69-89-6
Xanthine
CAS: 69-89-6
Molecular Formula: C5H4N4O2
69-89-6 - Names and Identifiers
| Name | Xanthine |
| Synonyms | Xanthine UREOUS ACID ISOXANTHINE 2,6-DIOXYPURINE 2,6-DIOXOPURINE 9H-PURINE-2,6-DIOL TIMTEC-BB SBB004054 2,6-Dihydroxypurine 2,6-DIHYDROXYPURINE 1H-purine-2,6-dione xanthine sigmaultra 2,6-Dihydroxy purine PURINE-2,6(1H,3H)-DIONE purine-2(3H),6(1H)-dione 3,7-dihydro-1H-purine-2,6-dione 3,5-dihydro-1H-purine-2,6-dione |
| CAS | 69-89-6 |
| EINECS | 200-718-6 |
| InChI | InChI=1/C5H2N4O2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H,9,10,11) |
| InChIKey | LRFVTYWOQMYALW-UHFFFAOYSA-N |
69-89-6 - Physico-chemical Properties
| Molecular Formula | C5H4N4O2 |
| Molar Mass | 152.11 |
| Density | 1.5452 (rough estimate) |
| Melting Point | 300 °C |
| Boling Point | 274.55°C (rough estimate) |
| Water Solubility | Soluble in water(0.067g/L). |
| Solubility | Soluble in sodium hydroxide solution, ammonia and acidic solution, slightly soluble in water and ethanol, insoluble in organic solvents. |
| Vapor Density | 5.3 (vs air) |
| Appearance | White powder |
| Color | White to slightly yellow |
| Odor | Odorless |
| Merck | 14,10059 |
| BRN | 8733 |
| pKa | pKa 9.95 (Uncertain) |
| Storage Condition | Keep in dark place,Sealed in dry,Room Temperature |
| Sensitive | Sensitive to light |
| Refractive Index | 1.8500 (estimate) |
| MDL | MFCD00078453 |
| Physical and Chemical Properties | Crystal with metallic luster. |
| Use | Can be used for food coloring, can also be added to the poultry feed, the egg yolk to enhance the yellow |
69-89-6 - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R36 - Irritating to the eyes R43 - May cause sensitization by skin contact R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S36/37 - Wear suitable protective clothing and gloves. S37/39 - Wear suitable gloves and eye/face protection S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
| RTECS | ZD7700000 |
| TSCA | Yes |
| HS Code | 29335990 |
69-89-6 - Reference
| Reference Show more | 1. Zhu Xiangxiang, Fang Yingying, Peng Minxia et al. Comparative study on the replication of hyperuricemia model in mice by different modeling factors [J]. Journal of Zhejiang University of Chinese Medicine 2018 02(v.42;No.280):50-56. 2. Gao Xiaohui, Tang Jingjing, Liu Haoran, etc. Screening of xanthine oxidase inhibitors by improved nitrotetrazolium blue colorimetric method [J]. Journal of Hunan Normal University (Medical Sciences), 2016, 13(3). 3. Ma Qian, Zhao pincheng, Lu Yongchang. Inhibition of xanthine oxidase activity by different extracts of Polygonum multiflorum [J]. Chinese national folk medicine, 2020(15). 4. Yu Junjun, Xu Deping. Components of Hovenia dulcis Thunb for reducing uric acid [J]. Food Science and Technology, 2019, v.44;No.337(11):234-238 244. 5. Wang zeci, Xiaoyan, Cui Tao, Wei Zi, Hong, Zhang Hongbing, Liu Rui, Li, yazuo, yixiulin, Zhang Tie-jun, Gu Yuan, Wu Wei Party, Liu Xiao-Chang. Inhibitory effects of different medicinal components on OAT4 and URAT1 and their effects on serum uric acid level in mice with acute hyperuricemia [J]. Chinese herbal medicine 2019 50(05):1157-1163. 6. Deng Baoqin, Zhou Jiangrong. Study on decolorization process of total saponins from saponines by reduction method [J]. Journal of Jiangxi Normal University (Natural Science), 2019, 43(01):94-99. 7. Zhang Lei, Wang Yanhua, Liu Chang, etc. Analysis and Evaluation of chemical quality of donkey skin glue and deer skin glue [J]. Food Science, 2018, 039(022):57-63. 8. He Yue, Xiao Hui-min, Kang Xiao-Gang, et al. Study on radiosensitization of earthworm capsule and its principal components on S_(180) transplanted tumor in mice [J]. Northwest Pharmaceutical Journal, 2019. 9. Gao Kun, Gong, Rui Ze, Li Shanshan, et al. Simultaneous determination of 13 nucleosides in ginseng by UPLC [J]. Food Industry 2019. 10. Feng hygienic, Li Fang, Guo menghuan, et al. A new pyrazine derivative from Dioscorea opposita [J]. Chinese Journal of Pharmacy, 2017(08):101-103. 11. Xie Xiong-Xiong, Xie Jing, Zeng Jin-xiang, Zhang Chen-Hui, Li Min, Liang Jian, Zhu Jixiao, Zhong Guo-yue, Luo Guang-ming, Yao Peng-Cheng, Gui Yaqi. Study on the migration components in blood of Tibetan Medicine short tube rabbit ear grass and its molecular docking with XOD [J]. Journal of Jiangxi University of Traditional Chinese Medicine, 2020,32(05):71-76 115. 12. Fang Yan, Xie Dingyuan, Ding Lu, Yu Yong Hao, Luo Xin. Determination of purine in chicken and chicken soup by optimized HPLC [J]. Chinese condiment, 2020,45(12):115-123. 13. Xu Mengqi, Xu Deping. Study on the active constituents of reducing uric acid in Smilax glabra [J]. Natural product research and development, 2020,32(11):1860-1865. 14. Ma Qian, Zhao pincheng, Lu Yongchang. Inhibition of xanthine oxidase activity by different extracts of Polygonum multiflorum [J]. Chinese national folk medicine, 2020,29(15):16-20. 15. Lu Yushun, Wang zeshuai, Bi Xiaodong, Xia Yunshi, Lu Si, Sun Yinshi. Establishment of extraction method for extract of pilose antler and application of multi-component determination in quality evaluation [J]. Chinese herbal medicine, 2021,52(02):357-366. 16. Liu Songxin, Gong Ruize, Wang zeshuai, Zhang Lei, Liu Chang, Lu Yushun, Sun Yinshi. Comparative study on 9 kinds of chemical constituents of pilose antler and pilose antler based on principal component analysis and discriminant analysis [J]. Chinese herbal medicine, 2021,52(01):82-90. 17. Wang Rongrong, Hu Xiaoyan, Wu Pinggu, single La Tian, Huang Jiawei, Wang Chunlei. Simultaneous determination of nucleosides and amino acids in extracts of Agkistrodon acutus by ultra performance liquid chromatography-tandem mass spectrometry [J]. Chinese Journal of Health inspection, 2020,30(15):1793-1797 1803. 18. Wu, Zhao-Yu, et al. "Evaluation of xanthine oxidase inhibitory activity of flavonoids by an online capillary electrophoresis‐based immobilized enzyme microreactor." Electrophoresis 41.15 (2020): 1326-1332.https://doi.org/10.1002/elps.202000083 19. [IF=7.711] Zhen Zhang et al."Mitochondria-Accessing Ratiometric Fluorescent Probe for Imaging Endogenous Superoxide Anion in Live Cells and Daphnia magna."Acs Sensors. 2018;3(3):735-741 20. [IF=7.514] Lizeng Cheng et al."Dynamic changes of metabolic profile and taste quality during the long-term aging of Qingzhuan Tea: The impact of storage age."Food Chem. 2021 Oct;359:129953 21. [IF=4.952] Yali Jiang et al."Bacillus amyloliquefaciens HZ-12 heterologously expressing NdmABCDE with higher ability of caffeine degradation."Lwt Food Sci Technol. 2019 Jul;109:387 22. [IF=4.952] Lizeng Cheng et al."Integration of non-targeted metabolomics and E-tongue evaluation reveals the chemical variation and taste characteristics of five typical dark teas."Lwt Food Sci Technol. 2021 Oct;150:111875 23. [IF=4.142] Wang Chenxi et al."Systematic quality evaluation of Peiyuan Tongnao capsule by offline two-dimensional liquid chromatography/quadrupole-Orbitrap mass spectrometry and adjusted parallel reaction monitoring of quality markers."Anal Bioanal Chem. 2019 Nov;4 24. [IF=3.535] Zhao-Yu Wu et al."Evaluation of xanthine oxidase inhibitory activity of flavonoids by an online capillary electrophoresis-based immobilized enzyme microreactor."Electrophoresis. 2020 Aug;41(15):1326-1332 25. [IF=3.24] Yinfang Gao et al."Uricase-deficient rats with similarly stable serum uric acid to human's are sensitive model animals for studying hyperuricemia."Plos One. 2022 Mar;17(3):e0264696 26. [IF=10.435] Xie Pei et al."Biodegradable MoSe2-polyvinylpyrrolidone nanoparticles with multi-enzyme activity for ameliorating acute pancreatitis."J Nanobiotechnol. 