Uracil 尿嘧啶

CAS 66-22-8 MFCD00006016

化学结构图

66-22-8
SMILES: O=c1cc[nH]c(=O)[nH]1

化学属性

Mol. FormulaC4H4N2O2
Mol. Weight112.09
Density1.321
Melting Point>300
TSCAYes
SolubilitySoluble in sodium hydroxide solution, hot H2O (1 mg/ml), ammonia water, alkalies, cold water (sparingly), and 1M NaOH (50 mg/ml). Insoluble in ethanol, and ether.
Stability对湿度敏感
Appearance 白色或浅黄色针状结晶。熔点338℃，易溶于热水，溶于稀氨水，微溶于冷水，不溶于乙醇和乙醚。

别名和识别编码

Chemical NameUracil
Synonym 3）-嘧啶二酮, 2,6-二羟基, 1,3-二氮杂苯 2,4(1H,3H)-嘧啶二酮 環丙烯醯尿 4-Hydroxy-2(1H)-pyrimidinone 2,4(1H,3H)-嘧啶二酮 2,4-二羟基嘧啶 灭胞素 尿嘧啶 2,4-Pyrimidinediol 由雪 2,4-Pyrimidinedione 2,4-二羟基嘧啶 杀胞素 2,4-PYRIMIDINEDIOL CCTGCCCTGUGCAGCTGTGGG Pirod 叶枯散 2,4-DIOXOPYRIMIDINE Pyrod Cellomate 2-Hydroxy-4(3H)-pyrimidinone 2,4-二羟基嘧啶, 2,4-（1 hybarx 2,(1H,3H)-Pyriminedione 2,6-Dihydroxypyrimidine
MDL NumberMFCD00006016
CAS Number66-22-8
EC Number200-621-9
Beilstein Registry Number24,312
PubChem Substance ID87577744
Merck Number9850
Chemical Name Translation尿嘧啶
Reaxys-RN606623
Wiswesser Line NotationT6MVMVJ
LabNetwork Molecule IDLN00153185
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分类

  • {SNA} Cell Culture, Miscellaneous Reagents and Supplements,
  • {SNA} Metabolic Pathways, Metabolites and Cofactors on the Metabolic Pathways Chart, Nucleotide, Panax ginseng, Phytochemicals by Plant (Food/Spice/Herb), 代谢组学, 细胞生物学, 营养研究
  • {SNA} Metabolic Pathways, Metabolites and Cofactors on the Metabolic Pathways Chart, Metabolomics, Nucleotide, Nutrition Research, Panax ginseng, Phytochemicals by Plant (Food/Spice/Herb)
  • {SNA} Miscellaneous Reagents and Supplements, 细胞培养, 试剂和添加剂
  • {SNA} Metabolic Pathways, Metabolites and Cofactors on the Metabolic Pathways Chart, Nucleotide, Nutrition Research, Panax ginseng,

产品应用

  • 用于有机合成和生化研究，主要合成鸟苷等。

相关文献及参考

  • For a review of the use of uracils as starting materials in heterocyclic synthesis, see: Adv. Het. Chem., 55, 130 (1992).
  • Merck: 14,9850
  • Merck: 14,9850 Beilstein:24,312
  • [1]. Pałasz A, et al. In search of uracil derivatives as bioactive agents. Uracils and fused uracils: Synthesis, biological activity and applications. Eur J Med Chem. 2015 Jun 5;97:582-611.

