2. Metabolic Enzyme/Protease NF-κB Immunology/Inflammation Cell Cycle/DNA Damage Epigenetics Autophagy Apoptosis
  3. Tyrosinase Reactive Oxygen Species (ROS) Keap1-Nrf2 PARP Autophagy Apoptosis
  4. 3',4'-Dihydroxyacetophenone

3',4'-Dihydroxyacetophenone  (Synonyms: 3,4-DHAP)

Cat. No.: HY-N1775 Purity: 99.87%
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3',4'-Dihydroxyacetophenone (3,4-DHAP) is a phenolic compound with oral bioavailability, possessing potent antioxidant, anti-inflammatory, anticancer and cardiovascular protective activities. 3',4'-Dihydroxyacetophenone inhibits mushroom Tyrosinase activity with an IC50 of 10 μM, thereby suppressing melanogenesis. 3',4'-Dihydroxyacetophenone inhibits platelet aggregation in platelet-rich plasma. 3',4'-Dihydroxyacetophenone reduces ROS levels in human umbilical vein endothelial cells treated with high glucose, upregulates the expression of Nrf2, HO-1 and PARP-1 in cells, and promotes the nuclear translocation of Nrf2. 3',4'-Dihydroxyacetophenone induces autophagy and apoptosis. 3',4'-Dihydroxyacetophenone inhibits seed germination/growth in most plants. 3',4'-Dihydroxyacetophenone can be used in the research of cancer, neurodegenerative diseases, non-alcoholic steatohepatitis, diabetes, obesity, skin pigmentation disorders, and cardiovascular and cerebrovascular diseases.

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3',4'-Dihydroxyacetophenone

3',4'-Dihydroxyacetophenone Chemical Structure

CAS No. : 1197-09-7

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Based on 1 publication(s) in Google Scholar

Other Forms of 3',4'-Dihydroxyacetophenone:

3',4'-Dihydroxyacetophenone Related Antibodies

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PARP PARP1 PARP2 PARP3 PARP4 TNKS1/PARP5A TNKS2/PARP5B PARP7 PARP10 PARP14 PARP15 PARP12 PARP16

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Description

3',4'-Dihydroxyacetophenone (3,4-DHAP) is a phenolic compound with oral bioavailability, possessing potent antioxidant, anti-inflammatory, anticancer and cardiovascular protective activities. 3',4'-Dihydroxyacetophenone inhibits mushroom Tyrosinase activity with an IC50 of 10 μM, thereby suppressing melanogenesis. 3',4'-Dihydroxyacetophenone inhibits platelet aggregation in platelet-rich plasma. 3',4'-Dihydroxyacetophenone reduces ROS levels in human umbilical vein endothelial cells treated with high glucose, upregulates the expression of Nrf2, HO-1 and PARP-1 in cells, and promotes the nuclear translocation of Nrf2. 3',4'-Dihydroxyacetophenone induces autophagy and apoptosis. 3',4'-Dihydroxyacetophenone inhibits seed germination/growth in most plants. 3',4'-Dihydroxyacetophenone can be used in the research of cancer, neurodegenerative diseases, non-alcoholic steatohepatitis, diabetes, obesity, skin pigmentation disorders, and cardiovascular and cerebrovascular diseases[1][2][3][4][5][6].

