Name | Cytidine |
Synonyms | CR Cytidin Cytidine Cytosine β-D-riboside 1-β-D-ribosylcytosine Cytosine, 1-beta-D-ribofuranosyl- 4-Amino-1-beta-D-ribofuranosyl-2(1H)-pyrimidinone 4-amino-1-alpha-D-lyxofuranosylpyrimidin-2(1H)-one 4-amino-1-(beta-D-xylofuranosyl)pyrimidin-2(1H)-one 4-amino-1-(beta-L-ribofuranosyl)pyrimidin-2(1H)-one Cytidine,Cytosine β-D-riboside, Cytosine-1-β-D-ribofuranoside 4-aMino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)pyriMidin-2(1H)-one |
CAS | 65-46-3 |
EINECS | 200-610-9 |
InChI | InChI=1/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6+,7+,8+/m1/s1 |
Molecular Formula | C9H13N3O5 |
Molar Mass | 243.22 |
Density | 1.3686 (rough estimate) |
Melting Point | 210-220 °C (dec.) (lit.) |
Boling Point | 386.09°C (rough estimate) |
Specific Rotation(α) | 31.5 º (c=0.6, H2O 25 ºC) |
Flash Point | 283.8°C |
Water Solubility | SOLUBLE |
Solubility | H2O : ≥ 50 mg/mL (205.58 mM);DMSO : 50 mg/mL (205.58 mM; Need ultrasonic) |
Vapor Presure | 3.5E-14mmHg at 25°C |
Appearance | White crystal |
Color | White to almost white |
Merck | 14,2786 |
BRN | 89173 |
pKa | 4.22, 12.5(at 25℃) |
Storage Condition | 2-8°C |
Stability | Stable. Incompatible with strong oxidizing agents. Protect from moisture. |
Sensitive | Hygroscopic |
Refractive Index | 34 ° (C=0.7, H2O) |
MDL | MFCD00006545 |
Physical and Chemical Properties | White crystalline powder, Melting Point: 210 ℃ ~ 217 ℃ |
Use | For the manufacture of cytarabine, cytidine, CTP, citicoline, etc |
Risk Codes | 68 - Possible risk of irreversible effects |
Safety Description | 24/25 - Avoid contact with skin and eyes. |
WGK Germany | 3 |
RTECS | UW7370000 |
FLUKA BRAND F CODES | 10-23 |
TSCA | Yes |
HS Code | 29349990 |
Toxicity | LD50 intraperitoneal in mouse: 2700mg/kg |
Reference Show more | 1. Peng Shi-Tao, Zhang Xian-ling, Yuan Jin-feng, et al. A comparative study of four processing methods of Fuzi based on Zhang Zhongjing's academic thought [J]. World Science and Technology-modernization of traditional Chinese medicine, 2018, 20(05):114-119. 2. Wang Ruoxuan, Xue Haiping, Ding Yue et al. Determination of nucleosides in ejiao compound effervescent tablets by HPLC [J]. Science and Technology of Chinese Medicine 2019 026(005):686-688. 3. 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. 4. 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 5. 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. 6. Tan Li, Kong Jing, Feng duo, Liu Lu, LV Shan, Zhang Yuan Yuan, Shi Renbing. Drug Quality Characterization Analysis of golden flower sunflower preparation based on anti-Myocardial ischemia effect [J]. World Science and Technology-modernization of traditional Chinese medicine, 2017,19(03):522-528. 7. 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. 8. Wen Jie Zhang, Shi Gang Liu, Lei Han, Hong Qun Luo, Nian Bing Li,A ratiometric fluorescent and colorimetric dual-signal sensing platform based on N-doped carbon dots for selective and sensitive detection of copper(II) and pyrophosphate ion,Sensors and Ac 9. [IF=7.46] Wen Jie Zhang et al."A ratiometric fluorescent and colorimetric dual-signal sensing platform based on N-doped carbon dots for selective and sensitive detection of copper(II) and pyrophosphate ion."Sensor Actuat B- Chem. 2019 Mar;283:215 10. [IF=5.923] Cuihua Chen et al."Variations in Physiology and Multiple Bioactive Constituents under Salt Stress Provide Insight into the Quality Evaluation of Apocyni Veneti Folium."Int J Mol Sci. 2018 Oct;19(10):3042 11. [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 12. [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 13. [IF=4.411] Mengxia Tan et al."Quality Evaluation of Ophiopogonis Radix from Two Different Producing Areas."Molecules. 