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3,6,9,12-Tetraoxapentadec-14-ynoic acid

3,6,9,12-Tetraoxapentadec-14-ynoic acid

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

CAS No.: 1694731-93-5

Cat No.: BP-500376

Purity: >95% 4.5

3,6,9,12-Tetraoxapentadec-14-ynoic acid is a polyethylene glycol–like, ether-rich linker bearing a terminal carboxylic acid and an internal alkyne (propargyl/alkynyl handle). Structurally, it provides a flexible, oxygenated chain that can project a warhead and an E3-ligase-binding moiety into productive spatial proximity while reducing steric clashes and maintaining conformational adaptability. The carboxylic acid enables robust amide or ester coupling to attach the linker to either partner of a PROTAC, whereas the alkyne functionality serves as a versatile chemical handle for orthogonal conjugation strategies (e.g., click-type derivatization) to introduce additional groups or to connect to complementary reactive fragments. In targeted protein degradation research, such ether-rich, functionalized linkers are widely used to tune linker length, rigidity, and hydrophilicity, thereby optimizing ternary complex formation and degradation potency. This compound is therefore a practical building block for constructing and systematically varying PROTAC architectures in mechanistic and structure–activity studies.

Structure of 1694731-93-5

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PROTAC Linker

Molecular Formula

C11H18O6

Molecular Weight

246.26

Appearance

Pale Yellow Oily Liquid

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

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Purity

>95%

Solubility

Soluble in DMSO

Appearance

Pale Yellow Oily Liquid

Storage

Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years)

Shipping

Room temperature in continental US; may vary elsewhere.

IUPACName

2-[2-[2-(2-prop-2-ynoxyethoxy)ethoxy]ethoxy]acetic acid

Synonyms

Propargyl-PEG4-CH2CO2H;Propargyl-PEG4-CH2COOH; Propargyl-PEG3-CH2COOH; Alkyne-PEG4-CH2COOH; 3,6,9,12-tetraoxapentadec-14-yn-1-oic acid

Boiling Point

375.0±32.0°C (Predicted)

Density

1.151±0.06 g/cm3 (Predicted)

InChI Key

MJRNNISHHNMYAE-UHFFFAOYSA-N

InChI

InChI=1S/C11H18O6/c1-2-3-14-4-5-15-6-7-16-8-9-17-10-11(12)13/h1H,3-10H2,(H,12,13)

SMILES

C#CCOCCOCCOCCOCC(=O)O

1. Intra-articular injections of platelet-rich plasma, hyaluronic acid or corticosteroids for knee osteoarthritis : A prospective randomized controlled study

Yong Huang, Xiaolu Liu, Xinliang Xu, Junbin Liu Orthopade. 2019 Mar;48(3):239-247.doi: 10.1007/s00132-018-03659-5.

Background:Knee osteoarthritis (KOA) is a degenerative joint disease leading to pain and disability for which no curative treatment exists. Intra-articular (IA) therapies are part of this multimodal approach and are approved by the Food and Drug Administration (FDA) and European Medicines Agency (EMA). Platelet-rich plasma (PRP), hyaluronic acid (HA), and corticosteroids (CS) have been increasingly used in recent years to treat KOA.Purpose:To determine whether IA-PRP was superior to IA-HA or IA-CS administration routes in these patients.Material and

2. ω-3 and ω-6 Fatty Acid Supplementation May Reduce Autism Symptoms Based on Parent Report in Preterm Toddlers

Sarah A Keim, Barbara Gracious, Kelly M Boone, Mark A Klebanoff, Lynette K Rogers, Joseph Rausch, Daniel L Coury, Kelly W Sheppard, Jesse Husk, Dale A Rhoda J Nutr. 2018 Feb 1;148(2):227-235.doi: 10.1093/jn/nxx047.

Background:Children born preterm are at increased risk of autism spectrum disorder (ASD). n-3 (ω-3) Combined with n-6 (ω-6) fatty acids including γ-linolenic acid (GLA) may benefit children born preterm showing early signs of ASD. Previous trials have reported that docosahexaenoic acid (DHA) promotes cognitive development in preterm neonates and n-3 fatty acids combined with GLA improve attention-deficit-hyperactivity disorder.Objectives:The objectives of the pilot Preemie Tots Trial were 1) to confirm the feasibility of a full-scale trial in toddlers born very preterm and exhibiting ASD symptoms and 2) to explore the effects of supplementation on parent-reported ASD symptoms and related behaviors.

3. The interaction of glycine, aspartic acid, and lysine by the protonated macrocyclic ligand 6,19-bis(2-hydroxypropyl)-3,6,9,16,19,22-hexaaza-tricyclo-[22.2.2.2(11,14)]triaconta-11,13,24,26,27,29-hexaene

Jin Huang, Shu-An Li, Dong-Feng Li, De-Xi Yang, Wei-Yin Sun, Wen-Xia Tang Bioorg Med Chem. 2004 Feb 1;12(3):529-35.doi: 10.1016/j.bmc.2003.11.020.

A new hexaaza macrocyclic ligand (L) bearing two 2-hydroxypropyl pendants, 6,19-bis(2-hydroxypropyl)-3,6,9,16,19,22-hexaaza-tricyclo-[22.2.2.2(11,14)]triaconta-11,13,24,26,27,29-hexaene has been synthesized and characterized. The macrocyclic ligand was isolated as a colorless crystal, monoclinic, P2(1)/n, with a=10.757(2), b=14.214(3), c=13.746(3) A, beta=101.40(3) degrees, V=2060.3(7) A3, Z=2, R1=0.0695, and wR2=0.1538 [I>2sigma(I)]. Potentiometric studies of the macrocyclic ligand and three types of amino acids, glycine (equal numbers of carboxylate and amino groups), aspartic acid (more carboxylate groups than amino group), and lysine (more amino groups than carboxylate group) have been performed. The stability constants for the new macrocycle and binary complexes of the amino acid with the macrocyclic ligand are reported. Binary complexes are formed in aqueous solution as a result of hydrogen bonding interaction and electrostatic attraction between the host and the guest. The binding Schemes for the recognition of amino acids are suggested. From the results, it seems that this new macrocyclic ligand is able to bind three different amino acids with selectivity in aqueous solution, and the strength of binding is of the order lysine < glycine < aspartic acid.

This linker, 3,6,9,12-Tetraoxapentadec-14-ynoic acid, is designed to provide a chemically addressable carboxylic acid handle within a poly(ether) framework, supporting robust attachment strategies used in PROTAC assembly. Its ether-rich scaffold can promote favorable conformational flexibility and solubility characteristics that are often beneficial for maintaining productive ternary-complex formation. The subsequent points describe its structural features and practical reactivity considerations for experimental PROTAC construction.

Structure: The molecule contains a long, tetra-ether (polyether) backbone incorporating oxygen atoms that confer polarity and potential conformational flexibility. A terminal carboxylic acid provides a reactive functional group for amide or ester formation. An alkyne functionality offers a site for chemoselective coupling strategies.

Reactivity: The carboxylic acid can be activated under standard peptide-coupling conditions to form amide linkages with amine-bearing targeting ligands, typically using carbodiimide-based activators and an appropriate base in polar aprotic solvents. The alkyne can be leveraged in click-type conjugations or other alkyne-tolerant coupling schemes, depending on the functional groups present on the partner molecules. Reaction design should prioritize mild conditions to preserve sensitive targeting moieties and maintain linker integrity.

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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