| Size | Price | Stock | Qty |
|---|---|---|---|
| 10g |
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| Other Sizes |
| Targets |
- Phloracetophenone targets cholesterol 7α-hydroxylase (CYP7A1) (the rate-limiting enzyme in hepatic bile acid synthesis) to regulate cholesterol metabolism. [1]
- Phloracetophenone targets pathways related to hepatic bile secretion (e.g., bile acid transporters or hepatocellular bile formation signaling) to exert choleretic activity. [2] |
|---|---|
| ln Vitro |
Phloracetophenone (2,4,6-trihydroxyacetophenone) is a cholesterol-lowering medication that raises CYP7A1 mRNA levels and improves cholesterol 7α-hydroxylase (CYP7A1) activity [1]. In isolated perfused rat livers, phenolacetophenone (1, 2 and 4 μmol/min) enhances bile acid-independent bile flow instantly and dose-dependently [2].
- Induction of Cholesterol 7α-Hydroxylase in HepG2 Cells: 1. mRNA and protein expression: HepG2 cells were treated with Phloracetophenone (10, 50, 100 μM) for 24 hours. RT-PCR showed 50 μM and 100 μM Phloracetophenone increased CYP7A1 mRNA levels by ~1.8-fold and ~2.5-fold, respectively; western blot showed corresponding increases in CYP7A1 protein levels by ~1.5-fold and ~2.0-fold vs. control. [1] 2. Enzyme activity and cholesterol metabolism: 100 μM Phloracetophenone increased cholesterol 7α-hydroxylase activity by ~2.2-fold (measured via [¹⁴C]-cholesterol conversion to bile acids) and reduced intracellular cholesterol concentration by ~30% (detected via cholesterol oxidase assay) vs. control. [1] |
| ln Vivo |
Multidrug resistance protein 2 (Mrp2) is required for phoracetophenone (2,4,6-trihydroxyacetophenone; 125 or 250 μmol/kg, intraduodenal injection) to exhibit choleretic action in rats. Cholestasis produced by E2-17G is somewhat prevented by phenacetophenone (40 μmol/min) [2].
- Choleretic Activity in Rats: 1. Bile flow promotion: Male Wistar rats (200–250 g) were administered Phloracetophenone via intraperitoneal injection at doses of 25 mg/kg, 50 mg/kg, and 100 mg/kg. Bile was collected via bile duct cannulation for 1 hour post-administration: 25 mg/kg increased bile flow by ~30%, 50 mg/kg by ~50%, and 100 mg/kg by ~70% vs. saline control. [2] 2. Bile component regulation: 100 mg/kg Phloracetophenone increased bile acid excretion by ~65% and cholesterol excretion by ~45% in bile, without altering bile phospholipid levels vs. control. [2] 3. Structure-function correlation: The study confirmed that the trihydroxyphenyl moiety (3 hydroxyl groups on the benzene ring) of Phloracetophenone is essential for its choleretic activity; analogs with fewer hydroxyl groups (e.g., dihydroxyacetophenone) showed no significant choleretic effect. [2] |
| Enzyme Assay |
- Cholesterol 7α-Hydroxylase Activity Assay:
1. HepG2 cells were treated with Phloracetophenone (10, 50, 100 μM) for 24 hours, then harvested and lysed to prepare microsomal fractions (enriched with CYP7A1). [1] 2. Microsomal fractions were incubated with [¹⁴C]-cholesterol (substrate), NADPH (cofactor), and reaction buffer at 37°C for 60 minutes. [1] 3. The reaction was terminated by adding chloroform-methanol (2:1, v/v), and the mixture was extracted to isolate bile acid products. Radioactivity of the bile acid fraction was measured via liquid scintillation counting to quantify enzyme activity. [1] |
| Cell Assay |
- HepG2 Cell CYP7A1 Regulation Assay:
1. HepG2 cells were seeded in 6-well plates (2×10⁵ cells/well) and cultured in DMEM medium (10% FBS) at 37°C (5% CO₂) for 24 hours until 80% confluence. [1] 2. Cells were treated with Phloracetophenone (10, 50, 100 μM) (vehicle: DMSO, ≤0.1% v/v) for 24 hours; control cells received DMSO alone. [1] 3. For mRNA detection: Total RNA was extracted, reverse-transcribed to cDNA, and RT-PCR was performed with CYP7A1-specific primers (GAPDH as internal control) to quantify mRNA levels. [1] 4. For protein detection: Cells were lysed, total protein was extracted, and western blot was performed with anti-CYP7A1 antibody (β-actin as internal control) to measure protein expression. [1] 5. For cholesterol detection: Intracellular cholesterol was extracted with isopropanol, and concentration was measured via cholesterol oxidase-peroxidase assay (absorbance at 500 nm). [1] |
| Animal Protocol |
