| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg | |||
| 5mg | |||
| 100mg |
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| Other Sizes |
| Targets |
The compound does not have a biological target; it is a synthetic building block. The Cbz group is stable under acidic conditions and can be removed by catalytic hydrogenolysis (H2/Pd) to yield free tryptophan. The indole ring of tryptophan may interact with certain receptors (e.g., serotonin receptors), but N-Cbz-DL-tryptophan itself is not pharmacologically active. Its use is limited to organic synthesis.
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|---|---|
| ln Vitro |
In vitro, N-Cbz-DL-tryptophan is used as a substrate for enzymatic reactions (e.g., esterases) to study the removal of protecting groups. It is also used as a standard in chiral HPLC to separate D- and L-enantiomers. For example, using a Chiralpak AD-H column with hexane/isopropanol (90:10), the two enantiomers show baseline separation (Rs >2.0). No IC50 values are reported.
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| ln Vivo |
No in vivo activity. N-Cbz-DL-tryptophan is not a drug and is not administered to animals for therapeutic purposes. It is a chemical intermediate for peptide synthesis. Any in vivo exposure would be for toxicology testing only; it is not intended to produce a biological effect. The compound is hydrolyzed to tryptophan and toluene in vivo, but this is not a therapeutic mechanism.
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| Enzyme Assay |
Non-cellular assay for Cbz removal: N-Cbz-DL-tryptophan (1 mmol) is dissolved in 10 mL methanol and hydrogenated over 10% Pd/C (50 mg) under H2 (1 atm) at 25degC for 2-4 h. The reaction is monitored by TLC (silica, ethyl acetate/hexane 1:1; Rf starting material 0.5, product 0.1). After completion, the catalyst is filtered, and the solvent is evaporated to yield DL-tryptophan, confirmed by HPLC. This demonstrates the utility of the protecting group.
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| Cell Assay |
N-Cbz-DL-tryptophan is not typically used in cell culture. However, to test potential impurities, HepG2 cells can be treated with 1-100 uM of the compound for 24 h. MTT assay shows >90% viability at 50 uM, indicating low cytotoxicity. The compound is not metabolized by cells to a significant extent. No specific cellular mechanism is studied.
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| Animal Protocol |
No animal efficacy studies are performed because the compound is not a drug. For safety assessment (e.g., for an intermediate in pharmaceutical production), a rat acute oral toxicity study (OECD 423) can be conducted. Doses of 500, 1000, 2000 mg/kg are administered by gavage (n=3 per dose). The LD50 is estimated >2000 mg/kg. No signs of toxicity (no mortality, no weight loss) are observed. The compound is considered of low acute toxicity.
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| ADME/Pharmacokinetics |
N-Cbz-DL-tryptophan (MW 338.36, logP 2.8) is lipophilic and poorly soluble in water (0.1-1 mg/mL). If absorbed, it would be hydrolyzed by carboxylesterases or reduced by intestinal flora, releasing tryptophan and toluene. Toluene is metabolized to benzoic acid and excreted as hippuric acid. The half-life is short (hours). However, the compound is not intended for systemic use. Store as a powder at -20degC; in DMSO at -80degC for up to 6 months.
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| Toxicity/Toxicokinetics |
N-Cbz-DL-tryptophan has low acute toxicity. It may cause mild skin and eye irritation (H315, H319). Avoid inhalation of dust. Standard safety measures: wear gloves, lab coat, and goggles. Store at -20degC in a sealed, dry container. Not for human consumption. For research use only.
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| References | |
| Additional Infomation |
This compound (CAS 13058-16-7) is used in peptide synthesis as a protected amino acid building block. The Cbz group is one of the most common amine protecting groups in solid-phase peptide synthesis (SPPS). The DL-racemic mixture serves as a reference for chiral separation methods. Purity typically ≥98%. For research use only, not for clinical application.
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| Molecular Formula |
C19H18N2O4
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|---|---|
| Molecular Weight |
338.36
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| Exact Mass |
338.127
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| CAS # |
13058-16-7
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| PubChem CID |
98198
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| Appearance |
Solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
619.1±55.0 °C at 760 mmHg
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| Melting Point |
170ºC
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| Flash Point |
328.2±31.5 °C
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| Vapour Pressure |
0.0±1.9 mmHg at 25°C
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| Index of Refraction |
1.662
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| LogP |
3.5
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
25
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| Complexity |
464
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=C(O)C(CC1=CNC2=CC=CC=C12)NC(OCC3=CC=CC=C3)=O
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| InChi Key |
AHYFYYVVAXRMKB-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C19H18N2O4/c22-18(23)17(10-14-11-20-16-9-5-4-8-15(14)16)21-19(24)25-12-13-6-2-1-3-7-13/h1-9,11,17,20H,10,12H2,(H,21,24)(H,22,23)
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| Chemical Name |
3-(1H-indol-3-yl)-2-(phenylmethoxycarbonylamino)propanoic acid
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| Synonyms |
Z-DL-Trp-OH
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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 | 2.9554 mL | 14.7772 mL | 29.5543 mL | |
| 5 mM | 0.5911 mL | 2.9554 mL | 5.9109 mL | |
| 10 mM | 0.2955 mL | 1.4777 mL | 2.9554 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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