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2,2-Dihydroxyacetic acid (glyoxylic acid hydrate)

Cat No.:V72355 Purity: ≥98%
2,2-Dihydroxyacetic acid is an endogenously produced metabolite.
2,2-Dihydroxyacetic acid (glyoxylic acid hydrate)
2,2-Dihydroxyacetic acid (glyoxylic acid hydrate) Chemical Structure CAS No.: 563-96-2
Product category: Endogenous Metabolite
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
2,2-Dihydroxyacetic acid is an endogenously produced metabolite.
2,2-Dihydroxyacetic acid (glyoxylic acid monohydrate) is an endogenous metabolite and the monohydrate form of glyoxylic acid. It is an intermediate in the glyoxylate cycle, which enables certain organisms to convert fatty acids to carbohydrates. It has been found to be associated with primary hyperoxaluria, an inborn error of metabolism.
Biological Activity I Assay Protocols (From Reference)
Targets
2,2-Dihydroxyacetic acid targets the glyoxylate cycle and metabolic pathways involving glyoxylate. As an aldehyde, it may modify proteins to form advanced glycation end products (AGEs). It may participate in microbial glyoxylate cycle and induce an increase in reactive oxygen species (ROS). It promotes cell differentiation.
ln Vitro
In vitro, 2,2-dihydroxyacetic acid induces an increase in reactive oxygen species and promotes cell differentiation. It may modify proteins to form AGEs. The compound is used to study the glyoxylate cycle and metabolic disorders such as primary hyperoxaluria. Its activity as an aldehyde makes it useful in studies of protein modification and oxidative stress.
ln Vivo
In vivo, 2,2-dihydroxyacetic acid is an endogenous metabolite involved in the glyoxylate cycle. It is associated with primary hyperoxaluria, a metabolic disorder characterized by excessive oxalate production. The compound may contribute to the pathophysiology of this condition. It is metabolized through glyoxylate pathways. As an aldehyde, it may have effects on protein function and oxidative stress in vivo.
Enzyme Assay
In vitro enzyme assays for glyoxylate cycle enzymes involve incubating the enzyme with 2,2-dihydroxyacetic acid in buffer at physiological pH. Glyoxylate is a substrate for alanine-glyoxylate aminotransferase and other enzymes. The compound's conversion to glycolate or oxalate is monitored by HPLC or enzymatic assays. For AGE formation studies, proteins are incubated with the compound at 37°C, and AGEs are detected by ELISA or fluorescence spectroscopy.
Cell Assay
For in vitro cell assays, cells are cultured in medium supplemented with 2,2-dihydroxyacetic acid at concentrations of 0.1-10 mM. Cell viability is assessed by MTT assay. ROS levels are measured using fluorescent probes such as DCFH-DA. Cell differentiation is evaluated by morphological changes and marker gene expression. Protein modification by AGEs is detected by Western blot or ELISA. Metabolic effects are analyzed by targeted metabolomics.
Animal Protocol
For in vivo animal studies, 2,2-dihydroxyacetic acid is administered to rodents via oral gavage or intraperitoneal injection at doses of 10-100 mg/kg. Blood and urine samples are collected for pharmacokinetic analysis. Oxalate and glycolate levels are quantified by HPLC or LC-MS/MS. In primary hyperoxaluria models, urinary oxalate excretion is measured. Tissue distribution and metabolic profiling are performed to understand its disposition.
ADME/Pharmacokinetics
2,2-Dihydroxyacetic acid has a molecular weight of 92.05. It is soluble in DMSO and water. The compound is stable under standard storage conditions. As the monohydrate of glyoxylic acid, it is an aldehyde that can undergo various chemical reactions. It is an intermediate in the glyoxylate cycle and is metabolized through glyoxylate pathways. Purity is typically ≥98% by HPLC.
Toxicity/Toxicokinetics
The compound is for research use only. No specific toxicity data are available in the search results. As an endogenous metabolite, it is expected to have low toxicity at physiological concentrations. However, as an aldehyde, it may be reactive and cause cellular damage at high concentrations through ROS generation and protein modification. Standard safety precautions should be followed.
Additional Infomation
2,2-Dihydroxyacetic acid (CAS# 563-96-2) is an endogenous metabolite and research reagent used primarily in studies of the glyoxylate cycle, primary hyperoxaluria, and protein glycation. It has not been investigated in clinical trials nor approved as a therapeutic drug. The compound is used in metabolic research and studies of oxidative stress and protein modification. It is also used as a chemical intermediate.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C2H4O4
Molecular Weight
92.05
Exact Mass
92.01
CAS #
563-96-2
Appearance
White to off-white solid powder
Density
1.33 g/mL at 20ºC
Boiling Point
100ºC
Melting Point
48-52ºC
Flash Point
>110ºC
Index of Refraction
n20/D 1.414
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: 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)
Solubility Data
Solubility (In Vitro)
DMSO: 100 mg/mL (1086.37 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (27.16 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 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 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to 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: ≥ 2.5 mg/mL (27.16 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 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
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.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (27.16 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 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 10.8637 mL 54.3183 mL 108.6366 mL
5 mM 2.1727 mL 10.8637 mL 21.7273 mL
10 mM 1.0864 mL 5.4318 mL 10.8637 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.

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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:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
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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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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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