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Guanidineacetic acid CAS 352-97-6

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  • Appearance: White powder
  • Assay: 99. 0%min
  • Stock: In stock
  • Sample: Available
  • Zhishang Chemical: Guanidineacetic acid Supplement
352-97-6

Basic Info of Guanidineacetic acid

What is Guanidineacetic acid?

Guanidinoacetic acid is the only prerequisite for creatine synthesis in vertebrates. Creatine is a temporary storage place for energy in the body. It and creatine phosphate form a phosphogen system. When the body’s ATP supply is insufficient, it can provide P and resynthesize ATP with ADP. In humans and animals, about 1.7% of the creatine-phosphocreatine system is inevitably converted into creatinine and secreted into the urine every day, so the body must continuously replenish creatine.

Animals can synthesize creatine endogenously, and the synthesis requires two steps: arginine and glycine are synthesized in the kidney by L-arginine:glycine amidinylase catalyzed by guanidinoacetic acid, and guanidinoacetic acid reaches the liver through blood circulation Under the action of N-dimethyltransferase, it reacts with S-adenosylmethionine to generate creatine. Animal endogenous synthetic creatine accounts for 66% to 75% of the creatine required by the body, which cannot meet the demand, so animal protein (fish meal or meat meal) needs to be added to the diet to supplement it. In my country, there is a shortage of high-quality animal protein raw materials such as fish meal, and the price remains high. However, plant raw materials do not contain creatine, and pure plant diets can easily lead to the lack of creatine in animals. Therefore, the development of the feed industry faces severe challenges. The addition of guanidinoacetic acid to the feed can compensate for the decline in animal production performance caused by pure plant diets to a certain extent. The research and application of guanidinoacetic acid has attracted the attention of the majority of animal husbandry technology practitioners.

In recent years, the value of guanidinoacetic acid in human nutrition has been re-emphasized as an experimental dietary additive, and researchers have begun to study its role in animal production. Clinical results show that guanidinoacetic acid can effectively prevent muscle loss in patients with chronic renal failure. In healthy volunteers, guanidinoacetic acid can effectively improve their muscle development; in patients with chronic fatigue syndrome, guanidinoacetic acid can also improve some related symptoms. Guanidinoacetic acid increases creatine synthesis and stimulates cellular energy metabolism. The study showed that creatine content in skeletal muscle was significantly increased (P<0.05) after injection of guanidinoacetic acid in humans and piglets.

Guanidineacetic acid Uses

As early as the 1950s, it was reported that exogenous addition of guanidinoacetic acid could improve the physiological function of patients with cardiac decompensation, and it was suggested that the improved physiological function of guanidinoacetic acid may be based on the biosynthesis of creatine. But in addition to being a precursor of creatine, guanidinoacetic acid has many physiological functions, including promoting insulin secretion, affecting neuromodulation, altering arginine metabolism, and affecting the body’s oxidative and antioxidant systems.

Guanidinoacetic acid can promote insulin secretion and was first discovered in animal experiments. In vitro injection of guanidinoacetic acid and guanidino derivatives can stimulate insulin secretion in rodent pancreas, and the guanidine group may be an important reason for stimulating insulin secretion.

The specific mechanism of guanidinoacetic acid-stimulated insulin secretion may be that the polarity of guanidinoacetic acid molecule can affect the depolarization of pancreatic islet cell membrane and enhance the activity of insulin receptors on the surface of target cell membranes through protein kinases A and C, thereby activating the insulin signaling pathway. The physiological function of insulin is mainly to lower blood sugar, therefore, exogenous addition of guanidinoacetic acid can reduce the level of glucose in plasma. Because of the insulinotropic effect of guanidinoacetic acid, it appears that guanidinoacetic acid may act as an antidiabetic anabolic agent by affecting insulin homeostasis, thereby maintaining blood glucose homeostasis.

Arginine is an essential amino acid for poultry, and studies have shown that guanidinoacetic acid can effectively replace arginine in feed. Because arginine is the precursor of guanidinoacetic acid, and a part of arginine is used for the synthesis of guanidinoacetic acid in poultry, so adding guanidinoacetic acid to broiler diets can save more dietary arginine and participate in spermatogenesis. Other physiological functions of amino acids, such as protein synthesis, release of hormones (such as growth hormone), increase breast muscle production. Second, arginine can also act as a precursor of nitric oxide (NO), so exogenous addition of guanidinoacetic acid can also affect the physiological function of NO-mediated growth-promoting.

Guanidinoacetic acid can activate γ-aminobutyric acid (GABA) receptors in the brain and peripheral tissues. This is because the structure of guanidinoacetic acid is very similar to that of γ-aminobutyric acid (Figure 2). Therefore, in patients with GAMT deficiency (an autosomal recessive genetic disease), endogenous guanidinoacetic acid cannot synthesize creatine in time. It leads to the accumulation of high concentrations (10-30 μmol·L-1) of guanidinoacetic acid in the serum or brain, and activates the voltage-gated or ligand-gated chloride channels of nerve cells, resulting in spontaneous neuronal damage. That is to say, guanidinoacetic acid can act as a competitive inhibitor of γ-aminobutyric acid, activating the excitability affecting the nervous system. Studies have shown that supplementation of 3 g of guanidinoacetic acid per day in healthy people results in a significant decrease in plasma gamma-aminobutyric acid levels after 3 weeks, which seems to indicate that guanidinoacetic acid supplementation can negatively regulate gamma-aminobutyric acid plasma levels. However, whether the addition of guanidinoacetic acid can activate GABA-mediated neuronal or muscle excitability requires further investigation.

At present, guanidinoacetic acid, as a high-quality food supplement or feed additive, is widely used in human health care and animal production. Guanidinoacetic acid can endogenously synthesize creatine (Cr) under the catalysis of enzymes. Creatine is a nitrogen-containing amino acid and is considered to be an energy buffer. Its main role is in creatine kinase (creatine). Kinase, CK) to form phosphorylated creatine (P-Creatine, PCr), involved in adenosine triphosphate (adenosine triphosphate, ATP) cycle. When the energy supply of ATP is insufficient, creatine phosphate transfers the phosphate group to adenosine diphosphate (ADP) at a very fast rate through creatine kinase and reconverts it to adenosine triphosphate. Supplementation with creatine is known to reduce methionine consumption in diabetic patients, while reducing the production of homocysteine ​​in the liver, preventing the accumulation of fat, and is therefore beneficial for patients with fatty liver and non-alcoholic liver disease. About 1.6% (2 g) of creatine and phosphocreatine in animals are irreversibly converted to creatinine and excreted in urine. Since the creatine synthesized in animals only accounts for 50% of the creatine required by the body, exogenous creatine needs to be added. However, the price of creatine is high and the half-life is short, so it is not suitable as a feed additive. As a creatine precursor, guanidinoacetic acid can synthesize creatine in the body and has been widely used in animal husbandry. Its main functions include improving the growth performance and pork quality of growing and finishing pigs, increasing the breast muscle yield of broilers, improving meat quality and Energy Metabolism.

Currently, some studies at the animal level suggest that guanidinoacetic acid may affect the oxidative-antioxidant system, acting as both a superoxide and an antioxidant compound. Mice were induced oxidative stress after injection of guanidinoacetic acid and accumulated excess oxygen free radicals in a pathological state. When the concentration of guanidinoacetic acid increased (about 100 μmol·L-1) and accumulated in the brain, guanidinoacetic acid exhibited obvious superoxidative effect. The conjugate base provides an electron to generate superoxide anion-oxygen free radical, thereby generating reactive oxygen species.

However, other studies have shown that dietary supplementation of guanidinoacetic acid can improve the body’s antioxidant status by increasing the total antioxidant capacity and activating antioxidant enzyme activities. The serum guanidinoacetic acid concentration (about 5 μmol· Antioxidative effect was only shown when L-1) was low. This is because the uptake of guanidinoacetic acid can quench the oxygen free radicals of its related metabolites (creatine and arginine), therefore, guanidinoacetic acid has an indirect antioxidant effect. That is to say, if the metabolism of guanidinoacetic acid remains the same or provides a low concentration of exogenous guanidinoacetic acid, it has an antioxidant effect, and when too much guanidinoacetic acid is produced in the body, it can act as a kind of Strong oxidant and induces oxidative stress.

In industry, it is mainly used in laboratory organic synthesis and chemical and pharmaceutical research and development. Guanidinoacetic acid, also known as guanidineacetic acid and N-amidinoglycine, is an amino acid analog and the only precursor for the synthesis of creatine in vertebrates. Creatine mainly exists in muscle cells and participates in the body’s energy metabolism. It forms the phosphogen system together with creatine phosphate. 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 supplementation does not require the participation of oxygen, and is much faster than the energy supplementation directly released by the oxidation of food, which can meet the rapid muscle growth of young animals and the energy needs of emergency physiological states. Therefore, livestock and poultry urgently need to supplement creatine. Animals can supplement creatine either through dietary supplementation of animal-derived protein (such as fish meal) or through endogenous synthesis in the body. The endogenous synthetic creatine of animals accounts for about 75% of the creatine they need, and the rest needs to be provided in the diet.” At present, fishmeal resources are in short supply, and meat and bone meal have food safety problems, causing animals to eat pure plants such as corn and soybean meal. The production performance decreased significantly after the creatine-type diet due to insufficient creatine supply. Exogenous creatine supplementation was expensive and unstable. In addition, exogenous creatine supplementation inhibited the production of L-arginine:glycine imidyltransferase. expression, thereby inhibiting the synthesis of endogenous creatine. The latest research found that guanidinoacetic acid is more effective than creatine in increasing tissue creatine load.

Studies have shown that the addition of 600 mg/kg guanidinoacetic acid to the whole plant-based diet improved the performance and breast muscle weight of broilers, and obtained the same results as the fish meal treatment group (6% fish meal in the early stage, and 3% fish meal in the middle and late stage). Production performance 4. Supplementing 1000 mg/kg natriacetic acid for 15 d in the diet of finishing pigs can improve energy utilization, delay the occurrence of glycolysis and improve pork quality15. The purpose of this experiment was to study the effects of guanidinoacetic acid on the growth performance, carcass quality and meat quality of finishing pigs, and to provide a basis for the effective use of guanidinoacetic acid.

Supplementation of dietary guanidinoacetic acid was initially used in human studies. Early studies have found that guanidinoacetic acid can have a good effect on patients with cardiometabolic disorders and depression and anxiety without obvious side effects. Dai Zhongshan et al. studied the mutagenicity of guanidinoacetic acid and found that the addition of guanidinoacetic acid would not cause mutagenesis or genotoxicity, nor would it cause harm to the environment.

Therefore, guanidinoacetic acid can be widely used in human health care and animal production. The administration of guanidinoacetic acid has no significant effect on the enzyme expression profile of human liver and muscle, and the side effects caused by administration are also acceptable, such as weight gain, nausea, abdominal distension, muscle cramps, abdominal pain. But it is worth noting that in addition to increasing serum creatinine and muscle creatine levels, taking guanidinoacetic acid can also increase serum homocysteine ​​levels. This is because guanidinoacetic acid is methylated to form creatine and can also form S-adenosylhomocysteine, which is then hydrolyzed to cysteine ​​and adenosine in vivo. Since homocysteine ​​in serum is an important indicator of clinical atherosclerosis and cardiovascular disease, the intake of guanidinoacetic acid increases the content of homocysteine ​​in plasma, which can be considered as a part of guanidinoacetic acid. a side effect. The methyl group required for the synthesis of creatine from guanidinoacetic acid is provided by S-adenosylmethionine, when guanidinoacetic acid is added as an additive together with methyl donors (eg betaine, choline, vitamin B) , can inhibit the elevation of serum homocysteine ​​after guanidinoacetic acid intake.

In addition, the European Food Safety Authority stated that feeding high doses of guanidinoacetic acid did not cause consumer effects on guanidinoacetic acid, creatine and homocysteine ​​in meat products from pigs and chickens. Since the intake of guanidinoacetic acid can increase the content of homocysteine ​​in serum, when guanidinoacetic acid is used as a sports health drug or animal feed additive, it is necessary to pay close attention to the concentration of homocysteine ​​in serum.

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Application of Guanidineacetic acid

The Synthetic Method of Guanidineacetic acid

  • Method 1: thiourea reacts with ethyl bromide to generate S-ethylthiourea hydrobromide: salt, neutralizes it with sodium hydroxide, and then reacts with glycine to obtain guanidinoacetic acid:
  • Method 2: Free: Guanidine is produced by neutralizing guanidine hydrochloride with solid sodium hydroxide, and then reacting with chloroacetic acid to obtain guanidinoacetic acid:

Reference

  1. Glycocyamine – PubChem
  2. Zhang Junling, Tian Yaoyao, Ma Jia, et al. Research progress on the physiological function of guanidinoacetic acid [J]. Feed Expo, 2017 (3): 20-22.
  3. Zhang Junling, Zhang Defu, Shi Fengyun, et al. Research progress of guanidinoacetic acid in animal production [J]. China Animal Husbandry, 2016, 52(4): 63-66.

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