Adenine 腺嘌呤

CAS 73-24-5 MFCD00041790

化学结构图

73-24-5
SMILES: Nc1ncnc2nc[nH]c12

化学属性

Mol. FormulaC5H5N5
Mol. Weight135.13
Melting Point>360°C
TSCAYes
Density1.612
Stability对湿度敏感
Flash Point220°C
Appearance 白色细粉末结晶,具有强烈的咸味。 难溶于冷水,溶于沸水、酸及碱,微溶于乙醇,不溶于乙醚及氯仿。
Solubility0.5 g/L (20 °C)
Boiling Point238.81 °C at 760 mmHg

别名和识别编码

Chemical NameAdenine
CAS Number73-24-5
Alfabeta NamePURINAMINE H76---
MDL NumberMFCD00041790
Synonym Adenine {LY} Adenine {} {LY} Adenine {} {} {LY} Adenine {} {} {} {LY} Adenine {} {} {} {} {LY} Adenine {} {} {} {} {} {LY} Adenine {} {} {} {} {} {} {LY} Adenine {} {} {} {} {} {} {} {LY} Adenine {} {} {} {} {} {} {} {} {LY} Adenine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Adenine {} {} {} {} {} {} {} {} {} {} {LY} Adenine {} {} {} {} {} {} {} {} {} {} {} {LY} Adenine {} {} {} {} {} {} {} {} {} {} {} {} {LY} Adenine {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Adenine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Adenine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Adenine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Adenine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Adenine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {}
PubChem Substance ID190
EC Number200-796-1
Beilstein Registry Number5777
Merck Number152
Chemical Name Translation腺嘌呤
Reaxys-RN608603
Wiswesser Line NotationT56 BM DN FN HNJ IZ
LabNetwork Molecule IDLN00008093
InChIInChI=1S/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10)
Canonical SMILESNC1=C2N=CNC2=NC=N1
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分类

  • {SNA} A-AM, Bioactive Small Molecules, Cell Biology, Cytokinins, Molecular Biology, Nutrition Research, Plant Biotechnology, Plant Growth Regulators,
  • {SNA} Analytical Standards, EP Standards, EP Standards A - B, Pharmacopeia Metrological Institutes Standards, 分析/色谱
  • {SNA} Cytokinins, Vitamin B, Vitamin B4, Vitamins, 分子生物学, 植物生物技术, 植物生长调节剂, 植物组织培养, 生化试剂
  • {SNA} Analytical Standards, Analytical/Chromatography, Chromatography, EP Standards, EP Standards A - B,
  • {SNA} Artemisia vulgaris,

产品应用

  • 具有植物激动素作用,其片剂或注射剂可用于粒性白血球减少症等。也可应用于组织培养和生化试剂及合成药如维生素B4,嘌呤类药物等原料。也用于生化和药物分析。

相关文献及参考

  • [2]. Griffiths AJF, et al. An Introduction to Genetic Analysis. 7th edition. New York: W. H. Freeman; 2000. Structure of DNA.
  • [3]. Reader V. The assay of vitamin B(4). Biochem J. 1930;24(6):1827-31.
  • Merck 14 ,152
  • Merck: 14,152
  • Merck: 14,152 Beilstein:26(3/4)3561
  • [1]. ORO J, et al. Synthesis of purines under possible primitive earth conditions. I. Adenine from hydrogen cyanide. Arch Biochem Biophys. 1961 Aug;94:217-27.
  • [1]. ORO J, et al. Synthesis of purines under possible primitive earth conditions. I. Adenine from hydrogen cyanide. Arch Biochem Biophys. 1961 Aug;94:217-27.
  • [2]. Griffiths AJF, et al. An Introduction to Genetic Analysis. 7th edition. New York: W. H. Freeman; 2000. Structure of DNA.
  • [3]. Reader V. The assay of vitamin B(4). Biochem J. 1930;24(6):1827-31.

安全信息

Warnings IRRITANT
GHS Symbol
WGK Germany3
Hazard Codes 6.1 Xn Xn,Xi
Hazard statements
  • H301 Toxic if swallowed 吞食有毒
  • H302 Harmful if swallowed 吞食有害
  • H315 Causes skin irritation 会刺激皮肤
  • H317 May cause an allergic skin reaction 可能导致皮肤过敏
  • 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
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Faceshields, Gloves
RTECSAU6125000
Precautionary statements
  • P201 Obtain special instructions before use. 使用前获取专门指示。
  • P202 Do not handle until all safety precautions have been read and understood. 已阅读并理解所有的安全预防措施之前,切勿操作。
  • 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。
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西,喝水或吸烟。
  • P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
  • P272 Contaminated work clothing should not be allowed out of the workplace. 污染的工作服不得带出工作场所。
  • 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。
  • P301 IF SWALLOWED: 如果吞下去
  • P301+P310
  • P301+P310+P330
  • P301+P312
  • P302
  • P302+P352
  • P302+P352+P332+P313+P362+P364
  • P304+P340
  • P305+P351+P338
  • P305+P351+P338+P337+P313
  • P308+P313
  • P312 Call a POISON CENTER or doctor/physician if you feel unwell. 如果你感觉不适,呼叫解毒中心或医生/医师。
  • P321 Specific treatment (see … on this label). 具体治疗(见本标签上的)。
  • P330 Rinse mouth. 漱口
  • P332 IF SKIN irritation occurs: 如果发生皮肤刺激:
  • P332+P313
  • P333+P313
  • P337+P313
  • 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
  • P363 Wash contaminated clothing before reuse. 被污染的衣服洗净后方可重新使用。
  • P403+P233
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Signal word Danger
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;
Packing GroupIII
UN Number 2811 UN 2811 6.1/PG 3
Risk Statements
  • R22 Harmful if swallowed 吞咽有害
Storage condition 2-8°C {LY} 2-8°C Store at RT. {} {LY} 2-8°C {} {} {LY} 2-8°C {} {} {} {LY} 2-8°C {} {} {} {} {LY} 2-8°C {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C
Hazard Class6.1
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 227 mg/kg
TOXIC EFFECTS :
   Behavioral - convulsions or effect on seizure threshold
   Behavioral - muscle weakness
   Lungs, Thorax, or Respiration - other changes
REFERENCE :
   TXAPA9 Toxicology and Applied Pharmacology.  (Academic Press, Inc., 1 E.
   First St., Duluth, MN 5580

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 198 mg/kg
TOXIC EFFECTS :
   Behavioral - altered sleep time (including change in righting reflex)
   Behavioral - muscle weakness
   Lungs, Thorax, or Respiration - cyanosis
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: 104,20,1952

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 100 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NTIS** National Technical Information Service.  (Springfield, VA 22161)
   Formerly U.S. Clearinghouse for Scientific & Technical Information.
   Volume(issue)/page/year: AD277-689

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Subcutaneous
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            : Sperm Morphology
ROUTE OF EXPOSURE       : Intraperitoneal
TEST SYSTEM             : Rodent - mouse
DOSE/DURATION           : 500 mg/kg/5D (Continuous)
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 200,249,1988

TYPE OF TEST            : Sex chromosome loss and nondisjunction
TEST SYSTEM             : Human Lymphocyte
DOSE/DURATION           : 2500 umol/L
REFERENCE :
   EMMUEG Environmental and Molecular Mutagenesis.  (Alan R. Liss, Inc., 41 E.
   11th St., New York, NY 10003)  V.10-    1987-  Volume(issue)/page/year:
   25,197,1995

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            : Gene conversion and mitotic recombination
TEST SYSTEM             : Protozoa - Chlamydomonas reinhardi
DOSE/DURATION           : 200 mg/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 4,147,1967

