97-59-6 Usage
Anti-inflammatory analgesic effects
Allantoin has anti-inflammatory analgesic effects, but it also has a weak partial paralysis effect, can effectively reduce stimuli of stimulus, can be used as a skin protectant and anti-irritant, can reduce skin irritation of cosmetic ingredients, China food and Drug Administration rank it as the first kind efficient active ingredient of skin care agent, now has been widely used in many products such as shampoo, sunscreen products, creams and lotions, shaving creams and oral care products.
Chemical properties
Colorless crystalline powder. Melting point is 238-240 ℃ (decomposition). Can be dissolved in hot water, hot alcohol and dilute sodium hydroxide solution, slightly soluble in water and alcohol, almost insoluble in ether and chloroform. Odorless, tasteless. In dry air is stable, prolonged boiling in the water. or strong base will be destroyed. pH of saturated aqueous solution is 5.5.
The above information is edited by the lookchem of Liu Yujie.
Uses
Different sources of media describe the Uses of 97-59-6 differently. You can refer to the following data:
1. 1. Allantoin can promote skin cell growth and rapid wound healing. Used as anti-ulcer drug, mixed with dry aluminum hydroxide gel, for gastrointestinal ulcers and inflammation. The product can soften keratin, making the skin retain moisture, moist and soft, is special effects of additive in cosmetic. Allantoin and its derivatives are the quality improver and additive of many household chemical products. Allantoin protein may be formulated anti-irritant, anti-dandruff, cleaning and wound healing scalp preparations, making hair soft, shiny and elastic. The product is an amphoteric compound, can bind to a variety of material form double salts, with dark, antiseptic, analgesic, deodorant, anti-oxidation effect, and therefore is household chemical products, additives of cosmetics such as freckle cream, acne solution, shampoo , soap, toothpaste, shaving lotion, convergence liquid and antiperspirant deodorant detergent. Allantoin also is a biochemical reagents.
2. For the roles such as skin care, oral products, anti-allergy, the treatment of skin ulcers promote wound healing.
3. Widely used in treatment of a variety of skin ulcers and trauma and additives of nutritional cosmetics.
2. diuretic
3. allantoin is a botanical extract said to be healing, calming, and soothing, it can also help protect the skin from harmful external factors (e.g., wind burn). It is considered an excellent temporary anti-irritant and is believed to stimulate new tissue growth, helping heal damaged skin. Allantoin is appropriate for sensitive, irritated, and acne skins. Derived from the comfrey root, it is considered non-allergenic.
Production methods
Allantoin presents in the sheath cyst fluid, fetal urine and some of the plants. However, the cost extracted Allantoin from these substances is too high. Currently synthesis methods of Allantoin are: potassium permanganate oxidation uric acid method: dichloroacetic acid and urea heated to synthesize Allantoin; direct condensation method of glyoxylic acid and urea.
1. technological process of dichloroacetic acid and urea as raw materials is as follows: The sodium methoxide solution and methanol were added into the reaction tank, and heated to 40-50 ℃, slowly dropwise added dichloroacetic acid, after added and reflux reaction for 2 h. Cooled to room temperature, filtered, washed with methanol and the filtrate was combined, washed, added methanol solution of sodium dimethoxyethane. The solution was reduced to dryness under reduced pressure , 2.8 portion of hydrochloric acid was added,heated and stirred into a paste in a water bath. Then heated to 90 ℃, and then cooled to about 10 ℃, filtered, 0.25 portion of hydrochloric acid and urea was added into , dissolved by heated, reacted at 80 ℃ for 2 h. Cooled and crystallization, and then maintained at 0 ℃ for above 3 h, centrifugation, washed ,spin-dried, dried to crude product. After The crude product was used 15 times of the water to recrystallize, Allantoin was obtained. As for the dichloroacetic acid, the total yield was 30.3%.
2. The direct condensation of glyoxylic acid and urea (glyoxylate derived by oxidation of glyoxal) operation example: (1) oxidation was in 500 ml four-hole boiling flask equipped with mechanical stirrer, condenser, thermometer and dropping funnel, added 193 g (1 mol) 30% glyoxal aqueous solution, controlled the internal temperature at 40 ± 2 ℃ and stirred to dropwise add 135.5 g ( 1 mol) 45% nitric acid, After addition, continued to stir at this temperature and reacted for 2-3 h, until reddish brown oxidation no longer escaped, the reaction solution was blue-green and immediately disappeared. Replaced by simple distillation apparatus, at about 2.76 kPa, the outside temperature did not exceed 60 ℃ and about 125 g water was evaporated, concentrate solution was standing overnight at room temperature, oxalic acid crystals were precipitated (dried to get 19 g, together 0.21 mol), concentration was 39% ). Continue to stir and react for about 8h at an internal temperature of 40 ± 2 ℃, the oxidation reaction was completed. (2) condensation In 500 ml three-hole boiling flask equipped with mechanical stirrer, condenser and thermomete, above 150 g glyoxylic acid aqueous solution was added, added 170 g (2.83 mol) urea and 23.3 g of concentrated hydrochloric acid, heated to an internal temperature of 80 ℃ under stirring. After about 15min urea was dissolved, the reaction solution was transparent, approximately another 30-45 min, the reactant appeared white cloudy, white precipitate was gradually increased, stirred at an inner temperature of 80 ℃ for 1 h, heating was stopped and the reactant was cooled to room temperature, The white precipitate was collected on a Buchner funnel, precipitated with cold water several times, obtained crude product of Allantoin. Used 1000 ml distilled water to recrystallize. 60-63% white fine crystalline Allantoin was obtained, melting point was 236 ℃ (decomposition). Calculated by glyoxal, the theoretical yield of Allantoin was 38-40% (weight yield was 103-108%).
Description
Allantoin is a product of purine and uric acid metabolism. It is formed through oxidation of uric acid by urate oxidase in most mammals but is formed only through non-enzymatic oxidation by free radicals in humans. Urinary levels of allantoin are increased prior to the onset of Alzheimer’s disease symptoms in mice expressing mutations in amyloid precursor protein and tau (APP/tau) but not during the early/middle stage of the disease, indicating its potential use as a biomarker for predicting Alzheimer’s disease onset. Due to the formation of allantoin by free radicals in humans, increased urinary levels are a potential biomarker for oxidative stress status.
Chemical Properties
White Solid
Originator
Allantoin ,Arocor Holdings Inc.
Definition
ChEBI: An imidazolidine-2,4-dione that is 5-aminohydantoin in which a carbamoyl group is attached to the exocyclic nitrogen.
Manufacturing Process
To a mixture of 13.14 kg 40% solution of glyoxal in water and a solution of
0.5 L of concentrated HCl in 3 L of water was added 1.8 g Co(NO3)2·6H2O.
The mixture was heated at 50-60°C, to the solution was added 20 g of
sodium nitrite and then at 40-60°C was added dropwise the mixture of 6 L of
concentrated HNO3, 4.2 L of water and 30 g of sodium nitrite. The product
obtained was mixed with 2.4 kg ammonium sulfate and filtrated. The filtrate
was heated with 14.5 kg urea at 70°C for 10 hours. Allantoin was filtrated and
recrystallized from the water; M.P. 233-235°C.
Therapeutic Function
Vulnerary, Antiulcer (topical), Antipsoriatic
General Description
Allantoin, the final catabolic product of purines in mammals, is a highly polar and amphoteric substance. Allantoin is mainly used for skin protection as the drug promotes cell proliferation and wound healing.Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
Flammability and Explosibility
Nonflammable
Biochem/physiol Actions
Purine metabolite via the uric acid pathway. Uric acid also reacts with free radicals to produce allantoin, thus allantoin may be a useful biomarker for oxidative stress.
Purification Methods
It crystallises from water or EtOH [Hartman et al. Org Synth Coll Vol II 21 1943]. [Beilstein 25 III/IV 4071.]
Check Digit Verification of cas no
The CAS Registry Mumber 97-59-6 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 7 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 97-59:
(4*9)+(3*7)+(2*5)+(1*9)=76
76 % 10 = 6
So 97-59-6 is a valid CAS Registry Number.
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
97-59-6Relevant articles and documents
Synergistic effect of 1-(2,5-dioxoimidazolidin-4-yl)urea and Tween-80 towards the corrosion mitigation of mild steel in HCl
Zhang, Weiwei,Li, Hui-Jing,Wang, Chen,Wang, Li-Juan,Li, Gen,Ma, Hengyu,Pan, Qianwen,Wu, Yan-Chao
, p. 13899 - 13910 (2019)
Herein, the synergistic effect of 1-(2,5-dioxoimidazolidin-4-yl)urea (DMU) and Tween-80 on the corrosion of mild steel in a 1 mol L-1 HCl solution was investigated by weight-loss tests, electrochemical methods and surface analysis (SEM/SECM). The experiments revealed that the combination of DMU and Tween-80 strongly inhibited the corrosion of mild steel as compared to individual inhibitors, and the adsorption mode belonged to the Langmuir isothermal type. Based on the electrochemical results, DMU and DMU-Tween-80 behaved as mixed-type inhibitors, and their best inhibition efficiencies were 77.31% and 96.35%, respectively. The calculated synergistic parameter value was larger than unity, indicating that the enhancement of inhibition efficiency was due to the synergistic effect of DMU and Tween-80. Surface analysis techniques confirmed the presence of inhibitors on the mild steel surface. Quantum chemical parameters based on density functional theory provided a further insight into the mechanism of inhibition. Moreover, molecular dynamics simulations were carried out to explore the configurational adsorption behaviour of DMU on an Fe(110) surface.
Ultrasensitive detection of uric acid in serum of patients with gout by a new assay based on Pt&at;Ag nanoflowers
Chen, Shujun,Lin, Daiqin,Qiu, Ping,Tang, Xiaomin,Wang, Xue
, p. 36578 - 36585 (2019)
A ultrasensitive assay for the determination of uric acid (UA) based on Pt&at;Ag nanoflowers (Pt&at;Ag NFs) was constructed. H2O2 was formed by the reaction of uricase and UA and produced the hydroxyl radical (OH). The system was catalyzed by Pt&at;Ag NFs to change the color of 3,3′,5,5′-tetramethylbenzidine (TMB) from colorless to blue, and the morphology and chemical properties of Pt&at;Ag NFs were characterized by transmission electron microscopy and X-ray photoelectron spectroscopy. Under the optimized conditions, a linear relationship between the absorbance and UA concentration was in the range of 0.5-150 μM (R2 = 0.995) with a limit of detection of 0.3 μM (S/N = 3). The method can be applied to detection of UA in actual samples with satisfactory results. The proposed assay was successfully applied to the detection of UA in human serum with recoveries over 96.8percent. Thus, these results imply that the UA assay provides an effective tool in fast clinical analysis of gout.
Correction: Absolute stereochemistry and preferred conformations of urate degradation intermediates from computed and experimental circular dichroism spectra (Org. Biomol. Chem. (2011) 9 (5149-5155))
Pipolo, Silvio,Percudani, Riccardo,Cammi, Roberto
, p. 3654 - 3654 (2016)
Correction for 'Absolute stereochemistry and preferred conformations of urate degradation intermediates from computed and experimental circular dichroism spectra' by Silvio Pipolo et al., Org. Biomol. Chem., 2011, 9, 5149-5155.
Uricase-catalyzed oxidation of uric acid using an artificial electron acceptor and fabrication of amperometric uric acid sensors with use of a redox ladder polymer
Nakaminami, Takahiro
, p. 1928 - 1934 (1999)
Electrochemical oxidation of uric acid catalyzed by uricase (uric acid oxidase, UOx; EC 1.7.3.3) was studied using several redox compounds including 5-methylphenazinium (MP) and 1-methoxy-5-methylphenazinium (MMP) as electron acceptors for UOx, which does not contain any redox cofactor. It was found that MP and MMP were useful to mediate electrons from UOx to an electrode in the enzymatic oxidation of uric acid. A novel redox polymer, poly(N-methyl-o-phenyIenediamine) (poly-MPD), containing the MP units was also found to possess the mediation ability for UOx, and poly-MPD was immobilized together with UOx onto an electrode substrate covered with a self-assembled monolayer of 2-aminoethanethiolate with use of glutaraldehyde as a binding agent The resulting electrode (pory-MPD/UOx/Au) exhibited amperometric responses to uric acid with very fast response of ~30 s, allowing reagentless amperometric determination in a concentration range covering that in the blood of a healthy human being. Kinetic parameters of the apparent Michaelis constant and the maximum current response obtained at the poly-MPD/UOx/Au suggested that electrochemical oxidation of uric acid was controlled by diffusion of uric acid into the enzyme film and that the redox polymer worked well in mediating between active sites of UOx molecules and the electrode substrate.
A Novel Cascade Nanoreactor Integrating Two-Dimensional Pd-Ru Nanozyme, Uricase and Red Blood Cell Membrane for Highly Efficient Hyperuricemia Treatment
Ming, Jiang,Zhu, Tianbao,Li, Jingchao,Ye, Zichen,Shi, Changrong,Guo, Zhide,Wang, Jingjuan,Chen, Xiaolan,Zheng, Nanfeng
, (2021/10/21)
Nanozyme-based cascade reaction has emerged as an effective strategy for disease treatment because of its high efficiency and low side effects. Herein, a new and highly active two-dimensional Pd-Ru nanozyme is prepared and then integrated with uricase and red blood cell (RBC) membrane to fabricate a tandem nanoreactor, Pd-Ru/Uricase@RBC, for hyperuricemia treatment. The designed Pd-Ru/Uricase@RBC nanoreactor displayed not only good stability against extreme pH, temperature and proteolytic degradation, but also long circulation half-life and excellent safety. The nanoreactor can effectively degrade UA by uricase to allantoin and H2O2 and remove H2O2 by using Pd-Ru nanosheets (NSs) with the catalase (CAT)-like activity. More importantly, the finally produced O2 from H2O2 decomposition can in turn facilitate the catalytic oxidation of UA, as the degradation of UA is an O2 consumption process. By integrating the high-efficiency enzymatic activity, long circulation capability, and good biocompatibility, the designed Pd-Ru/Uricase@RBC can effectively and safely treat hyperuricemia without side effects. The study affords a new alternative for the exploration of clinical treatment of hyperuricemia.
(2,5-Dioxoimidazolidin-4-ylidene)aminocarbonylcarbamic Acid as a Precursor of Parabanic Acid, the Singlet Oxygen-Specific Oxidation Product of Uric Acid
Iida, Sayaka,Yamamoto, Yorihiro,Fujisawa, Akio
, (2019/03/19)
Previously, we identified that parabanic acid (PA) and its hydrolysate, oxaluric acid (OUA), are the singlet oxygen-specific oxidation products of uric acid (UA). In this study, we investigated the PA formation mechanism by using HPLC and a time-of-flight mass spectrometry technique and identified unknown intermediates as (2,5-dioxoimidazolidin-4-ylidene)aminocarbonylcarbamic acid (DIAA), dehydroallantoin, and 4-hydroxyallantoin (4-HAL). DIAA is the key to PA production, and its formation pathway was characterized using 18O2 and H218O. Two oxygen atoms were confirmed to be incorporated into DIAA: the 5-oxo- oxygen from singlet oxygen and the carboxylic oxygen from water. Isolated DIAA and 4-HAL gave PA stoichiometrically. A plausible reaction scheme in which two pathways branch out from DIAA is presented, and the potential for PA as an endogenous probe for biological formation of singlet oxygen is discussed.