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| Targets |
H-D-Phe(4-NO2)-OH monohydrate targets peptide synthesis and biochemical research applications as a D-configured nitro-substituted phenylalanine analogue. The D-configuration can confer proteolytic stability to peptides. The para-nitro substituent provides a chromophore for UV detection and can be used in spectroscopic studies. It does not have a specific biological receptor target.
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| 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].
In vitro activity of H-D-Phe(4-NO2)-OH monohydrate is primarily related to its role as a research tool and synthetic building block. Amino acid derivatives have been used as ergogenic supplements, affecting the release of anabolic hormones and fuel availability. H-D-Phe(4-NO2)-OH can be used in cell culture to study D-amino acid metabolism and incorporation into peptides. |
| ln Vivo |
There is limited specific in vivo activity data available for H-D-Phe(4-NO2)-OH monohydrate. As a D-configured nitro-substituted amino acid, it may have different metabolic properties compared to L-amino acids. The D-configuration can provide resistance to proteolytic degradation. The compound may be used in animal studies to investigate the effects of D-amino acid incorporation on peptide stability and function.
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| Enzyme Assay |
General protocols for amino acid derivatives involve preparing stock solutions in water or suitable buffers. For spectroscopic studies, the compound's absorbance at characteristic wavelengths (typically around 280 nm for nitroaromatic compounds) can be measured. For incorporation into peptides, standard SPPS protocols apply. The compound has an optical rotation of -7° (c=2%, 1N HCl). Purity is ≥99.5% by HPLC with chiral purity.
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| Cell Assay |
Standard in vitro cell culture protocols involve dissolving H-D-Phe(4-NO2)-OH monohydrate in sterile water or cell culture medium at desired concentrations. Cells are plated in multi-well plates and allowed to adhere, then treated with varying concentrations of the compound for 24-72 hours. Cell viability can be assessed using MTT or CCK-8 assays. The nitro chromophore enables spectrophotometric detection in cellular assays.
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| Animal Protocol |
In vivo animal studies with amino acid derivatives typically involve oral gavage or intravenous injection of the compound dissolved in saline or other suitable vehicles. Dosing regimens may include single-dose or multi-dose schedules depending on the study objectives. Blood and tissue samples are collected at various time points for analysis of compound distribution and metabolism. The D-configuration may affect the pharmacokinetic profile compared to L-amino acids.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of H-D-Phe(4-NO2)-OH monohydrate are characteristic of small amino acid derivatives. The compound has a molecular weight of 228.20 g/mol, formula C₉H₁₀N₂O₄·H₂O, and melting point of 238-240°C (decomp). Optical rotation is -7° (c=2%, 1N HCl). Purity is ≥99.5% by HPLC with chiral purity. It is expected to be absorbed following administration and distributed throughout body water compartments. Elimination is expected primarily via renal excretion.
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| Toxicity/Toxicokinetics |
Toxicological data for H-D-Phe(4-NO2)-OH monohydrate is limited. As a nitro-substituted amino acid derivative, it may have different toxicological properties compared to unsubstituted amino acids. Standard safety precautions for handling laboratory chemicals should be observed. The compound is not intended for human therapeutic use and is classified for research purposes only. In vitro cytotoxicity studies may be performed to establish safe concentration ranges for cell-based assays.
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| 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):1793-898.
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| Additional Infomation |
H-D-Phe(4-NO2)-OH monohydrate (CAS#: 56613-61-7) is also known as 4-Nitro-D-phenylalanine monohydrate and (R)-2-amino-3-(4-nitrophenyl)propanoic acid hydrate. Its molecular formula is C₉H₁₀N₂O₄·H₂O and molecular weight is 228.20 g/mol. It is a D-configured nitro-substituted phenylalanine derivative used in peptide synthesis and biochemical research. It has no approved therapeutic indications.
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| Molecular Formula |
C9H10N2O4
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| Molecular Weight |
210.1867
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| Exact Mass |
228.074
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| CAS # |
56613-61-7
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| PubChem CID |
679497
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| Appearance |
White to off-white powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
414.1±35.0 °C at 760 mmHg
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| Flash Point |
204.2±25.9 °C
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| Vapour Pressure |
0.0±1.0 mmHg at 25°C
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| Index of Refraction |
1.614
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| LogP |
0.84
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
15
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| Complexity |
243
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| Defined Atom Stereocenter Count |
1
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| SMILES |
OC([C@@H](CC1C=CC(=CC=1)[N+](=O)[O-])N)=O
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| InChi Key |
GTVVZTAFGPQSPC-MRVPVSSYSA-N
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| InChi Code |
InChI=1S/C9H10N2O4/c10-8(9(12)13)5-6-1-3-7(4-2-6)11(14)15/h1-4,8H,5,10H2,(H,12,13)/t8-/m1/s1
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| Chemical Name |
(2R)-2-amino-3-(4-nitrophenyl)propanoic acid
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| Synonyms |
(R)-2-Amino-3-(4-nitrophenyl)propanoic acid; H-D-Phe(4-NO2)-OH monohydrate
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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 | 4.7576 mL | 23.7880 mL | 47.5760 mL | |
| 5 mM | 0.9515 mL | 4.7576 mL | 9.5152 mL | |
| 10 mM | 0.4758 mL | 2.3788 mL | 4.7576 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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