2022 Dec;20(1):1-18 27. [IF=6.529] Yarigui Bao et al."Therapeutic effects of Chinese medicine Di-Long (Pheretima vulgaris) on rheumatoid arthritis through inhibiting NF-κB activation and regulating Th1/Th2 balance."Biomed Pharmacother. 2022 Mar;147:112643 28. [IF=6.576] Rui Wang et al."Quality Characteristics and Inhibitory Xanthine Oxidase Potential of 21 Sour Cherry (Prunus Cerasus L.) Varieties Cultivated in China."Front Nutr. 2021; 8: 796294 29. [IF=13.273] Liying Zhang et al."2D MoSe2@PVP nanosheets with multi-enzyme activity alleviate the acute pancreatitis via scavenging the reactive oxygen and nitrogen species."CHEMICAL ENGINEERING JOURNAL. 2022 Oct;446:136792 30. [IF=4.24] Jun Li et al."In vitro xanthine oxidase inhibitory properties of Flos Sophorae Immaturus and potential mechanisms."Food Biosci. 2022 Jun;47:101711 31. [IF=4.072] Meng-zhen Zhou et al."Discovery and Biochemical Characterization of N-methyltransferase Genes Involved in Purine Alkaloid Biosynthetic Pathway of Camellia gymnogyna Hung T.Chang (Theaceae) from Dayao Mountain."Phytochemistry. 2022 Jul;199:113167 |
69-89-6 - Reference Information
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Introduction | xanthine (English: xanthine), Chinese alias 3, 7-dihydro-1h-purine -2, 6-dione, 2, 6-dihydroxypurine, xanthine is a purine base widely distributed in organs and body fluids of human and other organisms, commonly used as mild stimulants and bronchodilators, especially for the treatment of asthma symptoms. Common mild stimulants such as caffeine, theophylline and theobromine (found mainly in chocolate) are derived from xanthine. Xanthine is also a product of purine metabolism and is converted to uric acid by xanthine oxidase. |
| Clinical application | xanthine is a purine derivative and is rarely found in the composition of nucleic acids. Xanthine is formed by the action of guanine via guanine deaminase and hypoxanthine via xanthine oxidase, which is eventually oxidized to uric acid via xanthine oxidase. The concentration of xanthine and uric acid in human body can be used as biomarkers of various clinical diseases, such as periodic asphyxia, cerebral ischemia, especially hyperuricemia and gouty arthritis. Therefore, the detection of the content of xanthine in the body is helpful to the diagnosis and determination of related diseases. |
| Application | xanthine is mainly used in biochemical research and organic synthesis, and is an intermediate of theobromine, it can also be used to prepare other xanthine analogs. Common xanthine compounds include caffeine, theophylline and theobromine. Caffeine and theophylline are often used as natural adenosine antagonists, which can relieve pain or inhibit asthma. Since caffeine and theophylline both contain a common mother nucleus structure-xanthine, a large number of studies have begun to synthesize xanthine compounds as adenosine receptor antagonists, in particular, xanthine compounds substituted at the 8-position are favored. |
| preparation method | xanthine is obtained by reacting 4-amino-5-formylsemicarbazine with formamide at 180-185 °c. |
| detection method | 1) trisodium citrate solution and chloroauric acid solution were thoroughly mixed and reacted to obtain citrate-coated gold nanoparticles, after dilution with ultrapure water, sodium bisulfate solution is added, and this solution is used as a detection solution; The volume ratio of the trisodium citrate solution to the chloroauric acid solution is 3: 1 to 5: 1, preferably 3.88: 1. The gold nanoparticles have a particle size of 10 to 15 nm, preferably 13 nm. Gold nanoparticles strongly adsorb amine-containing substances, while xanthine contains four amine groups, providing multiple adsorption sites. The detection solution according to, wherein the final concentration of sodium hydrogen sulfate is 0 to 2mmol/L. The detection solution according to, wherein the concentration of the gold nanoparticles is 0 to 10nmol/L. 2) The xanthine standard