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Key Documents

SML0782

Sigma-Aldrich

(-)-Umbellulone

≥98% (HPLC)

Synonym(s):

(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

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About This Item

Empirical Formula (Hill Notation):
C10H14O
CAS Number:
546-78-1
Molecular Weight:
150.22
UNSPSC Code:
12352202

biological source

Umbellularia californica Nutt.

Assay

≥98% (HPLC)

form

oil

storage condition

desiccated

color

colorless to light brown

storage temp.

−20°C

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

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
083M4714V

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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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