89231

(−)-α-Thujon

≥96.0% (GC)

• Synonym(e): (1S,4R)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-on
• Empirische Formel (Hill-System): C₁₀H₁₆O
• Molekulargewicht: 152.23
• Beilstein: 4660369
• EG-Nummer: 208-912-2
• MDL-Nummer: MFCD00001313
• UNSPSC-Code: 12352115
• PubChem Substanz-ID: 57653336
• NACRES: NA.22

Eigenschaften

• Assay: ≥96.0% (GC)
• Form: liquid
• Optische Aktivität: [α]20/D −19.0±2.0°, neat
• Brechungsindex: n20/D 1.450
• Dichte: 0.914 g/mL at 20 °C (lit.)
• Funktionelle Gruppe: ketone
• Lagertemp.: 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
• InChIKey: USMNOWBWPHYOEA-MRTMQBJTSA-N

Beschreibung

Allgemeine Beschreibung

(-)-α-Thujone, a monoterpene ketone found in the essential oil of Thuja occidentalis, shows potent antitumorigenic effect.[1]

Anwendung

• 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. Wirkung

GABAA receptor antagonist.

Sonstige Hinweise

Chiral building block[2][3][4]

Sicherheitshinweise

• Piktogramme: GHS07
• Signalwort: Warning
• H-Sätze: H302
• P-Sätze: P264 - P270 - P301 + P312 - P501
• Gefahreneinstufungen: Acute Tox. 4 Oral
• Lagerklassenschlüssel: 10 - Combustible liquids
• WGK: WGK 1
• Flammpunkt (°F): 147.2 °F - closed cup
• Flammpunkt (°C): 64 °C - closed cup
• Persönliche Schutzausrüstung: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter