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CAS Number: 39537-23-0Picture of molecule3D/inchi
ECHA ELINCS - REACH Pre-Reg:475-290-9
Nikkaji Web:J475.207D
XlogP3-AA:-4.40 (est)
Molecular Weight:217.22535000
Formula:C8 H15 N3 O4
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:special dietary and nutritional additives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Scholar: with word "flavor"Search
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Perfumer and Flavorist:Search
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Pubchem Patents:Search
JECFA Food Flavoring:2121 L-alanyl-L-glutamine
FEMA Number:4712 L-alanyl-L-glutamine
FDA:No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF):39537-23-0 ; L-ALANYL-L-GLUTAMINE
Physical Properties:
Appearance:white crystalline powder (est)
Assay: 98.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 230.00 to 232.00 °C. @ 760.00 mm Hg
Boiling Point: 615.00 to 616.00 °C. @ 760.00 mm Hg (est)
Flash Point: 619.00 °F. TCC ( 326.00 °C. ) (est)
logP (o/w): -2.581 (est)
Soluble in:
 water, 3.983e+005 mg/L @ 25 °C (est)
Organoleptic Properties:
Odor Description:mild savory
Odor and/or flavor descriptions from others (if found).
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: humectants
skin conditioning
Ajinomoto USA
Flavor: characteristic
L-glutamine has very important roles in vivo. Glutamine supplies nutritional requirements, improves intestinal health and enhances the immune system. Glutamine is also being used in a variety of clinical studies ranging from cancer treatment, radiation and chemotherapy to treatment of shock and more. In biotechnology, L-glutamine is an essential component for mammalian cell culture medium.
Ajinomoto USA
Flavor: characteristic
Ala-Gln is a dipeptide with a glutamine amino group joined to an alanyl residue. It has excellent stability and is readily soluble in aqueous solutions.
BOC Sciences
For experimental / research use only.
For experimental / research use only.
Glentham Life Sciences
Jiangyin Healthway
Alanyl Glutamine
New functional food ingredients
Penta International
Qingdao Dacon Trading
Santa Cruz Biotechnology
For experimental / research use only.
Sigma-Aldrich: Sigma
For experimental / research use only.
Ala-Gln ≥98% (TLC)
For experimental / research use only.
L-Alanyl-L-glutamine >98.0%(HPLC)(T)
Safety Information:
Preferred SDS: View
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
Safety in Use Information:
special dietary and nutritional additives
Recommendation for laevo-alanyl-laevo-glutamine usage levels up to:
 not for fragrance use.
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 25
Click here to view publication 25
 average usual ppmaverage maximum ppm
baked goods: 1400.000003000.00000
beverages(nonalcoholic): 60.00000600.00000
beverages(alcoholic): 60.00000600.00000
breakfast cereal: 600.000003000.00000
cheese: 1400.000003000.00000
chewing gum: 100.00000500.00000
condiments / relishes: 2000.000005000.00000
confectionery froastings: 300.00000500.00000
egg products: 1000.000002000.00000
fats / oils: 200.00000600.00000
fish products: 1000.000002500.00000
frozen dairy: 1400.000003000.00000
fruit ices: 200.00000600.00000
gelatins / puddings: 200.00000500.00000
granulated sugar: --
gravies: 1400.000003000.00000
hard candy: 200.00000600.00000
imitation dairy: 1400.000003000.00000
instant coffee / tea: 300.00000600.00000
jams / jellies: 300.00000500.00000
meat products: 1400.000003000.00000
milk products: 1400.000003000.00000
nut products: 300.000001000.00000
other grains: 300.000002000.00000
poultry: 1000.000002000.00000
processed fruits: 60.000003000.00000
processed vegetables: 300.00000500.00000
reconstituted vegetables: 200.00000400.00000
seasonings / flavors: 20000.00000250000.00000
snack foods: 2000.000005000.00000
soft candy: 200.00000600.00000
soups: 1000.000005000.00000
sugar substitutes: 200.000001000.00000
sweet sauces: 200.00000500.00000
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :123935
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
(2S)-5-amino-2-[[(2S)-2-aminopropanoyl]amino]-5-oxopentanoic acid
 (2S)-5-amino-2-[[(2S)-2-aminopropanoyl]amino]-5-oxopentanoic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):123935
Pubchem (sid):135078516
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2924.19.1150
FDA Listing of Food Additive Status:View
VCF-Online:VCF Volatile Compounds in Food
Potential Blenders and core components note
None Found
Potential Uses:
None Found
Occurrence (nature, food, other):note
 found in nature
(S)-5-amino-2-[(S)-2-aminopropanamido]-5-oxopentanoic acid
(2S)-5-amino-2-{[(2S)-2-aminopropanoyl]amino}-5-oxopentanoic acid
(2S)-2-((2S)-2-aminopropanoylamino)-4-carbamoylbutanoic acid
 dipeptiven (l-alanyl-l-glutamine)
L-glutamine, L-alanyl-
L-glutamine, N2-L-alanyl-


PubMed:L-Glutamine or L-alanyl-L-glutamine prevents oxidant- or endotoxin-induced death of neonatal enterocytes
Leffingwell & Associates:Flavor Properties of FEMA GRAS List 25 flavor chemicals
PubMed:Evitar (l-Alanyl-l-Glutamine) Regulates Key Signaling Molecules in the Pathogenesis of Postoperative Tissue Fibrosis
PubMed:Quantification of l-alanyl-l-glutamine in mammalian cell culture broth: Evaluation of different detectors
PubMed:Effects of l-Alanyl-l-Glutamine Ingestion on One-Hour Run Performance
PubMed:Oral supplementations with L-glutamine or L-alanyl-L-glutamine do not change metabolic alterations induced by long-term high-fat diet in the B6.129F2/J mouse model of insulin resistance
PubMed:Production of L-alanyl-L-glutamine by immobilized Pichia pastoris GS115 expressing -amino acid ester acyltransferase
PubMed:Metabolic engineering of Escherichia coli for efficient production of L-alanyl-L-glutamine
PubMed:Supplementation with L-Glutamine and L-Alanyl-L-Glutamine Changes Biochemical Parameters and Jejunum Morphophysiology in Type 1 Diabetic Wistar Rats
PubMed:Production of l-alanyl-l-glutamine by recycling E. coli expressing -amino acid ester acyltransferase
PubMed:The role of L-alanyl-L-glutamine in the immune response in vitro
PubMed:L-alanyl-L-glutamine ingestion maintains performance during a competitive basketball game
PubMed:L-alanyl-L-glutamine-supplemented parenteral nutrition improves infectious morbidity in secondary peritonitis
PubMed:Fermentative production of L-alanyl-L-glutamine by a metabolically engineered Escherichia coli strain expressing L-amino acid alpha-ligase
PubMed:Safety studies of l-alanyl-l-glutamine (l-AG)
PubMed:Production of L-alanyl-L-glutamine by immobilized Escherichia coli expressing amino acid ester acyltransferase
PubMed:L-alanyl-L-glutamine-supplemented parenteral nutrition decreases infectious morbidity rate in patients with severe acute pancreatitis
PubMed:Elimination kinetics of L-alanyl-L-glutamine in ICU patients
PubMed:Parenteral L-alanyl-L-glutamine improves 6-month outcome in critically ill patients
PubMed:Degradation kinetics of L-alanyl-L-glutamine and its derivatives in aqueous solution
PubMed:Perioperative application of L-alanyl-L-glutamine in cardiac surgery: effect on the polarized T cell cytokine expression
PubMed:Protective Effects Oncorneal Endothelium During Intracameral Irrigation Using N-(2)-l-alanyl-l-Glutamine
PubMed:Supplementation of l-Alanyl-l-Glutamine and Fish Oil Improves Body Composition and Quality of Life in Patients With Chronic Heart Failure
PubMed:Preconditioning with L-alanyl-L-glutamine in a Mongolian gerbil model of acute cerebral ischemia/reperfusion injury
PubMed:Safety and efficacy of adding intravenous N-acetylcysteine to parenteral L-alanyl-L-glutamine in hospitalized patients undergoing surgery of the colon: a randomized controlled trial
PubMed:Alterations in neutrophil (PMN) free intracellular alpha-keto acid profiles and immune functions induced by L-alanyl-L-glutamine, arginine or taurine
PubMed:Determination of the anti-inflammatory and cytoprotective effects of l-glutamine and l-alanine, or dipeptide, supplementation in rats submitted to resistance exercise
PubMed:L-alanyl-L-glutamine dipeptide-supplemented total parenteral nutrition reduces infectious complications and glucose intolerance in critically ill patients: the French controlled, randomize
