Name | L-Glutamic acid |
Synonyms | H-Glu-OH Glutamic Acid L-Glutamic acid L(+)GLUTAMIC ACID L-Glutamine Acid Glutamic Acid (200 mg) L-2-Aminoglutaric acid L-Glutamic Acid (Alpha) L-GLUTAMIC ACID extrapure 4-amino-5-hydroxypentanamide L-GLUTAMIC ACIDRESEARCH GRADE (S)-2-Aminopentanedioic acid, Glu L-Glutamic acid, extra pure, Ph Eur, FCC L-Glutamic acid (S)-2-Aminopentanedioic acid L-Glutamic acid,(S)-2-Aminopentanedioic acid, Glu (S)-2-Aminopentanedioic acid, Acidum glutamicum, Glu L-Glutamic acid,(S)-2-Aminopentanedioic acid, Acidum glutamicum, Glu |
CAS | 56-86-0 |
EINECS | 200-293-7 |
InChI | InChI=1/C5H12N2O2/c6-4(3-8)1-2-5(7)9/h4,8H,1-3,6H2,(H2,7,9) |
InChIKey | WHUUTDBJXJRKMK-VKHMYHEASA-N |
Molecular Formula | C5H9NO4 |
Molar Mass | 147.13 |
Density | 1.54 g/cm3 at 20 °C |
Melting Point | 205 °C (dec.) (lit.) |
Boling Point | 267.21°C (rough estimate) |
Specific Rotation(α) | 32 º (c=10,2N HCl) |
Flash Point | 207.284°C |
JECFA Number | 1420 |
Water Solubility | 7.5 g/L (20 ºC) |
Solubility | Soluble in hydrochloric acid water |
Vapor Presure | 0mmHg at 25°C |
Appearance | Crystallization |
Color | White |
Maximum wavelength(λmax) | ['λ: 260 nm Amax: 0.1', , 'λ: 280 nm Amax: 0.1'] |
Merck | 14,4469 |
BRN | 1723801 |
pKa | 2.13(at 25℃) |
PH | 3.0-3.5 (8.6g/l, H2O, 25℃) |
Storage Condition | 2-8°C |
Sensitive | Easily absorbing moisture |
Refractive Index | 1.4300 (estimate) |
MDL | MFCD00002634 |
Physical and Chemical Properties | White or colorless scaly crystals. Slightly acidic. Density 1.538. Sublimation at 200 °c. Decomposition at 247-249 °c. Slightly soluble in cold water, soluble in boiling water, insoluble in ethanol, ether and acetone. Can treat hepatic Coma disease. glutamine acid |
Use | One of the sodium salt-sodium glutamate used as a condiment, goods with flavor and flavor elements. |
Hazard Symbols | Xi - Irritant |
Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
Safety Description | S24/25 - Avoid contact with skin and eyes. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
WGK Germany | 2 |
RTECS | LZ9700000 |
FLUKA BRAND F CODES | 10 |
TSCA | Yes |
HS Code | 29224200 |
Toxicity | LD50 orally in Rabbit: > 30000 mg/kg |
Downstream Products | Levamisole (S)-2,3,5,6-tetrahydro-6-phenylimidazo[2,1-b]thiazoletriylium phosphate L(+)-Glutamine |
there are asymmetric carbon atoms in glutamic acid, so several stereoisomers are formed, the more important is L-glutamic acid (I glutamic acid) and racemic glutamic acid (d/-glutamic acid), are non-toxic, its physical and chemical properties are described below. L-glutamic acid is white scaly crystals. Odorless, slightly special taste and sour taste. Slightly acidic. Slightly soluble in cold water, soluble in hot water, almost insoluble in ether, acetone and cold acetic acid, insoluble in ethanol and methanol. 200 degrees C sublimation, 247~249 degrees C decomposition. The relative density was 1. 538. This product and hydrochloric acid to generate I a glutamic acid hydrochloride, and alkali to generate I a glutamic acid sodium. Racemic glutamic acid is a white crystal. Slightly soluble in ether, ethanol and petroleum ether. The relative density (d20) was 1. 4601. Melting point 225~227 °c (decomposition). D-glutamic acid precipitates from water into flaky crystals with a melting point of 247-249 ° C. (decomposition).
