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Guanine

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CAS:73-40-5
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CAS:73-40-5
Purity:99% Package:176/KG
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CAS:73-40-5
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CAS:73-40-5
Purity:99% Package:100G,25G,500G
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Products Intro:Product Name:Guanine
CAS:73-40-5
Purity:>98.0%(T)(LC) Package:1g;25g;250g Remarks:G0169
Guanine Basic information
Organic bases 6-Thioguanine Chemical Properties Uses Production method
Product Name:Guanine
Synonyms:2-AMino-6-hydroxy-1H-purine;9H-Guanine;Valaciclovir EP Impurity A;Guanine Vetec(TM) reagent grade, 99%;2-amino-1H-purin-6(9H)-one;6H-Purin-6-one, 2-amino-1,7-dihydro- (9CI);6H-purin-6-one, 2-amino-3,7-dihydro-;Guanine (8CI)
CAS:73-40-5
MF:C5H5N5O
MW:151.13
EINECS:200-799-8
Product Categories:nucleoside;API;Pharmaceutical Intermediates;Intermediates;Purine;Purines;Acyclovir;Biochemistry;Nucleobases and their analogs;Nucleosides, Nucleotides & Related Reagents;Nucleic acids;Bases & Related Reagents;Nucleotides
Mol File:73-40-5.mol
Guanine Structure
Guanine Chemical Properties
Melting point >300 °C(lit.)
storage temp. 2-8°C
solubility 1 M NaOH: 0.1 M at 20 °C, clear, colorless
form Powder
pka9.92(at 40℃)
color White to cream
Water Solubility practically insoluble
Merck 14,4564
BRN 9680
Stability:Stable. Incompatible with strong oxidizing agents.
CAS DataBase Reference73-40-5(CAS DataBase Reference)
NIST Chemistry Reference6H-Purin-6-one, 2-amino-1,7-dihydro-(73-40-5)
EPA Substance Registry System6H-Purin-6-one, 2-amino-1,7-dihydro-(73-40-5)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36-37/39
WGK Germany 3
RTECS MF8260000
Hazard Note Irritant
TSCA Yes
HS Code 29335990
Hazardous Substances Data73-40-5(Hazardous Substances Data)
MSDS Information
ProviderLanguage
Guanine English
ACROS English
SigmaAldrich English
ALFA English
Guanine Usage And Synthesis
Organic basesGuanine is an organic base that is widespread in the animal and the plant kingdom. The chemical name is 2-amino-6-oxo-purin. It is colorless square crystals or crystalline powder. In the aqueous solution containing a large excess of ammonia, it will become small diamond crystal after slowly evaporating the water. It has a melting point of 360 ℃ (partially decomposed and sublimated). It can be dissolved in ammonia water, caustic soda and dilute mineral acid, slightly soluble in ethanol, ethyl ether, and insoluble in water. It has a strong UV absorption. It is the major composition of guanosine and guanylate. Its hydrochloride monohydrate is powdery crystals with water being loss at 100 ℃ and hydrogen chloride being loss at 200 ℃. It can be dissolved in acidified water but is insoluble in water, alcohol, and ether. Guanine can be obtained through the hydrolysis of scale in hydrochloric acid. It is an important base composition of nucleic acids, being one of the four major bases of DNA and RNA as well as the compassion of various kinds of guanylate. Its N9 can be connected with the C1 of ribose or deoxyribose with β-glycosidic bond to obtain guanosine or deoxy-guanosine.
[Major application]: for biochemical research and preparation of caffeine and other drugs.
Its chemical composition is 2-amino-6-mercaptopurine. It, together with adenine, constitutes the two major purines bases in the nucleic acid. Through binding to ribose guanosine or deoxyribose guanosine through the glycosidic linkages, the corresponding triphosphates are guanosine triphosphate or deoxyguanosine triphosphate, respectively. They are the precursor of guanine during the biosynthesis process of RNA and DNA.
