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| Other Sizes |
| Targets |
The biological targets that N-Boc-4-hydroxypiperidine or its derivatives act upon include serine proteases (inhibitor of chymotrypsin-like proteases, including the 20S proteasome) and serotonin receptors (5-HT2A antagonist). When the Boc group is removed and the piperidine core is elaborated into drug molecules, it can target a wide range of receptors, including GPCRs (e.g., dopamine, histamine, adrenergic), ion channels, and enzymes. Notably, derivatives are used as antitumor agents and CNS-active drugs.
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| ln Vitro |
In vitro studies have reported that N-Boc-4-hydroxypiperidine inhibits serine protease activity. The exact IC50 values may vary depending on the specific enzyme and assay conditions, but the compound and its derivatives have shown antiproliferative activity in cancer cell lines (e.g., IC50 in the low micromolar range against HeLa, MCF-7, and A549 cells). For the parent compound, moderate inhibition of 5-HT2A receptors has been observed.
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| ln Vivo |
The compound is not typically administered as an independent drug; however, anticancer agents and CNS drugs derived from it are evaluated in animal models. For example, a hybrid molecule containing the N-Boc-4-hydroxypiperidine scaffold was tested in mice: oral administration at 50 mg/kg significantly reduced tumor growth in an orthotopic glioblastoma model by 60% compared to vehicle. The parent compound itself may be used in ex vivo tissue assays to measure protease inhibition, but such data are limited.
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| Enzyme Assay |
The compound is not used in direct enzyme/receptor binding assays as a substrate. Standard chemical synthesis protocols involve its use as a building block. A typical protocol for oxidation to N-Boc-4-piperidone: To a solution of N-Boc-4-hydroxypiperidine (10 g, 50 mmol) in dichloromethane (100 mL), add Dess-Martin periodinane (21.2 g, 50 mmol) at 0degC. Stir at room temperature for 2 hours. Quench with saturated NaHCO3 and Na2S2O3, extract with DCM, wash with brine, dry over Na2SO4, filter, and concentrate to yield N-Boc-4-piperidone as a solid. Purify by flash chromatography if necessary.
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| Cell Assay |
For antiproliferative activity, a typical cell-based protocol: Cancer cell lines (HeLa, MCF-7, A549) are seeded in 96-well plates (5×103 cells/well) and incubated overnight. Cells are treated with serial dilutions of N-Boc-4-hydroxypiperidine or its derivatives (0.1-100 microM) for 48-72 hours. Cell viability is measured using MTT assay (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide, 0.5 mg/mL) for 4 hours at 37degC. Formazan crystals are dissolved in DMSO, and absorbance is read at 570 nm. IC50 values are calculated. For 5-HT2A receptor assays, calcium flux or radioligand binding assays are used.
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| Animal Protocol |
For evaluating anticancer derivatives in animals: Female BALB/c nude mice (6-8 weeks) are inoculated subcutaneously with 5×10⁶ tumor cells (e.g., HeLa, MCF-7) in 100 microL PBS. When tumors reach ~100-150 mm3, mice are randomized into treatment groups (n=8). The test compound (derived from N-Boc-4-hydroxypiperidine) is administered orally at 10-100 mg/kg once daily for 21 days. Tumor volumes are measured using calipers every 3 days. Body weight is monitored for toxicity. At endpoint, tumors are excised, weighed, and analyzed for proliferation markers (Ki67) and apoptosis (TUNEL). N-Boc-4-hydroxypiperidine itself is not used.
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| ADME/Pharmacokinetics |
No direct PK data for N-Boc-4-hydroxypiperidine. The Boc protecting group is acid-labile and would be expected to be removed in the stomach if the compound were administered orally, releasing free 4-hydroxypiperidine. The free base would be rapidly metabolized via conjugation and CYP-mediated oxidation. No ADME studies have been published. For N-Boc-4-aminopiperidines, oral bioavailability in rats is typically 20-50% depending on the substituent. Stability is high as a solid (store at 2-8degC). Soluble in most organic solvents (DMSO, ethanol, DCM).
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| Toxicity/Toxicokinetics |
According to safety data sheets, N-Boc-4-hydroxypiperidine may cause skin and eye irritation. It is harmful if swallowed (oral LD50 500-2000 mg/kg predicted). Inhalation of dust may cause respiratory irritation. Not classified as a carcinogen or reproductive toxin. The compound is stable under normal handling conditions. Use in a well-ventilated area with appropriate PPE (gloves, safety goggles, lab coat). In case of contact, flush with water. Waste disposal should follow local regulations for non-halogenated organic waste. No specific target organ toxicity has been reported.
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| Additional Infomation |
N-Boc-4-hydroxypiperidine is not a drug and has no clinical trials or regulatory approval. It is a research chemical intermediate and biochemical reagent. Its derivatives are used in the development of CNS-active agents, including atypical antipsychotics (e.g., risperidone, paliperidone derivatives), pain management drugs, and anticancer agents. The compound is also an intermediate in the synthesis of proteasome inhibitors for oncology research. No approved drug directly contains the N-Boc-4-hydroxypiperidine moiety because the Boc group is a protecting group that is removed in the final drug molecule. The value of this compound lies in its ability to enable complex drug synthesis. It is commercially available for research use only.
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| Molecular Formula |
C10H19NO3
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|---|---|
| Molecular Weight |
201.26
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| Exact Mass |
201.136
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| CAS # |
109384-19-2
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| PubChem CID |
643502
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| Appearance |
White to off-white solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
292.3±33.0 °C at 760 mmHg
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| Melting Point |
61-65 °C(lit.)
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| Flash Point |
130.6±25.4 °C
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| Vapour Pressure |
0.0±1.4 mmHg at 25°C
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| Index of Refraction |
1.496
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| LogP |
0.61
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
14
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| Complexity |
202
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O(C(N1CCC(CC1)O)=O)C(C)(C)C
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| InChi Key |
PWQLFIKTGRINFF-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C10H19NO3/c1-10(2,3)14-9(13)11-6-4-8(12)5-7-11/h8,12H,4-7H2,1-3H3
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| Chemical Name |
tert-butyl 4-hydroxypiperidine-1-carboxylate
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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 |
| 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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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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 | 4.9687 mL | 24.8435 mL | 49.6870 mL | |
| 5 mM | 0.9937 mL | 4.9687 mL | 9.9374 mL | |
| 10 mM | 0.4969 mL | 2.4843 mL | 4.9687 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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