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89231

Sigma-Aldrich

(−)-α-Thujone

≥96.0% (GC)

Sinonimo/i:

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

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CHF 318.00

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1 ML
CHF 84.30
5 ML
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About This Item

Formula empirica (notazione di Hill):
C10H16O
Peso molecolare:
152.23
Beilstein:
4660369
Numero CE:
Numero MDL:
Codice UNSPSC:
12352115
ID PubChem:
NACRES:
NA.22

CHF 84.30


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Saggio

≥96.0% (GC)

Stato

liquid

Attività ottica

[α]20/D −19.0±2.0°, neat

Indice di rifrazione

n20/D 1.450

Densità

0.914 g/mL at 20 °C (lit.)

Gruppo funzionale

ketone

Temperatura di conservazione

2-8°C

Stringa SMILE

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
USMNOWBWPHYOEA-MRTMQBJTSA-N

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Descrizione generale

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

Applicazioni

  • 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).

Azioni biochim/fisiol

GABAA receptor antagonist.

Altre note

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

Pittogrammi

Exclamation mark

Avvertenze

Warning

Indicazioni di pericolo

Classi di pericolo

Acute Tox. 4 Oral

Codice della classe di stoccaggio

10 - Combustible liquids

Classe di pericolosità dell'acqua (WGK)

WGK 1

Punto d’infiammabilità (°F)

147.2 °F - closed cup

Punto d’infiammabilità (°C)

64 °C - closed cup

Dispositivi di protezione individuale

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


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Adebola O Oyedeji et al.
Natural product communications, 4(6), 849-852 (2009-07-29)
Safety of Artemisia afar has been a controversial issue due to its high thujone content. Despite the declaration of the World Health Organization in the 1970s of the plant being unsafe for consumption, it is still commonly used in folklore
Canadian Journal of Chemistry, 74, 666-666 (1996)
Marcin Szczot et al.
Journal of natural products, 75(4), 622-629 (2012-03-01)
α-Thujone (1a), a constituent of wormwood, has been suspected to cause adverse psychoactive reactions in addicted drinkers of absinthe. While the content of 1a in absinthe is too low for such effects, at higher doses it can indeed induce seizures
Biljana Nikolić et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 49(9), 2035-2045 (2011-05-31)
The aim of this work was to examine the antigenotoxic potential of plant monoterpenes: camphor, eucalyptol and thujone in prokaryotic and eukaryotic cells and to elucidate their effect on DNA repair. We compared the effect of monoterpenes on spontaneous, UV-
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

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