5550-12-9 Usage
Description
Guanosine 5'-monophosphate disodium salt, also known as disodium guanylate or sodium 5-guanylate, is an organic sodium salt that is the disodium salt of guanosine 5'-monophosphate (GMP). It is a white crystalline powder, colorless or white, with a characteristic taste similar to mushrooms. It is soluble in water, sparingly soluble in alcohol, and practically insoluble in ether. It is obtained by chemical synthesis and is stable against acid, alkali, salt, and heat.
Uses
1. Flavor Enhancer in Foods:
Guanosine 5'-monophosphate disodium salt is used as a flavor enhancer in the food industry. It is often used in conjunction with monosodium glutamate (MSG) and disodium inosinate, where it has a multiplication effect on the taste. It contributes to a fundamental taste sensation called "savory" in both animal and vegetable foods, providing a smoother "fullness" and "thickness" compared to other flavor enhancers.
2. Pharmaceutical Secondary Standards:
Disodium guanylate serves as pharmaceutical secondary standards for application in quality control. It provides a convenient and cost-effective alternative to the preparation of in-house working standards for pharma laboratories and manufacturers.
3. Certified Reference Materials:
These secondary standards are qualified as Certified Reference Materials, suitable for use in several analytical applications, including but not limited to pharmaceutical release testing, pharmaceutical method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.
4. Flavor Potentiator:
Sodium guanylate acts as a salt replacement flavor enhancer and is used as a food additive to potentiate the flavor of various food products.
5. Occurrence in Foods:
Guanosine 5'-monophosphate disodium salt is naturally found in certain foods such as mushrooms (shiitake, enokidake, matsutake, syoro, hatsutake), pork, chicken, and whale, contributing to their unique savory taste.
6. Synergistic Effect in Cooking:
The synergistic effect between nucleotides like GMP and MSG in cooking has long been empirically established. It is used in traditional Japanese cooking, where soup stocks are made by simmering ingredients rich in glutamate, IMP, or GMP, along with vegetables containing glutamate. Similarly, Europeans make soup stocks by cooking animal meats rich in IMP or several kinds of mushrooms rich in GMP, along with vegetables containing glutamate.
Chemical Properties:
Disodium guanylate contains approximately seven molecules of water of crystallization.
It appears as colorless to white crystalline or crystalline powder, odorless, with a unique flavor similar to mushrooms.
It undergoes browning under 240°C and decomposition under 250°C.
It has strong moisture absorption property and is easily soluble in water (25°C, 25%).
The pH value of its 5% aqueous solution is 7.0 to 8.5, being slightly soluble in ethanol, acetone, and ether.
Identification test
UV absorbance: A 1/50000 sample solution was prepared with 0.01 mol/L hydrochloric acid solution, which had a maximum absorbance at a wavelength of 256 nm ± 2 nm. A250/A260 ratio is at the range of 0.95 to 1.03, and A280/A260 ratio is at the range of 0.63 to 0.71.
Ribose test exhibits positive result. Take 3 mL of 0.03% sample solution, add 0.2 mL of the ethanol solution of 10% dihydroxy toluene, and 3 mL 0.1% ammonium ferric sulfate hydrochloric acid (TS-100), heat in water bath for 10 min, the color of the solution should be green.
Organic phosphate test is positive. Take 5 mL of 1% sample solution plus 2 mL of magnesium oxide mixture solution (TS-133), there should be no precipitation occurred. Further add 7 mL of nitric acid and boil for 10min, neutralize with sodium hydroxide solution (TS-224) and should exhibit phosphate reaction (IT-26).
The sodium salt test was positive (IT-28).
Solubility: it is soluble in water, slightly soluble in ethanol but almost insoluble in acetone and ether (OT-42).
Content analysis
Accurately weigh 500 mg of sample and dissolve with 0.01 mol/L hydrochloric acid, and add the volume up to 1000 ml. Take 10 mL of this solution, and then add 0.01mol/L hydrochloric acid to a final volume of 250 ml and mix. Use 0.01mol/L hydrochloric acid as a control, place it in 1 cm cuvette and measure the absorbance A under the wavelength of 260nm and then calculated as follows:
Amount (%) = A/289.8 × 250,000/Sample amount (mg) × 100/(100-Moisture (%)) × 100
Toxicity
ADI is not subject to special provision (FAO/WHO, 2001).