This product is mainly produced by fermentation. With molasses or starch as raw material, with Corynebacterium glutamicum, or small cocci, or Arthrobacter as bacteria, with urea as nitrogen source, fermentation at 30~32 ℃, fermentation, after separating the cells from the fermentation broth, the pH was adjusted to 3 with hydrochloric acid. O, for isoelectric point extraction, the separation of glutamic acid crystals, glutamic acid in the mother liquor and then extracted by 732 ion exchange resin, after crystallization, drying, to get the finished product.
This product is L-2-amino-Glutaric acid. Calculated as dry product, containing no less than 98.5% of C5H9N04.
take this product, precision weighing, add 2mol/L hydrochloric acid solution to dissolve and quantitatively dilute to make a solution containing about 70mg per lml, and determine according to law (General 0621), the specific rotation was 31.5 ° to 32.5 °.
L-glutamic acid itself as a drug, can treat hepatic coma, but the effect is poor. Mainly used in the production of monosodium glutamate, spices, and used as a salt, nutritional supplements and biochemical reagents. Racemic glutamic acid is used for the production of pharmaceuticals, as well as biochemical reagents and the like.
take this product l. After adding 2mol/L hydrochloric acid solution (20ml) to be dissolved, measure the transmittance at the wavelength of 430nm by UV-visible spectrophotometry (General rule 0401), and the transmittance shall not be less than 98.0%.
take 0.30g of this product and check it according to law (General rule 0801). Compared with the control solution made of 6.0ml of standard sodium chloride solution, it should not be more concentrated (0.02%).
take 0.50g of this product, add 2ml of dilute hydrochloric acid and 5ml of water, shake to dissolve, check according to law (General rule 0802), and compare with the control solution made of standard potassium sulfate solution, no more concentrated (0.02%).
take 0.10g of this product and check it according to law (General rule 0808). Compared with the control solution made of 0.02% of standard ammonium chloride solution, it shall not be deeper ().
take this product, add 0.5mol/L hydrochloric acid solution to dissolve and dilute to prepare a solution containing about 10 mg per 1ml as a test solution; Take 1ml for precision measurement, in a 0.5 measuring flask, dilute to the scale with mol/L hydrochloric acid solution, shake well, and use as a control solution, A 0.5mol/L hydrochloric acid solution was added, dissolved and diluted to prepare a solution containing about 10 mg of glutamic acid and MG of aspartic acid per 1ml, respectively, as a system-suitable solution. According to the thin layer chromatography (General 0502) test, draw 5ul of each of the above three solutions, respectively, on the same silica gel G thin layer plate, with n-butanol-water-glacial acetic acid (2:1:1) to develop, spread, dry, spray with ninhydrin in acetone solution (1-50), heat at 80°C until spots appear, and immediately inspect. The control solution should show a clear spot, and the system applicable solution should show two completely separated spots. If the test solution shows impurity spots, the color should not be deeper (0.5%) than the main spot of the control solution.
take this product, dry to constant weight at 105°C, weight loss shall not exceed 0.5% (General rule 0831).
take l.Og of this product and check it according to law (General rule 0841). The residue left shall not exceed 0.1%.
take 2.0g of this product, add 6mL of dilute hydrochloric acid and an appropriate amount of water, heat to dissolve, cool, add water to 25ml, and check according to law (General rule 0807), it should not be deeper (0.0005%) than the control solution made of standard iron solution.
The residue left under the item of taking the ignition residue shall not contain more than 10 parts per million of heavy metal when examined by law (General Principles 0821, Law II).
take 2.0g of this product, add 5ml of hydrochloric acid and 23ml of water to dissolve, check according to law (General Principles 0822 first law), should comply with the provisions (0.0001%).
This product is diluted with sodium chloride injection to make a solution containing 20mg per lml, heated to dissolve, let cool to 37°C, and check according to law (General rule 1142), dose according to the rabbit body weight per lkg injection 10ml, should comply with the provisions. (For injection)
take this product about 0.25g, precision weighing, add boiling water 50ml to dissolve, let cool, add 5 drops of bromothymol blue indicator solution, and use sodium hydroxide titration solution (0.1 mol/L) titration to the solution from yellow to blue-green. Each 1 ml of sodium hydroxide titration solution (0.1 mol/L) corresponds to 14.71mg of C5H9N04.
amino acid drugs.
light shielding, sealed storage.
