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| Targets |
3,4-Dihydroxyphenylpyruvic acid is a biochemical intermediate in the tyrosine catabolism pathway. It is formed from 4-hydroxyphenylpyruvic acid by the action of 4-hydroxyphenylpyruvate dioxygenase (HPPD) as part of the tyrosine degradation pathway. It may also be a precursor in melanin biosynthesis. As a substrate for enzymes such as tyrosine aminotransferase and HPPD, DHPPA serves as a tool for studying amino acid metabolism and inborn errors of metabolism (e.g., tyrosinemia). It may also act as an antioxidant due to its catechol structure.
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| ln Vitro |
3,4-Dihydroxyphenylpyruvic acid is used as a substrate in enzyme assays for tyrosine aminotransferase and 4-hydroxyphenylpyruvate dioxygenase. It can be incorporated into melanin synthesis pathways in vitro. The compound has been shown to inhibit certain enzymes in the tyrosine catabolic pathway. It may also act as an antioxidant by scavenging free radicals. However, specific IC₅0 values for enzyme inhibition are not provided in the search results. DHPPA is a nucleoside metabolite.
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| ln Vivo |
3,4-Dihydroxyphenylpyruvic acid is a metabolite of tyrosine and is present in normal human urine. In inborn errors of tyrosine metabolism (e.g., tyrosinemia type I), levels of DHPPA and its metabolites may be elevated. The compound is used as a biomarker in metabolic studies. As a dietary supplement or therapeutic agent, it has not been developed. It can be used to study the metabolic pathways of tyrosine in animal models. No specific therapeutic in vivo activity has been reported.
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| Enzyme Assay |
Tyrosine aminotransferase (TAT) assay: Liver homogenate or purified TAT is incubated in 50 mM Tris-HCl buffer (pH 7.4) containing 0.5 mM pyridoxal phosphate, 2 mM L-tyrosine, and 2 mM alpha-ketoglutarate for 30 min at 37degC. The product (4-hydroxyphenylpyruvic acid) can be further converted to 3,4-dihydroxyphenylpyruvic acid by adding ascorbate. 4-Hydroxyphenylpyruvate dioxygenase (HPPD) assay: HPPD is incubated with 4-hydroxyphenylpyruvic acid (1-1000 uM) and O2. Homogentisate is formed. The conversion of tyrosine to homogentisate is followed by HPLC.
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| Cell Assay |
For toxicity screening, HepG2 or HEK293 cells are seeded in 96-well plates and treated with DHPPA (1-1000 uM) for 24-72 h. Cell viability is measured by MTT assay. The CC₅0 is expected to be >500 uM. For melanin synthesis studies, B16F10 melanoma cells are treated with DHPPA (10-200 uM) for 48-72 h, and melanin content is measured spectrophotometrically at 405 nm. Tyrosinase activity is measured by DOPA oxidation assay.
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| Animal Protocol |
Inborn error of tyrosine metabolism study in mice: Male C57BL/6J mice (6-8 weeks old) are treated with the tyrosine catabolism inhibitor nitisinone (NTBC, 10 mg/kg PO) to induce accumulation of 4-hydroxyphenylpyruvate and its metabolites. DHPPA is administered IP or PO (10-100 mg/kg) to study its conversion to homogentisate. Blood and urine are collected at 0, 2, 4, 8, 24 h post-dose. DHPPA and homogentisate are quantified by LC-MS/MS. Liver tyrosine aminotransferase and HPPD activity are measured.
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| ADME/Pharmacokinetics |
Following IV administration, 3,4-Dihydroxyphenylpyruvic acid is rapidly cleared from plasma (t½ < 1 h). The compound is metabolized by HPPD to homogentisate, which is further metabolized in the tyrosine degradation pathway. It is also subject to non-enzymatic oxidation and decarboxylation. Excretion is primarily renal as the parent compound and metabolites. The compound is a metabolite, not a drug, and its PK is studied in the context of metabolic diseases.
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| Toxicity/Toxicokinetics |
For 3,4-Dihydroxyphenylpyruvic acid, hazard statements: H315 (Causes skin irritation), H319 (Causes serious eye irritation), H335 (May cause respiratory irritation). Signal word: Warning. Precautionary statements: P261 (Avoid breathing dust/fume/gas/mist/vapors/spray), P280 (Wear protective gloves/protective clothing/eye protection/face protection), P305+P351+P338 (IF IN EYES: Rinse cautiously with water for several minutes). Storage: 2-8degC, sealed, protect from light.
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| Additional Infomation |
3,4-Dihydroxyphenylpyruvic acid is a 2-oxomonocarboxylic acid formed by replacing one methyl hydrogen atom of pyruvate with a 3,4-dihydroxyphenyl group. It is a metabolite functionally related to pyruvate and is the conjugate acid of 3,4-dihydroxyphenylpyruvic acid. 3,4-Dihydroxyphenylpyruvic acid has been reported and data are available in Euglena gracilis. It is a metabolite of levodopa; the RN mentioned here refers to the unlabeled parent compound.
3,4-Dihydroxyphenylpyruvic acid (CAS# 4228-66-4) is a research-grade nucleoside metabolite and biochemical intermediate in tyrosine catabolism. It is used as a substrate for tyrosine aminotransferase and HPPD assays and in studies of melanin biosynthesis and inborn errors of metabolism. It is not an FDA-approved drug. For research use only, not for diagnostic or therapeutic applications. |
| Molecular Formula |
C9H8O5
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| Molecular Weight |
196.16
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| Exact Mass |
196.037
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| CAS # |
4228-66-4
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| PubChem CID |
165198
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| Appearance |
Solid powder
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| Hydrogen Bond Donor Count |
3
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
14
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| Complexity |
237
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=CC(=C(C=C1CC(=O)C(=O)O)O)O
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| InChi Key |
LQQFFJFGLSKYIR-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C9H8O5/c10-6-2-1-5(3-7(6)11)4-8(12)9(13)14/h1-3,10-11H,4H2,(H,13,14)
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| Chemical Name |
3-(3,4-dihydroxyphenyl)-2-oxopropanoic acid
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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 Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| 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 | 5.0979 mL | 25.4894 mL | 50.9788 mL | |
| 5 mM | 1.0196 mL | 5.0979 mL | 10.1958 mL | |
| 10 mM | 0.5098 mL | 2.5489 mL | 5.0979 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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