CYTOSINE
Cytosine
CAS: 71-30-7
Molecular Formula: C4H5N3O
CYTOSINE - Names and Identifiers
| Name | Cytosine |
| Synonyms | Cytosine CYTOSINE Aurora Ka-682 AURORA KA-682 4-aminopyrimidin-2-ol 4-AMINO-2-PYRIMIDINOL 4-AMINO-2(1)-PYRIMIDONE 2-Oxy-4-amino pyrimidine 4-AMINO-2(1H)-PYRIMIDINONE 6-aminopyrimidin-2(1H)-one 4-Amino-2(1H)-Pyrimidinone 4-Amino-2-hydroxypyrimidine 4-AMINO-2-HYDROXYPYRIMIDINE 4-AMINO-2-OXO-1,2-DIHYDROPYRIMIDINE 4-Amino-2-oxo-1,2-dihydropyrimidine |
| CAS | 71-30-7 |
| EINECS | 200-749-5 |
| InChI | InChI=1/C4H5N3O/c5-3-1-2-6-4(8)7-3/h1-2H,(H3,5,6,7,8) |
| InChIKey | OPTASPLRGRRNAP-UHFFFAOYSA-N |
CYTOSINE - Physico-chemical Properties
| Molecular Formula | C4H5N3O |
| Molar Mass | 111.1 |
| Density | 0,48 g/cm3 |
| Melting Point | >300 °C (lit.) |
| Boling Point | 208.2°C (rough estimate) |
| Flash Point | 223.4°C |
| Water Solubility | soluble |
| Solubility | Soluble in methanol, ethanol, DMSO and other organic solvents |
| Vapor Presure | 1.46E-08mmHg at 25°C |
| Appearance | White crystalline powder |
| Color | White to slightly yellow |
| Merck | 14,2795 |
| BRN | 2637 |
| pKa | 4.60, 12.16(at 25℃) |
| Storage Condition | 2-8°C |
| Stability | Stable. Incompatible with strong oxidizing agents. |
| Refractive Index | 1.5000 (estimate) |
| MDL | MFCD00006034 |
| Physical and Chemical Properties | Melting point 300°C water-soluble soluble |
| Use | Used as a drug Intermediate |
CYTOSINE - Risk and Safety
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S37/39 - Wear suitable gloves and eye/face protection |
| WGK Germany | 1 |
| RTECS | UW7350150 |
| TSCA | Yes |
| HS Code | 29335910 |
| Hazard Note | Irritant |
CYTOSINE - Reference
| Reference Show more | 1. Wang Zhiguo, Wang Lei, Wang Zhigang. Synthesis of intermediate sofosbuvir [J]. Chemical reagents, 2016, 38(3):287-290. 2. Wang Huimin, Feng Xuesong. Separation of graphene oxide/Cationic Cellulose composites by capillary electrophoresis [J]. Analytical Laboratory, 2015, 34(012):1395-1398. 3. 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. 4. Gao Kun, Gong, Rui Ze, Li Shanshan, et al. Simultaneous determination of 13 nucleosides in ginseng by UPLC [J]. Food Industry 2019. 5. 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. 6. Huang, Dihui, et al. "Determination of global DNA methylation level by capillary electrophoresis using octyl-modified quaternized cellulose as an electrolyte additive." Analytical and bioanalytical chemistry 406.12 (2014): 2771-2777.https://doi.org/10.1007 7. Song, G., Zhang, R., Jiang X. et al. Nitrogen-doped reduced graphene oxide as a sensing platform for detection of guanine and application in cell necrosis. Chem. Pap. 74, 89-98 (2020). https://doi.org/10.1007/s11696-019-00856-0 8. [IF=4.464] Junqing Qin et al."Growth of monolayer and multilayer graphene on glassy carbon electrode for simultaneous determination of guanine, adenine, thymine and cytosine."J Electroanal Chem. 2021 Aug;895:115403 9. [IF=6.558] Tianrun Zhang et al."Molecularly imprinted Ni-polyacrylamide-based electrochemical sensor for the simultaneous detection of dopamine and adenine."Anal Chim Acta. 2022 Apr;1202:339689 |
CYTOSINE - 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 | Cytosine, white crystalline powder, slightly soluble in water and ethanol, insoluble in ether, melting point 300 ° C, 100 ° C when the loss of crystal water, 300 ° C when Brown, 320 ° C; Chemical name: 4-amino -2-hydroxy pyrimidine, is the organism involved in DNA, RNA synthesis is an important active raw material, which is one of the pyrimidine bases constituting the nucleic acid. |