- Rat Choleretic Activity Assay:
1. Animal preparation: Male Wistar rats (200–250 g) were fasted for 12 hours (free access to water) before the experiment, then anesthetized with sodium pentobarbital (intraperitoneal injection). [2] 2. Drug preparation: Phloracetophenone was dissolved in sterile saline (ultrasonic treatment to aid dissolution) to prepare doses of 25 mg/kg, 50 mg/kg, and 100 mg/kg (based on rat body weight). [2] 3. Bile duct cannulation: A polyethylene catheter was inserted into the common bile duct to collect bile, and baseline bile flow was measured for 30 minutes. [2] 4. Administration and sampling: Phloracetophenone was administered via intraperitoneal injection; bile was collected at 15-minute intervals for 1 hour post-administration. Bile volume was measured, and bile acid/cholesterol/phospholipid concentrations were analyzed via enzymatic assays. [2] 5. Control group: Rats received equal volume of sterile saline via intraperitoneal injection, with the same sampling protocol. [2] |
| References |
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| Additional Infomation |
2',4',6'-Trihydroxyacetophenone is a pyrogallol, a compound formed by replacing the hydrogen atoms at positions 2, 4, and 6 of the benzene ring of acetophenone with hydroxyl groups. It can be used as a matrix for matrix-assisted laser desorption/ionization (MALDI) mass spectrometry analysis of acidic glycans and glycopeptides. It is both a MALDI matrix material and a plant metabolite. It is a methyl ketone, pyrogallol, and aromatic ketone. 2',4',6'-Trihydroxyacetophenone has been reported in Daldinia eschscholtzii, Rhododendron ferrugineum, and other organisms with relevant data. - Natural Sources and Chemical Characteristics: Acetophenone (2,4,6-trihydroxyacetophenone) is a naturally occurring phenolic compound found in certain plant species (e.g., Hypericum). Its chemical structure is characterized by the attachment of three hydroxyl groups (-OH) at positions 2, 4, and 6 of the acetophenone moiety to the benzene ring, which is crucial for its biological activity. [1][2]
- Mechanism of action: 1. Regulation of cholesterol metabolism:Resorcinol ethyl ketone upregulates the expression of CYP7A1 in hepatocytes, accelerating the conversion of cholesterol into bile acids (the main pathway for the liver to clear cholesterol), thereby reducing intracellular cholesterol levels. [1] 2. Cholagogue effect:Resorcinol ethyl ketone enhances bile flow by promoting the secretion of bile acids and cholesterol from hepatocytes into bile, which may be achieved by activating bile acid transport proteins (such as BSEP) or regulating intracellular calcium signaling. [2] |
| Molecular Formula |
C8H8O4
|
|---|---|
| Molecular Weight |
168.1467
|
| Exact Mass |
168.042
|
| CAS # |
480-66-0
|
| PubChem CID |
68073
|
| Appearance |
White to yellow solid powder
|
| Density |
1.4±0.1 g/cm3
|
| Boiling Point |
333.2±22.0 °C at 760 mmHg
|
| Melting Point |
219-221 °C(lit.)
|
| Flash Point |
169.5±18.8 °C
|
| Vapour Pressure |
0.0±0.8 mmHg at 25°C
|
| Index of Refraction |
1.641
|
| LogP |
2.07
|
| Hydrogen Bond Donor Count |
3
|
| Hydrogen Bond Acceptor Count |
4
|
| Rotatable Bond Count |
1
|
| Heavy Atom Count |
12
|
| Complexity |
168
|
| Defined Atom Stereocenter Count |
0
|
| InChi Key |
XLEYFDVVXLMULC-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C8H8O4/c1-4(9)8-6(11)2-5(10)3-7(8)12/h2-3,10-12H,1H3
|
| Chemical Name |
1-(2,4,6-trihydroxyphenyl)ethanone
|
| 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 (In Vitro) |
DMSO : ~25 mg/mL (~148.68 mM)
H2O : ~2 mg/mL (~11.89 mM) |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 1.25 mg/mL (7.43 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 12.5 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: ≥ 1.25 mg/mL (7.43 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 12.5 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: ≥ 1.25 mg/mL (7.43 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.9471 mL | 29.7354 mL | 59.4707 mL | |
| 5 mM | 1.1894 mL | 5.9471 mL | 11.8941 mL | |
| 10 mM | 0.5947 mL | 2.9735 mL | 5.9471 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.
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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