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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:
57653336
EC Number:
208-912-2
Beilstein/REAXYS Number:
4660369
MDL number:
MFCD00001313
Assay:
≥96.0% (GC)
Form:
liquid
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Quality Level

100

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

SMILES string

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

InChI key

USMNOWBWPHYOEA-MRTMQBJTSA-N

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

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pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

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
BCBB9718
1103512V
BCBB9718V
1103512
014071/2

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Canadian Journal of Chemistry, 74, 666-666 (1996)
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
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
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全球贸易项目编号

货号GTIN
89231-5ML04061837397493
89231-1ML04061833075630