transformations. Starting compounds and their hydroarylation products, at a concentration of 64 µg/mL, demonstrate good antimicrobial activity against yeast-like fungi Candida albicans. Apart from that, these compounds suppress Escherichia coli and Staphylococcus aureus.
        2. The Mechanism Underlying the Influence of Indole-3-Propionic Acid: A Relevance to Metabolic Disorders
        Binbin Zhang, Minjie Jiang, Jianan Zhao, Yu Song, Weidong Du, Junping Shi Front Endocrinol (Lausanne). 2022 Mar 18;13:841703.doi: 10.3389/fendo.2022.841703.eCollection 2022.
        The increasing prevalence of metabolic syndrome has become a serious public health problem. Certain bacteria-derived metabolites play a key role in maintaining human health by regulating the host metabolism. Recent evidence shows that indole-3-propionic acid content can be used to predict the occurrence and development of metabolic diseases. Supplementing indole-3-propionic acid can effectively improve metabolic disorders and is considered a promising metabolite. Therefore, this article systematically reviews the latest research on indole-3-propionic acid and elaborates its source of metabolism and its association with metabolic diseases. Indole-3-propionic acid can improve blood glucose and increase insulin sensitivity, inhibit liver lipid synthesis and inflammatory factors, correct intestinal microbial disorders, maintain the intestinal barrier, and suppress the intestinal immune response. The study of the mechanism of the metabolic benefits of indole-3-propionic acid is expected to be a potential compound for treating metabolic syndrome.
        3. Synthesis, characterization and in vitro biological evaluation of novel organotin(IV) compounds with derivatives of 2-(5-arylidene-2,4-dioxothiazolidin-3-yl)propanoic acid
        Nebojša Đ Pantelić, Bojana B Zmejkovski, Bojan Božić, Biljana Dojčinović, Nebojša R Banjac, Ludger A Wessjohann, Goran N Kaluđerović J Inorg Biochem. 2020 Oct;211:111207.doi: 10.1016/j.jinorgbio.2020.111207.Epub 2020 Jul 26.
        Two novel triphenyltin(IV) compounds, [Ph3SnL1] (L1 = 2-(5-(4-fluorobenzylidene)-2,4-dioxotetrahydrothiazole-3-yl)propanoate (1)) and [Ph3SnL2] (L2 = 2-(5-(5-methyl-2-furfurylidene)-2,4-dioxotetrahydrothiazole-3-yl)propanoate (2)) were synthesized and characterized by FT-IR, (1H and 13C) NMR spectroscopy, mass spectrometry, and elemental microanalysis. The in vitro anticancer activity of the synthesized organotin(IV) compounds was determined against four tumor cell lines: PC-3 (prostate), HT-29 (colon), MCF-7 (breast), and HepG2 (hepatic) using MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-12 diphenyltetrazolium bromide) and CV (crystal violet) assays. The IC50 values are found to be in the range from 0.11 to 0.50 μM. Compound 1 exhibits the highest activity toward PC-3 cells (IC50 = 0.115 ± 0.009 μM; CV assay). The tin and platinum uptake in PC-3 cells showed a threefold lower uptake of tin in comparison to platinum (as cisplatin). Together with its higher activity this indicates a much higher cell inhibition potential of the tin compounds (calculated to ca. 50 to 100 times). Morphological analysis suggested that the compounds induce apoptosis in PC-3 cells, and flow cytometry analysis revealed that 1 and 2 induce autophagy as well as NO (nitric oxide) production.
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