L-Glutamine
- Iupac Name：(2S)-2,5-diamino-5-oxopentanoic acid
- CAS No.: 56-85-9
- Molecular Weight：146.1445
- Modify Date.: 2022-10-27 07:49
- Introduction: 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.
View more+
1. Names and Identifiers
- 1.1 Name
- L-Glutamine
- 1.2 Synonyms
(2S)-2-((2S)-2-Aminopropanoylamino)-4-carbamoylbutanoic acid (2S)-2-amino-4-carbamoylbutanoic acid (2S)-5-Amino-2-{[(2S)-2-aminopropanoyl]amino}-5-oxopentanoic acid (S)-(+)-Glutamine (S)-5-Amino-2-[(S)-2-aminopropanamido]-5-oxopentanoic acid 2,5-Diamino-5-oxopentanoic acid, (S)- 2,5-Diamino-5-oxpentanoicacid 2-Aminoglutaramic acid, L- 5-Hydroxy-5-imino-L-norvaline Ala-Gln Alanyl-glutamine Alanyl-glutamine,Glutamine-S EINECS 200-292-1 GLUTAMINE, L- Glutamine-S glutaminic acid H-Ala-Gln-OH H-Gln-OH l-(+)-glutamic acid-5-amide L(+)-GLUTAMIC ACID-5-AMIDE L-(+)-Glutamine L(+)-GLUTAMINE L-Ala-L-Gln l-alanyl-l-glutamin L-Alanyl-L-glutamine LEVOGLUTAMIDE L-GLN L-GLUTAMIC ACID 5-AMIDE L-GLUTAMIC ACID AMIDE L-Glutamic Acid g-Amide L-Glutamic acid Γ-amide L-Glutamine, L-alanyl- L-Glutamine, N2-L-alanyl- L-Glutamine,L-alanyl L-Norvaline, 5-hydroxy-5-imino- MFCD00008044 N(2)-L-alanyl-L-glutamine N-L-alanyl-L-glutamine Pentanoic acid, 2,5-diamino-5-oxo-, (S)- S(+)-Glutamic acid 5-amide UNII-U5JDO2770Z ZY1&VMYVQ2VZ &&L-L Form
- View all
- 1.3 CAS No.
- 56-85-9
- 1.4 CID
- 5961
- 1.5 EINECS(EC#)
- 200-292-1
- 1.6 Molecular Formula
- C5H10N2O3 (isomer)
- 1.7 Inchi
- InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/t3-/m0/s1
- 1.8 InChIkey
- ZDXPYRJPNDTMRX-VKHMYHEASA-N
- 1.9 Canonical Smiles
- C(CC(=O)N)C(C(=O)O)N
- 1.10 Isomers Smiles
- C(CC(=O)N)[C@@H](C(=O)O)N
2. Properties
- 2.1 Density
- 1.321
- 2.1 Melting point
- 185℃
- 2.1 Boiling point
- 445.6℃at760mmHg
- 2.1 Refractive index
- 6.8 ° (C=4, H2O)
- 2.1 Flash Point
- 185℃
- 2.1 Precise Quality
- 146.06900
- 2.1 PSA
- 106.41000
- 2.1 logP
- 0.06440
- 2.1 Solubility
- H2O: 25?mg/mL
- 2.2 Appearance
- white powder
- 2.3 Storage
- Ambient temperatures.
- 2.4 Chemical Properties
- White crystalline powder
- 2.5 Color/Form
- White
- 2.6 Decomposition
- When heated to decomposition it emits toxic fumes of /nitrogen oxides/
- 2.7 PH
- pH = 5-6 at 14.6 g/L at 25 °C
- 2.8 pKa
- 2.17(at 25℃)
- 2.9 Water Solubility
- H2O: 25 mg/mL
- 2.10 Stability
- Stability Moisture and light sensitive. Incompatible with moisture, strong oxidizing agents.
- 2.11 StorageTemp
- Store below +30°C.
3. Use and Manufacturing
- 3.1 Definition
- ChEBI: An optically active form of glutamine having L-configuration.
- 3.2 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.]
- 3.3 Usage
- 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.
4. Safety and Handling
- 4.1 Hazard Codes
- Xi
- 4.1 Risk Statements
- R36
- 4.1 Safety Statements
- S24/25
- 4.1 RIDADR
- NONH for all modes of transport
- 4.1 Safety Profile
- Mddly toxic by ingestion. Human systemic effects: euphoria. When heated to decomposition it emits toxic fumes of NOx.
- 4.2 WGK Germany
- 2
- 4.2 RTECS
- MA2275100
- 4.2 Report
- L-Glutamine (CAS NO.77668-42-9) is reported in EPA TSCA Inventory.
- 4.3 Safety
- Hazard Codes: L-Glutamine (CAS NO.77668-42-9): Xi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-24/25-36/37/39-27
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
HS Code:29241900
Mildly toxic by ingestion. Human systemic effects: euphoria. When heated to decomposition it emits toxic fumes of NOx
- 4.4 Specification
- 1. Fire Fighting Measures
Information of L-Glutamine (CAS NO.77668-42-9): As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam.
2. Handling and Storage
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage: Store in a cool, dry place. Store in a tightly closed container.
- 4.5 Toxicity
-
| Organism |
Test Type |
Route |
Reported Dose (Normalized Dose) |
Effect |
Source |
| man |
TDLo |
oral |
27mg/kg/1W-I (27mg/kg) |
BEHAVIORAL: EUPHORIA |
American Journal of Psychiatry. Vol. 141, Pg. 1302, 1984. |
| mouse |
LD50 |
oral |
21700mg/kg (21700mg/kg) |
|
Drugs in Japan Vol. 6, Pg. 228, 1982. |
| rat |
LD50 |
oral |
7500mg/kg (7500mg/kg) |
|
Drugs in Japan Vol. 6, Pg. 228, 1982. |
- View all
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Not classified.
2.2 GHS label elements, including precautionary statements
| Pictogram(s) | No symbol. |
| Signal word | No signal word. |
| Hazard statement(s) | none |
| Precautionary statement(s) | |
| Prevention | none |
| Response | none |
| Storage | none |
| Disposal | none |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
56-85-9Total: 8 Synthesis Route
8. Other Information
- 8.0 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
- 8.1 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 .
- 8.2 Chemical Properties
- White crystalline powder
- 8.3 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.
- 8.4 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.
- 8.5 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. - View all
- 8.6 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.
- 8.7 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
- 8.8 Uses
- amine protecting agent
- 8.9 Definition
- ChEBI: An optically active form of glutamine having L-configuration.
- 8.10 Preparation
- By isolation from sugar beet juice.
- 8.11 Brand name
- Nutrestore (Nutritional Restart).
- 8.12 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.
- 8.13 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
- 8.14 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.
- 8.15 Merck
- 14,4471
- 8.16 BRN
- 1723797
- 8.17 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.
- 8.18 Usage
- L-Glutamine is involved in many metabolic processes and regulates acid-base balance in the kidney. It is an important amino acid for the incorporation of ammonium ions into biomolecules. It is a vital component of culture media that serves as a major energy source for cells in culture. As a component in oral supplementation, it is useful for patients who have advanced stages of cancer to reverse cachexia (i.e. muscle wasting). It is also used for attention deficit-hyperactivity disorder (ADHD), a urinary condition called cystinuria, sickle cell anemia and for alcohol withdrawal support. It finds applications in patients with HIV (AIDS) to prevent weight loss.
9. Computational chemical data
- Molecular Weight: 146.1445g/mol
- Molecular Formula: C5H10N2O3
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 146.06914219
- Monoisotopic Mass: 146.06914219
- Complexity: 146
- Rotatable Bond Count: 4
- Hydrogen Bond Donor Count: 3
- Hydrogen Bond Acceptor Count: 4
- Topological Polar Surface Area: 106
- Heavy Atom Count: 10
- Defined Atom Stereocenter Count: 1
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADccBjMAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAHgAQCAAACCjBgAQACABAAgAIAAGQGAAAAAAAAAAAAIGAAAACABIAgAAAQAAEEAAAAACcFwAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
10. Question & Answer
-
Glutamine is an amino acid that serves as a building block for proteins in the body. It is the most abundant amino acid in the human body and is primarily produced in the muscles and distributed to or..
-
As L-Glutamine can be used as a food additive, we can find this substance in the ingredient list when purchasing many foods. With further understanding, we will discover more and know its crucial role..
-
Irregular eating habits, frequent overeating or severe picky eating can cause damage to the gastrointestinal mucosa. Although the symptoms may not be particularly obvious in a short period of time, ov..
-
Irritable Bowel Syndrome steals away at your joy, causing excruciating agony and shame. It has the potential to aggravate your situation to the point of no return. You should get care from your doctor..
11. Recommended Suppliers
-
- Products:Pharma &Food Intermediates
Water Treatment Chemicals
Industrial Specialties
Fine Chemicals
- Tel:86-27-85835203
- Email:steven@cspharmchem.com
-
- Products:Pharmaceutical Intermediate , Apis , Food Additives , Herbal Extracts , Fine Chemicals , ...
- Tel:00-86-13023277276
- Email:hanna@xljxcl.com
-
- Products:Top quality and high purity with safe transportation and low price pmk powder ;pmk oil ;bmk powder ;bmk oil
- Tel:+8617720-217898-+8617720217898
- Email:bonnie@whslchemical.com
-
- Products:We are engaged in the development, marketing and sales of apis, intermediates, natural products (extracts), fine chemicals, food additives, agricultural chemicals and other products.
- Tel:0086-0319-19131200228
- Email:17610795226@chengcaibio.com
-
- Products:Cosmetic Raw Materials,solvents,etc.
- Tel:86-311-66562153
- Email:breeduan@crovellbio.com
12. Realated Product Infomation
skype
2YRS
