1-(2,5-dioxoimidazolidin-4-yl)urea
Allantoin
CAS: 97-59-6
Molecular Formula: C4H6N4O3
1-(2,5-dioxoimidazolidin-4-yl)urea - Names and Identifiers
| Name | Allantoin |
| Synonyms | ALL Sebical Alantan Alphosyl Allantin Allegron Egopsoryl Allantion ALLANTOIN Allantoin Cordianine Alyonyldiurened 5-Ureidohydantoin 5-UREIDOHYDANTOIN (2,5-dioxo-4-imidazolidinyl)urea (2,5-dioxo-4-imidazolidinyl)-urea (2,5-Dioxo-4-Imidazo-Lidinyl)Urea 1-(2,5-dioxoimidazolidin-4-yl)urea 1-[(4S)-2,5-dioxoimidazolidin-4-yl]urea 1-[(4R)-2,5-dioxoimidazolidin-4-yl]urea |
| CAS | 97-59-6 |
| EINECS | 202-592-8 |
| InChI | InChI=1/C4H6N4O3/c5-3(10)6-1-2(9)8-4(11)7-1/h1H,(H3,5,6,10)(H2,7,8,9,11)/t1-/m0/s1 |
| InChIKey | POJWUDADGALRAB-UHFFFAOYSA-N |
1-(2,5-dioxoimidazolidin-4-yl)urea - Physico-chemical Properties
| Molecular Formula | C4H6N4O3 |
| Molar Mass | 158.12 |
| Density | 1.6031 (rough estimate) |
| Melting Point | 230 °C (dec.) (lit.) |
| Boling Point | 283.17°C (rough estimate) |
| Flash Point | 230-234°C |
| Water Solubility | Slightly soluble in water. Freely soluble in alkalis |
| Solubility | Soluble in hot water, hot alcohol and dilute sodium hydroxide solution. Slightly soluble in water and alcohol at room temperature, hardly soluble in organic solvents such as ether and chloroform. |
| Appearance | White crystal |
| Color | White |
| Merck | 14,258 |
| BRN | 102364 |
| pKa | 8.96(at 25℃) |
| Storage Condition | 2-8°C |
| Stability | Stable. Incompatible with strong oxidizing agents. |
| Sensitive | Easily absorbing moisture |
| Refractive Index | 1.8500 (estimate) |
| MDL | MFCD00005260 |
| Physical and Chemical Properties | Appearance: white crystalline powder Melting Point: 226-240 ° C |
| Use | Widely used in various skin ulcers, wound treatment and nutritional cosmetics additives |
1-(2,5-dioxoimidazolidin-4-yl)urea - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 1 |
| RTECS | YT1600000 |
| TSCA | Yes |
| HS Code | 29332100 |
1-(2,5-dioxoimidazolidin-4-yl)urea - Reference
| Reference Show more | 1. Su Xiaojun, Lu chengte, Wang Feng, Guo Shiyin, Li Wenjia, Li Qingming. Effect of heat treatment on physicochemical properties of yam cooked powder [J]. Food Science, 2020,41(05):80-86 2. Mai Wu Ju Dan, a Li Fu, Yang Jian-Hua, Cao Yuan, etc. TLC identification of two water-soluble components in Cistanche deserticola [J]. Journal of Anhui Agricultural Sciences, 2015, 43(19):55-55. 3. Chen Guitian, Guo Siqin, Shi Jun, et al. Determination and physicochemical properties of allantoin and glycolic acid in snail mucus [J]. Journal of Guangdong Pharmaceutical Sciences, 2018, 034(006):5-9. 4. Ma Rui, Yang Ke, Li Wenhui et al. Analysis of chemical constituents of Dioscorea opposita Thunb at different growth stages [J]. Food Research and development 2019. 5. Marui, Wang, Lulu, Chen, with Qing. Analysis of commercial specification and quality characteristics of Chinese yam [J]. Chinese patent medicine, Vol 42, No. 7, 2020, pp. 2020. 6. Chen Jingjing, Meng ran, Zhang Zhenling, Zheng xuya, Yang Jianing. Comparison of the effects of different wheat bran varieties from different habitats on the quality of Bran-fried yam based on fingerprint and composition analysis [J]. Chinese Journal of Traditional Chinese Medicine, 2021,39(01):217-222 305. 7. Liu, Lei, et al. "Exogenous allantoin improves the salt tolerance of sugar beet by increasing putrescine metabolism and antioxidant activities." Plant Physiology and Biochemistry 154 (2020): 699-713.https://doi.org/10.1016/j.plaphy.2020.06.034 8. [IF=4.27] Lei Liu et al."Exogenous allantoin improves the salt tolerance of sugar beet by increasing putrescine metabolism and antioxidant activities."Plant Physiol Bioch. 2020 Sep;154:699 9. [IF=3] Qu Lala et al."Phenotypic assessment and ligand screening of ETA/ETB receptors with label-free dynamic mass redistribution assay."N-S Arch Pharmacol. 2020 Jun;393(6):937-950 |
1-(2,5-dioxoimidazolidin-4-yl)urea - Nature
Open Data Verified Data
colorless crystalline powder. Melting point 238~240 °c (decomposition). Soluble in hot water, hot alcohol and dilute sodium hydroxide solution, slightly soluble in water and alcohol, almost insoluble in ether and chloroform. Odorless and tasteless. Stable in dry air, boiled in water for a long time or broken in strong alkali
Bad. The pH of the saturated aqueous solution was 5.5.
