SML0782
(-)-Umbellulone
≥98% (HPLC)
别名:
(1R, 5S)-4-Methyl-1-propan-2-ylbicyclo(3.1.0)hex-3-en-2-one, (1R,5S)-(-)-3-Thujen-2-one, Thujen-2-one, Thujenone
SMILES string
O=C1[C@@]2([C@@H](C2)C(=C1)C)C(C)C
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
InChI key
LTTVJAQLCIHAFV-WCBMZHEXSA-N
biological source
Umbellularia californica Nutt.
assay
≥98% (HPLC)
form
oil
storage condition
desiccated
color
colorless to light brown
storage temp.
−20°C
Biochem/physiol Actions
(-)-Umbellulone is a selective activator of Transient Receptor Potential Anykrin 1 (TRPA1) channels.
(-)-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.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Herbalism helps headache.
Peter J Goadsby
Brain : a journal of neurology, 135(Pt 2), 318-319 (2012-02-22)
Christian Starkenmann et al.
Journal of agricultural and food chemistry, 59(2), 677-683 (2010-12-31)
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, we virtually screened the chemical structures of terpenes and sesquiterpenes to find
Cristina Moldovan Loomis et al.
The Journal of pharmacology and experimental therapeutics, 369(1), 26-36 (2019-01-16)
Migraine is a debilitating disease that affects almost 15% of the population worldwide and is the first cause of disability in people under 50 years of age, yet its etiology and pathophysiology remain incompletely understood. Recently, small molecules and therapeutic
Lingdi Nie et al.
International journal of molecular sciences, 22(22) (2021-11-28)
Transient receptor potential ankyrin 1 (TRPA1) plays a role in migraine and is proposed as a promising target for migraine therapy. However, TRPA1-induced signaling in migraine pathogenesis is poorly understood. In this study, we explored the hypothesis that Src family
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