This product contains glutamic acid (C5H9N04) should be labeled the amount of 95.0% ~ 105.0%.
This product is white tablet.
Take 10 tablets of this product, precision weighing, fine grinding, precision weighing an appropriate amount (about 0.4g equivalent to glutamic acid), add 50ml of boiling water to dissolve glutamic acid, let it cool, add bromothymol blue indicator solution 0.5, with sodium hydroxide titration solution (0.1 mol/L) titration to the solution from yellow to blue-green. Each 1 ml of sodium hydroxide titration solution (0.1 mol/L) corresponds to 14.71mg of C5H9N04.
Same as glutamic acid.
(1)0.3g (2)0.5g
light shielding, sealed storage.
FEMA | 3285 | L-GLUTAMIC ACID |
NIST chemical information | information provided by: webbook.nist.gov (external link) |
EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
One of 20 common α-amino acids | glutamic acid is one of the 20 common α-amino acids constituting proteins. As a precursor of glutamine, proline and arginine. It is divided into three forms: levorotatory, dextrorotatory and racemic, L-glutamic acid, L-glutamic acid is the coding amino acid in protein synthesis, non-essential amino acids in mammals, in the body can be converted from glucose. At room temperature is a white or colorless scale Crystal, slightly acidic, non-toxic. Slightly soluble in cold water, soluble in hot water, almost insoluble in ether, acetone and cold acetic acid, also insoluble in ethanol and methanol. Sublimation at 200 C, 247 C -249 C decomposition, density 1.538g/cm3, rotation 37- 38.9(25 C). L-glutamic acid has a wide range of uses. As a medicine, it can treat hepatic coma, and can also be used to produce monosodium glutamate (sodium glutamate), food additives, spices and for biochemical research. L-glutamic acid is prepared by microbial fermentation using saccharides as raw materials and separation by "isoelectric point extraction" plus "ion exchange resin. glutamate is ubiquitous in nature. A variety of foods and the human body contain glutamate, which is one of the structural amino acids of proteins or peptides, and free amino acids, L-type amino acids are delicious. glutamic acid was discovered by risoxhson in 1856. It is colorless crystal with umami taste, slightly soluble in water, and soluble in hydrochloric acid solution, with an isoelectric point of 3.22. A large amount of protein in cereals, animal brain content is also more. Glutamate plays an important role in protein metabolism in living organisms and participates in many important chemical reactions in animals, plants and microorganisms. |
History of use | glutamic acid was named for its initial production from cereals. It is widely distributed and is present in almost all protein components. Glutamic acid is obtained by protein hydrolysis. Colorless plate-like crystals, isoelectric point of 3.3, soluble in water, insoluble in benzene, ether and other organic solvents, acidic aqueous solution is acidic amino acids. In physiology, glutamate can combine with glycine and cysteine to form glutathione, which has important physiological functions. Glutamic acid has umami flavor, and its sodium salt is monosodium glutamate. Monosodium glutamate will be decomposed in high heat, not strong heat. Monosodium glutamate was first discovered by Japanese chemist Ota. By chance, he drank kelp soup and felt delicious. After research, he used 100 of kelp to obtain 2 grams of sodium glutamate. Later Japan mass production of monosodium glutamate, known as the "taste of the elements". China in the 20th century, 30's by the Shanghai Tianqiao monosodium glutamate factory first produce monosodium glutamate, are exported to various countries to gain a reputation. Commonly used natural wheat protein or casein after hydrolysis, the solution pH value is adjusted to 3.3 to obtain glutamic acid precipitation, separation and then add the right amount of sodium hydroxide into monosodium glutamate. Monosodium glutamate can also be synthesized artificially, but the cost is expensive, and it is usually still obtained by the above protein hydrolysis method. In Japan, glutamic acid was produced by microbial fermentation after the 1960s. They put the bacteria of the genus Bacillus, Bacillus, and bacillus into the sugar compounds (mainly starch, glucose), plus urea, ammonium sulfate, ammonium chloride, and appropriate amounts of biotin and other nutrients, the above bacteria secrete large amounts of glutamic acid for the production of monosodium glutamate. At present, China has also used the fermentation method to produce monosodium glutamate. Glutamate can also be combined with ammonia in the blood to make it a non-toxic, but also for the treatment of liver coma and recovery of liver dysfunction and other diseases. |
significance in amino acid metabolism | 1. Glutamate is involved in glutamate dehydrogenase-centered co-deamination (glutamate is deaminated). 2. In the blood ammonia transport, glutamine synthetase catalyzes the combination of glutamic acid and ammonia to produce glutamine. Glutamine neutral non-toxic, easy to penetrate the cell membrane, is the main form of ammonia transport. 3. In the glucose-alanine cycle pathway, glutamate dehydrogenase in muscle catalyzes the combination of α-ketoglutarate with ammonia to form glutamate, glutamic acid then reforms α-ketoglutarate and alanine with pyruvate under the catalysis of alanine transaminase. 4. In the metabolic pathway of bioactive substances, glutamic acid itself is an excitatory neurotransmitter, which widely exists in the brain and spinal cord, it is widely present in living organisms. 5. Glutamic acid is an important precursor for the synthesis of glutamine, proline, arginine and lysine in the amino acid synthesis pathway. 6. In the ornithine cycle (urea synthesis) pathway, glutamate dehydrogenase in mitochondria removes the amino group of glutamic acid, providing free ammonia for the synthesis of carbamoyl phosphate; the glutamate transaminase in the cytoplasm transfers the amino group of glutamic acid to oxaloacetic acid, which then forms aspartic acid into the ornithine cycle, which indirectly provides a second amino group for the cycle. |
pharmacological action | glutamic acid is also named "glutamic acid". It can combine with blood ammonia to form harmless glutamine, so that the blood amine drops, thereby reducing the symptoms of hepatic coma, in addition, it participates in brain protein metabolism and glucose metabolism, and promotes the oxidation process, improves the function of the central nervous system. For the prevention and treatment of liver Coma, liver Coma recovery and severe liver dysfunction, glutamate can also be used for a variety of reasons caused by the Coma recovery period and nervous system diseases (schizophrenia and epilepsy, etc.) adjuvant therapy. Oral 2.5-5G, 4 times a day. |
identification test | take TS-224 mg sample, add 4ml water and 1 ml sodium hydroxide solution (), dissolve, 1 ml of indantrione test solution (TS-250) and mg of sodium acetate were added and heated in a boiling water bath for 10min to produce a violet color. Take 1g of sample, add 9ml of water to prepare suspension, warm slowly on the steam bath and stir until all dissolved, add 6.8ml of lmol/L hydrochloric acid solution, and re-suspend, then add 6.8ml of 1 mol/L sodium hydroxide solution. After stirring, glutamic acid should be completely dissolved. |
content analysis | method 1 accurately weigh about 0.2g of sample, dissolve in 3ml of formic acid, 50ml of glacial acetic acid and 2 drops of crystal violet solution (TS-74) were added and titrated with 0.1mol/L perchloric acid solution until the green or blue color completely disappeared. A blank test was also performed in the same manner. Each mL of 0.1mol/L perchloric acid solution corresponds to 14.71mg of L-glutamic acid (C5H9NO4). Method 2 accurately weigh sample 500mg, dissolve in 250mi water, add several drops of bromothymol blue solution (TS-56), titrate with 0.1mol/L sodium hydroxide solution to the blue end point. Each mL of 0.1 mol/L NaOH corresponds to 14.7mg of L-glutamic acid (C5H9N04). |
toxicity | ADI is not specified (FAO/WHO,2001). GRAS(FDA,§ 182.1045,2000). |
usage limit | FAO/WHO(1984): broth and soup for convenience food, 10g/kg. FEMA(mg/kg): Beverage, baked goods, meat, meat sausage, broth, milk and dairy products, seasoning, cereal products, all 400mg/kg. FDA,§ 172.320(2000): as a nutritional supplement, a limit of 12.4% (by weight of total protein in the food product). |
Use | used in pharmacy, food additives, Nutrition Fortifier used in biochemical research, used in medicine for hepatic coma, prevent epilepsy, reduce ketonuria and ketonemia. salt substitutes, nutritional supplements, and flavoring agents (mainly used in meat, soup, and poultry). Can also be used as shrimp, crab and other aquatic canned produce magnesium ammonium phosphate crystal prevention agent, the dosage of 0.3% ~ 1.6%. According to the provisions of China's GB 2760 96 can be used as spices. L-glutamic acid is mainly used in the production of monosodium glutamate, spices, and used as a salt substitute, nutritional supplements and biochemical reagents. L-glutamic acid itself can be used as a drug to participate in the metabolism of proteins and sugars in the brain and promote the oxidation process. The product is combined with ammonia in the body to form a non-toxic glutamine, which reduces blood ammonia, relieve hepatic coma. Mainly used for the treatment of hepatic coma and severe liver dysfunction, etc., but the effect is not very satisfactory; And anti-epileptic drugs, can be used to treat small seizures and psychomotor seizures. Racemic glutamic acid is used for the production of pharmaceuticals, as well as biochemical reagents and the like. One of the sodium salt-sodium glutamate used as a condiment, goods with flavor and flavor elements. white or colorless scaly crystals. Slightly acidic. Density 1.538. Sublimation at 200 °c. Decomposition at 247-249 °c. Slightly soluble in cold water, soluble in boiling water, insoluble in ethanol, ether and acetone. Can treat hepatic Coma disease. |
production method | glutamic acid can be produced by protein hydrolysis and synthesis, but fermentation is currently the main method for producing glutamic acid. The carbon source for the production of glutamic acid by fermentation is hydrolyzed sugar or molasses of starch such as potato, corn, cassava starch and coconut tree starch, acetic acid and liquid paraffin (C16 paraffin is the best) and other petrochemical products, carbon sources used to form microbial cells and metabolic products in the carbon shelf and energy of nutrients. The nitrogen source is ammonium salt, urea and the like, nitrogen is the main element constituting the cell protein, nucleic acid and the like, and nitrogen is also the main component element constituting the glutamic acid amino group of the fermentation product. Other auxiliary raw materials are inorganic salts, vitamins, etc., such as microorganisms need suitable phosphorus concentration, magnesium is an inorganic activator to stimulate cell growth, potassium salt to promote acid production, corn steep liquor to provide biotin and organic nitrogen source. Various accelerators and additives are also included. The producer bacteria are Brevibacterium, Corynebacterium pekinensis and the like. In a large fermenter, aeration and stirring fermentation, temperature 30-34 ℃,pH>7-8, after 30-40H fermentation, remove bacteria, glutamic acid in the fermentation broth extracted, refined for the finished product, in the above process, the isoelectric point method is used for extraction, and the ion exchange method, the hydrochloride method, the direct concentration method (when acetic acid is used as a raw material) and the like can also be used. The product produced by fermentation was L-glutamic acid, and the content was more than 98%. 80% of starch () was consumed per ton of glutamic acid, and the strain was 25kg. The advantage of the synthesis method is that it does not consume food, but the production process requires high pressure (about 20MPa), high temperature (above 120 ℃), the use of toxic raw materials, equipment investment is twice higher than the fermentation method, the obtained racemic glutamic acid also needs to be resolved, and the production process is complicated. According to the calculation of the production of 1T 99% of sodium glutamate (MSG), the production cost is close to that of the acid method when the synthesis method consumes 640kg of acrylonitrile and the annual output is more than 5000t. starch or molasses as raw material, obtained by fermentation and purification. The species used mainly include Micrococcus glutamicum, Corynebacterium, Brevibacterium, Bacillus and Arthrobacter. with gluten as raw material, L-glutamic acid was hydrolyzed by acid water, and then salted by hydrochloric acid, L-glutamic acid hydrochloride was obtained, and the crude product was obtained by neutralization reaction with L-glutamic acid hydrochloride and aniline, the product was filtered and dried. |
toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |