85-32-5
guanosine 5'-monophosphoric acid
CAS: 85-32-5
Molecular Formula: C10H14N5O8P
85-32-5 - Names and Identifiers
| Name | guanosine 5'-monophosphoric acid |
| Synonyms | 5'-gmp GUANILICACID GUANILLICACID Guanylic Aicd 5'-guanylic acid guanosine 5'-monophosphoric acid GUALOSINE 5'-PHOSPHATE (FEED ACID) guanosine 5-(dihydrogen phosphate) guanosine 5-monophosphate free acid*sigma grade [5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxyphosphonic acid |
| CAS | 85-32-5 |
| EINECS | 201-598-8 |
| InChI | InChI=1/C10H14N5O8P/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,16-17H,1H2,(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1 |
85-32-5 - Physico-chemical Properties
| Molecular Formula | C10H14N5O8P |
| Molar Mass | 363.22 |
| Density | 2.47±0.1 g/cm3(Predicted) |
| Melting Point | 220 - 223°C |
| Boling Point | 64 °C(Press: 0.05 Torr) |
| Flash Point | 492.2°C |
| Solubility | DMSO (Very Slightly, Heated, Sonicated), Water (Slightly, Sonicated) |
| Vapor Presure | 5.16E-34mmHg at 25°C |
| Appearance | Solid |
| Color | White to Off-White |
| pKa | 1.86±0.10(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,Store in freezer, under -20°C |
| Refractive Index | 1.946 |
| Physical and Chemical Properties | Colorless or white crystals, or white crystalline powder, odorless, with a special taste. |
| Use | Used as drug intermediates, health food and biochemical reagents, food additives |
85-32-5 - Risk and Safety
| Toxicity | LDLo intraperitoneal in mouse: 1500mg/kg |
85-32-5 - Upstream Downstream Industry
| Raw Materials | Ribonucleic Acid, Transfer |
85-32-5 - Reference Information
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Introduction | guanosine, also known as 5 '-guanosine5'-monophos-phate code (GMP), has the molecular formula C10H14N5O8P, phosphoric acid is condensed with a hydroxyl group at the 5th carbon atom on the nucleotide ribose, and is one of five kinds of nucleotides constituting a nucleic acid. Guanosine can be synthesized by the salvage pathway and can be synthesized de novo, and it is guanosine tetraphosphate (pp GPP), guanosine triphosphate (GTP), cyclic guanosine monophosphate (cGMP). And guanosine diphosphate (GDP) precursor molecules. The structural formula of guanylate is shown in the figure. |
| Application | as one of the five nucleotides constituting nucleic acid, guanosine has a unique mushroom-like umami flavor, is often used to enhance the flavor of food because its umami threshold is 0.0125g/dL. In the food industry, it is mainly used as a food additive in the form of its sodium salt (Bird disodium glycoside), which is used as a raw material for seasoning, soy sauce and monosodium glutamate, it is commonly used together with glutamate to enhance the fresh taste of food products. In the field of medicine, guanosine has a high degree of biological activity, can improve the body's immunity, anti-tumor auxiliary, promote growth and regulate the body's nutrition and metabolism, can promote the recovery of liver function, regulate the body's immune function, resistant to Cancer, etc., make guanosine as a pharmaceutical raw material with great development potential. In addition to this , the antioxidant activity of guanosine has a very large effect on the growth of nerves, and can protect cells from the attack of active free radicals. Guanylate plays an invaluable role in both the food and pharmaceutical industries. |
| taste mechanism | taste nucleotides include inosinic acid, guanosine monophosphate, cytidine acid, uridine acid, the flavor of the latter three is far less than the former two, so the flavor nucleotides in industrial production are mainly inosinic acid (IMP) and guanosine (GMP). Studies have shown that: the flavor of IMP and GMP depends on its chemical structure, only the nucleoside 5 '-on the-OH and phosphate group esterification to show umami activity, the-OH phosphorylations at the 2'-and 3 '-positions are without umami flavor. According to n(IMP): n(GMP)= 1: 1 mixing, the umami threshold (the lowest concentration that can sense umami) can be reduced to 0.0063%. In 1960, Dr. KUNINAKA of Japan found that 5 '-guanosine had umami flavor and high content in Lentinus edodes, and then used it from Penicillium citrimum. The extracted 5'-phosphodiesterase degrades RNA to produce 5 '-nucleotides. Industrial production of nucleotides has been initiated in Japan using this method. Guanosine has a significant role in increasing freshness, assisting anti-tumor, improving immunity and regulating the body's nutrition and metabolism, so it is widely used in the field of food and medicine. |
