89231

(−)-α-Thujone

≥96.0% (GC)

• Synonym(s): (-)-alpha-Thujone, (1S,4R)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-one
• Empirical Formula (Hill Notation): C₁₀H₁₆O
• Molecular Weight: 152.23
• Beilstein: 4660369
• EC Number: 208-912-2
• MDL number: MFCD00001313
• UNSPSC Code: 12352115
• PubChem Substance ID: 57653336
• NACRES: NA.22

Properties

• 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

Description

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

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H302
• Precautionary Statements: P264 - P270 - P301 + P312 - P501
• 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