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2-Hydroxyisobutyric acid

Cat No.:V82156 Purity: ≥98%
2-Hydroxyisobutyric acid is an endogenously produced metabolite.
2-Hydroxyisobutyric acid
2-Hydroxyisobutyric acid Chemical Structure CAS No.: 594-61-6
Product category: Endogenous Metabolite
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
250mg
500mg
Other Sizes

Other Forms of 2-Hydroxyisobutyric acid:

  • 2-Hydroxyisobutyric acid-d6
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
2-Hydroxyisobutyric acid is an endogenously produced metabolite.
2-Hydroxyisobutyric acid (2-HIBA) (CAS: 594-61-6) is a short-chain branched-chain hydroxyl fatty acid. It is a cellular metabolite detected at high levels in the urine of obese individuals and is associated with the presence of certain gut microbiota and type 2 diabetes.
Biological Activity I Assay Protocols (From Reference)
Targets
2-HIBA targets multiple metabolic pathways. It promotes beta-oxidation and inhibits fatty acid synthesis by upregulating SKN-1/NRF2 and downregulating SREBP-1c transcription factors. It also binds to mitochondrial complex I subunit ND3 (MT-ND3) to boost mitochondrial respiratory chain homeostasis. It serves as a biomarker for insulin resistance.
ln Vitro
In vitro, 2-Hydroxyisobutyric acid (0.1-10 mM) has been shown to regulate mitochondrial disorders, promote beta-oxidation, and inhibit fatty acid synthesis. It is used as a standard in metabolomics and as a tool to study the effects of short-chain fatty acids on cellular energy metabolism.
ln Vivo
In animal studies, 2-Hydroxyisobutyric acid is being studied for its potential applications in treating metabolic diseases such as obesity and diabetes. It has demonstrated anti-aging and lipid-lowering effects in vivo by upregulating NRF2 and downregulating SREBP-1c. It is also used to model metabolic acidosis.
Enzyme Assay
Non-cell assays are performed using purified enzymes to study 2-HIBA metabolism. It is a substrate for lactate dehydrogenase (LDH) and alpha-hydroxybutyrate dehydrogenase (alpha-HBDH), which catalyze its formation from alpha-ketobutyrate. Activity is measured by monitoring NADH oxidation at 340 nm in a coupled assay system.
Cell Assay
For cell studies, 2-Hydroxyisobutyric acid is dissolved in culture medium (0.1-10 mM, pH adjusted) and added to hepatocytes, adipocytes, or neuronal cells. Effects on mitochondrial respiration are assessed using a Seahorse analyzer. beta-oxidation is measured by the production of 3H2O from [3H]-palmitate. SREBP-1c and NRF2 expression are measured by qPCR.
Animal Protocol
In animal studies, 2-Hydroxyisobutyric acid is administered to rodents via oral gavage (50-500 mg/kg) or intraperitoneal injection. It is also added to drinking water for chronic studies. Blood glucose, insulin, and lipid profiles are measured. Liver and adipose tissue are collected for histology and gene expression analysis. Metabolic phenotyping is performed using indirect calorimetry.
ADME/Pharmacokinetics
2-Hydroxyisobutyric acid is water-soluble and is rapidly absorbed from the gut. It is metabolized via the citric acid cycle after conversion to propionyl-CoA. It is cleared primarily by the kidneys, with a plasma half-life of approximately 1-2 hours. It is also formed as a byproduct of glutathione synthesis and protein metabolism.
Toxicity/Toxicokinetics
2-Hydroxyisobutyric acid is of low toxicity, as it is a normal intermediate in propionate metabolism. At very high doses (>1 g/kg), it may cause metabolic acidosis and lethargy due to the accumulation of organic acids. The compound is generally considered safe for research use at physiological concentrations (50-500 microM).
Additional Infomation
2-Hydroxyisobutyric acid (2-HOH) is a 2-hydroxy monocarboxylic acid, consisting of isobutyric acid with a hydroxyl substituent at the 2-position. It is a metabolite of methyl tert-butyl ether (MTBE) and functions as an exogenous metabolite in the human body. Functionally, it is related to isobutyric acid and is the conjugate acid of 2-hydroxyisobutyrate esters. 2-HOH has been reported to be present in soybeans (Glycine max), chili peppers (Capsicum annuum), and several other organisms with relevant data.
2-Hydroxyisobutyric acid is used as a standard for metabolic profiling by GC-MS and LC-MS in clinical diagnostics, particularly as a biomarker for type 2 diabetes, pre-eclampsia, and obesity. It is also being investigated as a potential therapeutic agent for metabolic diseases with anti-aging and lipid-lowering effects. It is not an approved drug.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C4H8O3
Molecular Weight
104.11
Exact Mass
104.047
CAS #
594-61-6
Related CAS #
2-Hydroxyisobutyric acid-d6;40662-45-1
PubChem CID
11671
Appearance
White to off-white solid powder
Density
1.2±0.1 g/cm3
Boiling Point
212.0±0.0 °C at 760 mmHg
Melting Point
82.5 °C ; 82.5 °C
Flash Point
104.9±16.3 °C
Vapour Pressure
0.0±0.9 mmHg at 25°C
Index of Refraction
1.457
LogP
-0.35
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
1
Heavy Atom Count
7
Complexity
84.9
Defined Atom Stereocenter Count
0
SMILES
CC(C)(C(=O)O)O
InChi Key
BWLBGMIXKSTLSX-UHFFFAOYSA-N
InChi Code
InChI=1S/C4H8O3/c1-4(2,7)3(5)6/h7H,1-2H3,(H,5,6)
Chemical Name
2-hydroxy-2-methylpropanoic 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

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 (~960.52 mM)
H2O :≥ 100 mg/mL (~960.52 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (24.01 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 (24.01 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 (24.01 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 9.6052 mL 48.0261 mL 96.0523 mL
5 mM 1.9210 mL 9.6052 mL 19.2105 mL
10 mM 0.9605 mL 4.8026 mL 9.6052 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.

Calculator

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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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  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
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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.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

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)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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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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