Umbellulone

Names

[ CAS No. ]:
546-78-1

[ Name ]:
Umbellulone

[Synonym ]:
Thuj-3-en-2-on

Biological Activity

[Description]:

Umbellulone is an active constituent of the leaves of Umbellularia californica. Umbellulone stimulates the TRPA1 channel in a subset of peptidergic, nociceptive neurons, activating the trigeminovascular system via this mechanism[1].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> TRP Channel

Research Areas >> Neurological Disease

[Target]

TRPA1 channel[1]

[In Vitro]

Umbellulone, from µM to sub-mM concentrations, selectively stimulates transient receptor potential ankyrin 1-expressing HEK293 cells[1].

[In Vivo]

Umbellulone (50–250 nM/5ul) causes an acute nocioceptive response in a dose-dependent manner in Trpa1+/+ mice[1]. Umbellulone (150 µg/kg; intravenous or intranasal) do not affect systemic blood pressure[1]. Umbellulone (30-150 μg/kg; i.v.) increases meningeal blood flow in a dose-dependent manner[1]. Animal Model: Sprague-Dawley rats (male, 250 g)[1] Dosage: 30 μg/kg, 75 μg/kg, 150 μg/kg Administration: Intravenously Result: Increased meningeal blood flow in a dose-dependent manner.

[References]

[1]. Nassini R, et al. The 'headache tree' via umbellulone and TRPA1 activates the trigeminovascular system. Brain. 2012 Feb;135(Pt 2):376-90.

Chemical & Physical Properties

[ Molecular Formula ]:
C₁₀H₁₄O

[ Molecular Weight ]:
150.21800

[ Exact Mass ]:
150.10400

[ PSA ]:
17.07000

[ LogP ]:
2.17770

[ Storage condition ]:
-20°C

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Hazard Codes ]:
Xi

Precursor & DownStream

Precursor

DownStream

Articles

Hemisynthesis of dihydroumbellulols from umbellulone: new cooling compounds.

J. Agric. Food Chem. 59(2) , 677-83, (2011)

Although menthol is a common ingredient used in food products, other molecules also evoke coolness through stimulation of the somatosensory system. To discover new molecules having cooling properties,...

Herbalism helps headache.

Brain 135(Pt 2) , 318-9, (2012)

Related Compounds

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