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
UNSPSC Code:
12352115
NACRES:
NA.22
PubChem Substance ID:
EC Number:
208-912-2
Beilstein/REAXYS Number:
4660369
MDL number:
Assay:
≥96.0% (GC)
Form:
liquid
Quality Level
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
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
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Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral
Storage Class
10 - Combustible liquids
wgk
WGK 1
flash_point_f
147.2 °F - closed cup
flash_point_c
64 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
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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
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)
J.P. Kutney et al.
Helvetica Chimica Acta, 77, 1707-1707 (1994)