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
Beilstein:
4660369
EC 号:
MDL编号:
UNSPSC代码:
12352115
PubChem化学物质编号:
NACRES:
NA.22
质量水平
方案
≥96.0% (GC)
表单
liquid
旋光性
[α]20/D −19.0±2.0°, neat
折射率
n20/D 1.450
密度
0.914 g/mL at 20 °C (lit.)
官能团
ketone
储存温度
2-8°C
SMILES字符串
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
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一般描述
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。
应用
- 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)。
生化/生理作用
GABAA 受体拮抗剂。
其他说明
手性结构单元
警示用语：
Warning
危险声明
危险分类
Acute Tox. 4 Oral
储存分类代码
10 - Combustible liquids
WGK
WGK 1
闪点(°F)
147.2 °F - closed cup
闪点(°C)
64 °C - closed cup
个人防护装备
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
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)
Modulation of GABAergic synaptic currents and current responses by α-thujone and dihydroumbellulone.
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
K S Siveen et al.
International immunopharmacology, 11(12), 1967-1975 (2011-09-03)
Thujone, a naturally occurring monoterpene, was found to enhance the total WBC count, bone marrow cellularity, number of α-esterase positive cells, number of plaque forming cells in spleen and circulating antibody titer in Balb/c mice (1mg/kg body weight, intraperitoneally for
J.P. Kutney et al.
Canadian Journal of Chemistry, 72, 1570-1570 (1994)
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