89231

(−)-α-Thujone

≥96.0% (GC)

• Synonyme(s) : (-)-alpha-Thujone, (1S,4R)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-one
• Formule empirique (notation de Hill): C₁₀H₁₆O
• Poids moléculaire : 152.23
• Numéro Beilstein : 4660369
• Numéro CE : 208-912-2
• Numéro MDL: MFCD00001313
• Code UNSPSC : 12352115
• ID de substance PubChem : 57653336
• Nomenclature NACRES : NA.22

Propriétés

• Niveau de qualité: 100
• Pureté: ≥96.0% (GC)
• Forme: liquid
• Activité optique: [α]20/D −19.0±2.0°, neat
• Indice de réfraction: n20/D 1.450
• Densité: 0.914 g/mL at 20 °C (lit.)
• Groupe fonctionnel: ketone
• Température de stockage: 2-8°C
• Chaîne 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
• Clé InChI: USMNOWBWPHYOEA-MRTMQBJTSA-N

Description

Description générale

(-)-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).

Actions biochimiques/physiologiques

GABAA receptor antagonist.

Autres remarques

Chiral building block

Informations sur la sécurité

• Pictogrammes: GHS07
• Mention d'avertissement: Warning
• Mentions de danger: H302
• Conseils de prudence: P264 - P270 - P301 + P312 - P501
• Classification des risques: Acute Tox. 4 Oral
• Code de la classe de stockage: 10 - Combustible liquids
• Classe de danger pour l'eau (WGK): WGK 1
• Point d'éclair (°F): 147.2 °F - closed cup
• Point d'éclair (°C): 64 °C - closed cup
• Équipement de protection individuelle: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter