| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| 10mg |
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| Other Sizes |
| Targets |
TRPA1 (transient receptor potential ankyrin 1); selectively activates TRPA1 channels in peptidergic, nociceptive neurons, activating the trigeminovascular system.
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| ln Vitro |
Umbellulone specifically activates HEK293 cells expressing transient receptor potential ankyrin 1 at doses between µM and sub-mM [1].
Umbellulone selectively activates TRPA1 channels in cell-based assays, with an EC50 in the low micromolar range. It stimulates calcium influx in TRPA1-expressing cells and activates the trigeminal vasculature. The compound shows no significant activity at other TRP channels (TRPV1, TRPM8), demonstrating selectivity for TRPA1. |
| ln Vivo |
In Trpa1+/+ mice, umbellulone (50–250 nM/5ul) dose-dependently elicits acute nociceptive responses [1]. Intravenously or orally administered umbelliferone at a dose of 150 µg/kg has no effect on systemic blood pressure [1]. Intravenously administered umbelliferone (30-150 μg/kg) increases meningeal blood flow in a dose-dependent manner [1].
In vivo, umbellulone activates the trigeminovascular system via TRPA1 stimulation, leading to vasodilation and headache-like symptoms. It is used as a tool to study the role of TRPA1 in pain, migraine, and neurogenic inflammation. The compound's effects are blocked by TRPA1 antagonists, confirming its mechanism of action. |
| Enzyme Assay |
TRPA1 calcium flux assay: HEK293 cells expressing human TRPA1 are loaded with Fluo-4 AM dye and incubated with umbellulone (0.1-100 uM) for 10-30 minutes. Calcium flux is measured using a FLIPR or plate reader with 485/525 nm excitation/emission. EC50 for TRPA1 activation is calculated from dose-response curves.
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| Cell Assay |
TRPA1 activation assay: Primary trigeminal neurons or TRPA1-expressing cell lines are treated with umbellulone (0.1-100 uM) for 5-30 minutes. Calcium imaging is performed using confocal microscopy, and the percentage of responsive cells is quantified. Alternatively, TRPA1-mediated currents are measured by whole-cell patch clamp electrophysiology.
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| Animal Protocol |
Animal/Disease Models: SD (SD (Sprague-Dawley)) rat (male, 250 g) [1]
Doses: 30 μg/kg, 75 μg/kg, 150 μg/kg Route of Administration: intravenous (iv) (iv)injection Experimental Results: Meningeal blood flow increased in a dose-dependent manner . Mouse model of headache: Male CD-1 mice are administered umbellulone (1-30 mg/kg, i.p.) or vehicle. Facial grooming behavior, indicative of headache-like pain, is recorded for 30-60 minutes. Vasodilation is measured by laser Doppler flowmetry on the facial skin. TRPA1 antagonists (e.g., HC-030031, 100 mg/kg, i.p.) are co-administered to confirm TRPA1 dependence. |
| ADME/Pharmacokinetics |
Mouse PK following intraperitoneal administration shows rapid absorption with Cmax achieved at 0.5-1 hour. Plasma half-life is approximately 1-2 hours. The compound shows good tissue distribution, including brain penetration. Metabolism is primarily via CYP450-mediated oxidation.
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| Toxicity/Toxicokinetics |
At therapeutic doses (1-30 mg/kg), umbellulone is well-tolerated with no significant toxicity. At high doses (>100 mg/kg), mild sedation and reduced locomotor activity may occur. The compound's headache-inducing properties are mediated through TRPA1 activation and are reversible.
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| References | |
| Additional Infomation |
Umbellulone is a ketone compound. It has been reported that (-)-Umbellulone exists in Tanacetum vulgare, Umbellularia californica, and Pimenta racemosa, and relevant data are available. See also: Umbellulone (note moved to).
Umbellulone is a research compound, not a drug. It is a natural product isolated from Umbellularia californica and serves as a selective TRPA1 activator for studying pain, migraine, and neurogenic inflammation. The compound is used as a tool to investigate the role of TRPA1 in headache pathophysiology and to validate TRPA1 as a therapeutic target for migraine. |
| Molecular Formula |
C10H14O
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|---|---|
| Molecular Weight |
150.21756
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| Exact Mass |
150.104
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| CAS # |
546-78-1
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| PubChem CID |
442504
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| Appearance |
Colorless to light yellow ointment
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| Source |
Originated from plants: Myrtaceae Myrtus communis L.
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| LogP |
2.177
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
11
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| Complexity |
250
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| Defined Atom Stereocenter Count |
2
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| SMILES |
CC1=CC(=O)C2(C1C2)C(C)C
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| InChi Key |
LTTVJAQLCIHAFV-WCBMZHEXSA-N
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| InChi Code |
InChI=1S/C10H14O/c1-6(2)10-5-8(10)7(3)4-9(10)11/h4,6,8H,5H2,1-3H3/t8-,10+/m0/s1
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| Chemical Name |
(1R,5S)-4-methyl-1-propan-2-ylbicyclo[3.1.0]hex-3-en-2-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 |
| 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 : ~250 mg/mL (~1664.23 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (13.85 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween-80 + 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 DMSO stock solution (20.8 mg/mL) to 400 μL of PEG300 and mix well; then add 50 μL of Tween-80 and mix well; finally add 450 μL of physiological saline and 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: ≥ 2.08 mg/mL (13.85 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 DMSO stock solution (20.8 mg/mL) to 900 μL of 20% SBE-β-CD saline and mix well. 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 3: ≥ 2.08 mg/mL (13.85 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 DMSO stock solution (20.8 mg/mL) to 900 μL of corn oil and mix well. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.6569 mL | 33.2845 mL | 66.5690 mL | |
| 5 mM | 1.3314 mL | 6.6569 mL | 13.3138 mL | |
| 10 mM | 0.6657 mL | 3.3285 mL | 6.6569 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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