2019 Jan;24(18):3220 14. [IF=3.24] Zhichen Cai et al."Metabolomics characterizes the metabolic changes of Lonicerae Japonicae Flos under different salt stresses."Plos One. 2020 Dec;15(12):e0243111 15. [IF=3] Zong-Chao HONG et al."Compound Sophorae Decoction: treating ulcerative colitis by affecting multiple metabolic pathways."Chin J Nat Medicines. 2021 Apr;19:267 16. [IF=2.752] Yuting Zhang et al."Metabolomic Analysis and Identification of Sperm Freezability-Related Metabolites in Boar Seminal Plasma."Animals-Basel. 2021 Jul;11(7):1939 17. [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; 18. [IF=1.902] Yu Sun et al."Characterization of sleep-related neurochemicals at different developmental stages and insomnia models Drosophila melanogaster."Biomedical Chromatography. 2022 Feb 01 19. [IF=3.373] Yiyuan Luo et al."Quality evaluation of Tetrastigma hemsleyanum different parts based on quantitative analysis of 42 bioactive constituents combined with multivariate statistical analysis."PHYTOCHEMICAL ANALYSIS. 2022 Apr 05 |
NIST chemical information | information provided by: webbook.nist.gov (external link) |
EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
Introduction | cytidine is cytidine, which is a ribonucleoside (containing pyrimidine base cytosine), and constitute a unit of the genetic code. Cytidine pairs non-covalently with the corresponding avian (purine) glycoside in deoxyribonucleic and cellular ribonucleic acids. |
uses | as a pyrimidine nucleoside, cytidine is mainly used in the production of antitumor, antiviral drug intermediates, is the manufacture of cytarabine (Ara-CR), the main raw materials of cytidine (CycloC), Cytidine triphosphate (CTP), citicoline (CDP-Choline) and other drugs. raw materials for drug synthesis and biochemical reagents. For the preparation of CTP, CDP-choline, 2 ', 3'-dideoxycytidine, cytarabine and the like. used in the manufacture of cytarabine, cytidine, CTP, citicoline, etc. |
preparation | A preparation method of cytidine, comprising the following steps: ① silanization: N-(tert-butyldimethylsilyl)-2-(tert-butyldimethylsilyloxy)-4-pyrimidine Amine was obtained by The Silylation reaction of cytosine and tert-butyldimethylsilyl. N-(tert-butyldimethylsilyl)-2-(tert-butyldimethylsilyloxy) was obtained by dissolving -2-(tert-butyldimethylsilyloxy)-4-pyrimidine amine in chloroform. -4-pyrimidine amine chloroform solution; (2) glycoside synthesis: four acetyl ribose in chloroform dissolved in titanium tetrachloride solution, A solution of N-(tert-butyldimethylsilyl)-2-(tert-butyldimethylsilyloxy)-4-pyrimidineamine in trichloromethane is added dropwise at an ambient temperature of 18 °c to 30 °c, cytosine acetyl Ribose was obtained by glycoside reaction; ③ aminolysis: a methanol solution of ammonia (I. E., methanol ammonia solution) with a mass percentage of ammonia of 10% is added to cytosine acetyl ribose at an ambient temperature of 18 ° C. To 30 ° C, the crude cytidine was obtained by aminolysis reaction; ④ refining: the crude cytidine was added into ethanol, heated and refluxed under stirring, and then water was added, after crystallization by cooling to 0 °c ± 2 °c for at least 5h, the solid was isolated and dried to give a cytosine nucleoside. The specific synthetic route is as follows: |