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Carbobenzoxyphenylalanine

Alias: NSC 402059; Carbobenzoxy-L-phenylalanine; Carbobenzoxyphenylalanine
Cat No.:V17550 Purity: ≥98%
Z-Phe-OH is a phenylalanine analogue.
Carbobenzoxyphenylalanine
Carbobenzoxyphenylalanine Chemical Structure CAS No.: 1161-13-3
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
10g
25g
Other Sizes
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Product Description
Z-Phe-OH is a phenylalanine analogue.
Carbobenzoxyphenylalanine (CAS#: 1161-13-3), also known as N-carbobenzoxy-L-phenylalanine or Z-Phe-OH, is a protected amino acid derivative used in peptide synthesis. The compound contains a carbobenzoxy (Cbz, Z) protecting group attached to the amino group of L-phenylalanine. It is widely used as a building block in solid-phase and solution-phase peptide synthesis for the preparation of peptides and peptide-based pharmaceuticals.
Biological Activity I Assay Protocols (From Reference)
Targets
The compound itself does not have a specific pharmacological target as it is a synthetic intermediate (protected amino acid) rather than a therapeutic agent. Its value lies in its use as a building block for the synthesis of peptides and peptide-based pharmaceuticals. The carbobenzoxy (Cbz) protecting group is used to protect the amino group during peptide synthesis, preventing unwanted side reactions.
ln Vitro
Commercial ergot supplements have been made from amino acids and their derivatives. They affect the release of anabolic hormones, the availability of fuel for activity, the ability to think clearly under pressure, and the prevention of muscular damage brought on by exertion. They are regarded as advantageous synergistic food ingredients [1].
Carbobenzoxyphenylalanine itself is not known to possess direct therapeutic activity. Its significance is as a synthetic intermediate for the preparation of peptides and peptide-based pharmaceuticals. The compound is used in peptide synthesis to introduce the phenylalanine residue into peptide sequences while protecting the amino group with the Cbz group, which can be removed by hydrogenation or other methods after peptide assembly.
ln Vivo
There is no reported in vivo activity for carbobenzoxyphenylalanine itself, as it is primarily a chemical intermediate rather than a drug candidate. Its role in drug discovery is indirect, serving as a building block for the synthesis of peptides that are then evaluated for biological activity.
Enzyme Assay
As a chemical intermediate, there are no standardized in vitro enzyme/receptor binding assays for carbobenzoxyphenylalanine itself. The compound's utility is in peptide synthesis rather than biological assay development. Researchers may use carbobenzoxyphenylalanine as a starting material to synthesize peptides that are then evaluated in various biological assays.
Cell Assay
There are no reported in vitro cellular assays for carbobenzoxyphenylalanine itself, as it is not a drug candidate. The compound is used in peptide synthesis to prepare peptides that may subsequently be tested in cellular assays for various biological activities.
Animal Protocol
There are no reported in vivo animal studies for carbobenzoxyphenylalanine itself, as the compound is a synthetic intermediate rather than a therapeutic agent. Animal studies would be conducted on the final peptide products synthesized from carbobenzoxyphenylalanine rather than on the intermediate itself.
ADME/Pharmacokinetics
As a synthetic intermediate, there are no reported pharmacokinetic data for carbobenzoxyphenylalanine. Pharmacokinetic studies would be performed on the final peptide molecules synthesized from carbobenzoxyphenylalanine rather than on the intermediate itself.
Toxicity/Toxicokinetics
As a synthetic intermediate used in peptide synthesis, carbobenzoxyphenylalanine is not intended for human consumption, and there are no reported toxicity data for the compound itself. Toxicology studies would be conducted on the final peptide products synthesized from carbobenzoxyphenylalanine. Appropriate safety precautions should be followed when handling the compound in the laboratory.
References
[1]. Luckose F, et al. Effects of amino acid derivatives on physical, mental, and physiological activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-883.
Additional Infomation
Carbobenzoxyphenylalanine (Z-Phe-OH) is a protected amino acid derivative used as a building block in peptide synthesis. The compound contains a carbobenzoxy (Cbz) protecting group attached to L-phenylalanine and is widely used in solid-phase and solution-phase peptide synthesis. The Cbz group can be removed by hydrogenation, allowing for the selective deprotection of the amino group during peptide assembly. Carbobenzoxyphenylalanine is a valuable tool in medicinal chemistry for the preparation of peptide-based pharmaceuticals and research compounds.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C17H17NO4
Molecular Weight
299.32
Exact Mass
299.115
CAS #
1161-13-3
PubChem CID
70878
Appearance
Typically exists as solid at room temperature
Density
1.2±0.1 g/cm3
Boiling Point
511.5±50.0 °C at 760 mmHg
Melting Point
85-87 °C(lit.)
Flash Point
263.1±30.1 °C
Vapour Pressure
0.0±1.4 mmHg at 25°C
Index of Refraction
1.591
LogP
3.58
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
7
Heavy Atom Count
22
Complexity
360
Defined Atom Stereocenter Count
1
SMILES
O(C([H])([H])C1C([H])=C([H])C([H])=C([H])C=1[H])C(N([H])[C@]([H])(C(=O)O[H])C([H])([H])C1C([H])=C([H])C([H])=C([H])C=1[H])=O
InChi Key
RRONHWAVOYADJL-HNNXBMFYSA-N
InChi Code
InChI=1S/C17H17NO4/c19-16(20)15(11-13-7-3-1-4-8-13)18-17(21)22-12-14-9-5-2-6-10-14/h1-10,15H,11-12H2,(H,18,21)(H,19,20)/t15-/m0/s1
Chemical Name
(2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoic acid
Synonyms
NSC 402059; Carbobenzoxy-L-phenylalanine; Carbobenzoxyphenylalanine
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

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
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
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*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 : PEG300Tween 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).
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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)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL 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).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.3409 mL 16.7045 mL 33.4091 mL
5 mM 0.6682 mL 3.3409 mL 6.6818 mL
10 mM 0.3341 mL 1.6705 mL 3.3409 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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