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Key Documents

89231

Sigma-Aldrich

(−)-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.)

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

Pictograms

Exclamation mark

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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J.P. Kutney et al.
Canadian Journal of Chemistry, 72, 1570-1570 (1994)
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
Canadian Journal of Chemistry, 74, 666-666 (1996)
Marcin Szczot et al.
Journal of natural products, 75(4), 622-629 (2012-03-01)
α-Thujone (1a), a constituent of wormwood, has been suspected to cause adverse psychoactive reactions in addicted drinkers of absinthe. While the content of 1a in absinthe is too low for such effects, at higher doses it can indeed induce seizures
Biljana Nikolić et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 49(9), 2035-2045 (2011-05-31)
The aim of this work was to examine the antigenotoxic potential of plant monoterpenes: camphor, eucalyptol and thujone in prokaryotic and eukaryotic cells and to elucidate their effect on DNA repair. We compared the effect of monoterpenes on spontaneous, UV-

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