LD50:10 mg/kg (rat, oral). After chronic test feeding of 0.1% to 1% feed for 6 months, weight and tissue get no abnormal changes.
It can be safely used in food products (FDA, §172.530, 2000).
EEC-HACSG provides that it should not be used for infant food.
Usage limit
GB 2760-96: all kinds of food, take GMP limit.
FAO WHO: luncheon meat, ham, bacon, etc., 500 mg kg (in guanosine), broth and soup, GMP.
Standard for Maximum Allowable amount and maximal allowable residue of Food Additives
Name of additive??? Food allowed to use it as additive??? Function of additive??? Maximal allowable amount（g/kg）??? Maximal allowable amount（g/kg）
5'-guanylate disodium??? Food??? Food purpose flavor??? The perfume ingredients used in formulating fragrances shall not exceed the maximal allowable amount documented in GB 2760???
5'-guanylate disodium??? Food??? Flavoring agent??? Apply appropriate amount based on the demand of production except in cases where there is specific rule
Preparation
The production methods of guanylic acid mainly include enzymatic hydrolysis and fermentation method. In the fermentation method, there are two-step method and combination method with biosynthesis and chemical synthesis, two kinds which are of industrial significance.
(1) Ribonucleic acid (RNA) hydrolysis method. See the production method of 5'-inosinic acid disodium.
(2) Two-step method. Take glucose as the carbon source and ferment with the Bacillus subtilis mutant to obtain the guanosine. The production level was 10.5 g/L. Then guanosine, in pyridine solution, is acidified with phosphorus oxychloride phosphate to obtain guanylate.
(3) Biosynthesis and chemical synthesis.
At pH=7, apply Bacillus megaterium (No. 336) for fermentation of glucose (8%) for 90 h at pH = 7, producing 15 g/L 5-amino-4-carboxamide nucleoside (AICAr); then extract by ion exchange, followed by concentration and drying to be dissolved in methanol containing NaOH. Add carbon disulfide for co-heating so that it is converted into 2-thioglycoside; It is finally oxidized with hydrogen peroxide; add excess ammonia and heat to obtain guanosine which is further converted to guanylate through phosphorylation.
Preparation
This flavor enhancer is derived from fungal sources.
Biochem/physiol Actions
Guanosine 5′-monophosphate (GMP) is a ribonucleoside monophospate which upon phosphorylation to GTP becomes incorporated into ribonucleic acids (RNAs) by various RNA polymerase(s). Guanosine-5′-monophosphate (GMP) can be used to study modulation of glutamatergic neurotransmission.
Check Digit Verification of cas no
The CAS Registry Mumber 5550-12-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,5,5 and 0 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 5550-12:
(6*5)+(5*5)+(4*5)+(3*0)+(2*1)+(1*2)=79
79 % 10 = 9
So 5550-12-9 is a valid CAS Registry Number.
5550-12-9Relevant articles and documents
Enhanced nonenzymatic RNA copying with 2-aminoimidazole activated nucleotides
Li, Li,Prywes, Noam,Tam, Chun Pong,Oflaherty, Derek K.,Lelyveld, Victor S.,Izgu, Enver Cagri,Pal, Ayan,Szostak, Jack W.
, p. 1810 - 1813 (2017)
Achieving efficient nonenzymatic replication of RNA is an important step toward the synthesis of self-replicating protocells that may mimic early forms of life. Despite recent progress, the nonenzymatic copying of templates containing mixed sequences remains slow and inefficient. Here we demonstrate that activating nucleotides with 2-aminoimidazole results in superior reaction kinetics and improved yields of primer extension reaction products. This new leaving group significantly accelerates monomer addition as well as trimer-assisted RNA primer extension, allowing efficient copying of a variety of short RNA templates with mixed sequences.