| Application | cytosine is an important intermediate in fine chemicals, pesticides and pharmaceuticals, with a wide range of applications. In the pesticide, the first discovery of the cytosine nucleoside peptide type new antibiotic, it is a kind of high efficiency, low toxicity, low residue broad-spectrum agricultural antibiotics. In the field of medicine, cytosine is a kind of nucleic acid substance, can be used as an antiviral drug, mainly used for the synthesis of anti-AIDS drugs and anti-hepatitis B drug lamivudine, anticancer drug gemcitabine, and 5-fluorocytosine, etc. |
| preparation | the specific synthesis method of Intermediate 1 is as follows: In a 2500 ml round bottom flask, 180g (3.0 mol) of urea, 370g (2.5 mol) of triethyl orthoformate and 226g (2.0 mol) of ethyl cyanoacetate were added, and the mixture was stirred and refluxed for 4 hours. The reflux phenomenon was continuously observed to ensure that the reflux was uniform and stable. After stopping the reaction, cool Suction filtration, yellow-white solid was collected, and with acetone rinsing, drying, Intermediate 1, yellow white powder solid 294.5G, yield 81%. The specific synthesis method of intermediate 2 is as follows: to a 2500 ml round bottom flask, add 1000 mL of anhydrous methanol, add 23g (1 mol) of sodium metal in portions, after the metal sodium is completely dissolved, add 183(1 mol) G of Intermediate 1, 5.6g of nano calcium oxide powder (0.1 mol) was added, heated to 60 ° C. And refluxed for 3 hours, the reaction was stopped, cooled, and the yellow solid was collected by Suction filtration. The resulting solid was dissolved in 500 of water and water was added with stirring until the yellow solid was completely dissolved. With dilute hydrochloric acid (prepared from concentrated hydrochloric acid and water in a volume ratio of 1:3) acidification to pH = 6~7, there is precipitation, Suction filtration to collect white solid, and with a small amount of acetone washing. Drying gave Intermediate 2 as a white powdery solid, 53g, in 29% yield. The specific synthesis method of intermediate 3 is as follows: 10% of 800 NaOH solution is prepared, added to a 2500 round bottom flask, heated to 90 degrees Celsius, and 91.5(0.5 mol) of intermediate is added. Stir for 15 min. Quickly cooled to room temperature, and then add hydrochloric acid acidification pH = 5, there are white precipitate formation, Suction filtration, After washing with water and drying, 5-carboxycytosine was obtained as a white powdery solid, 73.6g, yield 95%. Synthesis of cytosine by decarboxylation: to a 1000 ml round-bottom flask, add 77.5G (0.5 mol) of intermediate 3,26.8g (0.5 mol) of ammonium chloride, 500 ml of N-methyl pyrrolidone, nitrogen protection, stirring the reaction evenly heated to 180 ° C, and heat for 8 hours, heat reflux until less bubbles are removed, stop the reaction, it was cooled to room temperature, 150 of diethyl ether was added, and the precipitated solid was filtered. The white solid was collected as the final product cytosine, which was dried. 49g of white crystalline solid was obtained in 87.0% yield. |
| biological activity | Cytosine (4-amino-2-hydroxy-ypyrimidine, cytosymine) is one of the four main bases present in DNA and RNA, it is used by cells to store and transmit genetic information. |
| Use | for pharmaceutical intermediates |
Last Update：2024-04-09 02:00:11
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View History
CYTOSINE
(1-甲基苯并咪唑-2-基)胺
2-NP-呋喃西林代谢物
食品级甲基环戊烯醇酮
DIMETHYL PIMELATE
(4-哌啶)乙酸甲酯盐酸盐
N-(3-IODOPYRIDIN-2-YL)PIVALAMIDE
CAPADIPINE
胶质源性连接蛋白 封闭多肽
甲氧基(环辛二烯)铑(I)二聚体
(1-甲基苯并咪唑-2-基)胺
2-NP-呋喃西林代谢物
食品级甲基环戊烯醇酮
DIMETHYL PIMELATE
(4-哌啶)乙酸甲酯盐酸盐
N-(3-IODOPYRIDIN-2-YL)PIVALAMIDE
CAPADIPINE
胶质源性连接蛋白 封闭多肽
甲氧基(环辛二烯)铑(I)二聚体