73-40-5

Basic information

• 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 NO: 73-40-5
• Molecular Formula: C₅H₅N₅O
• Molecular Weight: 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

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: 273.11°C (rough estimate)
• Flash Point: 311.4oC
• Appearance: White to cream/Powder
• Density: 1.4456 (rough estimate)
• Vapor Pressure: 5.86E-14mmHg at 25°C
• Refractive Index: 2.0000 (estimate)
• Storage Temp.: 2-8°C
• Solubility: 1 M NaOH: 0.1 M at 20 °C, clear, colorless
• PKA: 9.92(at 40℃)
• Water Solubility: practically insoluble
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,4564
• BRN: 9680
• CAS DataBase Reference: Guanine(CAS DataBase Reference)
• NIST Chemistry Reference: Guanine(73-40-5)
• EPA Substance Registry System: Guanine(73-40-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: MF8260000
• TSCA: Yes
• Hazardous Substances Data: 73-40-5(Hazardous Substances Data)

Usage

Uses

Used in Biochemical Studies:
Guanine is used as a biochemical research tool, aiding in the understanding of nucleic acid structures and functions.
Used in Pharmaceutical Industry:
Guanine serves as an intermediate in the synthesis of antiviral drugs such as acyclovir, contributing to the development of medications for viral infections.
Used as an Intermediate in Synthesis:
Guanine is used as an intermediate in the production of thioguanine and open-ringed guanine, which are important compounds in various chemical processes.
Used in Cosmetics Industry:
Guanine obtained from fish scales is used in cosmetics, particularly for eye cosmetics and nail polishes, to create a pearlized effect. It adds a unique iridescent quality to these products.
Used in Nail Polish:
Guanine is mixed in water and used primarily in nail polish to achieve a pearlized effect. Although it has been largely replaced by synthetic alternatives, it still holds a place in the market for its natural origin and properties.

Organic bases

Guanine 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-Thioguanine

6-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.

Production method

5-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.

History

Guanine is one of the two purines comprising the five nucleic acid bases. Much of the information regarding the general role of nucleic acid bases is covered in Adenine and Cytosine. Guanine gets its name from guano, from which it was first isolated in the 1840s. Albrecht Kossel (1853 1927) determined that guanine (as well as adenine, cytosine, thymine and uracil) was a component of nucleic acid in the last two decades of the 19th century. Similar to adenine, guanine combines with ribose to form a nucleoside. The nucleoside produced is guanosine, which in turn combines with one to three phosphoryls to yield the nucleotides guanosine monophosphate (GMP), guanosine diphosphate (GDP), and guanosine triphosphate (GTP), respectively. Guanine nucleotides play an important role in metabolism including the conversion of adenosine diphosphate (ADP) to adenosine triphosphate (ATP) and carbohydrate metabolism.

Biological Activity

guanine is one of the four main nucleobases found in the nucleic acids dna and rna.guanine is a purine derivative, consisting of a fused pyrimidine-imidazole ring system with conjugated double bonds.

InChI:InChI=1/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)

Upstream product

• 64-18-6 formic acid 
• 1004-75-7 2,5,6-triamino-3,4-dihydro-4-pyrimidinone 
• 141-53-7 sodium formate 
• 122-51-0 orthoformic acid triethyl ester 
• 23663-65-2 5-acetamido-2,4-diamino-6(1H)-pyrimidinone 
• 77287-34-4 formamide 
• 118-00-3 G 
• 56-40-6 glycine 
• 74972-72-8 cis-2,7-diamino-1-(5'-guanylyl)mitosine 
• 53225-79-9 2,8-dichloro-1,7-dihydro-purin-6-one 
• 7664-41-7 ammonia 
• 7664-93-9 sulfuric acid 
• 902-04-5 2'-deoxyguanosine 5'-monophosphate 
• 7732-18-5 water 

Downstream Products

• 961-07-9 2'-Deoxyguanosine 
• 26758-00-9 1,7-dimethylguanine 
• 28128-41-8 8-aminoguanine 
• 75056-37-0 4-(2-amino-6-oxo-6,7-dihydro-3H-purin-8-ylazo)-benzenesulfonic acid 
• 19962-37-9 N²-acetyl-N⁷(H)-guanine 
• 578-76-7 7-methylguanine 
• 118-00-3 G 
• 120-89-8 parabanic acid 
• 113-00-8 guanidine nitrate 
• 69-93-2 uric Acid 
• 154-42-7 thioguanin 
• 3066-84-0 8-bromoguanine 
• 41341-35-9 N⁹-(β-D-Glucopyranosyl)guanin 
• 41341-34-8 7-β-D-glucopyranosylguanine 

