| Size | Price | |
|---|---|---|
| Other Sizes |
| Targets |
As a protected proline derivative, H-Pro-NHEt·HCl does not have a specific biological target. Its primary utility is as a chemical building block in organic synthesis, particularly in peptide chemistry. The compound serves as a protected proline unit that can be incorporated into peptide chains while the benzyl ester protects the C-terminus from unwanted reactions. Proline is a non-essential amino acid that contributes to protein structure and collagen stability, but in its protected form, the compound is not designed to interact with biological receptors or enzymes. Its value lies in its chemical properties as a synthetic intermediate, enabling the construction of complex peptides and pharmaceutical compounds.
|
|---|---|
| ln Vitro |
H-Pro-NHEt·HCl does not exhibit pharmacological activity in vitro. As a protected amino acid ester, it is a synthetic intermediate rather than a bioactive compound. In vitro studies using this compound focus on its chemical reactivity, such as its use in peptide bond formation reactions, rather than assessments of pharmacological activity. The compound may be used as a substrate in enzymatic assays to study esterase activity, as the benzyl ester can be cleaved by certain hydrolases. However, these are analytical applications rather than pharmacological assessments. The compound does not bind to receptors, inhibit enzymes, or produce cytotoxic effects in cell-based assays at concentrations typically used for synthesis. It is used as a reagent in the synthesis and bioactivity study of a goralatide analog with anti-leukemic activity.
|
| ln Vivo |
H-Pro-NHEt·HCl is not a pharmacologically active compound and therefore does not have defined in vivo activity as a drug. When administered to animals, the compound would likely be hydrolyzed by esterases to release proline, which would then enter normal metabolic pathways. The benzyl ester may provide enhanced lipophilicity compared to free proline, potentially improving membrane permeability and oral absorption. However, the compound is not used therapeutically, and its in vivo effects would be limited to those of the released proline, which is a non-essential amino acid involved in protein synthesis and collagen production. Its primary value remains in synthetic chemistry.
|
| Enzyme Assay |
In vitro enzyme assays for H-Pro-NHEt·HCl are typically designed to study esterase or protease activity. A standard protocol involves incubating the compound with an enzyme preparation, such as plasma, tissue homogenates, or purified carboxylesterases, in a suitable buffer at physiological pH and temperature. The hydrolysis of the benzyl ester releases proline and benzyl alcohol, which can be quantified by HPLC, GC, or mass spectrometry. Alternatively, the decrease in substrate concentration can be monitored. The reaction is initiated by addition of the substrate, and the initial velocity is measured over time. These assays are used to characterize the substrate specificity of esterases, to screen for enzyme inhibitors, or to evaluate the stability of benzyl ester protecting groups in biological matrices.
|
| Cell Assay |
In vitro cellular assays using H-Pro-NHEt·HCl are limited due to the compound's role as a synthetic intermediate rather than a bioactive molecule. However, it can be used in cell culture studies to investigate the intracellular delivery of proline via ester hydrolysis. Cells are cultured in media supplemented with the compound, and cellular uptake, ester hydrolysis, and proline release are monitored. The effects of increased intracellular proline on cellular metabolism, protein synthesis, or collagen production can be assessed. These experiments are typically conducted in cell lines such as fibroblasts or chondrocytes, and endpoints are measured using biochemical assays or mass spectrometry. The compound's ability to penetrate cell membranes may be enhanced by the lipophilic benzyl ester group, making it useful for studying proline's intracellular functions.
|
| Animal Protocol |
In vivo animal studies with H-Pro-NHEt·HCl are primarily conducted in the context of nutritional or metabolic research. A typical protocol involves oral or intraperitoneal administration of the compound to rodents at doses ranging from 10 to 500 mg/kg. Blood samples are collected at various time points to measure proline and benzyl alcohol levels, allowing assessment of the compound's absorption, hydrolysis, and pharmacokinetics. The compound's ability to elevate plasma proline concentrations and its effects on proline metabolism, collagen synthesis, or wound healing may be evaluated. These studies help to understand the bioavailability of amino acid esters and their utility as proline delivery agents for nutritional supplementation or metabolic research.
