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Z-Hyp-OH

Alias: Z-Hyp-OH; N-Cbz-hydroxy-L-proline
Cat No.:V37479 Purity: ≥98%
N-Cbz-hydroxy-L-proline is a biochemical compound that can be used as a biomaterial or organic/chemical reagent for biomedical research.
Z-Hyp-OH
Z-Hyp-OH Chemical Structure CAS No.: 13504-85-3
Product category: Amino Acids
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
N-Cbz-hydroxy-L-proline is a biochemical compound that can be used as a biomaterial or organic/chemical reagent for biomedical research.
Z-Hyp-OH, also known as trans-N-Carbobenzoxy-4-hydroxy-L-proline or trans-N-Cbz-4-hydroxy-L-proline, is a protected hydroxyproline derivative. It is a biochemical compound that can be used as a biomaterial or organic/chemical reagent for biomedical research. The compound has a molecular weight of 265.27 g/mol and formula C₁₃H₁₅NO₅.
Biological Activity I Assay Protocols (From Reference)
Targets
Z-Hyp-OH targets peptide synthesis and biomedical research applications as a protected hydroxyproline derivative. The Z (benzyloxycarbonyl) group protects the amino group. Hydroxyproline is an important amino acid in collagen structure and function. The compound can be used as a biomaterial for biomedical research. It does not have a specific biological receptor target.
ln Vitro
In vitro activity of Z-Hyp-OH is primarily as a peptide synthesis reagent and biomaterial. Amino acid derivatives have been used as ergogenic supplements, affecting the release of anabolic hormones and fuel availability. Z-Hyp-OH itself is not directly biologically active. Its utility is in preparing hydroxyproline-containing peptides for structural and biological studies.
ln Vivo
There is no specific in vivo activity data for Z-Hyp-OH as a standalone compound. Peptides containing hydroxyproline residues synthesized using this building block may be evaluated in vivo for applications related to collagen structure and function. Animal studies would be performed on the final peptide products.
Enzyme Assay
In vitro protocols for Z-Hyp-OH involve its use in peptide synthesis. The compound is activated using coupling reagents and coupled to peptides. The Z group is removed by hydrogenation or HBr in acetic acid. Purity is >98% by HPLC. Melting point is 104-107°C. Boiling point (predicted) is 486.9±45.0°C. Density is 1.416±0.06 g/cm³.
Cell Assay
Cell-based protocols are not directly applicable to Z-Hyp-OH as it is a synthesis building block. Hydroxyproline-containing peptides synthesized using this reagent can be tested in cell culture. Peptides are dissolved in DMSO or appropriate buffers, sterile-filtered, and added to cells at concentrations of 0.1-100 µM. Incubation is typically 24-72 hours. Assays include cell viability, proliferation, and collagen-related readouts.
Animal Protocol
Animal studies with Z-Hyp-OH are not conducted directly. Peptides containing hydroxyproline residues synthesized using this building block may be evaluated in vivo. Protocols involve administration of the peptide via appropriate routes in animal models. Pharmacokinetic sampling, efficacy assessment, and toxicological evaluation follow standard preclinical study designs. Hydroxyproline residues can influence collagen stability and structure.
ADME/Pharmacokinetics
Pharmacokinetic data for Z-Hyp-OH as a standalone compound is not applicable. The compound has molecular weight 265.27 g/mol, formula C₁₃H₁₅NO₅, and melting point 104-107°C. Storage: room temperature. The Z group is removed by hydrogenation or acid treatment. The resulting hydroxyproline residue is important in collagen structure.
Toxicity/Toxicokinetics
Toxicological data for Z-Hyp-OH is limited. The compound is for research use only. Standard safety precautions should be observed. Acute toxicity is expected to be low. Store at room temperature. Proper personal protective equipment should be worn when handling. No specific toxicity studies have been reported. It is not intended for human therapeutic use.
References

[1]. Mild Method for Deprotection of the N-Benzyloxycarbonyl (N-Cbz) Group by the Combination of AlCl3 and HFIP. J Org Chem. 2024;89(8):5665-5674.

Additional Infomation
Z-Hyp-OH (CAS#: 13504-85-3) is also known as trans-N-Carbobenzoxy-4-hydroxy-L-proline, trans-N-Cbz-4-hydroxy-L-proline, and (2S,4R)-4-hydroxy-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid. Its molecular formula is C₁₃H₁₅NO₅ and molecular weight is 265.27 g/mol. It is a protected hydroxyproline used in peptide synthesis and biomedical research. It has no approved therapeutic indications.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C13H15NO5
Molecular Weight
265.26
Exact Mass
265.095
CAS #
13504-85-3
PubChem CID
391517
Appearance
White to off-white powder
Density
1.4±0.1 g/cm3
Boiling Point
486.9±45.0 °C at 760 mmHg
Melting Point
104-107 °C
Flash Point
248.3±28.7 °C
Vapour Pressure
0.0±1.3 mmHg at 25°C
Index of Refraction
1.612
LogP
-0.1
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
4
Heavy Atom Count
19
Complexity
340
Defined Atom Stereocenter Count
2
SMILES
C1=CC=CC=C1COC(N2C(CC(C2)O)C(O)=O)=O
InChi Key
WWVCWLBEARZMAH-MNOVXSKESA-N
InChi Code
InChI=1S/C13H15NO5/c15-10-6-11(12(16)17)14(7-10)13(18)19-8-9-4-2-1-3-5-9/h1-5,10-11,15H,6-8H2,(H,16,17)/t10-,11+/m1/s1
Chemical Name
(2S,4R)-4-hydroxy-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid
Synonyms
Z-Hyp-OH; N-Cbz-hydroxy-L-proline
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)
DMSO: ~100 mg/mL (~377.0 mM; with ultrasonication)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 5 mg/mL (18.85 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween-80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), Clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of DMSO stock solution (50.0 mg/mL) to 400 μL of PEG300 and mix well; then add 50 μL of Tween-80 and mix well; finally add 450 μL of physiological saline and adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 5 mg/mL (18.85 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), Clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of DMSO stock solution (50.0 mg/mL) to 900 μL of 20% SBE-β-CD saline and mix well.
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.

Solubility in Formulation 3: ≥ 5 mg/mL (18.85 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), Clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of DMSO stock solution (50.0 mg/mL) to 900 μL of corn oil and mix well.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.7699 mL 18.8494 mL 37.6989 mL
5 mM 0.7540 mL 3.7699 mL 7.5398 mL
10 mM 0.3770 mL 1.8849 mL 3.7699 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.

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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?
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  • 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:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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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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