6-Thioguanine6-Thioguanine belongs to another kind of common purine metabolism antagonist in the inhibition of the purine synthesis pathway and is a cell cycle specific drugs to which those cells locating in the cycle S period are most sensitive. In addition to inhibit the biosynthesis of cellular DNA, it also has mild inhibitory effect on the biosynthesis of RNA. This product is a kind of guanosine analogs. It becomes active only after being converted to 6-TG ribonucleotide via the phosphor-ribosyltransferase inside human body. The action process of this product is similar to that of mercapto-purine. In addition, 6-TG ribonucleotide, through its inhibitory effect on guanylate kinase, can prevent the phosphorylation of guanosine monophosphate (GMP) into guanosine diphosphate (GDP). This product, after being metabolized into deoxyribonucleoside triphosphate, can be embedded in DNA, thus further inhibiting the biosynthesis of nucleic acids while mercaptopurine having no effect. The product has cross-resistance with mercaptopurine while it can have its efficacy improved upon combination with other drugs such as cytarabine. Its oral absorption after oral administration is incomplete, at about 30%. Only a relatively small amount of the drug can shift from the blood to penetrate through the blood-brain barrier, therefore at generally oral dose, it is insufficient to prevent and treat meningeal leukemia. The activation and decomposition process of the product both proceeds in the liver with being de-activated through either shifting the amino-methyl mercaptopurine via methylation or shifting to mercaptopurine via deamination. However, the metabolic process of inactivation is not related to xanthine oxidase, therefore taking allopurinol has no significant inhibitory effect on the metabolism of this product. The half-life of intravenous injection is 25~240 min with the average period being 80 min. Through being excreted through the kidneys, for one time of oral administration, about 40% of the drug is excreted in urine in the form of metabolites within 24h with only trace amount of 6-Thioguanine being detected in the urine.
Chemical PropertiesIt is colorless needle crystal or amorphous powder. The melting point is 360 ℃ (decomposition). It is easily soluble in acid and alkali, slightly soluble in alcohol, ether, but insoluble in water.
The above information is edited by the chemicalbook of Dai Xiongfeng.
UsesIt can be used for biochemical studies.
It can be used as the intermediates of the antiviral drugs acyclovir.
It can be used as the intermediate of thioguanine and open-ringed guanine.
Production method5-amino-4-imidazolyl amide can have esterification reaction with isothiocyanate methylbenzene to generate ester, and then successfully reacted with methyl iodide, ammonia to synthesize it.
Chemical Propertieswhite to light yellow crystal powder
UsesGuanine is on one of the five nucleobases incorporated into biological nucleic acids. Guanine, along with adenine and cytosine, is present in both DNA and RNA, whereas thymine is usually seen only in DNA, and uracil only in RNA.
DefinitionChEBI: A 2-aminopurine carrying a 6-oxo substituent.
Guanine Preparation Products And Raw materials
Preparation Products6-Thioguanine-->6-O-Benzylguanine-->Acyclovir-->6-Chloroguanine-->Famciclovir
Raw materialsIodomethane-->2,5,6-Triaminopyrimidin-4-ol sulphate-->BENZYL ISOTHIOCYANATE
Tag:Guanine(73-40-5) Related Product Information
8-BROMO-9-[2'-(HYDROXY-ETHOXY)METHYL]GUANINE N2,2'-O-DIBUTYRYLGUANOSINE 3':5'-CYCLIC MONOPHOSPHATE SODIUM SALT 2-AMINO-8-BROMO-9-((2R,3R,4S,5R)-3,4-DIHYDROXY-5-HYDROXYMETHYL-TETRAHYDRO-FURAN-2-YL)-1,9-DIHYDRO-PURIN-6-ONE N2-ISOBUTYRYL-3'-O-BENZOYL-2'-DEOXYGUANOSINE TIMTEC-BB SBB006472 5'-O-Dimethoxytrityl-N-isobutyryl-deoxyguanosine 5'-O-(4,4'-DIMETHOXYTRITYL)-N2-ISOBUTYRYL-2'-DEOXYGUANOSINE-3'-(2-CYANOETHYL-N,N-DIISOPROPYL)PHOSPHORAMIDITE 8-AMINOGUANOSINE N2-Isobutyryl-2'-deoxyguanosine GUANOSINE 3':5'-CYCLIC MONOPHOSPHATE SODIUM SALT 1-METHYLGUANINE 8-BR-CGMP 2'-Deoxyguanosine-5'-diphosphate trisodium salt Guanylyl Imidodiphosphate Guanosine ADENYLYL-(3'-5')-GUANOSINE 8-BROMOGUANINE 2',3'-DIDEOXYGUANOSINE 5'-TRIPHOSPHATE TETRASODIUM SALT