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Merck

89231

Sigma-Aldrich

(−)-α-Thujone

≥96.0% (GC)

Sinónimos:

(-)-alpha-Thujone, (1S,4R)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-one

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About This Item

Fórmula empírica (notación de Hill):
C10H16O
Peso molecular:
152.23
Beilstein:
4660369
Número CE:
Número MDL:
Código UNSPSC:
12352115
ID de la sustancia en PubChem:
NACRES:
NA.22

Nivel de calidad

Ensayo

≥96.0% (GC)

Formulario

liquid

actividad óptica

[α]20/D −19.0±2.0°, neat

índice de refracción

n20/D 1.450

densidad

0.914 g/mL at 20 °C (lit.)

grupo funcional

ketone

temp. de almacenamiento

2-8°C

cadena 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

Clave InChI

USMNOWBWPHYOEA-MRTMQBJTSA-N

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Descripción general

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

Aplicación

  • 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).

Acciones bioquímicas o fisiológicas

GABAA receptor antagonist.

Otras notas

Chiral building block

Pictogramas

Exclamation mark

Palabra de señalización

Warning

Frases de peligro

Clasificaciones de peligro

Acute Tox. 4 Oral

Código de clase de almacenamiento

10 - Combustible liquids

Clase de riesgo para el agua (WGK)

WGK 1

Punto de inflamabilidad (°F)

147.2 °F - closed cup

Punto de inflamabilidad (°C)

64 °C - closed cup

Equipo de protección personal

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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Visite la Librería de documentos

Hakam Alkhateeb et al.
Applied physiology, nutrition, and metabolism = Physiologie appliquee, nutrition et metabolisme, 36(3), 361-367 (2011-05-18)
Rescue of palmitate-induced insulin resistance has been linked with improvements in fatty acid oxidation, but importantly, not always with concurrently altered AMPK or ACC2 phosphorylation. Therefore, we examined the interrelationships among AMPK, ACC2, and fatty acid oxidation under 12 controlled
Nour W Al-Haj Baddar et al.
Natural product research, 25(12), 1180-1184 (2011-07-12)
Thujone, which is the major constituent in Salvia sp. (Lamiaceae), was found to correct the lipid profile (cholesterol and triglycerides) in diabetic rats. Oral treatment with thujone (5 mg kg⁻¹ body weight dose) significantly adjusted cholesterol and triglyceride levels in
Ilioara Oniga et al.
Revista medico-chirurgicala a Societatii de Medici si Naturalisti din Iasi, 114(2), 593-595 (2010-08-13)
The quantitative and qualitative analysis of essential oils obtained from Salvia officinalis L. (Lamiaceae) cultivated in Romania is reported in this paper. The essential oils were obtained from fresh and dried material harvested from plants cultivated in Cluj (Romania) and
Hédi Mighri et al.
Chemistry & biodiversity, 7(11), 2709-2717 (2010-11-13)
The intraspecific chemical variability of essential oils (50 samples) isolated from the aerial parts of Artemisia herba-alba Asso growing wild in the arid zone of Southeastern Tunisia was investigated. Analysis by GC (RI) and GC/MS allowed the identification of 54
Dirk W Lachenmeier et al.
Regulatory toxicology and pharmacology : RTP, 58(3), 437-443 (2010-08-24)
Thujone is a natural substance found in plants commonly used in foods and beverages, such as wormwood and sage, as well as in herbal medicines. The current limits for thujone in food products are based on short-term animal studies from

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