(2S)-2-amino-4-carbamoylbutanoic acid

(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/c26-3(5(9)10)1-2-4(7)8/h23H,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)