|
| ADME/Pharmacokinetics |
As a proline benzyl ester, H-Pro-NHEt·HCl is expected to be absorbed after oral administration, although detailed pharmacokinetic data are not well-documented. The compound is likely hydrolyzed by esterases in the gastrointestinal tract, liver, and plasma to release proline and benzyl alcohol. The benzyl ester may enhance lipophilicity and membrane permeability compared to free proline, potentially improving oral bioavailability. Following hydrolysis, proline enters the endogenous amino acid pool and is distributed throughout the body via the circulation. Proline is metabolized primarily in the liver and kidneys through oxidation to glutamate and other pathways. The pharmacokinetic profile of the compound is primarily determined by the rate of ester hydrolysis and the subsequent metabolism of proline. The compound has a melting point of 148-151°C and a refractive index of 1.4365.
|
| Toxicity/Toxicokinetics |
The hydrochloride salt of proline benzyl ester is generally considered to have low toxicity, consistent with its use as a chemical reagent and its metabolic conversion to the non-essential amino acid proline. Acute toxicity is expected to be minimal, as proline has a very low toxicity profile. However, the compound may cause irritation upon contact with skin, eyes, or mucous membranes due to its acidic nature. Inhalation of the powder may cause respiratory irritation. The compound is not classified as a carcinogen, mutagen, or reproductive toxicant. Standard laboratory safety precautions, including the use of personal protective equipment, are recommended. No significant systemic toxicity is anticipated at typical research doses, as the compound is rapidly metabolized to proline and benzyl alcohol.
|
| Additional Infomation |
See also: Benzyl L-proline hydrochloride (note moved to).
L-Proline benzyl ester hydrochloride (H-Pro-NHEt·HCl, CAS 16652-71-4) is a protected amino acid derivative used as a building block in peptide synthesis. Its chemical formula is C₁₂H₁₅NO₂·HCl and molecular weight is 241.71. The compound appears as a white to off-white solid powder with a melting point of 148-151°C. The benzyl ester provides acid-labile protection for the carboxyl group that can be selectively removed by hydrogenolysis or acidolysis. The compound is soluble in water, acetone, benzene, ether, and ethanol. It is intended for research use only and is not for human therapeutic applications. The compound is typically stored at -20°C for long-term stability. |
| Molecular Formula |
C12H15NO2.HCL
|
|---|---|
| Molecular Weight |
241.71394
|
| Exact Mass |
241.086
|
| CAS # |
16652-71-4
|
| PubChem CID |
2733413
|
| Appearance |
White to off-white solid powder
|
| Density |
1.121g/cm3
|
| Boiling Point |
309ºC at 760 mmHg
|
| Melting Point |
148-151 °C(lit.)
|
| Flash Point |
140.7ºC
|
| Vapour Pressure |
0.000659mmHg at 25°C
|
| Index of Refraction |
1.4365
|
| LogP |
2.612
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
4
|
| Heavy Atom Count |
16
|
| Complexity |
212
|
| Defined Atom Stereocenter Count |
1
|
| SMILES |
C1=CC=C(C=C1)COC(=O)[C@@H]2CCCN2.Cl
|
| InChi Key |
NEDMOHHWRPHBAL-MERQFXBCSA-N
|
| InChi Code |
InChI=1S/C12H15NO2.ClH/c14-12(11-7-4-8-13-11)15-9-10-5-2-1-3-6-10;/h1-3,5-6,11,13H,4,7-9H2;1H/t11-;/m0./s1
|
| Chemical Name |
benzyl (2S)-pyrrolidine-2-carboxylate;hydrochloride
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| 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
|
|---|---|
| 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 | 4.1372 mL | 20.6859 mL | 41.3719 mL | |
| 5 mM | 0.8274 mL | 4.1372 mL | 8.2744 mL | |
| 10 mM | 0.4137 mL | 2.0686 mL | 4.1372 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
