| Identification | Back Directory | [Name]
[1R,5S,(-)]-4-Methyl-1-isopropylbicyclo[3.1.0]hexa-3-ene-2-one | [CAS]
546-78-1 | [Synonyms]
Thujenone
Thujen-2-one
(-)-Umbellulone
(1R,5S)-(-)-3-Thujen-2-one
(-)-Umbellulone >=98% (HPLC)
(1R, 5S)-4-Methyl-1-propan-2-ylbicyclo(3.1.0)hex-3-en-2-one
[1R,5S,(-)]-4-Methyl-1-isopropylbicyclo[3.1.0]hexa-3-ene-2-one | [MDL Number]
MFCD26961114 | [MOL File]
546-78-1.mol |
| Chemical Properties | Back Directory | [storage temp. ]
-20°C | [solubility ]
DMSO : 250 mg/mL (1664.23 mM; Need ultrasonic) | [form ]
Oil | [color ]
colorless to light brown | [biological source]
Umbellularia californica Nutt. |
| Hazard Information | Back Directory | [Uses]
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]. | [Definition]
ChEBI: Umbellulone is a ketone. | [Biochem/physiol Actions]
(-)-Umbellulone, isolated from the"headache tree" Umbellularia californica Nutt, is a selective activator of Transient Receptor Potential Anykrin 1 (TRPA1) channels. (-)-Umbellulone activates TRPA1 channels on nociceptive trigeminal afferents, resulting in release of CGRP and CGRP-mediated neurogenic vasodilatation, causing a painful cold sensation and headache/migraine. | [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. |
| [storage]
Store at -20°C | [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. DOI:10.1093/brain/awr272 |
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