89231
(−)-α-Thujone
≥96.0% (GC)
Synonym(s):
(-)-alpha-Thujone, (1S,4R)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-one
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About This Item
Empirical Formula (Hill Notation):
C10H16O
Molecular Weight:
152.23
Beilstein:
4660369
EC Number:
MDL number:
UNSPSC Code:
12352115
PubChem Substance ID:
NACRES:
NA.22
Assay
≥96.0% (GC)
form
liquid
optical activity
[α]20/D −19.0±2.0°, neat
refractive index
n20/D 1.450
density
0.914 g/mL at 20 °C (lit.)
functional group
ketone
storage temp.
2-8°C
SMILES string
CC(C)[C@@]12C[C@@H]1[C@@H](C)C(=O)C2
InChI
1S/C10H16O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6-8H,4-5H2,1-3H3/t7-,8-,10+/m1/s1
InChI key
USMNOWBWPHYOEA-MRTMQBJTSA-N
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General description
(-)-α-Thujone, a monoterpene ketone found in the essential oil of Thuja occidentalis, shows potent antitumorigenic effect.
Application
- A six-step total synthesis of α-thujone and d6-α-thujone, enabling facile access to isotopically labelled metabolites: This study presents a concise method for synthesizing α-thujone, useful for creating isotopically labeled derivatives for research purposes (Thamm et al., 2016).
- Enhancement of CD3AK cell proliferation and killing ability by α-thujone: Investigates α-thujone′s ability to enhance the proliferation and cytotoxic activity of CD3AK cells, suggesting potential immunological applications (Zhou et al., 2016).
- α-Thujone exhibits an antifungal activity against F. graminearum by inducing oxidative stress, apoptosis, epigenetics alterations and reduced toxin synthesis: Demonstrates the antifungal effects of α-thujone against Fusarium graminearum, which could make it a valuable alternative to traditional fungicides (Teker et al., 2021).
Biochem/physiol Actions
GABAA receptor antagonist.
Other Notes
Chiral building block
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral
Storage Class Code
10 - Combustible liquids
WGK
WGK 1
Flash Point(F)
147.2 °F - closed cup
Flash Point(C)
64 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Pro-apoptotic and anti-angiogenic properties of the a/?-thujone fraction from Thuja occidentalis on glioblastoma cells.
Torres A, et al.
Journal of Neuro-Oncology, 128(1), 9-19 (2016)
Ilioara Oniga et al.
Revista medico-chirurgicala a Societatii de Medici si Naturalisti din Iasi, 114(2), 593-595 (2010-08-13)
The quantitative and qualitative analysis of essential oils obtained from Salvia officinalis L. (Lamiaceae) cultivated in Romania is reported in this paper. The essential oils were obtained from fresh and dried material harvested from plants cultivated in Cluj (Romania) and
Nour W Al-Haj Baddar et al.
Natural product research, 25(12), 1180-1184 (2011-07-12)
Thujone, which is the major constituent in Salvia sp. (Lamiaceae), was found to correct the lipid profile (cholesterol and triglycerides) in diabetic rats. Oral treatment with thujone (5 mg kg⁻¹ body weight dose) significantly adjusted cholesterol and triglyceride levels in
Hakam Alkhateeb et al.
Applied physiology, nutrition, and metabolism = Physiologie appliquee, nutrition et metabolisme, 36(3), 361-367 (2011-05-18)
Rescue of palmitate-induced insulin resistance has been linked with improvements in fatty acid oxidation, but importantly, not always with concurrently altered AMPK or ACC2 phosphorylation. Therefore, we examined the interrelationships among AMPK, ACC2, and fatty acid oxidation under 12 controlled
Adebola O Oyedeji et al.
Natural product communications, 4(6), 849-852 (2009-07-29)
Safety of Artemisia afar has been a controversial issue due to its high thujone content. Despite the declaration of the World Health Organization in the 1970s of the plant being unsafe for consumption, it is still commonly used in folklore
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