Last Update：2024-01-02 23:10:35
1-(2,5-dioxoimidazolidin-4-yl)urea - Preparation Method
Open Data Verified Data
allantoin is present in the quiet fluid, fetal urine and some plants. However, the cost of extracting the capsule from these substances is too high. At present, allantoin is synthesized by potassium permanganate oxidation of urea acid; Allantoin is synthesized by heating with dichloroacetic acid and urea; Glyoxylic acid and urea are directly condensed.
- using dichloroacetic acid and urea as raw materials, the process was as follows: sodium methoxide solution and methanol were added into the reaction tank, heated to 40-50 ° C., dichloroacetic acid was slowly added dropwise, and the reaction was refluxed for 2 hours after the addition. It was cooled to room temperature, filtered, washed with methanol, and the filtrate was washed together to give a solution of sodium dimethoxide in methanol. The solution was reduced to dryness under reduced pressure, 2.8 parts of hydrochloric acid was added, and heated and stirred on a water bath to a paste. Then the temperature was raised to 90 ℃, then cooled to about 10 ℃, filtered, and the small solution was added with 0. 25 parts of hydrochloric acid and urea, heated and dissolved, and reacted at 80 ℃ for 2H. Cooling crystallization, and then maintained at 0 deg C for more than 3H, centrifugation, washing, spin drying, drying to obtain fine. The crude product was recrystallized with 15 times water to obtain allantoin. The overall yield of p-dichloroacetic acid was 30.3%.
- direct condensation of glyoxylic acid with urea (glyoxylic acid is obtained by oxidation of glyoxal) example of operation: oxidation in a 500ml four-mouth bottle equipped with mechanical stirring, condenser, thermometer and dropping funnel, 193g (1mol) of 30% aqueous glyoxal solution was added, 40±2g(1mol) of 135.5 nitric acid was added dropwise with stirring at controlled internal temperature (45%) ° C., and the reaction was continued at this temperature for 2-3H, until the oxidation of Red-Brown no longer escape, the reaction solution was blue-green and disappeared. Change to a simple distillation apparatus, in about 2. 76kPa; The external temperature is not more than 60 degrees Celsius, distilled out of water about 12 5G, concentrated liquid at room temperature overnight, precipitation of oxalic acid crystals (19g after drying, 0. 21mol, the concentration is 39%). The reaction was continued with stirring at an internal temperature (40±2) ° C. For about 8H, and the oxidation reaction was completed. (2) condensation in a 500ml three-necked flask equipped with mechanical stirring, condenser and thermometer, 150g of the above aqueous glyoxylic acid solution were added, and 170g of (2. 83mol) urea and 23. 3g of concentrated hydrochloric acid was heated with stirring to an internal temperature of 80 °c. After about 15 min, the urea was dissolved, and the reactant was a transparent liquid. After about 30~45min, the reactant appeared white turbidity, and then the white precipitate gradually increased, the heating was stopped and the reaction was cooled to room temperature. The white precipitate was collected using a Buchner funnel and precipitated several times with cold water to obtain the crude allantoin. The crystals were recrystallized with looml distilled water. White fine crystalline allantoin (60~63)%, melting point 236 C (decomposition). Allantoin yield is theoretical (38-40)% in terms of glyoxal
Last Update：2022-01-01 10:57:26
1-(2,5-dioxoimidazolidin-4-yl)urea - Use
Open Data Verified Data
allantoin can promote the growth of endothelial cells and make the wound heal quickly. It is used as an anti-ulcer drug, mixed with dried aluminum hydroxide gel, and used for peptic ulcer and inflammation. The product can soften keratan, so that the skin to maintain moisture, moisture and soft, is a special additive cosmetics. Allantoin and its derivatives are also quality improvers and additives for many daily chemical products. Allantoin protein can be formulated as an anti-irritant, anti-dandruff, cleansing, and wound-healing scalp preparation, making hair soft, shiny and elastic. The product is a kind of amphoteric compounds, can be combined with a variety of substances in the form of double salt, with light, sterilization, anti-corrosion, pain, deodorization, antioxidant effect, so it is a daily chemical products, beauty cosmetics such as pastille cream, additives for acne cream, shampoo, soap, toothpaste, shaving lotion, astringent liquid, anti-sweat deodorant detergent, etc. Allantoin is also a Biochemical reagent.
