Estragole
(Synonyms: 草蒿脑; 4-Allylanisole) 目录号 : GC46141
A volatile compound with diverse biological activities
Cas No.:140-67-0
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Estragole is a volatile compound that has been found in basil oil and has diverse biological activities.1,2,3,4 It induces mortality in 100% of adult C. capitata, B. dorsalis, and B. cucurbitae fruit flies exposed to wicks impregnated with estragole at concentrations greater than or equal to 2.5%.1 Estragole (60 mg/kg) reduces carrageenan-induced paw edema in mice.2 It increases survival in a mouse model of infection with the ME49 strain of T. gondii when administered at a dose of 100 mg/kg per day.3 Estragole (2.5 μmol/g, p.o., twice per week) increases the percentage of hepatoma-bearing mice and the average number of hepatomas per mouse in male, but not female, mice when administered prior to weaning.4
| Cas No. | 140-67-0 | SDF | |
| 别名 | 草蒿脑; 4-Allylanisole | ||
| Canonical SMILES | COC1=CC=C(CC=C)C=C1 | ||
| 分子式 | C10H12O | 分子量 | 148.2 |
| 溶解度 | DMF: 10 mg/ml,Ethanol: Partially soluble | 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。 |
||
| 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 | |||
 |
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。
Constituents of aromatic plants: II. Estragole
Fitoterapia 2000 Dec;71(6):725-9.PMID:11077188DOI:10.1016/s0367-326x(00)00153-2.
Estragole (ES) is a natural constituent of a number of plants (e.g. tarragon, sweet basil and sweet fennel) and their essential oils have been widely used in foodstuffs as flavouring agents. Several studies with oral, i.p. or s.c. administration to CD-1 and B6C3F1 mice have shown the carcinogenicity of ES. The 1-hydroxy metabolites are stronger hepatocarcinogens than the parent compound. Controversial results are reported for the mutagenicity of ES. However, the formation of hepatic DNA adducts in vivo and in vitro by metabolites of ES has been demonstrated.
Modeling the hydroxylation of Estragole via human liver cytochrome P450
J Mol Model 2021 Jun 11;27(7):199.PMID:34117581DOI:10.1007/s00894-021-04815-z.
Natural compounds derived from plants are generally regarded safe and devoid of adverse effects. However, there are individual ingredients that possess toxic, genotoxic, and carcinogenic activities. These compounds when exposed at specific level become hazardous to health. Estragole (1-allyl-4-methoxybenzene) is a common component of spice plants. Its toxicity gets activated with the hydroxylation at benzylic carbon (C1') position by P450 enzymes present in the human liver. The present study grounds to explore the reaction mechanism of conversion of Estragole to hydroxylated metabolite using computational methodology. Density functional theory (DFT)-based calculations were employed to explore the cytochrome P450-catalyzed mechanism at C1 position aliphatic hydroxylation of Estragole. Overall reaction energy profile, electronic configuration, and 3D structure of all intermediates, transition states, and product complexes formed during the reaction along with their free energies were tried to be investigated.
Bioactivation of Estragole and anethole leads to common adducts in DNA and hemoglobin
Food Chem Toxicol 2021 Jul;153:112253.PMID:34015424DOI:10.1016/j.fct.2021.112253.
Estragole and anethole are secondary metabolites occurring in a variety of commonly used herbs like fennel, basil, and anise. Estragole is genotoxic and carcinogenic in rodents, which depends on the formation of 1'-sulfoxyestragole after hydroxylation and subsequent sulfoconjugation catalyzed by CYP and SULT, respectively. It was hypothesized recently that anethole may be bioactivated via the same metabolic pathways. Incubating Estragole with hepatic S9-fractions from rats and humans, specific adducts with hemoglobin (N-(isoestragole-3-yl)-valine, IES-Val) and DNA (isoestragole-2'-deoxyguanosine and isoestragole-2'-deoxyadenosine) were formed. An isotope-dilution technique was developed for the quantification of IES-Val after cleavage with fluorescein isothiocyanate (FITC) according to a modified Edman degradation. The same adducts, albeit at lower levels, were also detected in reactions with anethole, indicating the formation of 3'-hydroxyanethole and the reactive 3'-sulfoxyanethole. Finally, we conducted a pilot investigation in which IES-Val levels in human blood were determined during and after the consumption of an estragole- and anethole-rich fennel tea for four weeks. A significant increase of IES-Val levels was observed during the consumption phase and followed by a continuous decrease during the washout period. IES-Val may be used to monitor the internal exposure to the common reactive genotoxic metabolites of Estragole and anethole, 1'-sulfoxyestragole and 3'-sulfoxyanethole, respectively.
