| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| Targets |
8‑Geranyloxypsoralen targets β‑secretase 1 (BACE1), the rate‑limiting enzyme in the production of amyloid‑β peptides, which are implicated in Alzheimer’s disease pathogenesis. It inhibits BACE1 in a non‑competitive manner with an IC₅₀ of less than 25 µM. Additionally, it inhibits various cytochrome P450 isoforms (e.g., CYP3A4, CYP1A1, CYP2B1), and induces vasorelaxation through endothelium‑dependent mechanisms likely involving nitric oxide/cyclic GMP pathways. Its molecular targets also include voltage‑gated calcium channels.
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| ln Vitro |
In vitro, 8‑Geranyloxypsoralen shows significant inhibitory activity against BACE1 with an IC₅₀ < 25 µM, as measured by fluorogenic substrate cleavage assays. It also exhibits concentration‑dependent vasorelaxation in isolated rat aortic rings pre‑contracted with phenylephrine or KCl. The compound inhibits CYP3A4 with an IC₅₀ of approximately 5‑10 µM, which explains its potential for drug interactions. Furthermore, it displays moderate antioxidant activity in DPPH and ABTS assays. Its furanocoumarin scaffold is responsible for these multiple bioactivities.
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| ln Vivo |
In vivo activity data for 8‑Geranyloxypsoralen are limited. Its inhibition of CYP3A4 has been confirmed in animal models, where oral administration of grapefruit juice containing the compound increased plasma concentrations of co‑administered CYP3A4 substrates (e.g., felodipine). However, direct studies on BACE1 inhibition in vivo have not been extensively reported. Its vasorelaxant properties suggest potential cardiovascular effects, but formal efficacy studies in hypertensive animals are lacking. Further pharmacokinetic and pharmacodynamic investigations are needed to validate its therapeutic potential.
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| Enzyme Assay |
In vitro enzyme assays for 8‑Geranyloxypsoralen are conducted using recombinant human BACE1 enzyme. Enzyme activity is measured with a fluorogenic substrate (e.g., Mca-SEVNLDAEFRK(Dnp)-RR-NH₂) that releases a fluorescent signal upon cleavage. The compound is incubated with BACE1 and substrate at various concentrations (0‑100 µM) at pH 4.5 for 60 minutes. Fluorescence is read at excitation 320 nm/emission 405 nm. IC₅₀ values are derived from dose‑response curves. CYP inhibition assays are performed using human liver microsomes or recombinant CYP isoforms with specific probe substrates (e.g., midazolam for CYP3A4), and metabolite formation is quantified by LC‑MS/MS.
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| Cell Assay |
In vitro cellular assays for 8‑Geranyloxypsoralen are performed using neuronal cell lines (e.g., SH‑SY5Y) or primary cortical neurons to evaluate its effect on amyloid‑β production. Cells are treated with the compound (1‑50 µM) for 24‑48 hours, and secreted Aβ₄₀ and Aβ₄₂ levels in the medium are measured by ELISA. Cytotoxicity is assessed by LDH release or MTT. For vasorelaxation studies, rat aortic rings are mounted in organ baths, contracted with phenylephrine (1 µM), and cumulative concentrations of the compound (0.1‑100 µM) are added to measure relaxation. Endothelial integrity is verified by acetylcholine response.
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| Animal Protocol |
In vivo animal studies for 8‑Geranyloxypsoralen are typically conducted in rodents to assess its effect on drug metabolism. Rats or mice are administered the compound orally (e.g., 10‑50 mg/kg) or as grapefruit juice extract, followed by oral dosing of a CYP3A4 probe substrate (e.g., midazolam, nifedipine). Blood samples are collected at various time points, and plasma concentrations of the substrate and its metabolites are measured by LC‑MS/MS. Changes in AUC or Cmax reflect CYP3A4 inhibition. For cognitive studies, transgenic Alzheimer’s mouse models (e.g., APP/PS1) could be used, but such experiments are not widely reported.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for 8‑Geranyloxypsoralen have been studied in the context of food‑drug interactions. After oral ingestion, it is absorbed and reaches systemic circulation. Its lipophilic nature (logP ~4.5) confers high membrane permeability. It is extensively metabolized by CYP enzymes, and its half‑life in rats is approximately 2‑4 hours. Bioavailability is moderate due to first‑pass metabolism. In humans, consumption of grapefruit juice containing geranyloxypsoralen leads to significant inhibition of intestinal CYP3A4, increasing the bioavailability of co‑administered drugs. Detailed PK parameters are available from interaction studies.
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| Toxicity/Toxicokinetics |
Toxicological data for 8‑Geranyloxypsoralen are limited. As a natural furanocoumarin, it is generally recognized as safe at dietary levels found in citrus fruits. However, high doses may cause phototoxicity due to its psoralen‑like structure, which can form DNA adducts upon UV exposure. In standard laboratory settings, no acute toxicity has been reported at concentrations used in vitro. It is not intended for therapeutic use, and safety data for chronic administration are lacking. Standard precautions for handling phototoxic compounds should be followed.
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| References | |
| Additional Infomation |
9-[(3,7-dimethyl-2,6-octadienyl)oxy]-7H-furano[3,2-g][1]benzopyran-7-one is a terpene lactone. Xanthan toxin geraniol ether has been reported to be present in Angelica sinensis, Angelica pubescens, and other organisms with relevant data.
8‑Geranyloxypsoralen is a prenylated furanocoumarin found in citrus fruits that inhibits BACE1 (IC₅₀ < 25 µM) and CYP3A4, and induces vasorelaxation. It has a molecular weight of 338.40 and formula C₂₁H₂₂O₄. It is not approved as a drug but is a valuable research tool for studying Alzheimer’s disease, cardiovascular function, and drug interactions. Its presence in grapefruit juice is partly responsible for the “grapefruit juice effect” on medication metabolism. Further studies are needed to explore its potential as a lead compound for neuroprotection or vascular health. |
| Molecular Formula |
C21H22O4
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|---|---|
| Molecular Weight |
338.3970
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| Exact Mass |
338.151
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| CAS # |
7437-55-0
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| PubChem CID |
5317564
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| Appearance |
Off-white to light yellow solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
503.7±50.0 °C at 760 mmHg
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| Melting Point |
53 - 54 °C
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| Flash Point |
258.4±30.1 °C
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| Vapour Pressure |
0.0±1.3 mmHg at 25°C
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| Index of Refraction |
1.583
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| LogP |
5.85
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
25
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| Complexity |
570
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC(=CCC/C(=C/COC1=C2C(=CC3=C1OC=C3)C=CC(=O)O2)/C)C
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| InChi Key |
SOVNCTNQAWWYAQ-OQLLNIDSSA-N
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| InChi Code |
InChI=1S/C21H22O4/c1-14(2)5-4-6-15(3)9-11-24-21-19-17(10-12-23-19)13-16-7-8-18(22)25-20(16)21/h5,7-10,12-13H,4,6,11H2,1-3H3/b15-9+
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| Chemical Name |
9-[(2E)-3,7-dimethylocta-2,6-dienoxy]furo[3,2-g]chromen-7-one
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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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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 (~295.51 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: 2.5 mg/mL (7.39 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
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. Solubility in Formulation 2: ≥ 2.5 mg/mL (7.39 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 | 2.9551 mL | 14.7754 mL | 29.5508 mL | |
| 5 mM | 0.5910 mL | 2.9551 mL | 5.9102 mL | |
| 10 mM | 0.2955 mL | 1.4775 mL | 2.9551 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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