Relevant articles and documents

Origin of difference between one-electron redox potentials of guanosine and guanine: Electrochemical and quantum chemical study

Cyclic voltammetry was used to measure the rates of the chemical oxidation of guanine (G), guanosine (Gs), 2a?2-deoxyguanosine (dG), and 2a?2-deoxyguanosine 5a?2-monophosphate (dGMP) by electrochemically generated tris(2,2a?2-bipyridyl)ruthenium(III). The numeric fit of voltammograms to an ECCCE type of mechanism provided the equilibrium and rate constants of the two-step chemical oxidation of the guanine species. One-electron redox potentials evaluated from the equilibrium constant of the first electron uptake follow the sequence G + and partly from the higher difference in the hydration energy between the deprotonated radical Gs(-H) and the parent Gs, which compensate for the lower ionization potential of Gs compared to that of G.

Kinetics of hydrolysis of 8-(arylamino)-2′-deoxyguanosines

The 8-(arylamino)-2′-deoxyguanosines, or C-8 adducts, are the major adducts formed by reaction of N-arylnitrenium ions derived from carcinogenic and mutagenic amines with 2′-deoxyguanosine (d-G) and guanosine residues of DNA. The hydrolysis kinetics of three C-8 adducts 1a-c were determined by UV and HPLC methods at 20 °C under acidic, neutral, and mildly alkaline conditions. At pH 2+2 (Scheme 2). The C-8 adducts are 2- to 5-fold more reactive than d-G under these conditions. At 3 +. Under these conditions the hydrolysis kinetics are accelerated by 40- to 1300-fold over that of d-G. The rate increase appears to be caused by a combination of steric acceleration of C-N bond cleavage and a decrease in the ionization constant of 1H+, Ka1, due to the electron-donating properties of the arylamino C-8 substituent. Under neutral pH conditions a slow (kobs ≈ 10-8 s-1 to 5 × 10-7 s-1) spontaneous cleavage of the C-N bond of the neutral nucleoside, 1, occurs that has not been previously reported for simple purine nucleosides. Finally, under mildly alkaline conditions a process consistent with spontaneous decomposition of the anion 1- or OH--induced decomposition of 1 is observed. The latter process has been observed for other purine nucleosides, including the closely related 1d, and involves nucleophilic attack of OH- on C-8 to cleave the imidazole ring of the purine.

π-Interactions of modified nucleobases. On mesomeric purine betaines with inversed charge properties

Intermolecular interactions of modified nucleobases with altered charge properties in relation to natural systems are studied. We prepared conjugated mesomeric betaines of purines and examined their properties by semiempirical calculations, IH

REACTION OF GUANOSINE DERIVATIVES WITH PHOSPHORUS TRICHLORIDE IN ACETONE

2',3'-Di-O-protected guanosine derivatives (Ia and Ib) were allowed to react with phosphorus trichloride in acetone to give the N-2-(1-methyl-1-phosphono)ethylguanosine derivatives (IIIa and 3b).

Novel use of a guanosine prodrug approach to convert 2′,3′-didehydro-2′,3′-dideoxyguanosine into a viable antiviral agent

Transient kinetic studies with human immunodeficiency virus (HIV) type 1 reverse transcriptase suggest that nucleotide analogs containing the 2′,3′-didehydro-2′,3′-dideoxy ribose ring structure present in D4T (stavudine) triphosphate are among the most effective alternative substrates. For unclear reasons, however, the corresponding purine nucleoside, 2′,3′-didehydro-2′,3′-dideoxyguanosine (D4G), was found to be inactive in cell culture. We have found that the previously reported lack of activity of D4G is primarily due to solution instability, and in this report we describe a novel use of a guanosine prodrug approach to stabilize the nucleoside. D4G was modified at the 6 position of the purine ring to contain a cyclopropylamino group yielding the prodrug, cyclo-D4G. An evaluation of cyclo-D4G revealed that the prodrug possessed anti-HIV activity. In addition, cyclo-D4G had increased stability, lipophilicity, and solubility, as well as decreased toxicity relative to D4G, suggesting that further study is warranted.