TYPE OF TEST            : Cytogenetic analysis
ROUTE OF EXPOSURE       : Intraperitoneal
TEST SYSTEM             : Rodent - mouse
DOSE/DURATION           : 451 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: 17,199,1974

TYPE OF TEST            : Cytogenetic analysis
ROUTE OF EXPOSURE       : Oral
TEST SYSTEM             : Rodent - mouse
DOSE/DURATION

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 300 mg/kg
SEX/DURATION            : female 10 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - eye/ear
REFERENCE :
   OFAJAE Okajimas Folia Anatomica Japonica.  (Keio Univ., School of Medicine,
   Dept. of Anatomy, 35 Shinano-machi, Shinjuku-ku, Tokyo 160, Japan)  V.14-
   1936-  Volume(issue)/page/year: 49,47,1972

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 200 mg/kg
SEX/DURATION            : female 10 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Fertility - post-implantation mortality (e.g. dead and/or
   resorbed implants per total number of implants)
   Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death,
   e.g., stunted fetus)
   Reproductive - Effects on Embryo or Fetus - fetal death
REFERENCE :
   OFAJAE Okajimas Folia Anatomica Japonica.  (Keio Univ., School of Medicine,
   Dept. of Anatomy, 35 Shinano-machi, Shinjuku-ku, Tokyo 160, Japan)  V.14-
   1936-  Volume(issue)/page/year: 49,75,1972

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 5040 mg/kg
SEX/DURATION            : male 4 week(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Paternal Effects - testes, epididymis, sperm duct
REFERENCE :
   TOIZAG Toho Igakkai Zasshi.  Journal of Medical Society of Toho University.
   (Toho Daigaku Igakkai, 21-16, Omori-nishi, 5-chome, Ota-ku, Tokyo 143,
   Japan)  V.1-    1954-  Volume(issue)/page/year: 32,36,1985

