yingweiwo

2-Hydroxybutyric acid

Cat No.:V29971 Purity: ≥98%
2-Hydroxybutyric acid (α-Hydroxybutyric acid) is converted from 2-Aminobutyric acid, and 2-oxobutyric acid is an intermediate metabolite.
2-Hydroxybutyric acid
2-Hydroxybutyric acid Chemical Structure CAS No.: 600-15-7
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
100mg
250mg
500mg
Other Sizes

Other Forms of 2-Hydroxybutyric acid:

  • (R)-2-Hydroxybutanoic acid ((R)-2-Hydroxybutyric acid; (R)-α-Hydroxybutyric acid)
  • Sodium 2-hydroxybutanoate
  • (S)-2-Hydroxybutanoic acid
Official Supplier of:
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Alternate Text
Top Publications Citing lnvivochem Products
Product Description
2-Hydroxybutyric acid (α-Hydroxybutyric acid) is converted from 2-Aminobutyric acid, and 2-oxobutyric acid is an intermediate metabolite.
2-Hydroxybutyric acid (CAS#: 600-15-7), also known as alpha-hydroxybutyrate, is an organic acid derived from alpha-ketobutyrate, which is produced by amino acid catabolism (threonine and methionine) and glutathione anabolism. It is formed as a byproduct from the formation of alpha-ketobutyrate via a reaction catalyzed by lactate dehydrogenase (LDH) or alpha-hydroxybutyrate dehydrogenase. 2-Hydroxybutyrate is an early marker for both insulin resistance and impaired glucose regulation that appears to arise due to increased lipid oxidation and oxidative stress. Its molecular formula is C4H8O3 with a molecular weight of 104.10 g/mol.
Biological Activity I Assay Protocols (From Reference)
Targets
2-Hydroxybutyric acid targets metabolic pathways involved in insulin resistance, glucose regulation, and oxidative stress. As an early marker for insulin resistance and impaired glucose regulation, its production is closely linked to increased lipid oxidation and oxidative stress. The compound is involved in propanoate metabolism and is primarily produced in mammalian hepatic tissues that catabolize L-threonine or synthesize glutathione. It is a potential biomarker for type 2 diabetes and preeclampsia.
ln Vitro
In vitro, 2-Hydroxybutyric acid is used as a biomarker for metabolic disorders. It prevents acetaminophen (AP)-induced liver injury. The compound is involved in the synthesis of glutathione, and its production is closely linked to oxidative stress and detoxification processes. It is an endogenous metabolite used in biochemical research to study insulin resistance, glucose regulation, and oxidative stress.
ln Vivo
In vivo, 2-Hydroxybutyric acid is a potential biomarker for type 2 diabetes and preeclampsia. It prevents acetaminophen-induced liver injury. Elevated levels of alpha-hydroxybutyrate in plasma are a good marker for early-stage type II diabetes. The compound is often found in the urine of patients suffering from lactic acidosis and ketoacidosis. It generally appears at high concentrations in situations related to deficient energy metabolism.
Enzyme Assay
In vitro enzyme assays for 2-Hydroxybutyric acid involve measuring its role as a metabolite in amino acid catabolism and glutathione synthesis. Enzymes such as lactate dehydrogenase (LDH) and alpha-hydroxybutyrate dehydrogenase catalyze the formation of 2-hydroxybutyric acid from alpha-ketobutyrate. Enzyme activity is assessed by monitoring the conversion of substrates to products. For biomarker studies, levels of 2-hydroxybutyric acid in biological samples are measured by HPLC or LC-MS. Assays are performed in appropriate buffer systems with positive controls.
Cell Assay
In vitro cell-based assays for 2-Hydroxybutyric acid are conducted in hepatic cells and other relevant cell types. Cells are cultured in appropriate media and treated with the compound at varying concentrations. For hepatoprotection studies, cells are treated with acetaminophen and 2-hydroxybutyric acid, and cell viability is assessed. Oxidative stress markers are measured. Glutathione levels are assessed to evaluate the compound's role in detoxification. Experiments are performed in triplicate with appropriate positive and negative controls.
Animal Protocol
2-Hydroxybutyric acid in vivo studies are conducted in animal models of metabolic disorders and liver injury. Animals are administered the compound via oral administration or injection. For biomarker studies, blood and urine samples are collected to measure 2-hydroxybutyric acid levels and assess its correlation with insulin resistance and diabetes. For hepatoprotection studies, animals are treated with acetaminophen and 2-hydroxybutyric acid, and liver injury markers are assessed. Animals are monitored for clinical signs. Tissues and blood samples are collected for biochemical analysis at study endpoints. Studies are conducted in accordance with institutional animal care guidelines.
ADME/Pharmacokinetics
2-Hydroxybutyric acid (MW 104.10 g/mol, C4H8O3) is an organic acid and endogenous metabolite. It is also known as alpha-hydroxybutyrate. The compound is soluble in water and other appropriate solvents. It is stable under recommended storage conditions. 2-Hydroxybutyric acid is a potential biomarker for type 2 diabetes and preeclampsia. Pharmacokinetic parameters such as half-life, bioavailability, and tissue distribution would be determined in species-specific studies.
Toxicity/Toxicokinetics
2-Hydroxybutyric acid is generally well-tolerated as an endogenous metabolite. The compound is an early marker for insulin resistance and impaired glucose regulation. It prevents acetaminophen-induced liver injury. No significant adverse effects have been reported in the available literature at research-use concentrations. The compound is intended for research use only. Standard laboratory safety practices should be employed when handling this compound. Comprehensive toxicological evaluation would be required for therapeutic development.
References

