| Size | Price | Stock | Qty |
|---|---|---|---|
| 250mg | |||
| 100g |
|
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| Other Sizes |
| ln Vitro |
1. Decomposition Experiment in Cosmetics and Patch Test Materials: Different cosmetic formulations (e.g., lotion, cream) and patch test materials containing Imidazolidinyl urea were stored at 4°C, 25°C, and 40°C for 0, 1, 3, 6, and 12 months. Samples were collected at each time point, and high-performance liquid chromatography (HPLC) was used to analyze the concentration of Imidazolidinyl urea and its decomposition products (formaldehyde, N-(2-hydroxyethyl)ethyleneurea, N-(2-hydroxyethyl)urea). The results showed that Imidazolidinyl urea decomposed gradually with increasing storage temperature and time; at 40°C for 12 months, its residual rate in lotions was only 35-45%, while formaldehyde content increased from initial 0.01-0.02% to 0.08-0.10% [1]
2. In Vitro Sensitization-Related Detection: Extracts of Imidazolidinyl urea-containing patch test materials were prepared using physiological saline. The extracts were tested for formaldehyde release using a formaldehyde-specific colorimetric kit. The data indicated that the amount of formaldehyde released from Imidazolidinyl urea was positively correlated with the storage time and temperature of the patch test materials; fresh materials released 0.03-0.05 μg/mg formaldehyde, while those stored at 40°C for 6 months released 0.12-0.15 μg/mg formaldehyde [1] |
|---|---|
| ln Vivo |
1. Human Patch Test for Sensitization: A total of 120 volunteers with a history of cosmetic contact dermatitis were selected for the patch test. The patch test materials contained Imidazolidinyl urea at concentrations of 0.5%, 1.0%, and 2.0% (dissolved in petrolatum). The patches were applied to the volar forearm of volunteers and removed after 48 hours; skin reactions were evaluated at 48 hours and 72 hours after application according to the International Contact Dermatitis Research Group (ICDRG) criteria. The results showed that the positive reaction rate (erythema, edema, or vesicles) was 8.3% (10/120) for 2.0% Imidazolidinyl urea, 3.3% (4/120) for 1.0%, and 0% (0/120) for 0.5%. No severe adverse reactions (e.g., blistering, ulceration) were observed [1]
|
| ADME/Pharmacokinetics |
Metabolism / Metabolites
Formaldehyde can be absorbed through inhalation, oral ingestion, or skin contact. It is an essential metabolic intermediate in all cells, produced during the normal metabolism of serine, glycine, methionine, and choline, and can also be produced through the demethylation of N-, S-, and O-methyl compounds. Exogenous formaldehyde is metabolized to formic acid by formaldehyde dehydrogenase at the site of contact. After formaldehyde is oxidized to formic acid, the carbon atoms are further oxidized to carbon dioxide, or incorporated into purines, thymidines, and amino acids through a tetrahydrofolate-dependent one-carbon biosynthesis pathway. Formaldehyde is not stored in the body; it is mainly excreted in urine as formic acid, incorporated into other cellular molecules, or exhaled as carbon dioxide. Nitrosamines can also enter the body through ingestion, inhalation, or skin contact. Once in the body, nitrosamines are metabolized by cytochrome P-450 enzymes, thus transforming into carcinogens. (L962, A2878, A2879) |
| Toxicity/Toxicokinetics |
Toxicity Summary
Imidurea is a formaldehyde releaser. When intracellular formaldehyde concentrations saturate with formaldehyde dehydrogenase activity, unmetabolized, intact formaldehyde molecules can exert their effects, leading to formaldehyde poisoning. Formaldehyde is known to form cross-links between proteins and DNA and to be metabolized and incorporated into macromolecules (DNA, RNA, and proteins). Imidurea is also a nitrosating agent. Nitrosating agents can decompose and/or react, leading to nitrosamine contamination. Nitrosamines are formed from secondary amines and amides in the presence of nitrite ions and are considered carcinogenic. Once in the body, nitrosamines are activated by cytochrome P-450 enzymes. Subsequently, they are believed to exert their carcinogenic effects