Umbellulone is an active ingredient in the leaves of Umbellularia californica. In a subpopulation of peptidergic, nociceptive neurons, Umbellulone stimulates TRPA1 channels and through this mechanism activates the trigeminal vasculature.

Physicochemical Properties

Molecular Formula	C10H14O
Molecular Weight	150.21756
Exact Mass	150.104
CAS #	546-78-1
PubChem CID	442504
Appearance	Colorless to light yellow ointment
LogP	2.177
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	1
Heavy Atom Count	11
Complexity	250
Defined Atom Stereocenter Count	2
SMILES	CC1=CC(=O)C2(C1C2)C(C)C
InChi Key	LTTVJAQLCIHAFV-WCBMZHEXSA-N
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
Chemical Name	(1R,5S)-4-methyl-1-propan-2-ylbicyclo[3.1.0]hex-3-en-2-one
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)

Biological Activity

ln Vitro	Umbellulone specifically activates HEK293 cells expressing transient receptor potential ankyrin 1 at doses between µM and sub-mM [1].
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].
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 .
References	[1]. The 'headache tree' via umbellulone and TRPA1 activates the trigeminovascular system. Brain. 2012 Feb;135(Pt 2):376-90.
Additional Infomation	Umbellulone is a ketone. (-)-Umbellulone has been reported in Tanacetum vulgare, Umbellularia californica, and Pimenta racemosa with data available. See also: Umbellulone (annotation moved to).

Solubility Data

Solubility (In Vitro)

DMSO : ~250 mg/mL (~1664.23 mM)

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *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. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (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.