Trans-Anethole ((E)-Anethole)
(Synonyms: 茴香烯,(E)?-Anethole) 目录号 : GC32428
A phenylpropanoid with antifungal and antioxidant activity
Cas No.:4180-23-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
(E)-Anethol is a phenylpropanoid that has been found in P. anisum seed oil and has antifungal and antioxidant activity.1,2,3 It is active against fermentatively growing S. cerevisiae under hypoxic, but not normoxic, conditions (MIC = 100 ?g/ml), and against C. parapsilosis when used at a concentration of 15% w/w.2,3 (E)-Anethol has antioxidant activity in a Trolox equivalent antioxidant capacity (TEAC) assay but does not scavenge 2,2-diphenyl-1-picrylhydrazel (DPPH) radicals in a cell-free assay.3
1.Embong, M.B., and Hadziyev, D.Essential oils from spices grown in Alberta: Anise oil (Pimpinella anisum)J. Plant Sci.57(3)681-688(1977) 2.Fujita, K., and Kubo, I.Potentiation of fungicidal activities of trans-anethole against Saccharomyces cerevisiae under hypoxic conditionsJ. Biosci. Bioeng.98(6)490-492(2004) 3.Donati, M., Mondin, A., Chen, Z., et al.Radical scavenging and antimicrobial activities of Croton zehntneri, Pterodon emarginatus and Schinopsis brasiliensis essential oils and their major constituents: Estragole, trans-anethole, β-caryophyllene and myrceneNat. Prod. Res.29(10)939-946(2014)
| Cas No. | 4180-23-8 | SDF | |
| 别名 | 茴香烯,(E)?-Anethole | ||
| Canonical SMILES | COC1=CC=C(/C=C/C)C=C1 | ||
| 分子式 | C10H12O | 分子量 | 148.2 |
| 溶解度 | DMSO: 100 mg/mL (674.76 mM); Water: 1 mg/mL (6.75 mM; ultrasonic and warming and heat to 80°C) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 6.7476 mL | 33.7382 mL | 67.4764 mL |
| 5 mM | 1.3495 mL | 6.7476 mL | 13.4953 mL |
| 10 mM | 0.6748 mL | 3.3738 mL | 6.7476 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Photocatalytic Isomerization of ( E\)-Anethole to ( Z)-Anethole
Molecules 2022 Aug 22;27(16):5342.PMID:36014580DOI:10.3390/molecules27165342.
Natural product (E\)-Anethole was isomerized to (Z)-anethole in a photocatalytic reaction. For this purpose, a self-designed cheap photoreactor was constructed. Among 11 photosensitizers (organo and metal complex compounds), Ir(p-tBu-ppy)3 led to the highest conversion. Triplet energies of (E)- and (Z)-anethole were predicted theoretically by DFT calculations to support the selection of appropriate photosensitizers. A catalyst loading of 0.1 mol% gave up to 90% conversion in gram scale. Further additives were not required and mild irradiation with light of 400 nm overnight was sufficient. As a proof of concept, (E)- and (Z)-anethole were dihydroxylated diastereoselectively to obtain diastereomerically pure like- and unlike-configured diols, respectively.
Essential Oils, Part III: Chemical Composition
Dermatitis 2016 Jul-Aug;27(4):161-9.PMID:27427817DOI:10.1097/DER.0000000000000193.
Data on the chemistry of essential oils which have caused contact allergy are provided. The largest group of chemicals found in essential oils consists of terpenes. The number of identified components usually ranges from 100 to 250, but in some oils (lavender, geranium, rosemary) 450 to 500 chemicals have been found. Many chemicals are present in a large number of oils, up to 98% for 尾-caryophyllene and 97% for limonene. Chemicals that are important constituents of >20 oils are limonene, linalool, and 伪-pinene. In many essential oils, there are 2 to 5 components which together constitute over 50% to 60% of the oil. In some oils, however, there is one dominant ingredient, making up more than 50% of the oil, including (E\)-Anethole in aniseed and star anise oil, carvone in spearmint oil, 1,8-cineole (eucalyptol) in Eucalyptus globulus oil, and (E)-cinnamaldehyde in cassia oil. The most important chemicals in 93 individual oils are specified.
Fumigant activity of (E\)-Anethole identified in Illicium verum fruit against Blattella germanica
Pest Manag Sci 2002 Feb;58(2):161-6.PMID:11852640DOI:10.1002/ps.435.
