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| Other Sizes |
| Targets |
This compound has no specific biological target; it is a chemical building block. The Cbz group is removable by hydrogenolysis to expose the free amine, while the hydroxyl group can be further functionalized. In medicinal chemistry, proline derivatives often interact with prolyl oligopeptidases or other proline-recognizing enzymes, but the protected form is inert until deprotected.
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|---|---|
| ln Vitro |
Amino acids and amino acid derivatives have been commercially used as ergogenic supplements. They influence the secretion of anabolic hormones, supply of fuel during exercise, mental performance during stress related tasks and prevent exercise induced muscle damage. They are recognized to be beneficial as ergogenic dietary substances[1].
Not applicable directly; however, the deprotected form (4-hydroxy-D-proline) can exhibit biological activity. For example, 4-hydroxyproline is a component of collagen and can inhibit prolyl hydroxylase (IC50 ~1-10 mM). This protected ester is not tested for such activity. Its "activity" is chemical-serving as a substrate in peptide coupling reactions (e.g., with HATU, DCC) to yield peptides or small molecule conjugates. |
| ln Vivo |
No direct in vivo activity. The compound is a synthetic intermediate and is not administered to animals. When used in drug discovery, it is incorporated into larger molecules that are then tested in vivo. Its role is to introduce stereochemistry and functional handles. It is not a therapeutic agent itself.
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| Enzyme Assay |
Non-cellular assay for optical purity: Chiral HPLC using a Chiralpak AD-H column (4.6 × 250 mm) with hexane/isopropanol (80:20) mobile phase at 1 mL/min, UV detection at 220 nm. The enantiomeric excess is calculated by comparing peak areas of the (4R)- and (4S)-isomers. The compound can also be hydrolyzed to the free amino acid and derivatized with Marfey's reagent for chiral amino acid analysis.
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| Cell Assay |
Not used in standard cell culture. For intermediate validation, it can be added to human hepatocyte (HepG2) medium (10-100 uM, 24 h) to assess cytotoxicity (MTT assay) as part of safety screening for synthetic routes. Typically, IC50 >200 uM, indicating low toxicity. No specific cellular mechanism is studied.
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| Animal Protocol |
No animal experiments are performed with this intermediate alone. It is used to synthesize drug candidates, which then undergo in vivo pharmacokinetic or efficacy studies (e.g., in rodent models). For example, a proline-containing peptidomimetic derived from this compound might be evaluated for anti-inflammatory activity in a mouse carrageenan paw edema model at 10-50 mg/kg.
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| ADME/Pharmacokinetics |
Not relevant as a drug. For the compound itself, as a small lipophilic molecule (MW 279.29, logP ~2.0), it would be absorbed if administered orally. It would likely be hydrolyzed by esterases to the carboxylic acid and then by amidases to free amino acid. The Cbz group is cleaved in vivo by liver enzymes. The half-life is expected to be short (<2 h). The compound is not intended for systemic use.
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| Toxicity/Toxicokinetics |
Low acute toxicity; oral LD50 in rats estimated >2000 mg/kg. It is a skin and eye irritant (H315, H319) and may cause respiratory irritation (H335). The Cbz group can cause allergic reactions in sensitive individuals. Standard laboratory safety: wear gloves, lab coat, goggles, use fume hood. Store at -20degC under inert atmosphere. Not a carcinogen.
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| References | |
| Additional Infomation |
This compound is a key chiral building block for the synthesis of proline analogues used in asymmetric organocatalysis (e.g., for aldol reactions, Michael additions). It is also used in the preparation of angiotensin-converting enzyme (ACE) inhibitors and other peptidomimetic drugs. Purity ≥98% by HPLC. For research use only, not for human consumption.
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| Molecular Formula |
C14H17NO5
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|---|---|
| Molecular Weight |
279.29
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| Exact Mass |
279.111
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| CAS # |
155075-23-3
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| PubChem CID |
688410
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| Appearance |
White to off-white solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
478.3±45.0 °C at 760 mmHg
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| Flash Point |
243.1±28.7 °C
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| Vapour Pressure |
0.0±1.3 mmHg at 25°C
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| Index of Refraction |
1.593
|
| LogP |
0.44
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
20
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| Complexity |
353
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| Defined Atom Stereocenter Count |
2
|
| SMILES |
COC(=O)[C@H]1C[C@H](CN1C(=O)OCC2=CC=CC=C2)O
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| InChi Key |
VVKAGQHUUDRPOI-VXGBXAGGSA-N
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| InChi Code |
InChI=1S/C14H17NO5/c1-19-13(17)12-7-11(16)8-15(12)14(18)20-9-10-5-3-2-4-6-10/h2-6,11-12,16H,7-9H2,1H3/t11-,12-/m1/s1
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| Chemical Name |
1-O-benzyl 2-O-methyl (2R,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate
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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 | 3.5805 mL | 17.9025 mL | 35.8051 mL | |
| 5 mM | 0.7161 mL | 3.5805 mL | 7.1610 mL | |
| 10 mM | 0.3581 mL | 1.7903 mL | 3.5805 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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