| production methods | the production methods of guanosine include enzymatic hydrolysis RNA method, cell autolysis method, four methods of fermentation and chemical synthesis. At present, the most widely used production process of guanosine is the fermentation conversion method, which uses certain microorganisms to produce guanosine with glucose as a carbon source, and then converts it into guanosine by biological or chemical methods, such as guanosine phosphorylation of guanosine, and the method of industrial production of guanosine is the two-step production method of guanosine fermentation. when the microorganism encounters unfavorable conditions for growth, the microorganism will start the ribosome autolysis system by using various RNA decomposing enzymes in the microbial cells, in order to obtain enough energy to maintain survival. Bacterial autolysis method is a method to obtain nucleotides by autolysis of bacteria to degrade their own ribonucleic acid under certain conditions. Because the efficiency is too low, and the extraction is difficult, the cell autolysis method is basically not used at present. Enzymatic hydrolysis of RNA method enzymatic hydrolysis of RNA method is the use of yeast or white mold cells as raw material, the use of phosphodiesterase hydrolysis of ribonucleic acid to prepare guanosine, it mainly includes the extraction of RNA from bacteria, the preparation of 5 '-phosphodiesterase, the enzymatic hydrolysis of RNA and the isolation and purification of single nucleic acid. This method originated in the early 60s of the 20th century, the country of Japan first discovered the use of Penicillium citrinum extracted 5 '- Phosphodiesterases can degrade RNA to produce 5 '-nucleotides. The key enzyme of enzymatic hydrolysis of RNA is the 5 '-phosphodiesterase of Penicillium. Because of the more by-products, this method is not commonly used [5]. The 5 '-phosphodiesterase is obtained by liquid submerged fermentation using Penicillium citrinum or Streptomyces aureus as the starting strain. The process flow is as follows: Slant culture → seed Culture → fermentation culture → filtrate. Chemical synthesis method The chemical synthesis method is usually a method in which a phosphoric acid-to-esterification reaction is carried out on a nucleoside using pyrophosphoric acid or an active derivative of phosphoric acid. Because of the need for a large number of organic solvents, there are problems such as environmental pollution and raw material sources, chemical synthesis is rarely used in production. The production of guanosine monophosphate by fermentation can be divided into two methods: direct fermentation and fermentation conversion. The direct fermentation method uses a certain number of microorganisms and uses glucose as carbon source to obtain guanosine monophosphate, but the yield of guanosine monophosphate obtained by this method is low and cannot meet the requirements of industrialization. At present, the most widely used method is the fermentation conversion method, which uses certain microorganisms to produce guanosine with polysaccharide or glucose as a carbon source, and then converts it into guanosine by biological or chemical methods. Generally, Bacillus subtilis is first subjected to slant culture, seed culture and fermentation culture to obtain guanosine, and then guanosine is prepared by using phosphorus oxychloride solution and pyridine solution. The Reaction formula is shown in the figure. At present, the yield of guanosine monophosphate in our country is lower than the advanced level abroad, and the industrial production of guanosine monophosphate is not yet mature. How to improve the yield of guanosine monophosphate has become the top priority of the research. obtained by decomposition and isolation of nucleic acids from yeast. From glucose by fermentation of guanosine, and then by phosphorylation. |
| identification test | UV absorbance 1: 0.01 sample solution was prepared with 50000 mol/L hydrochloric acid. The maximum absorbance was at 256Nm ± 2nm. The ratio of A250/A260 is 0.95~1.03; The ratio of A280/A260 is 0.63~0.71 (see ultraviolet spectrophotometry in GT-29). Ribose test with the "02006, two sodium guanosine" in the identification test in 2. Organic phosphate test take 1:400 sample solution 5ml, add magnesium oxide mixture test solution (TS-133)2ml, should be no precipitation. Then 7ml nitric acid was added, boiled for 10min, neutralized with NaOH solution (TS-224), then ammonium molybdate solution (TS-22) was added and warmed. A yellow precipitate should occur, which is dissolved in the NaOH or ammonia solution (TS-13). |
| content analysis | The method is the same as "02006, disodium guanosine", calculate: content (%) = A/325 × 25000/sample volume (mg)× 100/(100-loss on drying (%))× 100 |
| toxicity | ADI is not specified (FAO/WHO,2001). |
| usage limit | GB 2760-2001: infant formula milk powder 0.2-0.58g/kg (based on total nucleotides). |
| Use | flavoring agent used as pharmaceutical intermediates, health food and biochemical reagents, food additives |
Last Update：2024-04-09 02:00:12
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Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052
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Multiple Specifications
Product Name: Guanosine-5'-monophosphate, Free acid Request for quotationCAS: 85-32-5
Tel: +86-571-88162785
Email: Lucy@verypharm.com
Mobile: +86-13606544505
QQ: 472954302
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