[1]. The formation of 2-hydroxybutyric acid in experimental animals. Clin Chim Acta. 1975 Jan 6;58(1):23-32.

[2]. Improvement in insulin resistance after gastric bypass surgery is correlated with a decline in plasma 2-hydroxybutyric acid. Surg Obes Relat Dis. 2018 Aug;14(8):1126-1132.

[3]. Vancomycin pretreatment attenuates acetaminophen-induced liver injury through 2-hydroxybutyric acid. J Pharm Anal. 2020 Dec;10(6):560-570.

[4]. Metabolomic analysis-identified 2-hydroxybutyric acid might be a key metabolite of severe preeclampsia. Open Life Sci. 2023 Feb 28;18(1):20220572.

Additional Infomation
2-Hydroxybutyric acid (2-HHB) is a hydroxybutyric acid with a single hydroxyl group at the 2-position. Alcohol consumption or strenuous exercise increases the secretion of 2-HHB in urine, and it is associated with lactic acidosis and ketoacidosis in humans, as well as diabetes in animals. It is a metabolite in both humans and algae. It is a hydroxybutyric acid and a 2-hydroxy monocarboxylic acid. Functionally, it is related to butyric acid. It is the conjugate acid of 2-HHB. 2-HHB is a metabolite found or produced in Escherichia coli (K12 strain, MG1655 strain). It has also been reported to be present in African aloe vera, chili peppers, and other organisms with relevant data. 2-HHB is a metabolite found or produced in Saccharomyces cerevisiae.
2-Hydroxybutyric acid (alpha-hydroxybutyrate) is an organic acid derived from alpha-ketobutyrate and an early marker for insulin resistance and impaired glucose regulation. It is formed by lactate dehydrogenase or alpha-hydroxybutyrate dehydrogenase. The compound prevents acetaminophen-induced liver injury and is a potential biomarker for type 2 diabetes and preeclampsia. Its production is linked to oxidative stress and glutathione synthesis. All applications are limited to non-human research use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C4H8O3
Molecular Weight
104.10452
Exact Mass
104.047
CAS #
600-15-7
Related CAS #
(R)-2-Hydroxybutanoic acid;20016-85-7;Sodium 2-hydroxybutanoate;5094-24-6;(S)-2-Hydroxybutanoic acid;3347-90-8
PubChem CID
11266
Appearance
White to off-white <44.2°C solid powder,>44.2°C liquid
Density
1.2±0.1 g/cm3
Boiling Point
238.3±13.0 °C at 760 mmHg
Melting Point
44ºC
Flash Point
112.2±16.3 °C
Vapour Pressure
0.0±1.1 mmHg at 25°C
Index of Refraction
1.455
LogP
-0.17
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
2
Heavy Atom Count
7
Complexity
69.3
Defined Atom Stereocenter Count
0
SMILES
CCC(C(=O)O)O
InChi Key
AFENDNXGAFYKQO-UHFFFAOYSA-N
InChi Code
InChI=1S/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7)
Chemical Name
2-hydroxybutanoic 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 (~960.61 mM )
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (24.02 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 (24.02 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.

View More

Solubility in Formulation 3: ≥ 2.5 mg/mL (24.02 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 9.6061 mL 48.0307 mL 96.0615 mL
5 mM 1.9212 mL 9.6061 mL 19.2123 mL
10 mM 0.9606 mL 4.8031 mL 9.6061 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

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
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?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • 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)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
/

Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
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.)
+
+
+

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.

Contact Us