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:
产品名称
(-)-α-侧柏酮, ≥96.0% (GC)
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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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。
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。
Other Notes
手性结构单元
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
Ilioara Oniga et al.
Revista medico-chirurgicala a Societatii de Medici si Naturalisti din Iasi, 114(2), 593-595 (2010-08-13)
The quantitative and qualitative analysis of essential oils obtained from Salvia officinalis L. (Lamiaceae) cultivated in Romania is reported in this paper. The essential oils were obtained from fresh and dried material harvested from plants cultivated in Cluj (Romania) and
Hakam Alkhateeb et al.
Applied physiology, nutrition, and metabolism = Physiologie appliquee, nutrition et metabolisme, 36(3), 361-367 (2011-05-18)
Rescue of palmitate-induced insulin resistance has been linked with improvements in fatty acid oxidation, but importantly, not always with concurrently altered AMPK or ACC2 phosphorylation. Therefore, we examined the interrelationships among AMPK, ACC2, and fatty acid oxidation under 12 controlled
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
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)
J.P. Kutney et al.
Helvetica Chimica Acta, 77, 1707-1707 (1994)
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