guanidoacetic acid
Guanidineacetic acid
CAS: 352-97-6
Molecular Formula: C3H7N3O2
guanidoacetic acid - Names and Identifiers
| Name | Guanidineacetic acid |
| Synonyms | NSC 1901 BetacyaMine Glycocyamine N-Amidinoglycin N-Amidinoglycine guanidoacetic acid Guanidinoacetic acid Guanidineacetic acid N-(diaminomethylidene)glycine (Aminoiminomethyl)aminoacetic acid GLYCOCYAMINE(GUANIDINOACETIC ACID)(P) Guanidineacetic acid,glucocyamine,Glycocyamine Guanidineacetic acid,N-Amidinoglycine, N-Guanylglycine, Glycocyamine |
| CAS | 352-97-6 |
| EINECS | 206-529-5 |
| InChI | InChI=1/C3H7N3O2/c4-3(5)6-1-2(7)8/h1H2,(H,7,8)(H4,4,5,6) |
| InChIKey | BPMFZUMJYQTVII-UHFFFAOYSA-N |
guanidoacetic acid - Physico-chemical Properties
| Molecular Formula | C3H7N3O2 |
| Molar Mass | 117.11 |
| Density | 1.4020 (rough estimate) |
| Melting Point | 300°C(lit.) |
| Boling Point | 218.88°C (rough estimate) |
| Flash Point | 163.5°C |
| Water Solubility | 3.6g/L(15 ºC) |
| Solubility | 6 M NaOH : 50mg/mL, clear, colorless |
| Vapor Presure | 9.89E-06mmHg at 25°C |
| Appearance | White crystal |
| Color | White to Off-White |
| Merck | 14,4495 |
| BRN | 1759179 |
| pKa | 2.82(at 25℃) |
| Storage Condition | Keep in dark place,Inert atmosphere,Room temperature |
| Refractive Index | 1.4900 (estimate) |
| MDL | MFCD00004278 |
| Use | Used as food additives, intermediates in organic synthesis |
guanidoacetic acid - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| RTECS | MB7700000 |
| HS Code | 29252000 |
guanidoacetic acid - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| energy regulator | guanidinoacetic acid (Guanidino Acid, GAA) is a precursor of creatine in animals and participates in the regulation of energy metabolism in the body. As a new nutritional feed additive, guanidinoacetic acid has the functions of improving the growth performance of pigs, chickens and other animals, slaughtering and reproductive performance, and improving meat quality. |
| characteristics | guanidinoacetic acid is colorless leaf-like or needle-like crystals, soluble in water, slightly soluble in ethanol and ether. Decomposition at 280~284 ℃. General reagent content ≥ 97%(NT). |
| Mechanism of action | Guanidinoacetic acid, also known as guanidinoacetic acid and N-amidinylglycine, is an amino acid analog and is the only prerequisite for the synthesis of creatine in vertebrates. Creatine mainly exists in muscle cells and participates in the energy metabolism of the body. It and creatine phosphate together form the phosphoric acid system. When the body has excess ATP, creatine phosphate can store energy. When the body's ATP supply is insufficient, creatine phosphate can regenerate ATP. This kind of supplement does not require the participation of oxygen, and is much faster than the energy supplement released directly by food oxidation. It can meet the rapid muscle growth of young animals and the energy needs in emergency physiological conditions. |
| safety | guanidinoacetic acid has no obvious effect on the enzyme expression profile of human liver and muscle, and the side effects caused by taking it are acceptable, such as weight gain, nausea, abdominal distension, muscle cramps and abdominal pain. However, it is worth noting that taking guanidinoacetic acid can not only increase serum creatinine content and creatine content in muscle, but also increase the content of homocysteine in serum. This is because guanidinoacetic acid is methylated to form creatine and can also form S-adenosine homocysteine, which is then hydrolyzed into cysteine and adenosine in vivo. Since homocysteine in serum is an important indicator of atherosclerosis and cardiovascular disease in clinic, the intake of guanidinoacetic acid increases the content of homocysteine in plasma, which can be considered as a side effect of guanidinoacetic acid. |
| physiological function | 1. stimulating insulin secretion studies have shown that exogenous addition of guanidinoacetic acid can stimulate insulin secretion in rodents. compared with the synthesis of creatine and saving arginine, guanidinoacetic acid has a more powerful function in improving insulin secretion. The polarity of the guanidinoacetic acid molecule affects the depolarization of the pancreatic islet cell membrane and stimulates insulin secretion through protein kinase A and C sensitive mechanisms. In addition, exogenous guanidinoacetic acid increases insulin secretion by reducing the glucose content in the blood. It may be that the enhancement of guanidinoacetate protein kinase regulates the activity of insulin receptors on target cells. Therefore, guanidinoacetic acid can promote the secretion of insulin and affect insulin metabolism; it can also be used as an anti-diabetic compound to improve the symptoms of hyperglycemia. There are no clinical studies in humans to evaluate the function of guanidinoacetic acid to stimulate insulin secretion and its mechanism of action. 2. saving arginine in animal nutrition, adding guanidinoacetic acid to the diet can effectively save arginine. This saving effect allows more arginine to be used in other areas, including protein synthesis, cell signaling and hormone secretion. Recent studies have shown that adding guanidinoacetic acid to the diet can improve the growth performance and daily gain of broilers, and more arginine is involved in protein synthesis, including breast meat synthesis. At present, there is no research to evaluate its function of saving arginine and protein synthesis in human body. 3. Activate γ-aminobutyric acid receptors in the brain and nerves γ-aminobutyric acid is the main inhibitory neurotransmitter in the nervous system. Guanidinoacetic acid can be used as a neuroregulator to affect nerve Excitement, muscle tone and brain development. The interaction between guanidinoacetic acid and γ-aminobutyric acid receptor can be regarded as a substitute mechanism, which can be explained as an autosomal recessive genetic disease, a disease in which creatine synthesis is impaired due to lack of guanidinoacetic acid transferase. This disease can cause neurological dysfunction in patients. Guanidinoacetic acid and γ-aminobutyric acid have similar structures. Guanidinoacetic acid can activate voltage-gated and ligand-gated chloride ion channels in nerve cells, affecting nerve spontaneous activity. The above situation may occur under the condition of GAMT enzyme deficiency and accumulation of large amounts of guanidinoacetic acid in blood and brain. However, under physiological conditions, it is not clear whether guanidinoacetic acid can be used as a γ-aminobutyric acid receptor activator. Experimental studies have shown that given 3 g of guanidinoacetic acid per day to healthy people, the level of gamma aminobutyric acid in the blood decreased after 3 weeks. The regulatory mechanism of guanidinoacetic acid on γ-aminobutyric acid in diet needs further study. |
| use | guanidinoacetic acid is a precursor of creatine. creatine phosphate containing high phosphate group transfer potential energy is widely present in muscle and nerve tissues. it is the main energy supply substance in animal muscle tissue and can be used as food additive and organic synthesis intermediate. |
| Production method | The reaction of thiourea and bromoethane produces S-ethyl thiourea hydrobromide, and then reacts with glycine to produce guanidine acetic acid. Mix thiourea, bromoethane and absolute ethanol and warm them in a water bath for 3h to dissolve all thiourea. Then the ethanol and excess bromoethane are evaporated under reduced pressure to crystallize the residue and dry to obtain S-ethyl thiourea hydrobromide. Then add the sodium hydroxide solution to the resulting S-ethyl thiourea hydrobromide, and under cooling, quickly add the hot solution of glycine and water. After crystallization, add ether, leave it overnight, cool the mixture in an ice bath for 2 hours, and separate the ether layer. Suction and filtration, washing with ice water, ethanol, and ether in turn, and drying to obtain the finished product. |
Last Update：2024-04-09 02:00:08
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