IC50 & Target

IC50: 10 μM (Tyrosinase)[1].
In Vitro

3',4'-Dihydroxyacetophenone (3,4-DHAP) potently inhibits mushroom tyrosinase activity with an IC50 of 10 μM[2].
3',4'-Dihydroxyacetophenone (3,4-DHAP) (10-200 μM; 24 h) dose-dependently inhibits tyrosinase activity in α-MSH-stimulated B16 melanoma cells, with significant inhibition starting at 10 μM after 24 h of treatment[2].
3',4'-Dihydroxyacetophenone (3 min pre-incubation; 5 min aggregation monitoring) potently inhibits ADP-stimulated platelet aggregation in rabbit PRP with an IC50 of 99.22 µmol/l[3].
3',4'-Dihydroxyacetophenone (1-100 µmol/l; 6 h) increases viability of human umbilical vein endothelial cells at 10 µmol/l, while higher and lower concentrations reduce viability, and 10 µmol/l protects cells against high glucose-induced viability loss[5].
3',4'-Dihydroxyacetophenone (10 µmol/l; 6 h) significantly reduces reactive oxygen species levels in high glucose-treated human umbilical vein endothelial cells[5].
3',4'-Dihydroxyacetophenone (10 µmol/l; 6 h) significantly increases the LC3-II/LC3-I protein ratio, indicating enhanced autophagy, in high glucose-treated human umbilical vein endothelial cells[5].
3',4'-Dihydroxyacetophenone (3,4-DHAP) (0.1-10 mM; up to 21 days) dose-dependently inhibits Picea schrenkiana seed germination rate and vigor, with significant inhibition starting at 2.5 mM for germination rate and 1 mM for germination vigor, and complete elimination of vigor at 10 mM[6].
3',4'-Dihydroxyacetophenone (3,4-DHAP) (0.1-10 mM; up to 14 days) does not inhibit Oryza sativa seed germination rate, but significantly promotes germination vigor at 1, 2.5, and 10 mM[6].
3',4'-Dihydroxyacetophenone (3,4-DHAP) (0.1-10 mM; up to 30 days) dose-dependently inhibits Picea schrenkiana seedling shoot length, root length, and fresh weight, with significant inhibition starting at 5 mM for shoot length, 2.5 mM for root length and fresh weight[6].
3',4'-Dihydroxyacetophenone (3,4-DHAP) (0.1-10 mM; up to 10 days) dose-dependently inhibits Triticum aestivum seedling shoot length and root length (significant at 5 mM and 2.5 mM, respectively) and exhibits hormetic effects on fresh weight, promoting growth at 0.5 mM and inhibiting it at 2.5 mM and higher[6].
3',4'-Dihydroxyacetophenone (3,4-DHAP) (0.1-10 mM; up to 10 days) dose-dependently inhibits seedling root growth of Latuca sativa, Oryza sativa, Raphanus sativus, Cucumis sativus, and Phaseolus radiatus, with significant inhibition starting at concentrations ranging from 0.5 mM to 2.5 mM; it also promotes Raphanus sativus shoot growth at 10 mM[6].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

3',4'-Dihydroxyacetophenone Related Antibodies

Western Blot Analysis[2]

Cell Line: α-MSH-stimulated B16 melanoma cells
Concentration: 10, 50, and 250 μM
Incubation Time: 24 h
Result: Suppressed the amount of tyrosinase protein in α-MSH-stimulated B16 cells.

Cell Viability Assay[5]

Cell Line: human umbilical vein endothelial cells (HUVECs)
Concentration: 1, 10, 20, 50, 100 µM
Incubation Time: 6 h (pretreated prior to 12 h high glucose exposure; variable for viability assessment)
Result: Increased HUVEC viability significantly compared to the control group at 10 µmol/l.
Reduced cell viability at 1, 20, 50 µM and 100 µM.
Increased cell viability significantly compared to the high glucose group at 10 µM.

Western Blot Analysis[5]

Cell Line: human umbilical vein endothelial cells (HUVECs)
Concentration: 10 µM
Incubation Time: 6 h (pretreated prior to 12 h high glucose exposure)
Result: Increased total Nrf2 protein expression significantly compared to the high glucose group.\n
Increased nuclear Nrf2 protein expression significantly compared to the high glucose group.\n
Increased HO-1 protein expression significantly compared to the high glucose group.\n
Increased the LC3-II/LC3-I protein ratio significantly compared to the high glucose group.\n
Increased PARP-1 protein expression significantly compared to the high glucose group.

Real Time qPCR[5]

Cell Line: human umbilical vein endothelial cells (HUVECs)
Concentration: 10 µM
Incubation Time: 6 h (pretreated prior to 12 h high glucose exposure)
Result: Increased Nrf2 mRNA expression significantly compared to the high glucose group.
Increased HO-1 mRNA expression significantly compared to the high glucose group.

Immunofluorescence[5]

Cell Line: human umbilical vein endothelial cells (HUVECs)
Concentration: 10 µM
Incubation Time: 6 h (pretreated prior to 12 h high glucose exposure)
Result: Increased nuclear Nrf2 fluorescence intensity significantly compared to the high glucose group.
Parmacokinetics
Species Dose Route T1/2 CL/F AUC0-t AUC0-∞ MRT0-t T1/2 (Absorption) Bioavailability
Rat[3] 0.20 mM i.v. 0.15 h 2.30 L/h/kg 66.32 μM/L·h 87.48 μM/L·h 0.22 h / /
Rat[3] 0.39 mM i.m. 0.16 h 3.121 L/h/kg 124.22 μM/L·h 129.94 μM/L·h 0.46 h 0.14 h 93.81 %
Rat[3] 0.79 mM i.g. 0.16 h 17.39 L/h/kg 47.78 μM/L·h 48.64 μM/L·h 0.38 h 0.06 h 18.01 %
In Vivo

3',4'-Dihydroxyacetophenone (0.79 mM/kg; p.o.; single administration) exerts rapid and significant antiplatelet aggregation activity in healthy Wistar rats, but its activity decreases sharply at 40 min post-administration[3].
3',4'-Dihydroxyacetophenone (10 mg/kg; p.o.; daily; 8 weeks) improves endothelial function in rats with high-fat diet-induced obesity, as evidenced by enhanced endothelium-dependent vasodilation, upregulated activity of the eNOS-NO pathway, reduced oxidative stress and inflammatory responses, and improved lipid metabolism markers[4].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model: Wistar rats (male/female, 250-300 g)[3]
Dosage: 0.79 mmol/kg
Administration: i.g.; single dose
Result: Significantly inhibited platelet aggregation compared to vehicle controls at 10 minutes post-administration (P=0.003).
Showed significantly reduced antiplatelet aggregation activity at 40 minutes post-administration compared to 10 minutes post-administration (P=0.003).
Animal Model: Wistar (male, 6 weeks old, high-fat diet-induced obesity)[4]
Dosage: 10 mg/kg
Administration: p.o.; daily; 8 weeks
Result: Reduced plasma triglycerides, free fatty acids, serum tumor necrosis factor-α, and malondialdehyde.
Increased serum adiponectin.
Enhanced acetylcholine-induced endothelium-dependent vasodilatation.
Increased eNOS activity and NO production in endothelial cells.
Reduced NF-kB positive cells in the aorta.
Decreased superoxide anion production in the aorta.
Did not reduce body weight, visceral fat mass, or plasma insulin levels in obese rats.
Molecular Weight

152.15

Formula

C8H8O3
CAS No.
Appearance

Solid

Color

Light brown to brown

SMILES

CC(C1=CC=C(O)C(O)=C1)=O
Structure Classification
Initial Source
Shipping

Room temperature in continental US; may vary elsewhere.
Storage
Powder -20°C 3 years
4°C 2 years
In solvent -80°C 6 months
-20°C 1 month
Solvent & Solubility
In Vitro: 

DMSO : 50 mg/mL (328.62 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

Preparing
Stock Solutions
Concentration Solvent Mass 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
View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

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In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for in vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

  • Protocol 1

    Add each solvent one by one:  10% DMSO    40% PEG300    5% Tween-80    45% Saline

    Solubility: ≥ 2.5 mg/mL (16.43 mM); Clear solution

    This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).

    Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.

    Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
  • Protocol 2

    Add each solvent one by one:  10% DMSO    90% (20% SBE-β-CD in Saline)

    Solubility: ≥ 2.5 mg/mL (16.43 mM); Clear solution

    This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).

    Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.

    Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
In Vivo Dissolution Calculator
Please enter the basic information of animal experiments:

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Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Calculation results:
Working solution concentration: mg/mL
Method for preparing stock solution: mg drug dissolved in μL  DMSO (Stock solution concentration: mg/mL).
The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only. If necessary, please contact MedChemExpress (MCE).
Method for preparing in vivo working solution for animal experiments: Take μL DMSO stock solution, add μL . μL , mix evenly, next add μL Tween 80, mix evenly, then add μL Saline.
 If the continuous dosing period exceeds half a month, please choose this protocol carefully.
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Purity & Documentation

Purity: 99.92%

SDS (393 KB)

COA (249 KB) HNMR (127 KB) RP-HPLC (204 KB)

Handling Instructions (2659 KB)
References

Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Optional Solvent Concentration Solvent Mass 1 mg 5 mg 10 mg 25 mg
DMSO 1 mM 6.5725 mL 32.8623 mL 65.7246 mL 164.3115 mL
5 mM 1.3145 mL 6.5725 mL 13.1449 mL 32.8623 mL
10 mM 0.6572 mL 3.2862 mL 6.5725 mL 16.4312 mL
15 mM 0.4382 mL 2.1908 mL 4.3816 mL 10.9541 mL
20 mM 0.3286 mL 1.6431 mL 3.2862 mL 8.2156 mL
25 mM 0.2629 mL 1.3145 mL 2.6290 mL 6.5725 mL
30 mM 0.2191 mL 1.0954 mL 2.1908 mL 5.4771 mL
40 mM 0.1643 mL 0.8216 mL 1.6431 mL 4.1078 mL
50 mM 0.1314 mL 0.6572 mL 1.3145 mL 3.2862 mL
60 mM 0.1095 mL 0.5477 mL 1.0954 mL 2.7385 mL
80 mM 0.0822 mL 0.4108 mL 0.8216 mL 2.0539 mL
100 mM 0.0657 mL 0.3286 mL 0.6572 mL 1.6431 mL
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3',4'-Dihydroxyacetophenone Related Classifications

Help & FAQs
  • Do most proteins show cross-species activity?

    Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

Keywords:

3',4'-Dihydroxyacetophenone1197-09-73,4-DHAPTyrosinaseReactive Oxygen Species (ROS)Keap1-Nrf2PARPAutophagyApoptosispoly ADP ribose polymerase NF-κB pathwayJNK/Nrf2 pathwayAMPK pathway5-LOXFAKCOX-2MITFTLR4mushroom tyrosinaseeNOS-NO pathwayphenolic compoundHUVECsInhibitorinhibitorinhibit

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