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2,4-Dihydroxybenzoic acid

Cat No.:V28879 Purity: ≥98%
2,4-Dihydroxybenzoic acid is a degradation product of tart cheeries in cell culture.
2,4-Dihydroxybenzoic acid
2,4-Dihydroxybenzoic acid Chemical Structure CAS No.: 89-86-1
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
500mg
Other Sizes
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Product Description
2,4-Dihydroxybenzoic acid is a degradation product of tart cheeries in cell culture.
2,4-Dihydroxybenzoic acid (CAS: 89-86-1) is a degradation product of acid cherry anthocyanins during in vitro cell culture and an analogue of coenzyme Q precursor molecules. It is a dihydroxybenzoic acid with the molecular formula C7H6O4. It is also a plant metabolite and a potential environmental pollutant.
Biological Activity I Assay Protocols (From Reference)
Targets
2,4-Dihydroxybenzoic acid targets multiple enzymes. It inhibits soybean 15-lipoxygenase activity by 47.7% and human recombinant 5-lipoxygenase by 62% at 1 mM. It also inhibits mouse recombinant iNOS by 16% at 1 mM. It shows strong inhibitory effects against α-glucosidase with IC50 values of 549 μg/mL. It is also associated with carbonic anhydrase II (CA2) and androgen receptor (AR).
ln Vitro
In vitro, 2,4-Dihydroxybenzoic acid demonstrates enzyme inhibitory activities. It inhibits 5-lipoxygenase, 15-lipoxygenase, and iNOS. It also shows strong α-glucosidase inhibitory activity. These activities suggest potential anti-inflammatory and antidiabetic properties. It can improve the related symptoms of kidney diseases caused by ADCK4/Cog6 deficiency.
ln Vivo
In vivo, 2,4-Dihydroxybenzoic acid is a degradation product and a metabolite. It is found frequently as a pollutant in natural waters. Its potential to improve kidney disease symptoms suggests possible in vivo efficacy, but specific in vivo studies are limited. Its role as a coenzyme Q precursor analogue suggests it may have effects on mitochondrial function.
Enzyme Assay
The in vitro enzyme inhibition assay for 2,4-Dihydroxybenzoic acid involves incubating the compound with the target enzyme (e.g., 5-lipoxygenase, 15-lipoxygenase, iNOS, or α-glucosidase) and a specific substrate. The enzyme activity is measured by detecting the reaction product using spectrophotometry or fluorometry, and the IC50 or percentage inhibition is calculated.
Cell Assay
In vitro cell culture studies for 2,4-Dihydroxybenzoic acid are limited. Its effect on kidney cells can be studied in models of ADCK4/Cog6 deficiency. Its anti-inflammatory effects can be studied in macrophage cell lines by measuring the production of nitric oxide or cytokines. Its antidiabetic effects can be studied by measuring its inhibition of α-glucosidase activity in cell lysates.
Animal Protocol
In vivo animal experiments for 2,4-Dihydroxybenzoic acid are not extensively documented. However, its effects on kidney diseases could be studied in animal models of ADCK4/Cog6 deficiency. Its potential as an environmental pollutant is studied in ecotoxicological models. Its effects on inflammation could be studied in models of acute inflammation.
ADME/Pharmacokinetics
2,4-Dihydroxybenzoic acid has a molecular formula of C7H6O4 and a molecular weight of 154.12 g/mol. It is a solid compound that is soluble in water and organic solvents. It is typically stored as a powder at room temperature for long-term stability. Its stability is maintained under recommended storage conditions.
Toxicity/Toxicokinetics
Toxicological data for 2,4-Dihydroxybenzoic acid indicate that it is a potential environmental pollutant and is a precursor to the formation of highly toxic quinones. It may be an irritant. As a research compound, it is not intended for human therapeutic use, and comprehensive toxicity studies are not available. Standard safety precautions should be followed.
References

[1]. Degradation products of cyanidin glycosides from tart cherries and their bioactivities. J Agric Food Chem. 2001 Oct;49(10):4924-9.

Additional Infomation
It has been reported that potatoes, coconuts, and other organisms with available data contain 2,4-dihydroxybenzoic acid.
2,4-Dihydroxybenzoic acid is a research compound with no clinical approval. It is used as a reference standard in analytical chemistry and as a tool for studying enzyme inhibition. Its inhibitory effects on lipoxygenases and α-glucosidase make it a compound of interest for research into inflammation and diabetes. It is also studied for its role as a coenzyme Q precursor analogue and its potential effects on kidney diseases.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C7H6O4
Molecular Weight
154.12014
Exact Mass
154.026
CAS #
89-86-1
Related CAS #
17289-70-2 (mono-hydrochloride salt);41453-50-3 (lead salt)
PubChem CID
1491
Appearance
White to off-white solid powder
Density
1.6±0.1 g/cm3
Boiling Point
414.8±15.0 °C at 760 mmHg
Melting Point
208-211 °C (dec.)(lit.)
Flash Point
218.8±16.9 °C
Vapour Pressure
0.0±1.0 mmHg at 25°C
Index of Refraction
1.671
LogP
1.6
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
1
Heavy Atom Count
11
Complexity
157
Defined Atom Stereocenter Count
0
InChi Key
UIAFKZKHHVMJGS-UHFFFAOYSA-N
InChi Code
InChI=1S/C7H6O4/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,8-9H,(H,10,11)
Chemical Name
2,4-dihydroxybenzoic 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 (~648.85 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (16.22 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 (16.22 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 (16.22 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 6.4885 mL 32.4423 mL 64.8845 mL
5 mM 1.2977 mL 6.4885 mL 12.9769 mL
10 mM 0.6488 mL 3.2442 mL 6.4885 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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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:
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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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