安全信息

Signal word Warning
GHS Symbol
WGK Germany2
Safety Statements
  • S22 Do not breathe dust 不要吸入粉尘；
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触；
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护；
Risk Statements
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
Precautionary statements
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P305+P351+P338
Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
RTECSYQ8650000
Storage condition 密封保存。
Hazard Codes Xi 
TYPE OF TEST            : TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 378 gm/kg/30W-C
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Kidney, Ureter, Bladder - tumors
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   46,2062,1986

TYPE OF TEST

TYPE OF TEST            : TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 235 gm/kg/20W-C
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Kidney, Ureter, Bladder - tumors
REFERENCE :
   CALEDQ Cancer Letters (Shannon, Ireland).  (Elsevier Scientific Pub. Ireland
   Ltd., POB 85, Limerick, Ireland)  V.1-    1975- Volume(issue)/page/year:
   34,249,1987

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1905 gm/kg/96W-C
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Kidney, Ureter, Bladder - tumors
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   52,1675,1992

TYPE OF TEST            : TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 454 gm/kg/36W-C
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Kidney, Ureter, Bladder - tumors
REFERENCE :
   CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House,
   Southfield Road, Eynsham, Oxford OX8 1JJ, UK)  V.1-    1980-
   Volume(issue)/page/year: 12,35,1991

{hazar

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : >6 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   MDACAP Medicamentos de Actualidad.  (J.R. Prous, S.A., Apartado de Correos
   540, 08080 Barcelona, Spain)  V.1-    1965-  Volume(issue)/page/year:
   21,125,1985

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1513 mg/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Behavioral - changes in motor activity (specific assay)
REFERENCE :
   JPETAB Journal of Pharmacology and Experimental Therapeutics.  (Williams &
   Wilkins Co., 428 E. Preston St., Baltimore, MD 21202)  V.1-    1909/10-
   Volume(issue)/page/year: 207,504,1978

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : >8 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   OYYAA2 Oyo Yakuri.  Pharmacometrics.  (Oyo Yakuri Kenkyukai, CPO Box 180,
   Sendai 980-91, Japan) V.1-    1967-  Volume(issue)/page/year: 20,1009,1980

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rabbit
DOSE/DURATION           : >10 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   MDACAP Medicamentos de Actualidad.  (J.R. Prous, S.A., Apartado de Correos
   540, 08080 Barcelona, Spain)  V.1-    1965-  Volume(issue)/page/year:
   21,125,1985

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       :

TYPE OF TEST            : Phage inhibition capacity
TEST SYSTEM             : Bacteria - Escherichia coli
DOSE/DURATION           : 1 gm/L
REFERENCE :
   ZAPOAK Zeitschrift fuer Allgemeine Mikrobiologie.  (Akademie-Verlag GmbH,
   Postfach 1233, Berlin DDR-1086 Ger. Dem. Rep.)  V.1-    1960-
   Volume(issue)/page/year: 12,583,1972

TYPE OF TEST            : Cytogenetic analysis
ROUTE OF EXPOSURE       : Intraperitoneal
TEST SYSTEM             : Rodent - mouse
DOSE/DURATION           : 15 mg/kg
REFERENCE :
   NULSAK Nucleus (Calcutta).  (Dr. A.K. Sharma, Centre of Advanced Studies in
   Cell and Chromosome Research, Calcutta, 35 Baliygunge Circular Rd., Calcutta
   700 019, India)  V.1-    1958-  Volume(issue)/page/year: 19,40,1976

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 15400 mg/kg
SEX/DURATION            : female 7-17 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death,
   e.g., stunted fetus)
   Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
   OYYAA2 Oyo Yakuri.  Pharmacometrics.  (Oyo Yakuri Kenkyukai, CPO Box 180,
   Sendai 980-91, Japan) V.1-    1967-  Volume(issue)/page/year: 22,85,1981

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 616 mg/kg
SEX/DURATION            : female 7-17 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Newborn - sex ratio
REFERENCE :
   OYYAA2 Oyo Yakuri.  Pharmacometrics.  (Oyo Yakuri Kenkyukai, CPO Box 180,
   Sendai 980-91, Japan) V.1-    1967-  Volume(issue)/page/year: 22,85,1981

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 18 gm/kg
SEX/DURATION            : female 17-22 day(s) after conception
                          lactating female 21 day(s) post-birth
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - blood and lymphatic
   systems (including spleen and marrow)
   Reproductive - Specific Developmental Abnormalities - urogenital system
   Reproductive - Effects on Newborn - behavioral
REFERENCE :
   OYYAA2 Oyo Yakuri.  Pharmacometrics.  (Oyo Yakuri Kenkyukai, CPO Box 180,
   Sendai 980-91, Japan) V.1-    1967-  Volume(issue)/page/year: 22,109,1981

其他信息

  • 图谱信息:尿嘧啶(66-22-8)质谱(MS) 尿嘧啶(66-22-8)核磁图( 1 HNMR) 尿嘧啶(66-22-8)红外图谱(IR1) 尿嘧啶(66-22-8)核磁图( 13 CNMR) 尿嘧啶(66-22-8)红外图谱(IR2)
  • 下游产品:2,4-二氯嘧啶 --> 阿糖腺苷
  • TCI Shanghai:尿嘧啶 Uracil,>;98.0%(LC)(T)(66-22-8)
  • Sigma Aldrich:66-22-8(sigmaaldrich)
  • Acros Organics:尿嘧啶 Uracil, 99+%(66-22-8)
  • 有机碱:尿嘧啶是一种有机碱，是RNA中4种主要碱基之一，是核糖核酸中的一种主要嘧啶成分，也是各种尿苷酸的组成分。与核糖通过核苷键连接生成尿苷，其三磷酸化合物为尿三磷，尿三磷是核糖核酸生物合成过程中尿嘧啶的前体。尿三磷作为辅酶参与某些糖的生物合成。 尿嘧啶可阻断替加氟的降解作用，提高氟尿嘧啶的浓度，而增强抗癌作用。临床适应证与氟尿嘧啶同，主要用于消化系癌、乳腺癌及甲状腺癌等，与丝裂霉素合用于晚期胃癌疗效好。实验室通过尿素与甲酰乙酸乙酯环合而得尿嘧啶。用于医药及生化研究。 尿嘧啶存在互变异构现象： 酮式(2，4-2氧嘧啶) 烯醇式(2，4-2羟基嘧啶) 在生物细胞内主要以酮式存在。 自然界中的尿嘧啶存在于海洋生物、颗粒物和海水的溶解物中。在有机地球化学的研究中作为一种生源标示物。 嘧啶是指苯环分子的1,3位含两个氮杂原子的六元杂环化合物，与哒嗪和吡嗪互为同分异构体，由于嘧啶中存在共轭双键而具有特别的紫外光谱。嘧啶的碱性比吡啶弱，亲电取代反应也比吡啶难。但较易发生亲核取代，嘧啶衍生物广泛存在于自然界。例如维生素B1、尿嘧啶、胞嘧啶及胸腺嘧啶都含有嘧啶结构。 以上信息由Chemicalbook的晓楠编辑整理。
  • 氟尿嘧啶:氟尿嘧啶简称FU，是现有最常用的抗癌药之一。白色结晶，pKa=8.1，m.p.282～283℃，微溶于水(12mg/ml25℃)和乙醇，几不溶于氯仿和醚，溶于稀酸和稀碱。在强碱中水解，在生理盐水中稳定。由于电性很强的氟原子引入，使Fu的酸性比母体尿嘧啶强30倍。Fu的注射液为以氢氧化钠调至pH9的水溶液，对光敏感，在低温或长时期室温放置析出结晶。 根据大鼠瘤组织利用嘧啶的能力比正常组织强的现象，Duschinsky和Heidelberger于1957年设计将尿嘧啶5位氢以大小相近的氟原子取代而合成Fu，作为尿嘧啶的抗代谢物以达到有选择性地抗癌作用。FU对小鼠白血病L1210、L615、腺癌755等多种动物移植性肿瘤有抑制作用。瘤细胞对它与阿糖胞苷、甲氨蝶呤、巯嘌呤、环磷酰胺和卡氮芥等常用抗癌药无交叉抗药。 FU在组织中转变为5-氟脱氧尿嘧啶核苷单磷酸酯(FDUMP)和5-氟尿嘧啶核苷三磷酸酯(FUTP)。FDUMP通过与胸腺嘧啶核苷酸合成酶(TS)和5，10-次甲基四氢叶酸成复合物而抑制TS，造成细胞内胸腺嘧啶核苷酸缺乏，抑制DNA合成，导致细胞死亡。另一方面FUTP作为RNA多聚酶的底物而掺入RNA，影响RNA的正常合成和功能。在组织培养中胸腺嘧啶核苷(TdR)能逆转FU对细胞的毒性，故多年来认为FU对DNA的影响为其抑制细胞生长的首要作用机制。但发现TdR并不能完全逆转FU的细胞毒作用，且还发现FU和TdR合并时，显著地提高FU掺入RNA而提高FU的抗癌作用。 L1210白血病细胞与6—H3—5FU培养22小时后，106Cell中有80fmol的FDUMP-TS-5，10CH2-H4叶酸的复合物，而有400fmol的FU结合至RNA中，因此强调了FU掺入RNA对其抗肿瘤作用的重要性。FU是细胞周期特异性药物，对S相作用最显著。 参考资料：中国医学百科全书编辑委员会 编;黄量 主编.中国医学百科全书。
  • 100份25℃的水溶解本品0.358份。易溶于热水，微溶
  • 用途一:用作医药中间体，也用于有机合成
  • 尿嘧啶价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 65012332 尿嘧啶;由雪；2,4-二羟基嘧啶;2,4-(1,3)-嘧啶二酮;2,6-二羟基1,3-二氮杂苯 5g 30.8元 2011/04/16 U0013 尿嘧啶 Uracil 25G 240元 2011/04/16 U0013 尿嘧啶 Uracil 500G 2010元