The insecticidal activities of materials derived from the fruit of star anise, Illicium verum, against adults of Blattella germanica were examined by direct contact application and fumigation methods, and compared with those of DDVP, deltamethrin and hydramethylnon. The biologically active constituent of the Illicium fruit was characterized as the phenylpropene, (E\)-Anethole, by spectroscopic analysis. In a filter paper diffusion test with females, (E\)-Anethole caused 80.3% mortality at 0.159 mg cm-2 at 1 and 3 days after treatment (DAT), whereas 16.7% mortality at 3 DAT was achieved at 0.079 mg cm-2. DDVP and deltamethrin gave > 90% mortality at 0.019 mg cm-2 at 1 DAT. At 0.009 mg cm-2, DDVP and deltamethrin showed 73.3 and 60% mortality at 1 DAT, respectively, but 93.3 and 76.7% mortality at 3 DAT. Hydramethylnon exhibited 0 and 93.3% mortality at 0.159 mg cm-2 at 1 and 3 DAT, respectively, whereas 6.7% mortality at 3 DAT was observed at 0.079 mg cm-2. In a fumigation test with females, (E\)-Anethole was much more effective in closed cups than in open ones, indicating that the insecticidal activity of the compound was largely attributable to fumigant action. (E\)-Anethole and DDVP caused 100% mortality at 0.398 and 0.051 mg cm-2 4 and 1 h after treatment, respectively. (E\)-Anethole showed 46.7% mortality at 0.199 mg cm-2 at 3 DAT, whereas deltamethrin and hydramethylnon at 0.796 mg cm-2 was ineffective for 3-day period. As naturally occurring insect-control agents, the I verum fruit-derived materials described could be useful for managing populations of B germanica.
Fumigant Toxicity in Myzus persicae Sulzer (Hemiptera: Aphididae): Controlled Release of ( E)- anethole from Microspheres
Plants (Basel) 2020 Jan 18;9(1):124.PMID:31963690DOI:10.3390/plants9010124.
(E\)-Anethole is a phenylpropanoid that is the main compound found in the essential oils (EOs) of anise and fennel seeds, and either fumigant or direct contact activity of this compound has been demonstrated against aphids and stored product pests. In this work, solid microspheres were prepared by three methods-oil emulsion entrapment, spray-drying, and complexed with 尾-cyclodextrin. Fumigation activity of each microsphere preparation was tested against the green peach aphid, Myzus persicae Sulzer (Hemiptera: Aphididae), on pepper leaves. The best insecticidal activity was with (E\)-Anethole encapsulated in oil emulsion beads and introduced to aphids as a vapour over 24 h, with an LC50 of 0.415 渭L/L compared to 0.336 渭L/L of vapors from free (E\)-Anethole. Scanning electron microscopy of the beads revealed a compact surface with low porosity that produced a controlled release of the bioactive for more than 21 d, whilst most of the volatile was evaporated within two days if applied unformulated. Spray drying gave spherical particles with the greatest encapsulated yield (73%) of 6.15 g of (E\)-Anethole incorporated per 100 g of powder. Further work will be done on improving the formulation methods and testing the solid microspheres in all aphid stages scaling up the experimental assay. It is foreseen that nanotechnology will play a role in future developments of low risk plant protection products.
Chemical composition of the essential oil from different vegetative parts of Foeniculum vulgare subsp . piperitum (Ucria) Coutinho (Umbelliferae) growing wild in Sicily
Nat Prod Res 2022 Jul;36(14):3587-3597.PMID:33410338DOI:10.1080/14786419.2020.1870227.
In the present study, the chemical compositions of the essential oils from roots, stems, leaves and fruits of Foeniculum vulgare subsp. piperitum collected in Sicily were evaluated by GC and GC-MS. The main components of the roots were terpinolene (33.15%), 纬-terpinene (12.18%) and fenchyl acetate (11.23%). Stems and leaves were very rich in 伪-phellandrene (36.85% and 41.59%, respectively) and 尾-phellandrene (19.68% and 25.79%, respectively), whereas the main components of fruits were terpinolene (20.10%) and limonene (17.84%)These results were compared with those of the EOs of the same vegetative parts of Foeniculum vulgare subsp. vulgare, collected in the same station and in the same days. The oils of F. vulgare subsp. vulgare showed completely different compositions, with estragole, (E\)-Anethole and 伪-pinene as main compounds, clearly indicating the differentiation of the two subspecies. Our results were also compared with those reported in literature for other accessions of Foeniculum vulgare subsp. piperitum.