Imidazolidinyl urea
(Synonyms: 咪唑烷基脲) 目录号 : GC33960
Imidazolidinyl Urea (Imidurea) is an antimicrobial agent used as preservative in cosmetics.
Cas No.:39236-46-9
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
Imidazolidinyl Urea (Imidurea) is an antimicrobial agent used as preservative in cosmetics.
| Cas No. | 39236-46-9 | SDF | |
| 别名 | 咪唑烷基脲 | ||
| Canonical SMILES | O=C(NC(C(N1)=O)N(CO)C1=O)NCNC(NC(C(N2)=O)N(CO)C2=O)=O | ||
| 分子式 | C11H16N8O8 | 分子量 | 388.29 |
| 溶解度 | DMSO : ≥ 4 mg/mL (10.30 mM) | 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 | 2.5754 mL | 12.877 mL | 25.7539 mL |
| 5 mM | 0.5151 mL | 2.5754 mL | 5.1508 mL |
| 10 mM | 0.2575 mL | 1.2877 mL | 2.5754 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。
Imidazolidinyl urea activates mast cells via MRGPRX2 to induce non-histaminergic allergy
Toxicol Res (Camb) 2021 Apr 29;10(3):467-475.PMID:34141160DOI:10.1093/toxres/tfab035.
Imidazolidinyl urea (IU) is used as an antimicrobial preservative in cosmetic and pharmaceutical products. IU induces allergic contact dermatitis, however, the mechanism has not yet been elucidated. Mas-related G protein-coupled receptor-X2 (MRGPRX2) triggers drug-induced pseudo-allergic reactions. The aims of this study were to determine whether IU activated mast cells through MRGPRX2 to further trigger contact dermatitis. Wild-type (WT) and KitW-sh/HNihrJaeBsmJNju (MUT) mice were treated with IU to observe its effects on local inflammation and mast cells degranulation in vivo. Laboratory of allergic disease 2 cells were used to detect calcium mobilization and release of inflammatory mediators in vitro. WT mice showed a severe local inflammatory response and contact dermatitis, whereas only slight inflammatory infiltration was observed in MUT mice. Thus, MRGPRX2 mediated the IU-induced activation of mast cells. However, histamine, a typical allergen, was not involved in this process. Tryptase expressed by mast cells was the major non-histaminergic inflammatory mediator of contact dermatitis. IU induced anaphylactic reaction via MRGPRX2 and further triggering non-histaminergic contact dermatitis, which explained why antihistamines are clinically ineffective against some chronic dermatitis.
Contact Dermatitis to Medications and Skin Products
Clin Rev Allergy Immunol 2019 Feb;56(1):41-59.PMID:30145645DOI:10.1007/s12016-018-8705-0.
Consumer products and topical medications today contain many allergens that can cause a reaction on the skin known as allergic contact dermatitis. This review looks at various allergens in these products and reports current allergic contact dermatitis incidence and trends in North America, Europe, and Asia. First, medication contact allergy to corticosteroids will be discussed along with its five structural classes (A, B, C, D1, D2) and their steroid test compounds (tixocortol-21-pivalate, triamcinolone acetonide, budesonide, clobetasol-17-propionate, hydrocortisone-17-butyrate). Cross-reactivities between the steroid classes will also be examined. Next, estrogen and testosterone transdermal therapeutic systems, local anesthetic (benzocaine, lidocaine, pramoxine, dyclonine) antihistamines (piperazine, ethanolamine, propylamine, phenothiazine, piperidine, and pyrrolidine), topical antibiotics (neomycin, spectinomycin, bacitracin, mupirocin), and sunscreen are evaluated for their potential to cause contact dermatitis and cross-reactivities. Finally, we examine the ingredients in the excipients of these products, such as the formaldehyde releasers (quaternium-15, 2-bromo-2-nitropropane-1,3 diol, diazolidinyl urea, Imidazolidinyl urea, DMDM hydantoin), the non-formaldehyde releasers (isothiazolinones, parabens, methyldibromo glutaronitrile, iodopropynyl butylcarbamate, and thimerosal), fragrance mixes, and Myroxylon pereirae (Balsam of Peru) for contact allergy incidence and prevalence. Furthermore, strategies, recommendations, and two online tools (SkinSAFE and the Contact Allergen Management Program) on how to avoid these allergens in commercial skin care products will be discussed at the end.
