Guanine

Base Information

• Chemical Name: Guanine
• CAS No.: 73-40-5
• Molecular Formula: C5H5N5O
• Molecular Weight: 151.128
• Hs Code.: 2933.59 DERIVATION
• Mol file: 73-40-5.mol

Synonyms:6H-purin-6-one, 2-amino-3,7-dihydro-;C.I. Natural White 1;2-amino-3,7-dihydropurin-6-one;Hypoxanthine, 2-amino-;Pearl Essence;Guanine (2-Amino-6-hydroxypurine);Stella Polaris;CI 75170;CI Natural white 1;6H-Purin-6-one,2-amino-1,7-dihydro-;2-Aminohypoxanthine;Dew Pearl;2-Amino-1,7-dihydro-6H-purin-6-one;2-Amino-6-hydroxy-1H-purine;Mearlmaid AA;Gua;Mearlmaid;Guanine enol;6-Hydroxy-2-aminopurine;6H-Purin-6-one, 2-amino-1,7-dihydro- (9CI);6H-Purin-6-one, 2-amino-1,7-dihydro-;C.I. 75170;2-Amino-1,9-dihydro-purin-6-one;2-amino-1,9-dihydro-6H-purin-6-one;Guanin;2-Amino-6-purinol;2-Amino-6-hydroxypurine;Guanine (8CI);

Chemical Property of Guanine

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 5.86E-14mmHg at 25°C
• Melting Point: >300 °C(lit.)
• Refractive Index: 2.047
• Boiling Point: 591.4oC at 760 mmHg
• PKA: 9.92(at 40℃)
• Flash Point: 311.4oC
• PSA: 100.45000
• Density: 2.196 g/cm³
• LogP: -0.19040
• Storage Temp.: 2-8°C
• Solubility.: 1 M NaOH: 0.1 M at 20 °C, clear, colorless
• Water Solubility.: practically insoluble

Purity/Quality:

99% ^*data from raw suppliers

Guanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: It 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. Guanine is a crystalline amorphous substance that is found in guano, fish scales, and theliver of certain mammals. Guanine is responsible for the silvery iridescence of certain fishscales. Before its discovery, guanine was scraped from fish scales and used to coat beads to produceimitation pearls. Thus it was called pearl essence or pearly white in the 1700s. Guanineobtained from fish scales is used in cosmetics, especially for eye cosmetics and nail polishes. Guanine 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. guanine is mixed in water and used primarily in nail polish to achieve a pearlized effect. It has been greatly replaced by either synthetic pearl or aluminum and bronze particles. guanine is obtained from plant or animal sources.
• 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.

Technology Process of Guanine

There total 148 articles about Guanine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

G (118-00-3) → 2-amino-1,9-dihydro-6H-purin-6-one (73-40-5)

Guidance literature:

With sulfuric acid; In water; at 90 ℃; for 1.5h; Reagent/catalyst; Temperature; Solvent; Large scale;

Reference yield: 90.0%

acycloguanosine (59277-89-3) → 2-amino-1,9-dihydro-6H-purin-6-one (73-40-5)

Guidance literature:

With sodium hydroxide; In water;

Reference yield: 14.7%

2'-Deoxyguanosine (961-07-9) → spiroiminodihydantoin-2'-deoxyribonucleoside + 2-amino-1,9-dihydro-6H-purin-6-one (73-40-5) + 5-guanidinohydantoin (104184-01-2) + 2,2,4-triamino-2H-oxazol-5-one-2′-deoxyribonucleoside (1309569-79-6) + 5-carboxamido-5-formamido-2-iminohydantion-2′-deoxyribonucleoside + 5',8-cyclo-2'-deoxyguanosine + 7,8-dihydro-8-oxo-2'-deoxyguanosine (88847-89-6) + N1-(β-D-erythro-pentofuranosyl)-5-guanidinohydantoin

Guidance literature:

With N-acetylcystein; In aq. phosphate buffer; at 22 ℃; pH=7.4; Irradiation;

DOI:10.1021/acs.joc.5b00689

upstream raw materials:

formic acid

2,5,6-triamino-3,4-dihydro-4-pyrimidinone

sodium formate

orthoformic acid triethyl ester

Downstream raw materials:

2'-Deoxyguanosine

1,7-dimethylguanine

8-aminoguanine

4-(2-amino-6-oxo-6,7-dihydro-3H-purin-8-ylazo)-benzenesulfonic acid

Refernces

• 1、 Novak, Michael,Ruenz, Megan,Kazerani, Shahrokh,Toth, Krisztina,Nguyen, Thach-Mien,Heinrich, Brian. "Kinetics of hydrolysis of 8-(arylamino)-2′-deoxyguanosines". . p. 2303 - 2308. Retrieved 2002.
• 2、 Honjo, Mikio,Maruyama, Tokumi,Sato, Sumiko,Marumoto, Ryuji. "REACTION OF GUANOSINE DERIVATIVES WITH PHOSPHORUS TRICHLORIDE IN ACETONE". . p. 2663 - 2666. Retrieved 1981.
• 3、 Anderson,Chiang. "Physicochemical properties of carbovir, a potential anti-HIV agent". . p. 787 - 790. Retrieved 1990.
• 4、 Papadantonakis, George A.,Tranter, Robert,Brezinsky, Kenneth,Yang, Yanan,Van Breemen, Richard B.,LeBreton, Pierre R.. "Low-energy, low-yield photoionization, and production of 8-oxo-2a?2-deoxyguanosine and guanine from 2a?2-deoxyguanosine". . p. 7704 - 7712. Retrieved 2002.
• 5、 Liu, Peng,Shi, Dongxu,Wang, Ke,Zhang, Hong-yu,Zhang, Yuecheng,Zhao, Jiquan. "Nitrogen-Doped Carbon Supported Co/Ni Bimetallic Catalyst for Selectively Reductive N-Formylation of Nitroso in Guanine Synthesis". . . Retrieved 2021/11/22.
• 6、 -. "Method for synthesizing 2-amino-6-chloropurine". Paragraph 0021-0035. . Retrieved 2020/09/08.