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Merck
CN

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:
57653336
EC Number:
208-912-2
Beilstein/REAXYS Number:
4660369
MDL number:
MFCD00001313

Key Documents

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Product Name

(−)-α-Thujone, ≥96.0% (GC)

InChI key

USMNOWBWPHYOEA-MRTMQBJTSA-N

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

SMILES string

CC(C)[C@@]12C[C@@H]1[C@@H](C)C(=O)C2

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

Quality Level

100

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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.

General description

(-)-α-Thujone, a monoterpene ketone found in the essential oil of Thuja occidentalis, shows potent antitumorigenic effect.

Other Notes

Chiral building block

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

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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Certificates of Analysis (COA)

Lot/Batch Number
BCBB9718
1103512V
BCBB9718V
1103512
014071/2

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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
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
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)
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