solution and the sample solution with different concentrations are mixed with the detection solution respectively to fully react; The concentration range of the xanthine standard solution is 0-2.00ppm. A sufficient reaction is described with a reaction time of at least 2min. If it is less than 2min, if the concentration of xanthine contained in the sample is low, the adsorption between gold nano and xanthine is not complete, and the color change is not obvious. The sample solution may be an aqueous solution containing a sample of xanthine and other water-soluble impurities, or may be a biological sample such as a serum or urine sample treated to remove proteins. 3) after the reaction, the mixed droplets are placed on a paper-based chip, dried and photographed with a mobile phone and the RGB color intensity of the photograph is analyzed by software, so that the concentration of xanthine in the solution can be accurately calculated, further, the content of xanthine in the sample was determined, and the content refers to the mass-volume concentration. The content of xanthine in the solution is calculated as follows: the blue color value and the red color value in the color intensity are taken, and the ratio of them is taken as the ordinate, and the standard curve is established with different concentrations of xanthine as the abscissa, the color value ratio of the sample solution is brought into the standard curve, and the content of xanthine in the sample solution is calculated. |
| preparation | 33% G of purified water, 66g of concentrated hydrochloric acid, and G of guanine (0.1985mol) were sequentially placed in a ml flask, the reaction was stirred and heated to 85 °c for 0.5h. Then, 50g of a 40% sodium nitrite aqueous solution (MOL) was slowly added dropwise at 20 °c. After dropping, the reaction was continued at 45 ° C. For 2 hours, cooled to 15 ° C., filtered and washed to obtain 56g of AH01; 250g of purified water and 56g of AH01 were put into a 500ml flask, and stirred, the hydrolysis reaction was carried out at 80 ° C. For 2.0 hours, and the crude xanthine was obtained by filtration. The yield was 90% and the HPLC purity was 85%. add the above crude xanthine into a 1000mL three-necked flask, add 30% ml of purified water and 200g of concentrated hydrochloric acid (1.643mol), raise the temperature to 80~90 ℃, stir and dissolve, 5g of activated carbon was added, stirred and decolorized for 0.5h, filtered, and the filtrate was cooled to 20~25 °c for 1h to give xanthine-dehumidified product by filtration, with HPLC purity of 93%. add the xanthine dehumidified product into a 1000mL flask, add 30% ml of purified water and 200g of concentrated hydrochloric acid (1.643mol), and raise the temperature to 80~90 ℃, 5g of activated carbon was added, stirred and decolorized for 0.5h, filtered, and the filtrate was cooled to 20-25 °c for 1h for crystallization. Xanthine dehumidified product was obtained by filtration, with HPLC purity of 98%. put the xanthine dehumidified product into a 20% ml flask, add ml of purified water, raise the temperature to 75~85 °c, and add 30g of aqueous ammonia (0.3529mol) dropwise. pH = 7~8 was adjusted, stirred for 0.5h, filtered, washed with 50ml of water, dried, and dried under vacuum to obtain 24.3g of light yellow xanthine dry product with a molar yield of 75% and a purity of 98.1%. |
| Use | is used in biochemical research and organic synthesis, and is an intermediate of theobromine. can be used for food coloring, can also be added to the poultry feed, the egg yolk to enhance the yellow biochemical research, organic synthesis. |
| production method | is obtained by reacting 4-amino-5-formylsemicarbazine with formamide at 180-185 °c. 5-amino-4-imidazolamide was prepared by treatment with diethyl carbonate. |
Last Update：2024-04-09 02:00:10
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