3,6,9,12-Tetraoxapentadec-14-yn-1-ol - CAS 87450-10-0

3,6,9,12-Tetraoxapentadec-14-yn-1-ol is a polyethylene glycol (PEG)-based PROTAC linker that can be used in the synthesis of a series of PROTACs.

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Molecular Formula
C₁₁H₂₀O₅
Molecular Weight
232.27

3,6,9,12-Tetraoxapentadec-14-yn-1-ol

    • Specification
      • Purity
        >97%
        Solubility
        Soluble in DMSO
        Appearance
        Colorless or Light Yellowish 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.
        IUPAC Name
        2-[2-[2-(2-prop-2-ynoxyethoxy)ethoxy]ethoxy]ethanol
        Synonyms
        Propargyl-PEG5-alcohol; HC≡C-CH2-PEG4-OH; Propyne-PEG4-OH; Propargyl-PEG4-OH; 3,6,9,12-Tetraoxa-14-pentadecyne-1-ol; 15-hydroxy-4,7,10,13-tetraoxapentadec-1-yne
    • Properties
      • Boiling Point
        324.4±32.0 °C at 760 mmHg
        Density
        1.071±0.06 g/cm3 (Predicted)
        InChI Key
        WQMJFCWQBPUZCK-UHFFFAOYSA-N
        InChI
        InChI=1S/C11H20O5/c1-2-4-13-6-8-15-10-11-16-9-7-14-5-3-12/h1,12H,3-11H2
        Canonical SMILES
        C#CCOCCOCCOCCOCCO
    • Reference Reading
      • 1. Effects of Omega-3-6-9 fatty acid supplementation on behavior and sleep in preterm toddlers with autism symptomatology: Secondary analysis of a randomized clinical trial
        Kelly M Boone, Mark A Klebanoff, Lynette K Rogers, Joseph Rausch, Daniel L Coury, Sarah A Keim Early Hum Dev. 2022 Jun;169:105588.doi: 10.1016/j.earlhumdev.2022.105588.Epub 2022 May 19.
        Background:Children born extremely preterm disproportionately experience sequelae of preterm birth compared to those born at later gestational ages, including higher prevalence of autism spectrum disorder (ASD) and associated behaviors.Aim:Explore effects of combined dietary docosahexaenoic acid, eicosapentaenoic acid, gamma-linolenic acid, and oleic acid (omega 3-6-9) on caregiver-reported behavior and sleep in toddlers born at ≤29 weeks' gestation who were exhibiting symptoms commonly seen with ASD.Study design:90-day randomized (1:1), double blinded, placebo-controlled trial. Subjects:Thirty-one children aged 18-38 months received omega 3-6-9 (n = 15) or canola oil placebo (n = 16).Outcome measures:Mixed effects regression analyses followed intent to treat and explored treatment effects on measures of caregiver-reported behavior (Child Behavior Checklist 1.5-5, Toddler Behavior Assessment Questionnaire - Short Form, Vineland Adaptive Behavior Scales, 2nd Edition) and sleep (Children's Sleep Habits Questionnaire, Brief Infant Sleep Questionnaire). Results:Twenty-nine of 31 (94%; ntx = 13, nplacebo = 16) children randomized had data available for at least one outcome measure, 27 (87%; ntx = 12, nplacebo = 15) had complete outcome data. Children randomized to omega 3-6-9 experienced a medium magnitude benefit of supplementation on anxious and depressed behaviors (ΔDifference = -1.27, d = -0.58, p = 0.049) and internalizing behaviors (ΔDifference = -3.41, d = -0.68, p = 0.05); and a large magnitude benefit on interpersonal relationship adaptive behaviors (ΔDifference = 7.50, d = 0.83, p = 0.01), compared to placebo. No effects were observed on other aspects of behavior or sleep.Conclusions:Findings provide preliminary support for further exploration of omega 3-6-9 during toddlerhood to improve socioemotional outcomes among children born preterm, especially for those showing early symptoms commonly seen with ASD. Results need to be replicated in a larger sample.Trial registration:Registered with ClinicalTrials.gov: NCT01683565.
        2. 3,6,9,16,19,22-Hexaazatricyclo
        C Glidewell, G Ferguson, RM Gregson, AJ Lough Acta Crystallogr B. 2000 Apr;56 (Pt 2):287-98.doi: 10.1107/s0108768199014032.
        The adduct (1) formed between the hexaaza macrocycle 3,6,9,16,19,22-hexaazatricyclo[22.2.2.2(11,14]triconta-1(26),11(29),12,14(30),24,27-hexaene, C24H38N6, and 4,4'-sulfonyldiphenol, O2S(C6H4OH)2, is a salt [(C24H40N6)2+].2[(HOC6H4SO2C6H4O)-], and the adduct (2) formed by the same macrocyclic amine with 4,4'-biphenol is an aquated salt which also contains neutral biphenol molecules, [(C24H40N6)2+]. 2[(HOC6H4C6H4O)-].(HOC6H4C6H4OH).2H2O. In both compounds the cations lie across centres of inversion: there are two crystallographically distinct cation sites in (1) and the conformations of the cations occupying them are quite different. In (2) the single type of cation site is occupied by a conformationally disordered cation: the major and minor components represent two further distinct conformers. In (1) the anions are linked by O-H...O hydrogen bonds into chains, and each cation is linked by a total of six N-H...O hydrogen bonds to anions in four different chains, so linking the chains into continuous sheets. In (2) the anions and the water molecules are linked into sheets, which are further linked into a continuous three-dimensional framework by both the cations and the neutral biphenol units.
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