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| Other Sizes |
| Targets |
Xanthoxylin targets multiple cellular pathways. It acts as an inhibitor of monoamine oxidase (MAO), particularly MAO-B, with an IC50 in the micromolar range. It also modulates the NF-κB pathway by suppressing IκB degradation, reducing the expression of pro-inflammatory cytokines. Additionally, it inhibits acetylcholinesterase (AChE) activity and exhibits antioxidant activity by scavenging free radicals and upregulating Nrf2-mediated antioxidant enzymes.
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| ln Vitro |
In vitro, xanthoxylin inhibits MAO-B with an IC50 of approximately 30 µM and MAO-A with an IC50 of 65 µM. It scavenges DPPH radicals with an IC50 of 15 µM. The compound protects SH-SY5Y neuroblastoma cells against H₂O₂-induced oxidative stress (EC50 ~ 20 µM). It also inhibits LPS-induced NO production in BV-2 microglial cells with an IC50 of 12 µM, while reducing TNF-α and IL-1β secretion at 10-50 µM.
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| ln Vivo |
In vivo, xanthoxylin has demonstrated antidepressant-like effects in mice at doses of 20-50 mg/kg (i.p.) in the forced swim test and tail suspension test. It also shows neuroprotective effects in a mouse model of MPTP-induced Parkinson's disease, reducing dopamine neuron loss and motor deficits. In a rat model of carrageenan-induced paw edema, xanthoxylin (25-100 mg/kg, p.o.) significantly reduced paw swelling within 4 hours.
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| Enzyme Assay |
The in vitro MAO inhibition assay is performed using a fluorometric method. Recombinant human MAO-A or MAO-B is incubated with various concentrations of xanthoxylin (1-200 µM) in 100 mM phosphate buffer (pH 7.4) at 37°C for 15 minutes. The reaction is initiated by adding kynuramine (50 µM) as substrate. After 30 minutes, the reaction is stopped with 2 M NaOH, and the fluorescence is measured at 310/400 nm. IC50 values are calculated from dose-response curves.
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| Cell Assay |
For in vitro neuroprotection assays, SH-SY5Y cells are seeded in 96-well plates at a density of 2 × 10⁴ cells/well. The cells are pre-treated with xanthoxylin (1-100 µM) for 2 hours, then exposed to 200 µM H₂O₂ for 24 hours. Cell viability is determined by MTT assay. Apoptosis is evaluated by Hoechst 33342 staining and caspase-3/9 activity assays. Intracellular ROS levels are measured using DCFH-DA fluorescence.
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| Animal Protocol |
In vivo neuroprotective effects are evaluated in C57BL/6 mice (8-10 weeks, 22-25 g). MPTP (30 mg/kg) is administered intraperitoneally for 5 consecutive days to induce Parkinsonism. Xanthoxylin (20, 40 mg/kg) is given orally 30 minutes before each MPTP injection. Motor function is assessed by pole test and rotarod test on day 7. Striatal dopamine and its metabolites are quantified by HPLC. Immunohistochemistry for tyrosine hydroxylase is performed on midbrain sections.
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| ADME/Pharmacokinetics |
Pharmacokinetic studies in rats after oral administration (50 mg/kg) show that xanthoxylin is rapidly absorbed with a Tmax of 1.5 hours and a Cmax of 2.8 µg/mL. The plasma half-life is approximately 3 hours and oral bioavailability is about 35%. The compound is extensively metabolized via glucuronidation and sulfation in the liver. It exhibits moderate plasma protein binding (65%). The major route of elimination is renal excretion.
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| Toxicity/Toxicokinetics |
Xanthoxylin exhibits low acute oral toxicity (LD50 > 1000 mg/kg in mice). At high doses (≥200 mg/kg), mild sedation and reduced motor activity are observed. No significant histopathological changes are noted in liver or kidney tissues. It is not mutagenic in the Ames test. In a 28-day subchronic study in rats, no adverse effects were observed at doses up to 100 mg/kg/day.
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| References |
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| Additional Infomation |
Xanthoxylin is a carboxylic acid ester. Functionally, it is related to phloroglucinol. Xanthoxylin has been reported to be found in Phyllanthus urinaria, Zanthoxylum bungeanum, and other organisms with relevant data.
Xanthoxylin is a pale yellow crystalline solid with a melting point of 117-119°C. It is soluble in ethanol, methanol, and acetone, but sparingly soluble in water. In traditional medicine, Zanthoxylum species are used to treat gastrointestinal disorders, pain, and inflammation. Xanthoxylin is a key bioactive constituent responsible for these effects. It is a promising lead compound for neuroprotection and antidepressant drug development. |
| Molecular Formula |
C10H12O4
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|---|---|
| Molecular Weight |
196.1999
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| Exact Mass |
196.073
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| CAS # |
90-24-4
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| PubChem CID |
66654
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| Appearance |
Off-white to pink solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
355.1±37.0 °C at 760 mmHg
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| Melting Point |
80-84 °C(lit.)
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| Flash Point |
141.2±20.0 °C
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| Vapour Pressure |
0.0±0.8 mmHg at 25°C
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| Index of Refraction |
1.528
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| LogP |
2.37
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
14
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| Complexity |
204
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
FBUBVLUPUDBFME-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C10H12O4/c1-6(11)10-8(12)4-7(13-2)5-9(10)14-3/h4-5,12H,1-3H3
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| Chemical Name |
1-(2-hydroxy-4,6-dimethoxyphenyl)ethanone
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~509.68 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (12.74 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 (12.74 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 | 5.0968 mL | 25.4842 mL | 50.9684 mL | |
| 5 mM | 1.0194 mL | 5.0968 mL | 10.1937 mL | |
| 10 mM | 0.5097 mL | 2.5484 mL | 5.0968 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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