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Merck
CN

89231

(-)-α-侧柏酮

≥96.0% (GC)

别名:

(1S,4R)-1-异丙基-4-甲基双环[3.1.0]己-3-酮

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关于此项目

经验公式(希尔记法):
C10H16O
分子量:
152.23
UNSPSC Code:
12352115
NACRES:
NA.22
PubChem Substance ID:
EC Number:
208-912-2
Beilstein/REAXYS Number:
4660369
MDL number:
Assay:
≥96.0% (GC)
Form:
liquid
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InChI key

USMNOWBWPHYOEA-MRTMQBJTSA-N

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

SMILES string

CC(C)[C@@]12C[C@@H]1[C@@H](C)C(=O)C2

assay

≥96.0% (GC)

form

liquid

optical activity

[α]20/D −19.0±2.0°, neat

refractive index

n20/D 1.450

density

0.914 g/mL at 20 °C (lit.)

functional group

ketone

storage temp.

2-8°C

Quality Level

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General description

Thuja occidentalis 的精油中发现的单萜酮 (-)-α-Thujone 显示出强效的抗肿瘤作用。

Application

  • A six-step total synthesis of α-thujone and d6-α-thujone, enabling facile access to isotopically labelled metabolites:提供合成α-侧柏酮的准确方法,用于制备研究用的同位素标记衍生物(Thamm et al., 2016)。
  • Enhancement of CD3AK cell proliferation and killing ability by α-thujone:研究α-侧柏酮增强CD3AK细胞增殖和细胞毒性的作用,说明其可用于免疫领域(Zhou et al., 2016)。
  • α-Thujone exhibits an antifungal activity against F. graminearum by inducing oxidative stress, apoptosis, epigenetics alterations and reduced toxin synthesis:证明α-侧柏酮对禾谷镰刀菌具有抗真菌活性,令其可作为传统杀真菌剂的有效替代品(Teker et al., 2021)。

Biochem/physiol Actions

GABAA 受体拮抗剂。

Other Notes

手性结构单元

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

存储类别

10 - Combustible liquids

wgk

WGK 1

flash_point_f

147.2 °F - closed cup

flash_point_c

64 °C - closed cup

ppe

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


历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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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)
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-
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
M J Eadie
The journal of the Royal College of Physicians of Edinburgh, 39(1), 73-78 (2009-10-17)
Absinthe is an alcoholic liquor containing extracts from the wormwood plant. It was widely consumed in France in the late nineteenth century. Its production was banned in 1915, partly because it was thought to cause neurological disturbances, including mental changes

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