Guanine 鸟嘌呤

CAS 73-40-5 MFCD00071533

化学结构图

73-40-5
SMILES: Nc1nc2[nH]cnc2c(=O)[nH]1

化学属性

Mol. FormulaC5H5N5O
Mol. Weight151.13
Density2.19
Melting Point>300°C
TSCAYes
Solubility难溶
Appearance 五色针状结晶或无定性粉末。Mp360℃(分解)。易溶于酸和碱，微溶于乙醇、乙醚，不溶于水。
Boiling Point273.11 °C at 760 mmHg

别名和识别编码

Chemical NameGuanine
CAS Number73-40-5
Synonym Guanine {LY} Guanine {} {LY} Guanine {} {} {LY} Guanine {} {} {} {LY} Guanine {} {} {} {} {LY} Guanine {} {} {} {} {} {LY} Guanine {} {} {} {} {} {} {LY} Guanine {} {} {} {} {} {} {} {LY} Guanine {} {} {} {} {} {} {} {} {LY} Guanine {} {} {} {} {} {} {} {} {} {LY} Guanine {} {} {} {} {} {} {} {} {} {} {LY} Guanine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Guanine {} {} {} {} {} {} {} {} {} {} {} {} {LY} Guanine {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Guanine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Guanine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Guanine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Guanine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Guanine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Guanine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {}
MDL NumberMFCD00071533
EC Number200-799-8
Beilstein Registry Number9680
PubChem Substance ID135398634
Merck Number4564
Reaxys-RN147911
Chemical Name Translation鸟嘌呤
Wiswesser Line NotationT56 BM DN FVM INJ HZ
LabNetwork Molecule IDLN00192899
InChIInChI=1S/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
Canonical SMILESO=C1N=C(N)NC2=C1NC=N2
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分类

  • {SNA} Biochemicals and Reagents, Nucleosides, Nucleosides, Nucleotides, Oligonucleotides
  • Bases & Related Reagents
  • Nucleotides
  • {SNA} Building Blocks, Chemical Synthesis, Heterocyclic Building Blocks, Panax ginseng, Phytochemicals by Plant (Food/Spice/Herb), Purines, 细胞生物学, 营养研究
  • {Chemicalbook} 生物化学品: 生化试剂: 核糖、核苷酸及其他类
  • {SNA} Analytical Standards, Analytical/Chromatography, Chromatography, Pharmaceutical Secondary Standards, Pharmaceutical Standards
  • {SNA} Additional Standards, Analytical Standards, Chromatography, Pharmaceutical Secondary Standards, Pharmaceutical Standards,
  • {uni_hamburg} no charge; nitrogen heterocycle; aromatic; large ring; fused rings; 5ring; 6ring; 9ring; amide; lactame; 1fragment
  • {SNA} Nucleosides, 核苷，核苷酸和寡核苷酸, 生化试

产品应用

  • 生化研究。

相关文献及参考

  • Short: III/20a
  • Merck: 14,4564
  • Short: III/31a
  • Manini, P., et al.: Toxicol. Lett., 190, 41 (2009),
  • Geslain, R., et al.: J. Biol. Chem., 284, 27760 (2009),

安全信息

Signal word Warning
GHS Symbol
WGK Germany3
Safety Statements
  • 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 Wear suitable protective clothing 穿戴适当的防护服；
  • 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；
  • S37 Wear suitable gloves 戴适当手套；
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。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P305+P351+P338
  • P362 Take off contaminated clothing and wash before reuse. 脱掉污染的衣服，清洗后方可重新使用
Hazard statements
  • H315 Causes skin irritation 会刺激皮肤
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
RTECSMF8260000
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes Xi
Storage condition 2-8°C, protect from light {LY} 2-8°C, protect from light {} {LY} 2-8°C, protect from light {} {} {LY} 2-8°C, protect from light {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} 
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 1300 mg/kg/26W-I
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Skin and Appendages - tumors
   Reproductive - Tumorigenic effects - ovarian tumors
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   27,925,1967

TYPE OF TEST            : LD - Lethal dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : >3333 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   FMXXAJ French Medicament Patent Document.  (U.S. Patent and Trademark
   Office, Foreign Patents, Washington, DC 20231)  Discontinued.
   Volume(issue)/page/year: #2698M

TYPE OF TEST            : LD - Lethal dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : >1 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   ANYAA9 Annals of the New York Academy of Sciences.  (New York Academy of
   Sciences, 2 E. 63rd St., New York, NY 10021)  V.1-    1877-
   Volume(issue)/page/year: 60,251,1954

TYPE OF TEST            : Sex chromosome loss and nondisjunction
TEST SYSTEM             : Human Lymphocyte
DOSE/DURATION           : 30 umol/L
REFERENCE :
   MUTAEX Mutagenesis. (Oxford Univ. Press, Pinkhill House, Southfield Road,
   Eynsham, Oxford OX8 1JJ, UK) V.1- 1986-  Volume(issue)/page/year: 1,99,1986

