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L-Glutamine

CAS No.
56-85-9
Chemical Name:
L-Glutamine
Synonyms
GLUTAMINE;GLN;H-GLN-OH;L-GLN;L-Glutamin;L-Gln-OH;L-GLUTAMIC ACID AMIDE;Concentrated Soy Protein;(S)-2,5-DIAMINO-5-OXOPENTANOIC ACID;L-GUTAMINE
CBNumber:
CB6280105
Molecular Formula:
C5H10N2O3
Molecular Weight:
146.14
MDL Number:
MFCD00008044
MOL File:
56-85-9.mol
MSDS File:
SDS
Last updated:2023-12-24 21:24:35

L-Glutamine Properties

Melting point 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 | L-GLUTAMINE
refractive index 6.8 ° (C=4, H2O)
Flash point 185°C
storage temp. Store below +30°C.
solubility H2O: 25 mg/mL
form solution
pka 2.17(at 25℃)
color White
PH 5.0-6.0 (25℃, 0.1M in H2O)
Odor at 100.00 %. very mild milky custard cocoa oily
Odor Type milky
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
JECFA Number 1430
Merck 14,4471
BRN 1723797
Stability Moisture and light sensitive. Incompatible with moisture, strong oxidizing agents.
InChIKey ZDXPYRJPNDTMRX-VKHMYHEASA-N
LogP -1.67
Substances Added to Food (formerly EAFUS) L-GLUTAMINE
FDA 21 CFR 172.320
CAS DataBase Reference 56-85-9(CAS DataBase Reference)
EWG's Food Scores 1
NCI Dictionary of Cancer Terms glutamine
FDA UNII 0RH81L854J
NCI Drug Dictionary glutamine
ATC code A16AA03
NIST Chemistry Reference L-Glutamine(56-85-9)
EPA Substance Registry System L-Glutamine (56-85-9)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P305+P351+P338
Hazard Codes  Xi
Risk Statements  36-36/37/38
Safety Statements  26-24/25-36/37/39-27
WGK Germany  2
RTECS  MA2275100
TSCA  Yes
HS Code  29241900
Toxicity LD50 orally in Rabbit: 7500 mg/kg
NFPA 704
0
2 0

L-Glutamine price More Price(109)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 8.16016 (S)-(+)-Glutamine for synthesis 56-85-9 25g $32.8 2024-03-01 Buy
Sigma-Aldrich 8.16016 (S)-(+)-Glutamine for synthesis 56-85-9 100g $88.6 2024-03-01 Buy
Sigma-Aldrich 49419 L-Glutamine BioUltra, ≥99.5% (NT) 56-85-9 25g $70.4 2024-03-01 Buy
Sigma-Aldrich 1294808 Glutamine United States Pharmacopeia (USP) Reference Standard 56-85-9 100mg $466 2024-03-01 Buy
Sigma-Aldrich 1.00289 L-Glutamine for biochemistry 56-85-9 1kg $618 2024-03-01 Buy
Product number Packaging Price Buy
8.16016 25g $32.8 Buy
8.16016 100g $88.6 Buy
49419 25g $70.4 Buy
1294808 100mg $466 Buy
1.00289 1kg $618 Buy

L-Glutamine Chemical Properties,Uses,Production

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

Description

Glutamine (abbreviated as Gln or Q) is one of the 20 amino acids encoded by the standard genetic code. It is not recognized as an essential amino acid, but may become conditionally essential in certain situations, including intensive athletic training or certain gastrointestinal disorders.Its side-chain is an amide formed by replacing the side-chain hydroxyl of glutamic acid with an amine functional group, making it the amide of glutamic acid. Its codons are CAA and CAG. In human blood, glutamine is the most abundant free amino acid, with a concentration of about 500–900 μmol / l .

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, 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.

Chemical Properties

White crystalline powder

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

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.

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

amine protecting agent

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.

Safety Profile

Mddly toxic by ingestion. Human systemic effects: euphoria. When heated to decomposition it emits toxic fumes of NOx.

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.

13726-85-7
56-85-9
Synthesis of L-Glutamine from N-(tert-Butoxycarbonyl)-L-glutamine
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View Lastest Price from L-Glutamine manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
L-Gln-OH pictures 2024-03-19 L-Gln-OH
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US $20.00 / KG 1KG 99% 6000KG Shandong Luning Pharmaceutical Co., Ltd.
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2,5-Diamino-5-oxpentanoicacid L(+)-GLUTAMINE L-GLUTAMINE L(+)-GLUTAMIC ACID-5-AMIDE L-GLUTAMIC ACID 5-AMIDE L-ALPHA-AMINOGLUTAMIC ACID L-2-AMINOGLUTARAMIC ACID 2-aminoglutaramic acid 2-AMINOGLUTARIC ACID-3-MONOAMIDE Miglu-P Pentanoic acid, 2,5-diamino-5-oxo-, (S)- Stimulina H-L-GLN-OH SAB CHLORAM. CONTACT BLISTER DOUBLE-WRAP L-Glutamine Hybri-Max L-Glutamine Vetec(TM) reagent grade, >=99% CHLOROFORM BP GLUTAMINE, L- FEMA 3684 (S)-(+)-GLUTAMINE (S)-2,5-Diamino-5-oxopentanoic (S)-2,5-Diamino-5-oxopentanoic acid, L-Glutamic acid 5-amide (S)-2,5-Diamino-5-oxopentanoic acid, L-Glutamic acid 5-amide, L-Glutamine L-Glutamine Powder Glycine, Pyrogen-Free H-Gln-OH ,≥99% L-Glutamine (H-Gln-OH) L-Glutamine,(S)-2,5-Diamino-5-oxopentanoic acid, L-Glutamic acid 5-amide L-Glutamine, extra pure L-GLUTAMINE, USP L-GlutaMine base L-GLUTAMINERESEARCH GRADE MultiPharM (TM) L-GlutaMine, USP L-GLUTAMINE (3,4-13C2) L-GLUTAMINE (2,3,3,4,4-D5, 15N2) L-Glutamine, Animal-Free alpha-glutamine L-GLUTAMINE BIOTECHNOLOGY PERFORMANC L-Glutamine≥ 99% (anhydrous assay) L-Glutamine USP from non-animal source99.0-101.0% (Titration: anhydrous basis) L-Glutamine, 99-100% α-Aminoglutamic acid L-Glutamine, FCC Grade L-2-Aminoglutaramic acid, FCC Grade L-Glutaminee L-GLUTAMINE 200 MM SOLUTION HYBRI-MAX L-GLUTAMINE 98.5+% FCC L-GLUTAMINE, REAGENTPLUS TM, >= 99% L-GLUTAMINE BIOTECHNOLOGY PERFORMANCE & L-GLUTAMINE GAMMA-IRRADIATED CELL*CULTUR E TESTED GLUTAMINE (L) 200 MM L-GLUTAMINE 200 MM STERILE FILTERED*CELL CULTURE TE L-GlutamineForBiochemistry99+% L-GlutamineForBiochemistry L-Glutamine,99% l-glutamine solution L-GLUTAMINE,FCC (2S)-2-amino-4-carbamoyl-butanoic acid L-Glutamine (9CI)