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H-Tyr-Phe-OH

Cat No.:V43878 Purity: ≥98%
H-Tyr-Phe-OH (L-Tyrosyl-L-phenylalanine) is an orally bioactive ACE inhibitor (antagonist) with an inhibition rate of 48% at 50 μM.
H-Tyr-Phe-OH
H-Tyr-Phe-OH Chemical Structure CAS No.: 17355-11-2
Product category: New3
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
250mg
500mg
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Product Description
H-Tyr-Phe-OH (L-Tyrosyl-L-phenylalanine) is an orally bioactive ACE inhibitor (antagonist) with an inhibition rate of 48% at 50 μM. H-Tyr-Phe-OH can be used as a biomarker to differentiate between benign thyroid nodules (BTN) and thyroid cancer (TC). H-Tyr-Phe-OH has xanthine oxidase inhibitory (uric acid-lowering) activity and can act as a regulator of IL-8 production in neutrophil-like cells.
H-Tyr-Phe-OH (CAS: 17355-11-2), also known as L-Tyrosyl-L-phenylalanine, is a dipeptide composed of tyrosine and phenylalanine linked by a peptide bond. The molecular formula is C18H20N2O4 and the molecular weight is 328.36. H-Tyr-Phe-OH is an orally active inhibitor of angiotensin-converting enzyme (ACE) with an inhibition rate of 48% at 50 μM. It has xanthine oxidase inhibitory (uric acid-lowering) activity and can act as a regulator of IL-8 production in neutrophil-like cells. It can be used as a biomarker to differentiate between benign thyroid nodules (BTN) and thyroid cancer (TC).
Biological Activity I Assay Protocols (From Reference)
Targets
H-Tyr-Phe-OH targets multiple enzymes and pathways. It inhibits angiotensin-converting enzyme (ACE) with an inhibition rate of 48% at 50 μM, suggesting potential antihypertensive activity. It also exhibits xanthine oxidase inhibitory (uric acid-lowering) activity. Additionally, it regulates IL-8 production in neutrophil-like cells. These diverse activities make it a compound of interest for studying cardiovascular, metabolic, and inflammatory processes.
ln Vitro
In vitro, H-Tyr-Phe-OH demonstrates ACE inhibitory activity with an inhibition rate of 48% at 50 μM. It also shows xanthine oxidase inhibitory activity and regulates IL-8 production in neutrophil-like cells. These activities suggest potential applications in hypertension, gout, and inflammation research. The compound's ability to inhibit ACE and xanthine oxidase makes it a valuable tool for studying these enzymes.
ln Vivo
In vivo, H-Tyr-Phe-OH is orally active, suggesting it may have potential as an orally bioavailable therapeutic agent. Its ACE inhibitory activity could translate to antihypertensive effects in vivo. However, specific in vivo efficacy data are not extensively documented. The compound is used as a biomarker for thyroid cancer research.
Enzyme Assay
In vitro enzyme assays are used to characterize H-Tyr-Phe-OH's activity. ACE inhibition assays measure the compound's ability to inhibit ACE-mediated cleavage of a substrate. Xanthine oxidase inhibition assays measure the compound's ability to inhibit the conversion of xanthine to uric acid. IL-8 production can be measured in neutrophil-like cells treated with the compound.
Cell Assay
Cell-based assays for H-Tyr-Phe-OH are conducted in neutrophil-like cells to assess its effects on IL-8 production. Cells are treated with the compound at various concentrations, and IL-8 levels in the supernatant are measured by ELISA. Cytotoxicity is assessed in parallel. These assays characterize the compound's immunomodulatory effects.
Animal Protocol
In vivo animal experiments with H-Tyr-Phe-OH are not extensively documented. As an orally active ACE inhibitor, it could be tested in hypertensive animal models to assess its blood pressure-lowering effects. It could also be evaluated in models of gout to assess its uric acid-lowering effects. Specific protocols are not available.
ADME/Pharmacokinetics
Pharmacokinetic properties of H-Tyr-Phe-OH include oral activity, indicating reasonable oral bioavailability. The compound has a molecular formula of C18H20N2O4 and a molecular weight of 328.36. It is a solid. Storage: powder at -20°C for 3 years; in solvent at -80°C for 6 months. Specific PK parameters are not available.
Toxicity/Toxicokinetics
Safety and toxicology data for H-Tyr-Phe-OH are limited. As a dipeptide, it is expected to have low toxicity. The compound is for research use only and is not approved for human therapeutic use. Standard laboratory safety precautions should be followed. No specific toxicity data are available.
References

[1]. Biomarker containing keratin type II cytoskeleton 1b for differentiating benign thyroid nodules and thyroid cancer: China, CN114264828A[P]. 2022-04-01.

[2]. Angiotensin converting enzyme (ACE)-inhibiting peptides, ACE inhibitors containing the peptides, their uses, and manufacture of the peptides from shark cartilage: Japan, JP2005154326A[P]. 2005-06-16.

[3]. Method for preparing cod fish peptide with xanthine oxidase inhibitory activity: China, CN113005166A[P]. 2021-06-22.

[4]. Metabolomic profiling of parapneumonic effusion reveals a regulatory role of dipeptides in interleukin-8 production in neutrophil-like cells. Anal Chim Acta. 2020 Sep 1;1128:238-250.

Additional Infomation
Tyr-Phe is a dipeptide formed from L-tyrosine and L-phenylalanine residues; it is a metabolite.
H-Tyr-Phe-OH has CAS number 17355-11-2, molecular formula C18H20N2O4, and molecular weight 328.36. It is a dipeptide composed of tyrosine and phenylalanine. It is an orally active ACE inhibitor (48% inhibition at 50 μM), has xanthine oxidase inhibitory activity, and regulates IL-8 production. It can be used as a thyroid cancer biomarker. Not for human use; for research purposes only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C18H20N2O4
Molecular Weight
328.3624
Exact Mass
328.142
CAS #
17355-11-2
PubChem CID
7009600
Appearance
White to off-white solid powder
Density
1.3 g/cm3
Boiling Point
642.2ºC at 760 mmHg
Flash Point
342.2ºC
Vapour Pressure
2.27E-17mmHg at 25°C
Index of Refraction
1.625
LogP
2.165
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
7
Heavy Atom Count
24
Complexity
415
Defined Atom Stereocenter Count
2
SMILES
C1=CC=C(C=C1)C[C@@H](C(=O)O)NC(=O)[C@H](CC2=CC=C(C=C2)O)N
InChi Key
CGWAPUBOXJWXMS-HOTGVXAUSA-N
InChi Code
InChI=1S/C18H20N2O4/c19-15(10-13-6-8-14(21)9-7-13)17(22)20-16(18(23)24)11-12-4-2-1-3-5-12/h1-9,15-16,21H,10-11,19H2,(H,20,22)(H,23,24)/t15-,16-/m0/s1
Chemical Name
(2S)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-3-phenylpropanoic acid
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

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
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 : ~5 mg/mL (~15.23 mM)
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 3.0454 mL 15.2272 mL 30.4544 mL
5 mM 0.6091 mL 3.0454 mL 6.0909 mL
10 mM 0.3045 mL 1.5227 mL 3.0454 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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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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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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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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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