by forming adducts at the N and O atoms of DNA. (L962, L1889, L1890, A2878, A2879, A2880, L1894) Toxicity Data LC50 (rat)> 5,000 mg/m3/1hr 1. Contact Sensitization Toxicity: Human patch tests have confirmed that Imidurea has potential contact sensitization, especially at concentrations ≥1.0%. The sensitization mechanism is related to its decomposition product formaldehyde, which can react with skin proteins to generate haptens, thereby triggering an immune response [1] 2. Decomposition Product-Related Toxicity: Imidurea decomposes to release formaldehyde, a known irritant and sensitizer. Studies have shown that samples containing Imidurea, after long-term storage at high temperatures (40°C, ≥6 months), have formaldehyde levels exceeding the recommended safety limit (0.05%), increasing the risk of skin irritation and sensitization [1] |
| References | |
| Additional Infomation |
Imidurea belongs to the urea family and has antibacterial properties. Imidurea is an antibacterial preservative used in cosmetics that releases formaldehyde. Imidurea is a standardized chemical allergen. Its physiological effects are achieved through increased histamine release and cell-mediated immunity. Imidurea is an antibacterial preservative used in cosmetics that releases formaldehyde. Imidurea may cause contact dermatitis. Its toxicity also stems from its ability to react with and release formaldehyde and nitrosamines, both of which are considered carcinogens. (L1890, L1894) See also: Aloe vera leaf; Imidurea; Water (ingredient)... See more... 1. Background and Applications: Imidurea is a common formaldehyde-releasing preservative widely used in cosmetics (lotions, creams, shampoos) and personal care products to inhibit the growth of bacteria and fungi. Its preservative effect is achieved by the slow release of formaldehyde [1]
2. Decomposition mechanism: Imidurea decomposes through hydrolysis under the influence of temperature, humidity and pH. The hydrolysis process destroys the imidazolium ring, generating formaldehyde and other byproducts (N-(2-hydroxyethyl)vinylurea, N-(2-hydroxyethyl)urea). Higher temperatures and longer storage times accelerate this decomposition [1] 3. Regulatory and safety impacts: Due to its potential sensitization risk (related to formaldehyde release), the use of imidazolyl urea in cosmetics is restricted in some regions; for example, the European Union (EU) limits its maximum concentration in leave-on products to 1.0%. This study provides data support for optimizing the storage conditions (low temperature, short shelf life) of products containing imidazolyl urea to reduce safety risks [1] |
| Molecular Formula |
C11H16N8O8
|
|---|---|
| Molecular Weight |
388.2935
|
| Exact Mass |
388.109
|
| CAS # |
39236-46-9
|
| Related CAS # |
71042-94-9 (mono-hydrochloride salt)
|
| PubChem CID |
38258
|
| Appearance |
White to off-white solid powder
|
| Density |
1.9±0.1 g/cm3
|
| Index of Refraction |
1.715
|
| LogP |
-5.36
|
| Hydrogen Bond Donor Count |
8
|
| Hydrogen Bond Acceptor Count |
8
|
| Rotatable Bond Count |
6
|
| Heavy Atom Count |
27
|
| Complexity |
627
|
| Defined Atom Stereocenter Count |
0
|
| InChi Key |
ZCTXEAQXZGPWFG-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C11H16N8O8/c20-2-18-4(6(22)16-10(18)26)14-8(24)12-1-13-9(25)15-5-7(23)17-11(27)19(5)3-21/h4-5,20-21H,1-3H2,(H2,12,14,24)(H2,13,15,25)(H,16,22,26)(H,17,23,27)
|
| Chemical Name |
1-[3-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]-3-[[[3-(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]carbamoylamino]methyl]urea
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO : ≥ 100 mg/mL (~257.54 mM)
H2O : ~100 mg/mL (~257.54 mM) |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.44 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (6.44 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (6.44 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 100 mg/mL (257.54 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.5754 mL | 12.8770 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 |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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