Estragole DNA adduct accumulation in human liver HepaRG cells upon repeated in vitro exposure
Toxicol Lett 2021 Feb 1;337:1-6.PMID:33189830DOI:10.1016/j.toxlet.2020.11.009.
Accumulation of N2-(trans-isoestragol-3'-yl)-2'-deoxyguanosine (E-3'-N2-dG) DNA adducts derived from the alkenylbenzene Estragole upon repeated dose exposure was investigated since the repair of this adduct was previously shown to be inefficient. To this end human HepaRG cells were exposed to repeating cycles of 2 h exposure to 50 μM Estragole followed by 22 h repair to mimic daily exposure. The E-3'-N2-dG DNA adduct levels were quantified by LC-MS/MS after each cycle. The results show accumulation of E-3'-N2-dG DNA adducts at a rate of 17.53 adducts/108 nts/cycle. This rate at the dose level calculated by physiologically based kinetic (PBK) modeling to result in 50 μM was converted to a rate expected at average human daily intake of Estragole. The predicted time estimated to reach adduct levels reported at the BMD10 of the related alkenylbenzene methyleugenol of 10-100 adducts /108 nts upon average human daily intake of Estragole amounted to 8-80 (in rat) or 6-57 years (in human). It is concluded that the persistent nature of the E-3'-N2-dG DNA adducts may contribute to accumulation of substantial levels of DNA adducts upon prolonged dietary exposure.
Effect of Estragole over the RN4220 Staphylococcus aureus strain and its toxicity in Drosophila melanogaster
Life Sci 2021 Jan 1;264:118675.PMID:33127513DOI:10.1016/j.lfs.2020.118675.
Among the bacterial resistance mechanisms, efflux pumps are responsible for expelling xenobiotics, including bacterial cell antibiotics. Given this problem, studies are investigating new alternatives for inhibiting bacterial growth or enhancing the antibiotic activity of drugs already on the market. With this in mind, this study aimed to evaluate the antibacterial activity of Estragole against the RN4220 Staphylococcus aureus strain, which carries the MsrA efflux pump, as well as Estragole's toxicity in the Drosophila melanogaster arthropod model. The broth microdilution method was used to perform the Minimum Inhibitory Concentration (MIC) tests. Estragole was used at a Sub-Inhibitory Concentration (MIC/8) in association with erythromycin and ethidium bromide to assess its combined effect. As for Estragole's toxicity evaluation over D. melanogaster, the fumigation bioassay and negative geotaxis methods were used. The results were expressed as an average of sextuplicate replicates. A Two-way ANOVA followed by Bonferroni's post hoc test was used. The present study demonstrated that Estragole did not show a direct antibacterial activity over the RN4220 S. aureus strain, since it obtained a MIC ≥1024 μg/mL. The association of Estragole with erythromycin demonstrated a potentiation of the antibiotic effect, reducing the MIC from 512 to 256 μg/mL. On the other hand, when Estragole was associated with ethidium bromide (EtBr), an antagonism was observed, increasing the MIC of EtBr from 32 to 50.7968 μg/mL, demonstrating that Estragole did not inhibited directly the MsrA efflux pump mechanism. We conclude that Estragole has no relevant direct effect over bacterial growth, however, when associated with erythromycin, this reduced its MIC, potentiating the effect of the antibiotic.