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

其他信息

  • 上游原料:碘甲烷 --> 2,5,6-三氨基-4-羟基嘧啶硫酸盐 --> 十二(烷)酸苄酯苯基酯
  • 硫鸟嘌呤:硫鸟嘌呤属于抑制嘌呤合成途径的另一种常用嘌呤代谢拮抗物，是细胞周期特异性药物，对处于S周期的细胞最敏感，除能抑制细胞DNA的合成外，对RNA的合成亦有轻度抑制作用。本品是鸟嘌呤的同类物，在人体内必需由磷酸核糖转移酶转为6-TG核糖核苷酸后方具活性。本品的作用环节与巯嘌呤相似。此外，6-TG核糖核苷酸通过对鸟苷酸激酶的抑制作用，可阻止一磷酸鸟苷 (GMP)磷酸化为二磷酸鸟苷 (GDP)。本品经代谢为脱氧核糖三磷酸后，能嵌入DNA，因而进一步抑制核酸的生物合成，巯嘌呤无此作用。本品与巯嘌呤有交叉耐药性，而与阿糖胞苷等药物合用，可提高疗效。口服后吸收不完全，约30%。仅有较小量药物能从血液渗透入血-脑脊液屏障，因而一般口服量不足以预防和治疗脑膜白血病。本品的活化及分解过程均在肝脏内进行，经甲基化作用转为氨甲基巯嘌呤或经脱氨作用转为巯嘌呤而失去活性，但灭活的代谢过程与黄嘌呤氧化酶无关，因而服用别嘌醇对本品的代谢并无明显的抑制作用。静脉注射的半衰期为25～240min，平均为80min。经肾脏排泄，一次口服，约40%的药物在24h内以代谢产物形式经尿液排出，尿中仅能测出微量的硫鸟嘌呤。
  • 方法一:5-氨基-4-咪唑酰胺与异硫氰酸苯甲酯进行酯化成酯，再与碘甲烷、氨水依次反应制得。
  • TCI Shanghai:鸟嘌呤 Guanine,>;98.0%(LC)(T)(73-40-5)
  • 有机碱:鸟嘌呤是一种有机碱，广泛存在于动、植物界。化学名称为2-氨基-6-氧嘌呤，无色正方形晶体或结晶性粉末，在含有大大过量氨存在的水溶液中，慢慢蒸去水得小菱形晶体，熔点360℃(分解并部分升华)。溶于氨水、苛性碱及稀矿酸液，微溶于乙醇、乙醚，不溶于水，对紫外线有强烈的吸收性，为鸟苷和鸟苷酸的组成成分。其盐酸盐为单水合粉末状晶体，在100℃时失水，200℃时失去氯化氢，溶于酸化的水，不溶于水、乙醇、乙醚。鸟嘌呤可由鱼鳞经盐酸水解而得。为组成核酸的重要碱基，是DNA和RNA中4种主要碱基之一，也是各种鸟苷酸的组成分。其N9与核糖或脱氧核糖C1以β-糖苷键连接而成鸟苷或脱氧鸟苷。 【主要用途】:用于生化研究及制备咖啡因等药物。 化学成分为2-氨基-6-酮基嘌呤。与腺嘌呤一起构成核酸中的两种主要嘌呤碱。通过糖苷键与核糖或脱氧核糖结合与鸟苷或脱氧鸟苷，其三磷酸化合
  • 用途一:用作抗病毒药物阿昔洛韦中间体
  • Sigma Aldrich:73-40-5(sigmaaldrich)
  • 有机碱:鸟嘌呤是一种有机碱，广泛存在于动、植物界。化学名称为2-氨基-6-氧嘌呤，无色正方形晶体或结晶性粉末，在含有大大过量氨存在的水溶液中，慢慢蒸去水得小菱形晶体，熔点360℃(分解并部分升华)。溶于氨水、苛性碱及稀矿酸液，微溶于乙醇、乙醚，不溶于水，对紫外线有强烈的吸收性，为鸟苷和鸟苷酸的组成成分。其盐酸盐为单水合粉末状晶体，在100℃时失水，200℃时失去氯化氢，溶于酸化的水，不溶于水、乙醇、乙醚。鸟嘌呤可由鱼鳞经盐酸水解而得。为组成核酸的重要碱基，是DNA和RNA中4种主要碱基之一，也是各种鸟苷酸的组成分。其N9与核糖或脱氧核糖C1以β-糖苷键连接而成鸟苷或脱氧鸟苷。 【主要用途】:用于生化研究及制备咖啡因等药物。 化学成分为2-氨基-6-酮基嘌呤。与腺嘌呤一起构成核酸中的两种主要嘌呤碱。通过糖苷键与核糖或脱氧核糖结合与鸟苷或脱氧鸟苷，其三磷酸化合物分别为鸟苷三磷
  • 易溶于氢氧化铵、氢氧化钠碱液和稀酸溶液，微溶于乙醇和乙醚，实际上不溶于水。360℃以上分解并部分升华。有刺激性。
  • 下游产品:6-硫鸟嘌呤 --> O-6-苄基鸟嘌呤 --> 阿昔洛韦 --> 2-氨基-6-氯嘌呤 --> 泛昔洛韦
  • 图谱信息:鸟嘌呤(73-40-5)质谱(MS) 鸟嘌呤(73-40-5)红外图谱(IR2) 鸟嘌呤(73-40-5)红外图谱(IR1)
  • 用途二:生化研究。
  • Hazard Note:Irritant
  • Acros Organics:鸟嘌呤 Guanine, 99+%(73-40-5)
  • MSDS 信息:Guanine(73-40-5).msds

系列性分类

  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Nucleosides, Nucleotides, Oligonucleotides - Biochemicals and Reagents
  4. Nucleosides - Nucleosides, Nucleotides, Oligonucleotides
  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Nucleosides, Nucleotides, Oligonucleotides - Biochemicals and Reagents
  4. Nucleosides - Nucleosides, Nucleotides, Oligonucleotides
  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. Piperidones 哌啶酮
  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. Purines 嘌呤
  1. Analytical & Chromatography 分析化学与色谱
  2. Analytical Standards
  3. Chromatography - Analytical Standards
  4. Pharmaceutical Standards - Chromatography
  5. Pharmaceutical Secondary Standards - Pharmaceutical Standards
  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. Nucleosides, Nucleotides, Oligonucleotides
  4. Nucleoside Analogs
  1. Medical Research Areas
  2. Metabolism
  3. Endogenous Metabolite  (内源性代谢物)