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intr

其他信息

  • 方法二:方法一、以次黄嘌呤为原料的合成法 6-氯嘌呤的制备 次黄嘌呤精品24g,二甲基苯胺80ml及三氯氧化磷300ml,150℃油浴,回流50min,换水浴加热至70-80℃,真空浓缩至蒸不出为止。浓缩液倒人300g冰块中,剧烈搅拌至全溶,用10mol/L氢氧化钠液中和至 pH 11-12,用甲苯提取至甲苯层无色,中途用10mol/L氢氧化钠调节水层pH值保持pH11-12。冷却,用浓盐酸酸化水层至pH1-2,加氯化钠70g,使之饱和,冰箱冷却24h,过滤,用少量冰水冲洗滤渣,再以8-10倍热水溶解,加活性炭4g脱色(活性炭用无水乙醇200ml洗脱,浓缩,回收部分产品),趁热过滤,滤液冷却结晶。再用12倍量蒸馏水重结晶,100℃烘干,得6-氯嘌呤8.5-9g。 次黄嘌呤[三氯氧磷,二甲基苯胺]→[150℃, 5min]6-氯嘌呤 6-羟胺嘌吟的制备 盐酸羟胺19.74g溶于无水乙醇中,加氢氧化钾18.69g,加热回流15 min,将冷却生成的氯化钾沉淀过滤并用无水乙醇洗涤,合并滤液及洗液,得中性澄清溶液。加入6-氯嘌呤,水浴回流6h后室温过夜,将析出的6-羟胺嘌呤过滤,依次用水及无水乙醇洗涤,干燥器干燥,得产品8.8g,mp 245-251℃。 6-氯嘌呤[盐酸羟胺,氢氧化钾,无水乙醇]→[pH7, 6h]6-羟胺嘌呤 6-氨基嘌呤磷酸盐的制备 6-羟胺嘌呤5g,加水80ml,用10%氢氧化钠溶液调pH值至9,90℃搅拌下分批加入工业用保险粉20g,并保持pH 9,搅拌1h反应至溶液澄清,冷却,室温放置过夜,过滤,水洗滤饼,100℃干燥,得6-氨基嘌呤1.75g。取6-氨基嘌呤4.05g加蒸馏水100ml,磷酸4.2g,加热溶解,浓缩,过滤,无水乙醇洗涤,真空干燥,得6-氨基嘌呤磷酸盐6.3g。 6-羟胺嘌呤[连二亚硫酸钠,氢氧化钠]→[pH9,90℃,1h]6-氨基嘌呤[磷酸]→6-氨基嘌呤磷酸盐 方法二、以丙二酸二乙酯为原料的合成法 4,6-二羟基嘧啶的制备 投料比(质量比)为乙醇钠:甲酰胺:丙二酸二乙酯=7:2.13:1。 $乙醇钠先加入反应器中,再加入甲酰胺,加热至30℃加丙二酸二乙酯,加热至75-80℃使有馏分蒸出,快干时换减压蒸馏装置浓缩至干,加水溶解,冷却,盐酸酸化至pH 4,冷却过滤,冰水洗涤,烘干,得黄色产品。 丙二酸二乙酯[甲酰胺,乙醇钠]→[30℃; 74-81℃, pH4]4.6-二羟基嘧啶 4, 6-二羟基-5-硝基嘧啶的制备 将100ml硝酸冷却,搅拌下加入浓硫酸36ml,冷至30℃后分次加入4,6-二羟基嘧啶48g,加料时保持内温为30-35℃,加完后水浴加热至37-40℃搅拌反应1.5h,将反应液倾人25g碎冰中,放置,过滤,冰水洗涤至中性,抽滤烘干得淡黄色产品。 4, 6-二羟基嘧啶[硝酸,硫酸]→[37-40℃,1.5h]4, 6-二羟基-5-硝基嘧啶 4,6-二氯-5-硝基嘧啶的制备 三氯氧磷120ml,搅拌下加入4,6-二氨基-5-硝基嘧啶60g,加热至50℃,滴加二甲基苯胺,滴完后回流反应1h,将反应液倾入900g碎冰中,放置至冰块全部溶解,过滤,冰水洗涤,得淡黄色产品。 4, 6-二羟基-5-硝基嘧啶[三氯氧磷,二甲基苯胺]→4, 6-二氯-5-硝基嘧啶 4,6-二氨基-5-硝基嘧啶的制备 将4,6-二氯-5-硝基嘧啶用300ml乙醇溶解,水浴缓慢回流并缓慢滴加氨水400ml,滴加时保持温度65℃左右,加完后继续回流1.5h,冷却放置过夜后过滤,冰水洗涤干燥得棕色产品。4, 6-二氯-5-硝基嘧啶[乙醇,氨水]→4,6-二氨基-5-硝基嘧啶 6-氨基嘌呤磷酸盐的制备 甲酰胺200ml,搅拌下加入4,6-二氨基-5-硝基嘧啶26g和甲酸30ml,升温至110℃后分次加入保险粉25g,并控制内温为110-120℃,加完后升温至180-190℃,反应2.5h,冷却过夜后抽滤分别用乙醇和冰水洗涤至中性,再用600ml蒸馏水重结晶,抽滤烘干得淡黄色6-氨基嘌呤。加蒸馏水250ml,加磷酸0.0125g,调节pH为1-2,加热,活性炭脱色,趁热抽滤,滤液冷却后抽滤,干燥得产品。 4, 6-二氨基-5-硝基嘧啶[甲醇,甲酰胺,连二亚硫酸钠]→6-氨基嘌呤[磷酸]→6-氨基嘌呤磷酸盐。
  • 图谱信息:腺嘌呤(73-24-5)Raman光谱 腺嘌呤(73-24-5)核磁图( 1 HNMR) 腺嘌呤(73-24-5)核磁图( 13 CNMR) 腺嘌呤(73-24-5)质谱(MS) 腺嘌呤(73-24-5)红外图谱(IR1) 腺嘌呤(73-24-5)红外图谱(IR2)
  • 方法三:4,6

系列性分类


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