(2S)-2-amino-4-carbamoylbutanoic acid
L(+)-Glutamine
CAS: 56-85-9
Molecular Formula: C5H10N2O3
(2S)-2-amino-4-carbamoylbutanoic acid - Names and Identifiers
| Name | L(+)-Glutamine |
| Synonyms | L-GLN H-Gln-OH L-Glutamine L-GLUTAMINE glutamine, L- levoglutamide LEVOGLUTAMIDE L(+)-Glutamine L(+)-GLUTAMINE alpha-glutamine glutaminic acid L-(+)-glutamine (S)-(+)-glutamine L-GLUTAMIC ACID AMIDE L-GLUTAMIC ACID 5-AMIDE L-Glutamic acid 5-amide L-2-Aminoglutaramic acid L(+)-Glutamic acid-5-amide L(+)-GLUTAMIC ACID-5-AMIDE 2-Aminoglutaramic acid, L- L-(+)-glutamic acid-5-amide 2,5-Diamino-5-oxpentanoicacid 2,5-Diamino-5-oxopentanoic acid, (S)- (2S)-2-amino-4-carbamoylbutanoic acid |
| CAS | 56-85-9 |
| EINECS | 200-292-1 |
| InChI | InChI=1/2C5H10N2O3/c2*6-3(5(9)10)1-2-4(7)8/h2*3H,1-2,6H2,(H2,7,8)(H,9,10) |
| InChIKey | ZDXPYRJPNDTMRX-VKHMYHEASA-N |
(2S)-2-amino-4-carbamoylbutanoic acid - Physico-chemical Properties
| Molecular Formula | C5H10N2O3 |
| Molar Mass | 146.14 |
| Density | 1.47 g/cm3 (20℃) |
| Melting Point | 185 °C (dec.) (lit.) |
| Boling Point | 265.74°C (rough estimate) |
| Specific Rotation(α) | 32.25 º (c=10, 2 N HCl) |
| Flash Point | 185°C |
| JECFA Number | 1430 |
| Water Solubility | Soluble in water, dimethyl sulfoxide and ethanol. Insoluble in methanol, ether, benzene, acetone, ethyl acetate and chloroform. |
| Solubility | Soluble in water (the solubility in water at 25°C is 3.6%), slightly soluble in ethanol, insoluble in ether, methanol, benzene, acetone, chloroform, ethyl acetate and glacial acetic acid |
| Vapor Presure | 3.3E-24mmHg at 25°C |
| Appearance | Colorless crystal |
| Color | White |
| Maximum wavelength(λmax) | ['λ: 260 nm Amax: 0.01', , 'λ: 280 nm Amax: 0.01'] |
| Merck | 14,4471 |
| BRN | 1723797 |
| pKa | 2.17(at 25℃) |
| PH | 5.0-6.0 (25℃, 0.1M in H2O) |
| Storage Condition | Store below +30°C. |
| Stability | Stability Moisture and light sensitive. Incompatible with moisture, strong oxidizing agents. |
| Refractive Index | 6.8 ° (C=4, H2O) |
| MDL | MFCD00008044 |
| Physical and Chemical Properties | White needle-like crystals. Melting point 184-185 °c (decomposition). Soluble in methanol, ethanol, ether, benzene, acetone, chloroform and ethyl acetate. Stable in neutral solution, in acid, alkali or hot water easily decomposed into glutamic acid, or lactone into pyrrole carboxylic acid. Odorless and slightly sweet. |
| Use | The product in the body into sugar Amine, as a precursor of synthetic mucin, can promote ulcer healing, mainly used as peptic ulcer medicine. In addition, it can also be used as a brain function improving agent and for the treatment of alcoholism. |
(2S)-2-amino-4-carbamoylbutanoic acid - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R36 - Irritating to the eyes R36/37/38 - 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. S24/25 - Avoid contact with skin and eyes. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S27 - Take off immediately all contaminated clothing. |
| WGK Germany | 2 |
| RTECS | MA2275100 |
| TSCA | Yes |
| HS Code | 29241900 |
| Toxicity | LD50 orally in Rabbit: 7500 mg/kg |
(2S)-2-amino-4-carbamoylbutanoic acid - Upstream Downstream Industry
| Raw Materials | L-Glutamic acid-5-methyl ester |
(2S)-2-amino-4-carbamoylbutanoic acid - Nature
Open Data Verified Data
This product is white crystal or crystalline powder, odorless, tasteless. Melting point 185 °c (decomposition). Soluble in water (3.6%,25 ° C), insoluble in ethanol, insoluble in methanol, ether, benzene, acetone, chloroform, ethyl acetate and acetic acid. Unstable to acid, alkali, hot water, hydrolysis into L-glutamic acid. It is involved in the biosynthesis of glucosamine, a component of mucin in the digestive tract, thus promoting the repair of mucosal epithelial tissue and contributing to the elimination of ulcer lesions. At the same time, it can promote brain metabolism through the blood brain barrier, improve brain function, and glutamate is an important nutrient for brain metabolism.
Last Update：2024-01-02 23:10:35
(2S)-2-amino-4-carbamoylbutanoic acid - Preparation Method
Open Data Verified Data
- synthesis method.
- fermentation method.
Last Update：2022-01-01 11:10:08
(2S)-2-amino-4-carbamoylbutanoic acid - Use
Open Data Verified Data
amino acid drugs. For low acid, peptic ulcer. Oral 0. 5G, 3-4 times a day. For the improvement of intellectual development of children and Mental Disorder, alcoholism, epilepsy brain function. Daily 0.1~0. 72g.
Last Update：2022-01-01 11:10:08
(2S)-2-amino-4-carbamoylbutanoic acid - Safety
Open Data Verified Data
- adverse reactions included sleepiness, facial flushing and constipation.
- sealed and protected from light.
Last Update：2022-01-01 11:10:08
(2S)-2-amino-4-carbamoylbutanoic acid - Reference Information
| FEMA | 3684 | L-GLUTAMINE |
| Decomposition | 185 ºC |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| trait | L-glutamine is a white crystalline or crystalline powder substance. |
| identification test | take 0.1% sample solution and add 1ml of ninhydrin test solution (TS-250), after heating and dissolving in a boiling water bath, it should be purplish red. |
| content analysis | accurately weigh about 150mg of sample pre-dried at 80 ℃ for 3H, after dissolving in 3ml of formic acid and 50ml of glacial acetic acid, titrated with 0.1mol/L perchloric acid, the end point was determined by potentiometer. At the same time, the blank test was carried out and the necessary correction was made. Perchloric acid corresponds to 14.62mg of L-glutamine (C5H10N2O3) per mL of 0.1mol/L. |
| toxicity | can be used safely in foods (FDA § 172.320,2000). LD507500mg/kg (rat, oral). |
| usage limit | accounts for 12.4% of the total protein in food (FDA § 172.320,2000). FEMA: baked products, meat products, soft candy, meat soup, nut products, seasoning, all 350(mg/kg). |
| uses | for biochemical research, medicine for peptic ulcer, Mental Disorder, alcoholism, epilepsy, brain dysfunction and other diseases, for the improvement of intellectual development of children. nutritional supplement, flavoring and flavoring agent. It is used in medicine to treat peptic ulcer, alcohol poisoning and improve brain function. nutritional supplements, flavoring and flavoring agents. It is used in medicine to treat digestive organs, ulcers, alcohol poisoning and improve brain function. The product is converted into a sugar amine in the body. As a precursor of synthetic mucin, it can promote ulcer healing and is mainly used as a digestive ulcer medicine. In addition, it can also be used as a brain function improving agent and for the treatment of alcoholism. |
| production method | L-glutamine widely exists in nature, for example, in Free State in pumpkin, in the seedlings of sunflower, the N-ethyl compound (theanine) is contained in tea leaves. Although glutamine can be extracted from natural products, mass production is carried out by fermentation and synthesis. 1. Synthesis from L-glutamic acid -5-methyl ester ([1499-55-4]) by condensation, addition, salt, hydrolysis. Glutamic acid was esterified with methanol in the presence of concentrated sulfuric acid, and the resulting esterified droplets were added to a mixed solution of methanol and carbon disulfide, and ammonia was passed under cooling while dropping. After completion of the addition of the esterified droplets, ammonia was continued, and then triethylamine was added, and the mixture was kept in a closed state at 30 ° C. For 40 hours. After Ammonia removal by concentration under reduced pressure, γ-methyl ester-L-glutamic acid-N-ammonia acid diammonium salt concentrate was obtained. It was heated to 40-45 °c and acetic acid was added. After stirring for 30min, the carbon disulfide was removed under reduced pressure, at which point a large amount of crystals were crystallized. An equal volume of methanol was then added, placed at 0 °c for 12h, and filtered to give crude glutamine. After activated carbon decolorization, recrystallization to obtain the finished product. 2. Fermentation method glucose, acetic acid and ethanol were used as the carbon source of the medium, and the yield was 39g/L based on glucose, and the yield was 39%. L-glutamic acid is obtained via γ-hydrazide, usually by amidation of L-glutamic acid-γ-methyl ester in the presence of carbon disulfide. -glutamic acid as raw materials, dissolved in methanol and sulfuric acid, ammonia neutralization after adding carbon disulfide, and then neutralized with ammonia, Ammonia removal after adding acetic acid, distilled off sulfur compounds, then add methanol, filtration, the product was dried. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:29:15
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Raw Materials for (2S)-2-amino-4-carbamoylbutanoic acid