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Merck
CN

89231

Sigma-Aldrich

(-)-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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About This Item

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

象形图

Exclamation mark

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


历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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J.P. Kutney et al.
Helvetica Chimica Acta, 77, 1707-1707 (1994)
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
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
Pro-apoptotic and anti-angiogenic properties of the a/?-thujone fraction from Thuja occidentalis on glioblastoma cells.
Torres A, et al.
Journal of Neuro-Oncology, 128(1), 9-19 (2016)
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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