Urasil

Urasil - Names and Identifiers

Name	Uracil
Synonyms	U Uracil Uracyl hybarx Urasil Hybar X 2,4-pyrimidinediol 2,4-dioxy pyrimidine 2,4-Dihydroxypyrimidine 2,6-Dihydroxypyrimidine 2,4(1H,3H)-Pyrimidinedione 2,4-(1H,3H-Pyrimidinedione) pyrimidine-2,4(1H,3H)-dione 4-Hydroxy-2(1H)-pyrimidinone 2-Hydroxy-4(3H)-pyrimidinone ALUMINIUM CAN WITH HANDLE AND STOPPER COATED SAFETY BOTTLE 2,5LWITHOUT CAP ISO
CAS	66-22-8
EINECS	200-621-9
InChI	InChI=1/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)
InChIKey	ISAKRJDGNUQOIC-UHFFFAOYSA-N

Urasil - Physico-chemical Properties

Molecular Formula	C4H4N2O2
Molar Mass	112.09
Density	1.4421 (rough estimate)
Melting Point	>300 °C (lit.)
Boling Point	209.98°C (rough estimate)
Flash Point	220.2°C
Water Solubility	SOLUBLE IN HOT WATER
Solubility	Easily soluble in hot water, soluble in dilute ammonia water, slightly soluble in cold water, insoluble in ethanol and ether
Vapor Presure	2.27E-08mmHg at 25°C
Appearance	White or white-like crystalline powder
Color	White to slightly yellow
Merck	14,9850
BRN	606623
pKa	9.45(at 25℃)
Storage Condition	2-8°C
Stability	Stable. Incompatible with strong oxidizing agents.
Refractive Index	1.4610 (estimate)
MDL	MFCD00006016
Physical and Chemical Properties	Melting point 335°C WATER-SOLUBLE IN HOT WATER
Use	Used as pharmaceutical intermediates, also used in organic synthesis

Urasil - Risk and Safety

Hazard Symbols	Xi - Irritant
Safety Description	S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes.
WGK Germany	2
RTECS	YQ8650000
TSCA	Yes
HS Code	29335990

Urasil - Reference

Reference

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2. Zhao Chen. Synthesis of very-long-chain fatty acids by engineered yeast strains and the effect of temperature [J]. Microbiology, 2020, 47(1):13-23.
3. Chen Fazhong, Liao Dongqing, Li Xiaoming, etc. Construction of genetic engineering transformation system of Aspergillus oryzae AS3.800 [J]. Light Industry Technology, 2013, 26 (06):12-15.
4. 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.
5. 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.
6. Zhang Yanli, Yang Yanyun, Bai Zhiyao et al. Simultaneous determination of 8 nucleosides in radix rehmanniae Preparata by UPLC-MS/MS [J]. Journal of Pharmaceutical Analysis, 2019, 039(004):608-614.
7. Zhang Yanli, Yang Yanyun, Bai Zhiyao et al. Simultaneous determination of seven nucleosides in Codonopsis pilosula by UPLC-MS/MS [J]. China Medical Science 2018 v.8;No.181(13):68-71.
8. Zheng Xiaoke, Yang Yanyun, Zhang Yanli, etc. Simultaneous determination of seven nucleosides in radix rehmanniae by UPLC-MS/MS [J]. Chinese herbal medicine 2018 041(005):1142-1144.
9. Kong Jing, He Jing, Tan Li, Shen Lifeng, Li Qian, Zhang Yuanyuan, Lu Shan, Wu Qiuhong, Chen Mengjie, Liu Lu, Li Wenxia, Lu Dongbo, Shi Renbing, Jiang Yanyan. Study on correlation analysis of nucleosides based on the quality characterization of golden flower sunflower [J]. Journal of Beijing University of Chinese Medicine, 2017,40(05):420-427
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. Liu Zhengbo, Zhang yayuwang, Qiuxia et al. Effects of different potassium levels on the contents of nucleosides in panax ginseng [J]. Journal of Jilin Agricultural University, 2019, 41(4):432-437.
12. On behalf of Lily, Jin Shanxia, fan Mengying, etc. Application of quaternized β-cyclodextrin grafted chitosan coating in capillary electrophoresis separation [J]. Analytical Laboratory, 2017, 08(v.36):15-18.
13. 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.
14. 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.
15. Wang Pan, total storage root, xuanyun, Cai Zhengyin. Study on fingerprint of didangxianxiong decoction HPLC-MS [J]. Shi Zhen, National Medicine, 2020,31(12):2937-2940.
16. [IF=4.411] Cuihua Chen et al."Quality Evaluation of Apocyni Veneti Folium from Different Habitats and Commercial Herbs Based on Simultaneous Determination of Multiple Bioactive Constituents Combined with Multivariate Statistical Analysis."Molecules. 2018 Mar;23(3):5
17. [IF=4.411] Yujiao Hua et al."Quality Evaluation of Pseudostellariae Radix Based on Simultaneous Determination of Multiple Bioactive Components Combined with Grey Relational Analysis."Molecules. 2017 Jan;22(1):13
18. [IF=2.896] Ya-yun Chen et al."Determination of free amino acids and nucleosides and nucleobases in Annona squamosa L. fruitages from different regions in China by LC-QTRAP-MS/MS."Anal Methods-Uk. 2017 Jun;9(25):3862-3869
19. [IF=4.466] Yao Tan et al."Multiomics Integrative Analysis for Discovering the Potential Mechanism of Dioscin against Hyperuricemia Mice."J Proteome Res. 2021;20(1):645-660
20. [IF=4.411] Mengxia Tan et al."Quality Evaluation of Ophiopogonis Radix from Two Different Producing Areas."Molecules. 2019 Jan;24(18):3220
21. [IF=1.618] Wang Shengnan et al."Simultaneous Determination of Iridoid Glycosides, Phenylpropanoid Glycosides, Organic Acids, Nucleosides and Amino Acids in Scrophulariae Radix Processed by Different Processing Methods by HPLC-QTRAP-MS/MS."J Chromatogr Sci. 2021 Jun;
22. [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

Urasil - Nature

Open Data Verified Data

white or light yellow needle-like crystals. Melting point 338 °c. Soluble in hot water, slightly soluble in cold water, soluble in dilute ammonia, insoluble in ethanol and ether.

Last Update：2024-01-02 23:10:35

Urasil - Hair-making

Open Data Verified Data

from malic acid, sulfuric acid and urea by reaction process in the reaction kettle, in the stirring and below 10 deg C, the urea is added to 15% fuming sulfuric acid, and then add malic acid; the mixture was heated with a steam bath for 1H to release carbon monoxide; After reaction, the reactants were poured into water to cool and crystallize, and filtered; The filter cake was washed with water, and then dissolved in boiling water and decolorized with activated carbon, after filtration, cooling crystallization, and uracil product, the yield of more than 50%.

Last Update：2022-01-01 10:53:18

Urasil - 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)
Organic Base	uracil is an organic base, one of the four main bases in RNA, ribonucleic acid is a major component of pyrimidine, but also various components of uridic acid. It is linked to ribose by a nucleoside bond to produce uridine, and its triphosphate compound is urinary triphosphate, which is the precursor of uracil in the biosynthesis of ribonucleic acid. Urinary triphosphorus is involved as a coenzyme in the biosynthesis of certain sugars. uracil can block the degradation of tegafur, increase the concentration of fluorouracil, and enhance the anticancer effect. Clinical indications and fluorouracil, mainly used for digestive system cancer, breast cancer and thyroid cancer, etc., combined with mitomycin for advanced gastric cancer curative effect is good. Uracil was obtained in the laboratory by cyclization of urea with ethyl formyl acetate. Used in medicine and biochemical research. tautomerism of uracil exists: ketonic formula (2,4-2 oxypyrimidine) enol formula (2,4-2 hydroxypyrimidine) exists mainly as ketonic formula in biological cells. uracil is found in nature in marine organisms, particulate matter, and dissolved matter in seawater. As a biogenic marker in the study of organic geochemistry. pyrimidine is a six-membered heterocyclic compound containing two nitrogen heteroatoms at 1,3 positions of the benzene ring molecule, which is isomeric with pyridazine and pyrazine, there is a particular UV spectrum due to the presence of conjugated double bonds in the pyrimidine. The basicity of pyrimidine is weaker than that of pyridine, and the electrophilic substitution reaction is more difficult than that of pyridine. But more prone to nucleophilic substitution, pyrimidine derivatives widely exist in nature. For example, vitamin B1, uracil, cytosine and thymine all contain a pyrimidine structure.
fluorouracil	fluorouracil (FU) is one of the most commonly used anticancer drugs. White crystals, pKa = 8.1,m.p.282~283 ℃, slightly soluble in water (12 mg/mL 25 ℃) and ethanol, a few insoluble in chloroform and ether, soluble in dilute acid and dilute alkali. Hydrolysis in strong base, stable in physiological saline. Due to the introduction of the electrically strong fluorine atom, Fu is 30 times more acidic than the parent uracil. The injection of Fu is an aqueous solution adjusted to pH 9 with sodium hydroxide, which is sensitive to light and precipitates at low temperature or room temperature for a long period of time. Based on the phenomenon that rat tumor tissues have a stronger ability to utilize pyrimidine than normal tissues, it was designed in 1957 by dschinsky and Heidelberger to synthesize Fu by replacing the hydrogen at the 5-position of uracil with a fluorine atom close to each other, as an antimetabolite of uracil to achieve a selective anti-cancer effect. FU has inhibitory effect on transplanted tumor of mice leukemia L1210, L615, adenocarcinoma 755 and other animals. Tumor cells with cytarabine, methotrexate, mercaptopurine, cyclophosphamide and carbazole and other commonly used anticancer drugs without cross-resistance. FU is converted to 5-fluorodeoxyuridine monophosphate (FDUMP) and 5-fluorouracil nucleoside triphosphate (FUTP) in tissues. FDUMP inhibits TS by forming a complex with thymine nucleotide synthase (TS) and 5,10-Methylenetetrahydrofolate, resulting in a deficiency of intracellular thymine nucleotides, inhibiting DNA synthesis, results in cell death. On the other hand, FUTP is incorporated into RNA as a substrate for RNA polymerase, Affects the normal synthesis and function of RNA. Thymidine (TdR) can reverse the toxicity of FU to cells in tissue culture, so the effect of FU on DNA has been considered as the primary mechanism of cell growth inhibition for many years. However, it was found that TdR could not completely reverse the cytotoxic effect of FU, and it was also found that when FU and TdR were combined, the incorporation of FU into RNA was significantly increased to enhance the anticancer effect of FU. L1210 leukemia cells were incubated with 6-H3-5FU for 22 hours, FDUMP-TS-5 fmol of the, 10CH2-H4 folate complex was present in the 106Cell, while 400fmol of FU was bound to RNA, the importance of the incorporation of FU into RNA for its anti-tumor effect is therefore emphasized. FU is a cell cycle-specific drug that has the most significant effect on the S phase. Reference Materials: Editorial board of Chinese Medical Encyclopedia; Huang-Liang, Chinese medical encyclopedia.
Use	for biochemical studies. used in the synthesis of drugs used as pharmaceutical intermediates, also used in organic synthesis
production method	is prepared by reacting malic acid, sulfuric acid and urea.