系列性分类

  1. Life Science 生命科学
  2. Cell Culture 细胞培养
  3. Reagents and Supplements - Cell Culture
  4. Miscellaneous Reagents and Supplements - Reagents and Supplements
  1. Life Science 生命科学
  2. Nutrition Research 营养研究
  3. Phytochemicals by Plant (Food/Spice/Herb) - Nutrition Research
  4. Panax ginseng - Phytochemicals by Plant (Food/Spice/Herb)
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Heterocyclic Building Blocks 杂环合成砌块
  4. Pyrimidines 嘧啶
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Heterocyclic Building Blocks 杂环合成砌块
  4. Pyrimidines 嘧啶
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Heterocyclic Building Blocks 杂环合成砌块
  4. Others 其他杂环
  1. Life Science 生命科学
  2. Metabolomics 代谢组学
  3. Metabolic Pathways - Metabolomics
  4. Metabolites and Cofactors on the Metabolic Pathways Chart - Metabolic Pathways
  5. Nucleotide - Metabolites and Cofactors on the Metabolic Pathways Chart
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Heterocyclic Building Blocks 杂环合成砌块
  4. Pyrimidines 嘧啶
  5. C4 to C5 - Pyrimidines
  1. C9 to C46
  1. Life Science 生命科学
  2. Biochemistry / Glyco-Chemistry
  3. DNA / RNA Synthesis
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Cell Culture
  4. Lipids and Lipid Carriers
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Microscopy Reagents
  4. Stains and Dyes
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Reagents and Supplements
  4. Lipids and Lipid Carriers
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Cell Culture
  4. Reagents and Supplements
  5. Lipids and Lipid Carriers
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Metabolomics
  4. Metabolic Pathways
  5. Metabolites and Cofactors on the Metabolic Pathways Chart
  6. Lipid
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Enzymes, Inhibitors, and Substrates
  4. Metabolomics
  5. Metabolic Pathways
  6. Metabolites and Cofactors on the Metabolic Pathways Chart
  7. Lipid
  1. Medical Research Areas
  2. Metabolism
  3. Endogenous Metabolite  (内源性代谢物)