Characterization and chemistry of Imidazolidinyl urea and diazolidinyl urea
Contact Dermatitis 2006 Jan;54(1):50-8.PMID:16426294DOI:10.1111/j.0105-1873.2006.00735.x.
For several decades, the cosmetic preservatives Imidazolidinyl urea (IU) and diazolidinyl urea (DU) have not only been poorly characterized but have also had misleading chemical structures assigned to them. The most common trade names of IU and DU are Germall 115 and Germall II, respectively. This publication gives an insight into what these 2 well-known contact allergens consist of and their degradation patterns. Approximately, 30-40% of both products can be characterized by mixtures of allantoin (synthetic starting material), (4-hydroxymethyl-2,5-dioxo-imidazolidin-4-yl)-urea (compound HU) and presumably 1-(3,4-bis-hydroxymethyl-2,5-dioxo-imidazolidin-4-yl)-1,3-bis-hydroxymethyl-urea (compound BHU). A full chemical characterization of compound HU is shown. The remaining part of both IU and DU are believed to be polymers of allantoin-formaldehyde condensation products. The analytical methods used to characterize IU and DU are capillary electrophoresis and nuclear magnetic resonance and mass spectroscopy studies.
Characterization of the decomposition of compounds derived from Imidazolidinyl urea in cosmetics and patch test materials
Contact Dermatitis 2012 Nov;67(5):284-92.PMID:22564140DOI:10.1111/j.1600-0536.2012.02073.x.
Background: Imidazolidinyl urea releases formaldehyde through decomposition. However, there have been few reports on the chemistry of Imidazolidinyl urea in cosmetics. Objectives: The aim of this study was to characterize imidazolidinyl urea-derived compounds in cosmetics and to determine which compounds are responsible for the cross-reactivity with diazolidinyl urea. Methods: We analysed Imidazolidinyl urea dissolved in aqueous solutions, Imidazolidinyl urea patch test materials and imidazolidinyl urea-preserved cosmetics by high-performance liquid chromatography/photodiode array detection and liquid chromatography/mass spectrometry. The results were compared with those obtained with a diazolidinyl urea aqueous solution. Results: In the analysed cosmetic samples and patch test materials, Imidazolidinyl urea was primarily composed of allantoin, (4-hydroxymethyl-2,5-dioxo-imidazolidine-4-yl)-urea (HU), (3,4-bis-hydroxymethyl-2,5-dioxo-imidazolidine-4-yl)-urea (3,4-BHU), and (3-hydroxymethyl-2,5-dioxo-imidazolidine-4-yl)-urea. Conclusions: Two of the imidazolidinyl urea-derived major decomposition compounds - HU and 3,4-BHU - are common in the diazolidinyl urea-decomposed compound present in cosmetics. These compounds are possible causative agents of the cross-reactivity between diazolidinyl urea and Imidazolidinyl urea.
Construction of supramolecular hydrogels using Imidazolidinyl urea as hydrogen bonding reinforced factor
J Mater Chem B 2020 Apr 21;8(15):3058-3063.PMID:32201874DOI:10.1039/d0tb00331j.
The development of a new hydrogen bonding reinforced factor is of importance for the design and application of supramolecular hydrogels. Herein, we use a new reinforced factor, Imidazolidinyl urea (IU), for the construction of hydrogen bonding supramolecular hydrogels. Poly(ethylene glycol) (PEG), three types of diisocyanates (isophorone diisocyanate (IPDI), 4,4'-methylene bis(cyclohexyl isocyanate) (HMDI) and 4,4'-methylene bis(phenyl isocyanate) (MDI)) and IU were employed to synthesize a series of polymers through hydroxyl-isocyanate chemistry. We found that increased IU content and hydrophobicity of the diisocyanates led to a higher gel-sol transition temperature of the polymer aqueous solutions, and the formed hydrogel showed great self-healing capability in response to external mechanical forces. Moreover, we found that improved diisocyanate hydrophobicity could endow the hydrogel with promising mechanical strength, with 1.6 MPa tensile stress and 460% elongation at the break. The advanced hydrogel can also efficiently dissipate energy during deformation and can quickly recover from 200% strain at room temperature without any assistance. Since IU is commercially available and ready for polymer preparation, our work provides a simple and convenient method for the development of hydrogen bonding supramolecular hydrogels with advanced properties.