Methyl Eugenol
(Synonyms: 甲基丁香酚) 目录号 : GC38962
Methyl eugenol (4-allylveratrole, eugenyl methyl ether, O-methyleugenol), as a constituent in leaves, fruits, stems, and/or roots, is used as a flavoring agent, as a fragrance and as an anesthetic in rodents.
Cas No.:93-15-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Methyl eugenol (4-allylveratrole, eugenyl methyl ether, O-methyleugenol), as a constituent in leaves, fruits, stems, and/or roots, is used as a flavoring agent, as a fragrance and as an anesthetic in rodents.
| Cas No. | 93-15-2 | SDF | |
| 别名 | 甲基丁香酚 | ||
| Canonical SMILES | COC1=CC(CC=C)=CC=C1OC | ||
| 分子式 | C11H14O2 | 分子量 | 178.23 |
| 溶解度 | DMSO : 100 mg/mL (561.07 mM; Need ultrasonic); H2O : < 0.1 mg/mL (insoluble) | 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 | 5.6107 mL | 28.0536 mL | 56.1073 mL |
| 5 mM | 1.1221 mL | 5.6107 mL | 11.2215 mL |
| 10 mM | 0.5611 mL | 2.8054 mL | 5.6107 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。
Methyl Eugenol attenuates liver ischemia reperfusion injury via activating PI3K/Akt signaling
Int Immunopharmacol 2021 Oct;99:108023.PMID:34358859DOI:10.1016/j.intimp.2021.108023.
Background: Liver ischemia reperfusion injury (LIRI) often occurs during liver transplantation, resection, and various circulatory shock procedures, leading to severe metabolic disorders, inflammatory immune responses, oxidative stress injury, and cell apoptosis. Methyl Eugenol (ME) is structurally similar to eugenol and has anti-inflammatory and apoptotic pharmacological effects. However, whether ME protects the liver from LIRI damage requires further investigation. Methods: We established a partially warm LIRI model by subjecting C57BL/6J mice to 60 min of ischemia, followed by reperfusion for 6 h. We also established a hypoxia-reoxygenation injury (H/R) cell model by subjecting AML12 (a mouse liver cell line) cells to 24 h hypoxia, followed by 18 h normoxia. The extent of liver injury was assessed by serum transaminase concentrations, hematoxylin and eosin staining, quantitative real-time PCR, myeloperoxidase activity, and TUNEL analysis. Apoptosis was detected using flow cytometry. The protein levels of p-PI3K, PI3K, p-Akt, Akt, p-Bad, Bad, Bcl-2, Bax, and cleaved caspase-3 were detected by western blotting. LY294002, an inhibitor of PI3K/Akt signaling, was used to elucidate the relationship between ME and PI3K/Akt signaling. Results: ME successfully alleviated LIRI-induced liver injury, inflammatory response, and apoptosis induced, as well as liver cell injury induced by hypoxia reoxygenation. ME is known to activate the PI3K/Akt signaling pathway in hepatocyte injury in vivo and in vitro, and when this signaling pathway is inhibited, the protective effect of ME is abrogated. Conclusions: The use of ME is a potential therapeutic approach for regulating LIRI by activating PI3K/Akt signaling.
Methyl Eugenol: its occurrence, distribution, and role in nature, especially in relation to insect behavior and pollination
J Insect Sci 2012;12:56.PMID:22963669DOI:10.1673/031.012.5601.
This review discusses the occurrence and distribution (within a plant) of Methyl Eugenol in different plant species (> 450) from 80 families spanning many plant orders, as well as various roles this chemical plays in nature, especially in the interactions between tephritid fruit flies and plants.
A Cautionary tale for using read-across for cancer hazard classification: Case study of isoeugenol and Methyl Eugenol
Regul Toxicol Pharmacol 2022 Dec;136:105280.PMID:36367523DOI:10.1016/j.yrtph.2022.105280.
