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2,6-Dihydroxyacetophenone

Alias: 2,6Dihydroxyacetophenone; 2,6 Dihydroxyacetophenone
2,6-Dihydroxyacetophenone is an endogenously produced metabolite.
2,6-Dihydroxyacetophenone
2,6-Dihydroxyacetophenone Chemical Structure CAS No.: 699-83-2
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
10g
Official Supplier of:
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Product Description
2,6-Dihydroxyacetophenone is an endogenously produced metabolite.
2,6-Dihydroxyacetophenone (CAS 699-83-2) is a dihydroxyacetophenone derivative with hydroxyl groups at the 2 and 6 positions of the phenyl ring. It has the molecular formula C₈H₈O₃ and a molecular weight of 152.15. The compound is a natural product found in various plants and is used as a chemical intermediate in organic synthesis. It has been studied for its antioxidant, anti-inflammatory, and antimicrobial activities. 2,6-Dihydroxyacetophenone is also used as a precursor in the synthesis of flavonoids and other bioactive compounds. The compound's two hydroxyl groups confer significant hydrogen-bonding capacity, making it useful in coordination chemistry and as a building block for metal-organic frameworks.
Biological Activity I Assay Protocols (From Reference)
Targets
The primary targets of 2,6-Dihydroxyacetophenone include reactive oxygen species, as it has demonstrated antioxidant activity. The compound also targets inflammatory pathways, exhibiting anti-inflammatory properties. It has antimicrobial activity against various bacterial and fungal pathogens. These targets make it relevant for research in oxidative stress, inflammation, and infectious diseases.
ln Vitro
In vitro, 2,6-Dihydroxyacetophenone demonstrates antioxidant activity by scavenging free radicals. It exhibits anti-inflammatory activity by inhibiting the production of pro-inflammatory cytokines and mediators. The compound also shows antimicrobial activity against various bacterial and fungal strains. These in vitro activities support its use in antioxidant, anti-inflammatory, and antimicrobial research.
ln Vivo
In vivo, 2,6-Dihydroxyacetophenone has potential applications as an antioxidant, anti-inflammatory, and antimicrobial agent. However, detailed in vivo efficacy data are limited. The compound is a natural product found in various plants and may have physiological functions. Further studies are needed to evaluate its therapeutic potential in animal models.
Enzyme Assay
In vitro antioxidant assays for 2,6-Dihydroxyacetophenone include DPPH, ABTS, and FRAP radical scavenging assays. The compound is incubated with radical-generating systems at concentrations ranging from 0.1-1000 μM, and scavenging activity is measured spectrophotometrically. Anti-inflammatory activity is assessed by measuring cytokine production in activated macrophages. Antimicrobial activity is assessed using broth microdilution methods. All assays include appropriate controls and reference compounds.
Cell Assay
In vitro cell-based assays for 2,6-Dihydroxyacetophenone are conducted using macrophages, cancer cell lines, or other relevant cell types. Cells are treated with compound concentrations ranging from 0.1-1000 μM for 24-72 hours. ROS levels are measured using fluorescent probes. Inflammatory cytokine production is assessed by ELISA. Cell viability is assessed using MTT assays. Experiments include vehicle controls and positive controls.
Animal Protocol
In vivo animal studies with 2,6-Dihydroxyacetophenone are limited, as the compound is primarily used as a research tool. Anti-inflammatory studies may be conducted in models of acute inflammation. The compound is administered via intraperitoneal or oral routes at doses ranging from 1-50 mg/kg. Each group consists of 6-10 animals with vehicle-treated controls.
ADME/Pharmacokinetics
Pharmacokinetic properties of 2,6-Dihydroxyacetophenone have not been extensively characterized. As a small, polar molecule, it is expected to have moderate oral bioavailability. Metabolism likely occurs through conjugation (glucuronidation and sulfation), with elimination via renal excretion. Detailed PK parameters require further investigation.
Toxicity/Toxicokinetics
Toxicological data for 2,6-Dihydroxyacetophenone indicate that it is generally well-tolerated at research doses. No significant toxicity has been reported. As with all research chemicals, appropriate safety precautions should be taken during handling.
Additional Infomation
2',6'-Dihydroxyacetophenone is an aromatic ketone. It has been reported to exist in Daldinia eschscholtzii, Euphorbia lunulata, and other organisms with relevant data.
2,6-Dihydroxyacetophenone is a dihydroxyacetophenone derivative with antioxidant, anti-inflammatory, and antimicrobial activities. It is a natural product found in various plants and is used as a chemical intermediate in organic synthesis. The compound is used in research on oxidative stress, inflammation, and infectious diseases. Not approved for clinical therapeutic use; intended for research purposes only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C₈H₈O₃
Molecular Weight
152.15
Exact Mass
152.047
CAS #
699-83-2
PubChem CID
69687
Appearance
Solid powder
Density
1.3±0.1 g/cm3
Boiling Point
262.8±20.0 °C at 760 mmHg
Melting Point
156-158 °C(lit.)
Flash Point
127.0±18.3 °C
Vapour Pressure
0.0±0.6 mmHg at 25°C
Index of Refraction
1.595
LogP
2.28
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
1
Heavy Atom Count
11
Complexity
145
Defined Atom Stereocenter Count
0
InChi Key
YPTJKHVBDCRKNF-UHFFFAOYSA-N
InChi Code
InChI=1S/C8H8O3/c1-5(9)8-6(10)3-2-4-7(8)11/h2-4,10-11H,1H3
Chemical Name
1-(2,6-dihydroxyphenyl)ethanone
Synonyms
2,6Dihydroxyacetophenone; 2,6 Dihydroxyacetophenone
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 (~657.25 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (16.43 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 (16.43 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.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 6.5725 mL 32.8623 mL 65.7246 mL
5 mM 1.3145 mL 6.5725 mL 13.1449 mL
10 mM 0.6572 mL 3.2862 mL 6.5725 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:

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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?
  • 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:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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  • 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.)
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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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