Isoeugenol
(Synonyms: 异丁香酚; iso-Eugenol) 目录号 : GC60946
Isoeugenol (4-Propenylguaiacol), an essential oil constituent of nutmeg, clove, and cinnamon, shows antimicrobial activity.
Cas No.:97-54-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Isoeugenol (4-Propenylguaiacol), an essential oil constituent of nutmeg, clove, and cinnamon, shows antimicrobial activity.
| Cas No. | 97-54-1 | SDF | |
| 别名 | 异丁香酚; iso-Eugenol | ||
| Canonical SMILES | OC1=CC=C(/C=C/C)C=C1OC | ||
| 分子式 | C10H12O2 | 分子量 | 164.2 |
| 溶解度 | DMSO : 100mg/mL | 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 | 6.0901 mL | 30.4507 mL | 60.9013 mL |
| 5 mM | 1.218 mL | 6.0901 mL | 12.1803 mL |
| 10 mM | 0.609 mL | 3.0451 mL | 6.0901 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。
Isoeugenol-functionalized nanogels inhibit peri-implantitis associated bacteria in vitro
Anaerobe 2022 Jun;75:102552.PMID:35367366DOI:10.1016/j.anaerobe.2022.102552.
Objectives: Obligate and facultative anaerobic bacteria adhering to dental implants are a major cause for peri-implant inflammation, which, if left untreated, can lead to implant loss. Previously, our group developed a new route for the synthesis of isoeugenol-functionalized aqueous nanogels for implant coatings. Methods: Here, the antimicrobial activity of several new nanogels differing in spacer length (n = 6, 9, 44), radius (60-200 nm), and amount of Isoeugenol functional substance (1-20 mol%) was tested against the following peri-implantitis-associated species: Fusobacterium nucleatum, Porphyromonas gingivalis, Prevotella intermedia, Aggregatibacter actinomycetemcomitans, Escherichia coli, Actinomyces viscosus, Enterococcus faecalis, Staphylococcus aureus, Streptococcus oralis, S. parasanguinis, and the yeast Candida albicans. The minimal bactericidal concentration (MBC) and fungicidal concentration (MFC) were determined for each combination. In addition, transmission electron microscopy (TEM) and fluorescence microscopy after live-dead-staining (LD-S) were performed to visualize nanogel-microbe interactions. Results: Two nanogels, NG9-3 and NG9-4 (colloids of 80-150 nm, with a spacer length of n = 9 and feeding between 5 and 10 mol% Isoeugenol), had an inhibitory effect on all Gram-positive species and on P. gingivalis and P. intermedia with MBC ≥31.25 μg/ml. TEM and LD-S images showed that cellular adhesion and uptake of nanogels resulted in swelling, shedding, or even complete detachment of the cell wall and then to bursting (see graphical abstract). Conclusions: Functional nanogels can be used as building blocks in the design of bioactive coatings on implants to prevent infection and accelerate tissue regeneration, but the concentrations required are higher than for antibiotics.
Isoeugenol suppresses multiple quorum sensing regulated phenotypes and biofilm formation of Pseudomonas aeruginosa PAO1
Nat Prod Res 2022 Mar;36(6):1663-1667.PMID:33719769DOI:10.1080/14786419.2021.1899174.
The potential strategy to prevent bacterial pathogenicity is disabling quorum sensing circuits with structural mimicking molecules. Here, we analyzed a synthetic molecule Isoeugenol, for inhibition of quorum sensing regulated phenotype and biofilm formation. Isoeugenol was an effective inhibitor, i.e., more than 70% of virulence factors were inhibited including pyocyanin, rhamnolipid, exopolysaccharide, swarming motility and biofilm formation. Interestingly, these quorum sensing regulated phenotypes in Pseudomonas aeruginosa PAO1 were inhibited without affecting the planktonic cells. Moreover, the presence of Isoeugenol exhibited more than 70% inhibition of biofilm formation through inhibition of the quorum sensing systems. Furthermore, docking studies suggest that Isoeugenol bound to the quorum sensor regulators such as LasI, LasR PqsE and SidA with considerable binding interactions. Our results demonstrate the utility of Isoeugenol as a blocker of quorum sensing, which will be functioning as an antivirulence compound.
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.
[Deodorants and antiperspirants]
Ann Dermatol Venereol 2020 May;147(5):387-395.PMID:32248967DOI:10.1016/j.annder.2020.01.003.
The terms deodorants and antiperspirants very frequently used interchangeably despite the fact that they employ completely different active substances and mechanisms of action. Antiperspirants are necessarily deodorants due to the lack of substrate to decompose. They nevertheless represent a group of very specific substances that create particular problems due to the presence of aluminium chlorohydrate, or ACH, (Al2(OH)5Cl, 2H2O), aluminium sesquichlorohydrate and aluminium-zirconium complex, which, after hydrolysis, causes intense acidification of the skin, hence the importance of inclusion of emollients and pH regulators in formulations. Moreover, systemic aluminium is thought to be genotoxic and to promote breast cancer, and it is thus at the centre of numerous scientific controversies. Nevertheless, its potential toxicity following topical application is related to its ability to penetrate skin, which is as yet poorly understood but considered very low, a fact that may provide some degree of reassurance regarding its use in cosmetic products. Its role in Alzheimer's disease has not been proven. On the other hand, zirconium salts are considered toxic and are partly regulated in Europe. The problems associated with deodorants are those arising from the presence of antiseptics (triclosan, usnic acid) capable of inducing bacterial resistance, but more particularly, the presence of axillary dermatitis due to the allergenic potential of the fragrances and essential oils used (e.g. Isoeugenol, citronellal, lyral, cinnamic aldehyde, etc.).
RIFM fragrance ingredient safety assessment, Isoeugenol, CAS Registry Number 97-54-1
Food Chem Toxicol 2016 Nov;97S:S49-S56.PMID:26723296DOI:10.1016/j.fct.2015.12.021.
The use of this material under current use conditions is supported by the existing information. This material was evaluated for genotoxicity, repeated dose toxicity, developmental toxicity, reproductive toxicity, local respiratory toxicity, phototoxicity, skin sensitization potential, as well as, environmental safety. Repeated dose toxicity was determined to have the most conservative systemic exposure derived NO[A]EL of 37.5 mg/kg/day. A gavage 13-week subchronic toxicity study conducted in mice resulted in a MOE of 5769 while considering 38.4% absorption from skin contact and 100% from inhalation. A MOE of >100 is deemed acceptable.