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| Other Sizes |
| Targets |
(3R)-3-Pyrrolidinemethanol is a PROTAC linker and has no defined biological target as a drug. As a PROTAC linker, it serves as a spacer connecting an E3 ubiquitin ligase ligand (e.g., CRBN or VHL) to a target protein ligand, enabling targeted protein degradation. The chirality of the molecule may influence the orientation and flexibility of the PROTAC, affecting its degradation potency. The primary alcohol group can be activated (e.g., as a tosylate or NHS carbonate) for conjugation to carboxylic acid-containing ligands, while the secondary amine (after deprotection if needed) can be used for amide bond formation.
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| ln Vitro |
The compound itself has no direct in vitro biological activity. It is a chemical intermediate and a PROTAC linker. Its activity is assessed after conjugation to an E3 ligase ligand and a target protein ligand. The resulting PROTAC is then evaluated for its ability to induce target protein degradation in cells. The pyrrolidine ring is a common scaffold in medicinal chemistry, and its incorporation can influence the pharmacokinetic properties of the final molecule.
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| ln Vivo |
The compound is not a drug; it is a PROTAC linker. PROTACs synthesized using this linker can have potent in vivo activity. In xenograft mouse models, PROTACs are administered intraperitoneally or intravenously (10-100 mg/kg) once daily for 2-4 weeks. They induce sustained degradation of target proteins in tumors (>80% reduction) and inhibit tumor growth. The linker contributes to the overall solubility, permeability, and PK of the PROTAC.
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| Enzyme Assay |
Not applicable. (3R)-3-Pyrrolidinemethanol is a PROTAC linker, not a standard enzyme inhibitor. Its purity (>97%) is assessed by GC or HPLC. The structure is confirmed by ¹H NMR (pyrrolidine protons delta 2.5-3.5 ppm, CH2OH delta 3.6-3.8 ppm) and mass spectrometry (ESI-MS, expected [M+H]+ m/z 102). Physicochemical properties: MW 101.15, colorless to off-white liquid, soluble in DMSO, ethanol, and water, stored at 2-8degC. No biological assays are applicable.
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| Cell Assay |
Not applicable. (3R)-3-Pyrrolidinemethanol is not used directly in cell-based assays; it is a building block for PROTAC synthesis. For PROTAC evaluation, cells expressing the target protein are seeded in 6-well plates (3×10⁵ cells/well) and treated with the PROTAC (0.1-1000 nM) for 4-24 h. Target protein degradation is assessed by Western blotting. DC₅0 is calculated from the dose-response curve. Cell viability is measured by MTT or CellTiter-Glo.
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| Animal Protocol |
In vivo efficacy of PROTACs incorporating (3R)-3-Pyrrolidinemethanol can be evaluated in xenograft mouse models. Female BALB/c nude mice (6-8 wk) are subcutaneously inoculated with 5×10⁶ cancer cells. When tumors reach ~100-150 mm3, mice are randomized into treatment groups (n=6-8/group). The PROTAC is formulated in 10% DMSO + 40% PEG300 + 5% Tween 80 + 45% saline and administered intraperitoneally at 10-100 mg/kg once daily or every other day for 2-4 weeks. Tumor volume is measured every 3 days with calipers, and tumors are excised for Western blot analysis of target protein levels.
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| ADME/Pharmacokinetics |
No specific PK data is available for (3R)-3-Pyrrolidinemethanol alone. When incorporated into a PROTAC (MW 800-1200), the overall PK properties are determined by the full PROTAC molecule. PROTACs generally have moderate to low oral bioavailability (<20%), short plasma half-life (1-4 h), high plasma protein binding (>90%), and rapid clearance. The chiral pyrrolidine linker may affect PROTAC permeability and solubility.
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| Toxicity/Toxicokinetics |
For (3R)-3-Pyrrolidinemethanol, hazard statements: H315 (Causes skin irritation), H319 (Causes serious eye irritation), H335 (May cause respiratory irritation). Signal word: Warning. Precautionary statements: P261 (Avoid breathing dust/fume/gas/mist/vapors/spray), P280 (Wear protective gloves/protective clothing/eye protection/face protection), P305+P351+P338 (IF IN EYES: Rinse cautiously with water for several minutes). Storage: at 2-8degC, sealed, protect from light.
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| References | |
| Additional Infomation |
(3R)-3-Pyrrolidinemethanol ((R)-3-(Hydroxymethyl)pyrrolidine; CAS# 110013-18-8) is a research-grade chiral building block and PROTAC linker. It is not an FDA-approved drug. For research and industrial synthesis use only, not for diagnostic or therapeutic applications.
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| Molecular Formula |
C5H11NO
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|---|---|
| Molecular Weight |
101.15
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| Exact Mass |
101.084
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| CAS # |
110013-18-8
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| PubChem CID |
7446913
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| Appearance |
Colorless to off-white liquid
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| Density |
1.0±0.1 g/cm3
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| Boiling Point |
176.1±13.0 °C at 760 mmHg
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| Flash Point |
89.6±10.5 °C
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| Vapour Pressure |
0.3±0.7 mmHg at 25°C
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| Index of Refraction |
1.455
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| LogP |
-0.85
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
7
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| Complexity |
56
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| Defined Atom Stereocenter Count |
1
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| SMILES |
O([H])C([H])([H])[C@@]1([H])C([H])([H])N([H])C([H])([H])C1([H])[H]
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| InChi Key |
QOTUIIJRVXKSJU-RXMQYKEDSA-N
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| InChi Code |
InChI=1S/C5H11NO/c7-4-5-1-2-6-3-5/h5-7H,1-4H2/t5-/m1/s1
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| Chemical Name |
[(3R)-pyrrolidin-3-yl]methanol
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| Synonyms |
(R)-3-(Hydroxymethyl)pyrrolidine
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~175 mg/mL (~1730.10 mM; with ultrasonication)
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 9.8863 mL | 49.4315 mL | 98.8631 mL | |
| 5 mM | 1.9773 mL | 9.8863 mL | 19.7726 mL | |
| 10 mM | 0.9886 mL | 4.9432 mL | 9.8863 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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