Last Update：2022-01-01 10:57:25
1-(2,5-dioxoimidazolidin-4-yl)urea - Reference Information
| Decomposition | 230-234 ºC |
| LogP | -2.26 at 20℃ |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| What is allantoin? | Allantoin belongs to an imidazole heterocyclic compound, is a derivative of uric acid, and belongs to a component of human skin. Uric acid acts as an antioxidant, and produces allantoin after free radical action. In 1912, Mocllster extracted allantoin from the underground stem of the plant. Allantoin can promote cell tissue growth, metabolism, softening stratum corneum protein. These properties are particularly pronounced when allantoin is applied to ulcerated and purulent skin, so it has the ability to accelerate wound healing and is a good active agent in the treatment of skin lesions. allantoin, once known as an anti-irritant, can effectively reduce the stimulation of irritants; At the same time, it is also an antioxidant, and like other water-soluble vitamins, its ability to aggregate free radicals is similar to that of vitamin C, so it can enhance the antioxidant capacity of cells. Therefore, the U. S. Food and Drug Administration FDA will be listed as the first class of efficient active component skin care agent, its non-toxic, non-irritating, no allergic reaction. |
| properties | pure product is a non-toxic, tasteless, non-irritating, non-allergic white crystals, crystallized in water as a single prism or colorless crystalline powder. Melting Point: 226-240 °c. Soluble in hot water, hot alcohol and dilute sodium hydroxide solution. Slightly soluble in water and alcohol at room temperature, difficult to dissolve in ether and chloroform and other organic solvents; Its saturated aqueous solution (concentration of 0.6%) is slightly acidic; PH 5.5. It is stable in an aqueous solution with a pH of 4 to 9. It is also stable in non-aqueous solvents and dry air; It can be decomposed by boiling in strong alkaline solution and sunlight exposure. |
| efficacy and function | 1. Emollient repair efficacy allantoin has good emollient effect, especially for the rough chapped skin, it can restore its smooth and moist, at the same time, it can enhance the water absorption capacity of the outermost layer of skin and hair, and improve the hydrophilicity of keratin molecules, the damaged stratum corneum is repaired to restore its natural water absorption capacity. 2. Moisturizing effect allantoin can promote the water absorption capacity of the outermost layer of skin and hair, reduce the evaporation of skin moisture, and form a layer of lubricating film on the skin surface, closed moisture, so as to achieve the role of skin moisturizing. 3, softening keratin effect allantoin has a unique nature of dissolving keratin, so it has the role of softening keratin protein, it stripped the metabolic waste at the same time, the intercellular spaces are filled with water to bring the skin to a hydrated, shiny state. 4. Anti-inflammatory and antioxidant effects allantoin is a kind of amphoteric compound, which can combine with a variety of substances to form double salt, and has the effects of avoiding light, sterilization, preservation, pain relief and antioxidation, it is widely used as an additive for pescing cream, stinging liquid, shampoo, soap, toothpaste, shaving lotion, hair conditioner, astringent, anti-sweat deodorant lotion and the like. |
| Use | allantoin is an important fine chemical product, which is widely used in medicine, light industry, agriculture, in medicine: allantoin can promote cell growth, accelerate wound healing, soften keratin and other physiological functions, it is a good healing agent and anti-ulcer agent for skin wounds. It can be used to relieve and treat xerosis, scaly skin disease, skin ulcer, digestive tract ulcer and inflammation, and has good curative effect on osteomyelitis, diabetes, cirrhosis and acne. 2, in cosmetics: allantoin is a kind of amphoteric compounds, can combine a variety of substances to form a double salt, with light, sterilization, anti-corrosion, pain, anti-oxidation effect, can keep the skin moisture, moisturizing and soft, is a cosmetic effect additives such as beauty. allantoin has the effect of promoting the growth of endothelial cells and rapid wound healing. Used as an anti-ulcer drug, mixed with dry aluminum hydroxide gel, used for peptic ulcer and inflammation. The product can soften keratan, so that the skin to maintain moisture, moisture and soft, is a special additive cosmetics. Allantoic Mutual and its derivatives or many daily chemical products quality improvers, additives. Allantoin protein can be formulated as an anti-irritant, anti-dandruff, cleansing, and wound-healing scalp preparation, making hair soft, shiny and elastic. The product is a kind of amphoteric compounds, can be combined with a variety of substances in the form of double salt, with light, sterilization, anti-corrosion, pain, deodorization, antioxidant effect, so it is a daily chemical products, beauty cosmetics such as pastille cream, face cream, shampoo, soap, toothpaste, An additive such as a astringent solution, an antiperspirant