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| Other Sizes |
| Targets |
DL-Tyrosine targets multiple enzymes and transporters. It activates various human carbonic anhydrase (CA) isoenzymes, including CA1 and CA2 with high potency (KA values of 0.02 μM and 0.011 μM, respectively), as well as CA7, CA14, and bacterial and fungal CAs. The compound inhibits mushroom tyrosinase, an enzyme involved in melanin synthesis. It also inhibits the full-length recombinant human CYP46A1, interfering with cholesterol hydroxylation. Furthermore, DL-Tyrosine interacts with human LAT1 (L-type amino acid transporter 1), exhibiting both inhibition and stimulation activities.
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| ln Vitro |
DL-Tyrosine demonstrates diverse in vitro activities. It exhibits antiviral activity against SARS-CoV-2, showing 30.42% inhibition of virus-induced cytotoxicity in Caco-2 cells at 10 μM concentration. The compound shows antibacterial and antifungal properties against pathogens including Staphylococcus aureus and Candida albicans, as evidenced by inhibition zones in agar well diffusion assays. It inhibits the full-length recombinant human CYP46A1 at 43 μM with 80% activity. DL-Tyrosine also shows potent inhibition of L-tryptophan uptake in Xenopus laevis oocytes by up to 100% and possesses antioxidant capabilities, scavenging various radicals in multiple assays.
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| ln Vivo |
In animal models, the effects of DL-Tyrosine vary with different dosages. For instance, in a dog shock model, the vasoactive effects of tyrosine depend on the animal's starting blood pressure. DL-Tyrosine has been shown to mitigate the physiological effects of stress by enhancing catecholamine synthesis. Studies involving animal models demonstrated that tyrosine administration could prevent behavioral inhibition caused by stressors, indicating its potential as a protective agent against stress-induced cognitive decline. Incorporation of total C14 into muscle protein was reduced in infected mice fed dl-tyrosine-2-C-14.
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| Enzyme Assay |
The activation of carbonic anhydrase isoenzymes can be assessed using esterase activity assays measuring p-nitrophenyl acetate hydrolysis. Tyrosinase inhibition is evaluated using L-DOPA or tyrosine as substrates in spectrophotometric assays. CYP46A1 inhibition is assessed by measuring cholesterol hydroxylation activity. LAT1 interaction can be studied using radiolabeled substrate uptake assays in Xenopus oocytes or cell lines expressing the transporter. Binding and inhibition assays are employed to characterize the compound's interactions with various targets.
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| Cell Assay |
DL-Tyrosine is evaluated in Caco-2 cells to assess antiviral activity against SARS-CoV-2, measuring inhibition of virus-induced cytotoxicity at 10 μM concentration. Antibacterial and antifungal activities are assessed using agar well diffusion assays against pathogens including Staphylococcus aureus and Candida albicans. The compound's effects on cellular processes, including cell signaling pathways, gene expression, and cellular metabolism, are studied in various cell models. DL-Tyrosine is also used in cell culture and protein chemistry as a building block for peptide and protein synthesis.
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| Animal Protocol |
In vivo studies with DL-Tyrosine typically involve dietary supplementation or precursor loading experiments in animal models to assess effects on neurotransmitter synthesis, stress response, and endocrine regulation. Rodent models are commonly used to study tyrosine's role in catecholamine biosynthesis under stress conditions. For instance, in a dog shock model, the vasoactive effects of tyrosine were evaluated depending on the animal's starting blood pressure. In vivo formulation calculators are available to prepare clear solutions for animal experiments.
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| ADME/Pharmacokinetics |
DL-Tyrosine is absorbed from the gastrointestinal tract and competes with other large neutral amino acids for transport across the blood-brain barrier via LAT1. It is metabolized to catecholamines, thyroid hormones, and melanin. As a substrate for LAT1, it can cross the blood-brain barrier, blood-retinal barrier, and other barriers. No specific pharmacokinetic parameters are reported for the racemic mixture. The compound is a natural metabolite found in various organisms including Drosophila melanogaster.
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| Toxicity/Toxicokinetics |
DL-Tyrosine is a naturally occurring amino acid with a well-established safety profile. As a research chemical, it may cause skin irritation (H315), serious eye irritation (H319), and respiratory irritation (H335). Standard laboratory safety precautions should be followed, including wearing protective gloves and eye protection. The toxicological properties have not been fully investigated. The compound is considered a mild irritant and should be handled with care.
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| References | |
| Additional Infomation |
Tyrosine is an α-amino acid, a form of phenylalanine with a hydroxyl substituent at the 4-position of the benzene ring. It is a metabolite of the large flea (Daphnia magna). Tyrosine is an α-amino acid, a polar amino acid, and an aromatic amino acid. It contains a 4-hydroxybenzyl group. Functionally, it is associated with propionic acid. It is the conjugate base of tyrosine salts. It is the conjugate acid of the tyrosine anion (1-). DL-tyrosine has been reported to exist in Drosophila melanogaster, Mycoplasma gallisepticum, and other organisms with relevant data.
DL-Tyrosine is a natural product and research compound, not an approved pharmaceutical drug. It is widely used in biochemical, neurological, and metabolic research to study neurotransmitter synthesis, stress response, and endocrine regulation. The compound is also used in traditional Chinese medicine research and is found in various herbal medicines such as Panax ginseng. It serves as a crucial research compound in neuroscience and biochemistry for studying neurotransmitter synthesis, protein function, and cellular signaling pathways. No clinical trials have been reported for this compound. |
| Molecular Formula |
C9H11NO3
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|---|---|
| Molecular Weight |
181.19
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| Exact Mass |
181.073
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| CAS # |
556-03-6
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| Related CAS # |
DL-Tyrosine-13C9,15N; 202407-26-9; DL-Tyrosine-d7; 402835-78-3; DL-Tyrosine-d2; 35693-18-6; DL-Tyrosine-d3; 73036-42-7
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| PubChem CID |
1153
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| Appearance |
White to off-white solid
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
385.2±32.0 °C at 760 mmHg
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| Melting Point |
>300ºC
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| Flash Point |
186.7±25.1 °C
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| Vapour Pressure |
0.0±0.9 mmHg at 25°C
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| Index of Refraction |
1.614
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| LogP |
0.38
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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 |
3
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| Heavy Atom Count |
13
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| Complexity |
176
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O([H])C(C([H])(C([H])([H])C1C([H])=C([H])C(=C([H])C=1[H])O[H])N([H])[H])=O
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| InChi Key |
OUYCCCASQSFEME-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)
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| Chemical Name |
2-amino-3-(4-hydroxyphenyl)propanoic acid
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| Synonyms |
DL-Tyrosine
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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) |
0.1 M NaOH: 10 mg/mL (55.19 mM)
0.1 M HCL: 5 mg/mL (27.60 mM) DMSO: < 1 mg/mL H2O: < 0.1 mg/mL |
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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 | 5.5191 mL | 27.5953 mL | 55.1907 mL | |
| 5 mM | 1.1038 mL | 5.5191 mL | 11.0381 mL | |
| 10 mM | 0.5519 mL | 2.7595 mL | 5.5191 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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