3-(2-Carboxyethoxy)propanoic acid

 CAS No.: 5961-83-1  Cat No.: BP-501597  Purity: 95% 4.5  

3-(2-Carboxyethoxy)propanoic acid is a bifunctional aliphatic linker bearing two carboxylic acid groups connected through an ether-containing spacer, providing a flexible, hydrophilic chain suitable for conjugation chemistry. Structurally, it offers a terminal carboxyl group for coupling to one PROTAC module (e.g., a ligand or warhead) and a second carboxyl group that can be activated for attachment to the complementary module, enabling construction of degraders with controlled spatial separation. In PROTAC design, such linkers help tune the effective distance and relative orientation between the target-binding ligand and the E3 ligase recruiter, which can strongly influence ternary complex formation and downstream ubiquitination efficiency. As a research-grade building block, it is valuable for preparing linker variants for systematic structure–activity studies, facilitating reproducible synthesis of targeted protein degradation constructs and supporting optimization of solubility and linker flexibility in vitro.

3-(2-Carboxyethoxy)propanoic acid

Structure of 5961-83-1

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Category
PROTAC Linker
Molecular Formula
C6H10O5
Molecular Weight
162.14
Related CAS
51178-68-8 (polymer)
Appearance
Pale Yellow to Light Yellow Low-melting Solid

* For research and manufacturing use only. Not for human or clinical use.

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Popular Publications Citing BOC Sciences Products
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.
IUPACName
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-
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)
SMILES
C(COCCC(=O)O)C(=O)O
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.

3-(2-Carboxyethoxy)propanoic acid, provides a chemically versatile, carboxylate-rich scaffold suitable for constructing bifunctional degraders. Its functional groups enable robust conjugation strategies that support controlled spatial presentation of ligands in targeted protein degradation workflows. The linker’s hydrophilic character and multiple reactive handles can improve coupling efficiency and compatibility with common PROTAC assembly sequences. Detailed structural and reactivity considerations are provided below.

Structure: The linker contains a propanoic acid core bearing an ether-linked carboxyethoxy substituent, providing two carboxylic acid functionalities and an internal ether linkage. The molecule features polar O–H and C–O bonds, with a flexible aliphatic backbone that supports conformational adaptability.

Reactivity: For PROTAC synthesis, the carboxylic acids are typically activated toward amide or ester bond formation using standard coupling chemistries, such as carbodiimide-based activation with appropriate additives, or acid chloride formation under controlled conditions. Reactions are commonly performed in polar aprotic solvents with base to promote nucleophilic acyl substitution. The flexible ether-containing scaffold can be retained during coupling, while protecting-group strategies may be used to achieve selective functionalization when both acids are present.

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It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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