deodorant detergent, and the like. Allantoin is also a Biochemical reagent. for skin care, oral products, anti-allergy, treatment of skin ulcers to promote wound healing and other effects widely used in a variety of skin ulcers, cosmetic additives for the treatment and nutrition of wounds effective biomarkers for oxidative stress reactions; Mannich bases for synthesis as antibacterial agents; used in the synthesis of sulfonylchlorophenylurea analogs as antitumor agents; Used as plant growth regulators has amphoteric properties, can form metal salts and adducts with many substances and can maintain the original characteristics. The saturated aqueous solution (0.6%) is slightly acidic (pH = 6), which can remain stable in the aqueous solution of pH = 4~9, and decomposition occurs when boiling in alkaline solution for a long time. The pH of the saturated aqueous solution was 5.5. purine metabolites through the uric acid pathway. Uric acid can also react with free radicals to produce allantoin, thus allantoin can be used as an effective biomarker for oxidative stress. |
| Anti-inflammatory analgesic effect | allantoin has anti-inflammatory analgesic effect, and it also has weak local paralysis effect, can effectively reduce the stimulation of irritants, can be used as a skin protective agent and anti-irritant, can reduce the irritation of cosmetic ingredients to the skin, the Chinese Food and Drug Administration listed it as the first type of efficient active component skin care agent, which has been widely used in shampoo, sunscreen products, cream lotion, shaving cream and oral care products. |
| production method | allantoin is present in the quiet fluid, fetal urine and some plants. However, the cost of extracting the capsule from these substances is too high. At present, the methods for synthesizing allantoin include: the method of oxidation of urea acid by potassium permanganate; The method of heating allantoin with dichloroacetic acid and urea; The method of direct condensation of glyoxylic acid and urea. 1. Using dichloroacetic acid and urea as raw materials, the process is as follows: sodium methoxide solution and methanol are added into the reaction tank, heated to 40-50 ° C., dichloroacetic acid is slowly added dropwise, and the reaction is refluxed for 2 hours after the addition. It was cooled to room temperature, filtered, washed with methanol, and the filtrate was washed together to give a solution of sodium dimethoxide in methanol. The solution was reduced to dryness under reduced pressure, 2.8 parts of hydrochloric acid was added, and heated and stirred on a water bath to a paste. Then the temperature was raised to 90 ° C., then cooled to about 10 ° C., filtered, the small solution was added with 0.25 parts of hydrochloric acid and urea, heated and dissolved, and reacted at 80 ° C. For 2H. Cooling crystallization, and then at 0 deg C for more than 3H, centrifugation, washing, spin drying, drying to obtain fine. The crude product was recrystallized with 15 times water to obtain allantoin. The overall yield of p-dichloroacetic acid was 30.3%. 2. Direct condensation of glyoxylic acid with urea (glyoxylic acid is obtained by oxidation of glyoxal) example operation:(1) oxidation in a 500ml four-mouth bottle equipped with mechanical stirring, condenser, thermometer and dropping funnel, 193g(1mol) of 30% aqueous glyoxal solution was added, 40±2g(1mol) of 135.5 nitric acid was added dropwise with stirring at controlled internal temperature of 45% ° C., and the reaction was continued at this temperature for 2-3H, until the oxidation of Red-Brown no longer escape, the reaction solution was blue-green and disappeared. Change to a simple distillation device, at about 2.76kPa, outside the temperature does not exceed 60 ℃ distilled out of water about 125g, concentrated liquid at room temperature overnight, precipitation of oxalic acid crystals (19g after drying, 0.21mol), the concentration of 39%). The reaction was continued with stirring at an internal temperature of 40±2 ° C. For about 8H, and the oxidation reaction was completed. (2) condensation in a 2.83 ml three-necked flask equipped with mechanical stirring, condenser and thermometer, 150g of the aqueous glyoxylic acid solution described above was added followed by 170g (mol) of urea and 23.3g of concentrated hydrochloric acid, heat to an internal temperature of 80 °c with stirring. After about 15min, the urea was dissolved, and the reactant was a transparent liquid. After about 30-45min, the reactant appeared white turbidity, and then the white precipitate gradually increased, the heating was stopped and the reaction was cooled to room temperature. The white precipitate was collected using a Buchner funnel and precipitated several times with cold water to obtain the crude allantoin. Recrystallization was performed with 1000mL of distilled water. White fine crystal allantoin 60-63%, melting point 236 deg C (decomposition). The allantoin yield is 38-40% of theory in terms of glyoxal (weight yield 103-108%). |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:01:54
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