Chemical grouping and read-across are frequently used non-animal alternatives for filling toxicological data gaps. When grouping chemicals, it is critical to define the applicability domain because minor differences in chemical structure can lead to significant differences in toxicity. Here, we present a case study on isoeugenol and Methyl Eugenol, which are scheduled for review by IARC in June 2023, to illustrate that structural similarity alone may not be sufficient to group chemicals for hazard classification. Isoeugenol and Methyl Eugenol are plant-derived phenylpropenes that share similar physicochemical properties. The major metabolic pathway for isoeugenol includes conjugation of the phenolic hydroxyl group with sulfate and glucuronic acid as an efficient detoxification process, whereas the major metabolic pathway for Methyl Eugenol involves benzylic hydroxylation and formation of the 1'-sulfoxymethyleugenol which leads to carbocation formation. The carbocation can form DNA adducts and induce genotoxicity and carcinogenicity. Consistently, genotoxicity and carcinogenicity alerts are identified from in silico prediction tools for Methyl Eugenol but not isoeugenol. Moreover, the available toxicogenomic, genotoxicity, and carcinogenicity studies confirm that these chemicals have significantly different bioactivities. Data on other structurally similar chemicals further supports our conclusion that it is not appropriate to group these two chemicals for cancer hazard classification.
Methyl Eugenol Binds Recombinant Gamma-Aminobutyric Acid Receptor-Associated Protein from the Western Flower Thrips Frankliniella occidentalis
J Agric Food Chem 2022 Apr 27;70(16):4871-4880.PMID:35385288DOI:10.1021/acs.jafc.1c07431.
The western flower thrips (Frankliniella occidentalis) is a major pest insect in agriculture. However, few insecticides are effective for their control. The recombinant gamma-aminobutyric acid receptor-associated protein (rGABARAP) was examined as a potential target of the monoterpenoids responsible for their insecticidal activities. The insecticidal activity of anethole, linalool, and Methyl Eugenol (ME) was evaluated in the laboratory. The half-maximum lethal concentration (LC50) of ME against second-instar nymphs of F. occidentalis was 5.5 mg/L using membrane and leaf immersion methods, while that of spinosyn A was 1.0 mg/L. The dissociation constants of ME binding to rGABARAP were 1.30 and 4.22 μmol/L, respectively, according to microscale thermophoresis (MST) and isothermal titration calorimetry (ITC) measurements. A molecular docking study showed interactions between ME and Tyr174 via π-π stacking. The MST and ITC experiments showed loss of specific binding between ME and the rGABARAPY174A mutant. Therefore, Tyr174 is a key amino acid residue of rGABARAP involving ME binding. The results revealed GABARAP as a potential target for the development of monoterpenoid insecticides.
Use of biomonitoring data to evaluate Methyl Eugenol exposure
Environ Health Perspect 2006 Nov;114(11):1797-801.PMID:17107870DOI:10.1289/ehp.9057.
Methyl Eugenol is a naturally occurring material found in a variety of food sources, including spices, oils, and nutritionally important foods such as bananas and oranges. Given its natural occurrence, a broad cross-section of the population is likely exposed. The availability of biomonitoring and toxicology data offers an opportunity to examine how biomonitoring data can be integrated into risk assessment. Methyl Eugenol has been used as a biomarker of exposure. An analytical method to detect Methyl Eugenol in human blood samples is well characterized but not readily available. Human studies indicate that Methyl Eugenol is short-lived in the body, and despite the high potential for exposure through the diet and environment, human blood levels are relatively low. The toxicology studies in animals demonstrate that relatively high-bolus doses administered orally result in hepatic neoplasms. However, an understanding is lacking regarding how this effect relates to the exposures that result when food containing Methyl Eugenol is consumed. Overall, the level of Methyl Eugenol detected in biomonitoring studies indicates that human exposure is several orders of magnitude lower than the lowest dose used in the bioassay. Furthermore, there are no known health effects in humans that result from typical dietary exposure to Methyl Eugenol.