Name: 3,6,9,12-Tetraoxatetradecane-1,14-dioic acid
Brand: BOC Sciences
Rating: 5 (1 reviews)

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Price

Stock

Quantity

$--

In stock

Purity

≥95%

Appearance

Liquid

Storage

Store at 2-8°C

Shipping

Room temperature in continental US; may vary elsewhere.

IUPACName

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

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)

SMILES

C(COCCOCC(=O)O)OCCOCC(=O)O

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.

3,6,9,12-Tetraoxatetradecane-1,14-dioic acid, provides a chemically robust, poly(ethylene glycol)-like spacer featuring terminal carboxylic acid handles for reliable conjugation. Its ether-rich backbone supports solubility and conformational flexibility, which can improve productive ternary complex formation in targeted protein degradation workflows. The linker is well suited for constructing degraders through standard amide or ester-forming coupling strategies; detailed structural and reactivity considerations are provided below.

Structure: The linker contains a linear ether-rich scaffold with multiple oxygen atoms and two terminal carboxylic acid functional groups. It features stable C–O ether linkages and carboxyl groups capable of forming amide bonds. The flexible polyether character supports favorable hydrophilicity and conformational adaptability.

Reactivity: The carboxylic acids enable PROTAC synthesis via activation and coupling to amine-containing ligands, typically through carboxylate activation using peptide-coupling reagents. Reaction conditions are commonly chosen to preserve sensitive functional groups and to drive amide-bond formation, often in polar aprotic solvents with base. Mechanistically, activation forms an acyl intermediate that is attacked by the nucleophilic amine to yield stable conjugates.

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* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C₁V₁ = C₂V₂