Physicochemical properties of carbovir, a potential anti-HIV agent

(±)-Carbovir [(±)-9-[4α-(hydroxymethyl)-cyclopent-2-ene-1α-yl]guanine; NSC 614846] is a novel carbocyclic nucleoside analogue which has been shown to be a potent and selective inhibitor of HIV in vitro. As part of an effort to develop a parenteral formulation for subsequent clinical and toxicological evaluation of this compound, the aqueous solution stability of carbovir as a function of pH and temperature and various physicochemical properties of carbovir including its pK(a), solubility versus pH and solvent composition, and octanol-water partition coefficient have been examined. Ultraviolet spectrophotometry indicated that carbovir has pK(a) values of 3.15 and 9.68, respectively, at 25°C and 0.01 ionic strength. The acqueous solubility of carbovir over the pH range 7-10.5 was consistent with that expected of a weak acid with a pK(a) of 9.65 and an intrinsic solubility of 1.24 mg/mL. Due to the limited solubility of carbovir at physiological pH, methods for solubilizing carbovir in aqueous solution were explored, including propylene glycol-water cosolvents and complexation with hydroxypropyl-β-cyclodextrin. As expected for carbovir, a semipolar compound with an octanol-water partition coefficient of 0.29, propylene glycol:water cosolvents were not highly effective in enhancing solubility. Complex formation between carbovir and 2-hydroxypropyl-β-cyclodextrin was found to be more effective, with a K(1:1) of 105 M-1 for the complexation. The pH profiles generated at 50, 70, and 90°C were accounted for by acid-catalyzed degradation at low pH leading to the formation of quanine and a neutral degradation pathway which dominates above pH 4. Prototype lyophilized formulations containing (after reconstitution) 10 mg/mL of carbovir at a pH of 10.6 were developed and evaluated.

THE EFFECT OF METAL ION COMPLEX FORMATION ON ACIDIC DEPURINATION OF 2'-DEOXYADENOSINE AND 2'-DEOXYGUANOSINE

The substitution inert N7-(dien)Pt(II) complex of 2'-deoxyguanosine has been shown to undergo acidic depurination 200 times less readily than the uncomplexed nucleoside, whereas the corresponding N1- and N7-complexes of 2'-deoxyadenosine are depurinated almost as rapidly as the nucleoside itself.These observations have been compared to the influences that several substitution labile metal ions exerted on the rate of depurination.Accordingly, the effects of (dien)Pd(II), Co(II), Ni(II), Cu(II), Zn(II) and Cd(II) ions on the acidic hydrolysis of 2'-deoxyadenosine and 2'-deoxyguanosine have been accounted for by competitive attachment of protons and metal ions to the N1 and N7 sites.The applicability of metal ions in chemical DNA sequencing is briefly discussed.

Low-energy, low-yield photoionization, and production of 8-oxo-2a?2-deoxyguanosine and guanine from 2a?2-deoxyguanosine

Experiments employing electron scavenging methods and high performance liquid chromatography with mass spectrometry detection indicate that electrons, formed via one-photon ionization, guanine (G) and small amounts of 8-oxo-2a?2-deoxyguanosine (8-oxo-dG)

Nitrogen-Doped Carbon Supported Co/Ni Bimetallic Catalyst for Selectively Reductive N-Formylation of Nitroso in Guanine Synthesis

A nitrogen-doped carbon supported Co/Ni bimetallic catalyst 2wt%Co/Ni@NC-700-10 was prepared and found to be efficient in the reductive N-formylation of 2,4-diamino-5-nitroso-6-hydroxypyrimidine (DANHP) to 2,4-diamino-5-formyl-6-hydroxypyrimidine (DAFHP) for the synthesis of guanine. Under optimal conditions, the conversion of DANHP reached up to 95.6% with a DAFHP selectivity of 97.6%. The characterization results revealed that the cobalt/nickel nanoparticles of the catalyst uniformly dispersed and encapsulated in the nitrogen-dopped carbon, and the catalyst has the characters of large surface area, as well as uniform dispersion and small diameters of metal nanoparticles in the form of Co/Ni alloy, which endowed its good catalytic performance in the reaction. Graphical abstract: [Figure not available: see fulltext.]

Preparation method and application of 2, 4-diamino-6-hydroxy-5-formamidopyrimidine

The invention discloses a preparation method of 2, 4-diamino-6-hydroxy-5-carboxamido pyrimidine. The preparation method comprises the following step: carrying out an acylation reaction on 2, 4-diamino-5-nitroso-6-hydroxypyrimidine in formamide and water under the catalytic action of a catalyst A to obtain the 2, 4-diamino-6-hydroxy-5-carboxamido pyrimidine. The invention also discloses a preparation method of guanine formate or guanine. The preparation method of guanine formate or guanine comprises the following step: reacting the 2, 4-diamino-6-hydroxy-5-formamidopyrimidine in formic acid toobtain guanine. According to the synthesis methods of the 2, 4-diamino-6-hydroxy-5-formamidopyrimidine and guanine, the production process is greatly shortened, the generation amount of three wastes is greatly reduced, the product quality of the guanine product meets related quality requirements, and the molar yield is higher than that of the guanine product prepared by the prior art. Therefore, the preparation methods disclosed by the invention are efficient, economic, green and environment-friendly preparation methods.