89231

(−)-α-Thujone

≥96.0% (GC)

• Sinônimo(s): (-)-alpha-Thujone, (1S,4R)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-one
• Fórmula empírica (Notação de Hill): C₁₀H₁₆O
• Peso molecular: 152.23
• Beilstein: 4660369
• Número CE: 208-912-2
• Número MDL: MFCD00001313
• Código UNSPSC: 12352115
• ID de substância PubChem: 57653336
• NACRES: NA.22

Propriedades

• Nível de qualidade: 100
• Ensaio: ≥96.0% (GC)
• Formulário: liquid
• atividade óptica: [α]20/D −19.0±2.0°, neat
• índice de refração: n20/D 1.450
• densidade: 0.914 g/mL at 20 °C (lit.)
• grupo funcional: ketone
• temperatura de armazenamento: 2-8°C
• cadeia de caracteres SMILES: 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
• chave InChI: USMNOWBWPHYOEA-MRTMQBJTSA-N

Descrição

Descrição geral

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

Aplicação

• 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).

Ações bioquímicas/fisiológicas

GABAA receptor antagonist.

Outras notas

Chiral building block

Informações de segurança

• Pictogramas: GHS07
• Palavra indicadora: Warning
• Frases de perigo: H302
• Declarações de precaução: P264 - P270 - P301 + P312 - P501
• Classificações de perigo: Acute Tox. 4 Oral
• Código de classe de armazenamento: 10 - Combustible liquids
• Classe de risco de água (WGK): WGK 1
• Ponto de fulgor (°F): 147.2 °F - closed cup
• Ponto de fulgor (°C): 64 °C - closed cup
• Equipamento de proteção individual: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter