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56-85-9

56-85-9 Structure

56-85-9 Structure
IdentificationMore
[Name]

L-Glutamine
[CAS]

56-85-9
[Synonyms]

2-aminoglutaramic acid
2-AMINOGLUTARIC ACID-3-MONOAMIDE
FEMA 3684
GLN
GLUTAMINE
GLUTAMINE, L-
H-GLN-OH
H-L-GLN-OH
L-2-AMINOGLUTARAMIC ACID
L-ALPHA-AMINOGLUTAMIC ACID
LEVOGLUTAMIDE
L-GLN
L(+)-GLUTAMIC ACID-5-AMIDE
L-GLUTAMIC ACID 5-AMIDE
L-GLUTAMIC ACID AMIDE
L(+)-GLUTAMINE
L-GLUTAMINE
RARECHEM AB PP 1119
(S)-2,5-DIAMINO-5-OXOPENTANOIC ACID
(S)-(+)-GLUTAMINE
[EINECS(EC#)]

200-292-1
[Molecular Formula]

C5H10N2O3
[MDL Number]

MFCD00008044
[Molecular Weight]

146.14
[MOL File]

56-85-9.mol
Chemical PropertiesBack Directory
[Appearance]

White crystalline powder
[Melting point ]

185 °C (dec.) (lit.)
[mp ]

185 °C (dec.)(lit.)
[Boiling point ]

265.74°C (rough estimate)
[alpha ]

32.25 º (c=10, 2 N HCl)
[density ]

1.47 g/cm3 (20℃)
[FEMA ]

3684
[refractive index ]

6.8 ° (C=4, H2O)
[Fp ]

185°C
[storage temp. ]

−20°C
[solubility ]

H2O: 25 mg/mL
[form ]

solution
[pka]

2.17(at 25℃)
[color ]

White
[Stability:]

Stability Moisture and light sensitive. Incompatible with moisture, strong oxidizing agents.
[PH]

5.0-6.0 (25℃, 0.1M in H2O)
[optical activity]

[α]20/D +33.0±1°, c = 5% in 5 M HCl
[Water Solubility ]

Soluble in water, dimethyl sulfoxide and ethanol. Insoluble in methanol, ether, benzene, acetone, ethyl acetate and chloroform.
[Decomposition ]

185 ºC
[λmax]

λ: 260 nm Amax: 0.01
λ: 280 nm Amax: 0.01
[Merck ]

14,4471
[JECFA Number]

1430
[BRN ]

1723797
[InChIKey]

ZDXPYRJPNDTMRX-VKHMYHEASA-N
[CAS DataBase Reference]

56-85-9(CAS DataBase Reference)
[NIST Chemistry Reference]

L-Glutamine(56-85-9)
[EPA Substance Registry System]

56-85-9(EPA Substance)
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

R36:Irritating to the eyes.
R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

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
[Safety Profile]

Mddly toxic by ingestion. Human systemic effects: euphoria. When heated to decomposition it emits toxic fumes of NOx.
[Hazardous Substances Data]

56-85-9(Hazardous Substances Data)
[Toxicity]

LD50 orally in Rabbit: 7500 mg/kg
Raw materials And Preparation ProductsBack Directory
【Raw materials】

Carbon disulfide-->L-Glutamic acid-->Metaclazepam-->L-Glutamic acid 5-methyl ester-->Octanoic hydrazide-->Carbodithioic acid
【Preparation Products】

(2S)-2-amino-3-(5-bromo-1H-indol-3-yl)propanoic acid-->5-Methyl-L-tryptophan-->N-Acetyl-L-glutamine-->5-amino-2,5-dioxo-pentanoic acid-->H-GAMMA-GLU-VAL-OH-->N-Carbobenzyloxy-L-glutamine-->Carbamic acid, (2,6-dioxo-3-piperidinyl)-, phenylmethyl ester (9CI)-->3-AMINO-PIPERIDINE-2,6-DIONE-->AMINO ACID HYDROXAMATES L-GLUTAMIC ACID GAMMA-MONOHYDROXAMATE
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

2-Aminoglutaramic acid(56-85-9).msds
Questions And AnswerBack Directory
[Description]

L-glutamine (chemical formula: C5H10N2O3) is an alpha-amino acid that is one of the 20 amino acids consisting proteins. L-glutamine is a non-essential amino acids and is also the most abundant amino acids in human bodies. It is involved in many important biological processes. For example, it is a building block for the protein synthesis as one key amino acid; it is used in the biosynthesis of urea and purines for nucleic acid synthesis; it is a substrate for the biosynthesis of neurotransmitters; it is also an important sources of cellular energy generation. L-glutamine provides many benefits to the body such as improving gastrointestinal health, aiding the treatment of ulcer and leaky gut, promoting muscle growth, improving diabetes and blood sugar as well as aiding in the treatment of cancer.
[References]

https://en.wikipedia.org/wiki/Glutamine
https://draxe.com/l-glutamine-benefits-side-effects-dosage/
https://pubchem.ncbi.nlm.nih.gov/compound/5961#section=Interactions
Hazard InformationBack Directory
[Chemical Properties]

L-glutamine is odorless, but has a slightly sweet taste L-glutamine performs a major role in DNA synthesis and sup- ports the immune system by means of glutathione synthesis.
[Chemical Properties]

White crystalline powder
[Chemical Properties]

White, odorless crystals or crystalline powder having a slightly sweet taste. It is soluble in water and practically insoluble in alcohol and in ether. Its solutions are acid to litmus. It melts with decomposition at about 185°C.
[Occurrence]

Occurrences in nature
Glutamine is the most abundant naturally occurring, nonessential amino acid in the human body, and one of the few amino acids that can directly cross the blood-brain barrier.In the body, it is found circulating in the blood, as well as stored in the skeletal muscles. It becomes conditionally essential (requiring intake from food or supplements) in states of illness or injury.Dietary sources
Dietary sources of L-glutamine include beef, chicken, fish, eggs, milk, dairy products, wheat, cabbage, beets, beans, spinach, and parsley. Small amounts of free L-glutamine are also found in vegetable juices.
Aiding gastrointestinal functionGlutamine-enriched diets have been linked with maintenance of gut barrier function and cell differentiation, suggesting glutamine may help to protect the lining of the gastrointestinal tract or mucosa. People who have inflammatory bowel disease (ulcerative colitis and Crohn' s disease) may not have enough glutamine, but two clinical trials found taking glutamine supplements did not improve symptoms of Crohn' s disease.
[Uses]

amine protecting agent
[Uses]

L-Glutamine is one of the 20 amino acids encoded by the standard genetic code. Its codons are CAA and CAG. Glutamine is a substance naturally produced in the body to help regulate cell growth and function. There may also be man-made versions of these subs
[Uses]

L-Glutamine is an essential amino acid that is a crucial component of culture media that serves as a major energy source for cells in culture. L-Glutamine is very stable as a dry powder and as a frozen solution. In liquid media or stock solutions, however, L-glutamine degrades relatively rapidly. Optimal cell performance usually requires supplementation of the media with L-glutamine prior to use.
[Preparation]

By isolation from sugar beet juice.
[Definition]

ChEBI: An optically active form of glutamine having L-configuration.
[Brand name]

Nutrestore (Nutritional Restart).
[Biological Functions]

Glutamine plays a role in a variety of biochemical functions, including :
Protein synthesis, as any other of the 20 proteinogenic amino acids
Regulation of acid-base balance in the kidney by producing ammonium
Cellular energy, as a source, next to glucose
Nitrogen donation for many anabolic processes, including the synthesis of purines
Carbon donation , as a source , refilling the citric acid cycle
Nontoxic transporter of ammonia in the blood circulation.
[Synthesis Reference(s)]

Tetrahedron: Asymmetry, 17, p. 245, 2006 DOI: 10.1016/j.tetasy.2005.12.023
Journal of the Chemical Society, p. 3315, 1949 DOI: 10.1039/JR9490003315
[General Description]

Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards. L-glutamine is the most abundant amino acid in the body. It is essential for the synthesis of L-asparagine. It also helps in muscle growth through protein synthesis and increased growth hormone levels.
[Biochem/physiol Actions]

L-Glutamine is an essential amino acid that is a crucial component of culture media that serves as a major energy source for cells in culture. L-Glutamine is very stable as a dry powder and as a frozen solution. In liquid media or stock solutions, however, L-glutamine degrades relatively rapidly. Optimal cell performance usually requires supplementation of the media with L-glutamine prior to use.
[Veterinary Drugs and Treatments]

Glutamine has been used as a GI protectant and in an attempt to enhance GI healing in conditions where GI epithelium is damaged (Parvo enteritis, chemotherapy, etc.).
A study that evaluated the efficacy of glutamine supplementation in cats with methotrexate-induced enteritis found no difference between cats supplemented with glutamine and those that were not. (Marks, Cook et al. 1999)
[Purification Methods]

Likely impurities are glutamic acid, ammonium pyroglutamate, tyrosine, asparagine, isoglutamine, arginine. Crystallise it from water or aqueous EtOH. [Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 pp 1929-1925 1961, Beilstein 4 IV 3038.]
[Producing and consuming organs]

Producers
Glutamine is synthesized by the enzyme glutamine synthetase from glutamate and ammonia. The most relevant glutamine-producing tissue is the muscle mass, accounting for about 90% of all glutamine synthesized. Glutamine is also released, in small amounts, by the lung and the brain. Although the liver is capable of relevant glutamine synthesis, its role in glutamine metabolism is more regulatory than producing, since the liver takes up large amounts of glutamine derived from the gut.
Consumers
The most eager consumers of glutamine are the cells of intestines, the kidney cells for the acid - base balance, activated immune cells, and many cancer cells. In respect to the last point mentioned, different glutamine analogues, such as DON, Azaserine or Acivicin, are tested as anticancer drugs.
Examples for the usage of glutamine
In catabolic states of injury and illness, glutamine becomes conditionally essential (requiring intake from food or supplements). Glutamine has been studied extensively over the past 10–15 years, and has been shown to be useful in treatment of injuries, trauma, burns, and treatment - related side effects of cancer, as well as in wound healing for postoperative patients. Glutamine is also marketed as a supplement used for muscle growth in weight lifting , body building, endurance, and other sports. Evidence indicates glutamine, when orally loaded, may increase plasma HGH levels by stimulating the anterior pituitary gland. In biological research, L-glutamine is commonly added to the media in cell culture. However, the high level of glutamine in the culture media may inhibit other amino acid transport activities.
Spectrum DetailBack Directory
[Spectrum Detail]

L-Glutamine(56-85-9)MS
L-Glutamine(56-85-9)1HNMR
L-Glutamine(56-85-9)13CNMR
L-Glutamine(56-85-9)IR1
L-Glutamine(56-85-9)IR2
L-Glutamine(56-85-9)Raman
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

L(+)-Glutamine, 99%(56-85-9)
[Alfa Aesar]

L-Glutamine, 99%(56-85-9)
[Sigma Aldrich]

56-85-9(sigmaaldrich)
[TCI AMERICA]

L-Glutamine,>99.0%(T)(56-85-9)
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