Name: 3,6,9-Trioxaundecanedioic acid
Brand: BOC Sciences
Rating: 5 (1 reviews)

Size

Price

Stock

Quantity

$--

In stock

Purity

>95%

Solubility

Soluble in DCM, DMF, DMSO, Water

Appearance

Liquid or solid

Storage

Store at 2-8°C

Shipping

Room temperature in continental US; may vary elsewhere.

IUPACName

2-[2-[2-(carboxymethoxy)ethoxy]ethoxy]acetic acid

Synonyms

COOH-CH2-PEG3-CH2-COOH; COOH-CH2-PEG2-CH2-COOH; 2,2'-((Oxybis(ethane-2,1-diyl))bis(oxy))diacetic acid; O,O'-Oxydiethylene-diglycolic acid; Acetic acid, 2,2'-[oxybis(2,1-ethanediyloxy)]bis-; 2,2'-(2,2'-Oxybis(ethane-2,1-diyl)bis(oxy))diacetic acid

Boiling Point

443.7±30.0°C at 760 mmHg

Density

1.3 g/mL at 20°C

InChI Key

HJZZQNLKBWJYPD-UHFFFAOYSA-N

InChI

InChI=1S/C8H14O7/c9-7(10)5-14-3-1-13-2-4-15-6-8(11)12/h1-6H2,(H,9,10)(H,11,12)

SMILES

C(COCC(=O)O)OCCOCC(=O)O

1. The Antibacterial and Anti-biofilm Activity of Metal Complexes Incorporating 3,6,9-Trioxaundecanedioate and 1,10-Phenanthroline Ligands in Clinical Isolates of Pseudomonas Aeruginosa from Irish Cystic Fibrosis Patients

Megan O'Shaughnessy, Pauraic McCarron, Livia Viganor, Malachy McCann, Michael Devereux, Orla Howe Antibiotics (Basel). 2020 Oct 5;9(10):674. doi: 10.3390/antibiotics9100674.

Chronic infections of Pseudomonas aeruginosa in the lungs of cystic fibrosis (CF) patients are problematic in Ireland where inherited CF is prevalent. The bacteria's capacity to form a biofilm in its pathogenesis is highly virulent and leads to decreased susceptibility to most antibiotic treatments. Herein, we present the activity profiles of the Cu(II), Mn(II) and Ag(I) tdda-phen chelate complexes {[Cu(3,6,9-tdda)(phen)2].3H2O.EtOH}n (Cu-tdda-phen), {[Mn(3,6,9-tdda)(phen)2].3H2O.EtOH}n (Mn-tdda-phen) and [Ag2(3,6,9-tdda)(phen)4].EtOH (Ag-tdda-phen) (tddaH2 = 3,6,9-trioxaundecanedioic acid; phen = 1,10-phenanthroline) towards clinical isolates of P. aeruginosa derived from Irish CF patients in comparison to two reference laboratory strains (ATCC 27853 and PAO1). The effects of the metal-tdda-phen complexes and gentamicin on planktonic growth, biofilm formation (pre-treatment) and mature biofilm (post-treatment) alone and in combination were investigated. The effects of the metal-tdda-phen complexes on the individual biofilm components; exopolysaccharide, extracellular DNA (eDNA), pyocyanin and pyoverdine are also presented. All three metal-tdda-phen complexes showed comparable and often superior activity to gentamicin in the CF strains, compared to their activities in the laboratory strains, with respect to both biofilm formation and established biofilms. Combination studies presented synergistic activity between all three complexes and gentamicin, particularly for the post-treatment of established mature biofilms, and was supported by the reduction of the individual biofilm components examined.

3,6,9-Trioxaundecanedioic acid, provides a flexible, oxygen-rich spacer architecture that can support productive spatial alignment between an E3 ligase ligand and a target-binding warhead. Its diacid functionality enables robust conjugation strategies commonly used in targeted protein degradation workflows. The linker’s ether-containing backbone and terminal carboxyl groups offer practical handles for linker diversification, facilitating structure–activity exploration and optimization in PROTAC design. Detailed structural and synthetic considerations are provided below.

Structure: 3,6,9-Trioxaundecanedioic acid is a linear linker featuring an ether-rich, tri-oxygen motif embedded within an aliphatic chain and terminal carboxylic acid groups. It contains stable C–O and C–C bonds, with carboxylate functionalities capable of hydrogen bonding and salt formation. The oxygenated backbone increases polarity and conformational flexibility.

Reactivity: The terminal carboxylic acids are suitable for standard amide or ester coupling routes used in PROTAC synthesis. Typical approaches involve activating the acids with coupling reagents (for example, carbodiimides or uronium-based activators) in the presence of a base, followed by reaction with amine- or alcohol-bearing partners to form stable linkages. Solvents such as polar aprotic media are commonly employed, and mild conditions are generally favored to preserve sensitive ligands; reaction progress is monitored by chromatographic methods.

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It is commonly abbreviated as: C₁V₁ = C₂V₂