PubMed:Route of administration (enteral or parenteral) affects the contribution of L-glutamine to de novo L-arginine synthesis in mice: a stable-isotope study
PubMed:Effect of the route of nutrition and L-alanyl-L-glutamine supplementation in amino acids' concentration in trauma patients
PubMed:Enzymatic production of L-alanyl-L-glutamine by recombinant E. coli expressing -amino acid ester acyltransferase from Sphingobacterium siyangensis
PubMed:Effects of arginine, L-alanyl-L-glutamine or taurine on neutrophil (PMN) free amino acid profiles and immune functions in vitro
PubMed:Prophylactic inhalation of L-alanyl-L-glutamine enhances heat shock protein 72 and attenuates endotoxin-induced lung injury in rats
PubMed:[Effect of L-alanyl-L-glutamine on expression of insulin-like growth factor-1 in intestinal tissues of low-birth-weight newborn rats with hypoxia/reoxygenation-induced intestinal injury]
PubMed:Effect of parenteral l-alanyl-l-glutamine administration on phagocytic responses of polymorphonuclear neutrophilic leukocytes in dogs undergoing high-dose methylprednisolone sodium succina
PubMed:Protective effects of N(2)?L?alanyl?L?glutamine mediated by the JAK2/STAT3 signaling pathway on myocardial ischemia reperfusion
PubMed:Double-blinded, placebo-controlled trial on intravenous L-alanyl-L-glutamine in the incidence of oral mucositis following chemoradiotherapy in patients with head-and-neck cancer
PubMed:Effect of acute L-Alanyl-L-Glutamine and electrolyte ingestion on cognitive function and reaction time following endurance exercise
PubMed:Cost containment through L-alanyl-L-glutamine supplemented total parenteral nutrition after major abdominal surgery: a prospective randomized double-blind controlled study
PubMed:The effect of L-alanyl-L-glutamine dipeptide supplemented total parenteral nutrition on infectious morbidity and insulin sensitivity in critically ill patients
PubMed:Availability of amino acids supplied intravenously in healthy man as synthetic dipeptides: kinetic evaluation of L-alanyl-L-glutamine and glycyl-L-tyrosine
PubMed:Kinetically controlled enzymatic synthesis of dipeptide precursor of L-alanyl-L-glutamine
PubMed:l-glutamine and l-alanine supplementation increase glutamine-glutathione axis and muscle HSP-27 in rats trained using a progressive high-intensity resistance exercise
PubMed:In vivo utilization of intravenously supplied L-alanyl-L-glutamine in various tissues of the rat
PubMed:Formulation and characterization of ethylcellulose microparticles containing .L-alanyl- L-glutamine peptide
PubMed:L-glutamine supplementations enhance liver glutamine-glutathione axis and heat shock factor-1 expression in endurance-exercise trained rats
PubMed:Examination of the efficacy of acute L-alanyl-L-glutamine ingestion during hydration stress in endurance exercise
PubMed:Alanyl-glutamine and glutamine plus alanine supplements improve skeletal redox status in trained rats: involvement of heat shock protein pathways
PubMed:Design of composite microparticle systems based on pectin and waste material of propolis for modified l-alanyl-l-glutamine release and with immunostimulant activity
PubMed:Effect of the route of nutrition and L-alanyl-L-glutamine supplementation in amino acids' concentration in trauma patients
PubMed:[Efficacy of the dipeptide N(2)-L-Alanyl-L-glutamine in traumatic patients admitted to the ICU: a prospective, randomized, double-blind, multicentre study]
PubMed:Glutamine and alanyl-glutamine promote crypt expansion and mTOR signaling in murine enteroids
PubMed:Alanyl-glutamine improves pancreatic ?-cell function following ex vivo inflammatory challenge
PubMed:Effects of oral supplementation with glutamine and alanyl-glutamine on glutamine, glutamate, and glutathione status in trained rats and subjected to long-duration exercise
PubMed:Improvements of immune status, intestinal integrity and gain performance in the early-weaned calves parenterally supplemented with L-alanyl-L-glutamine dipeptide
PubMed:Effect of alanyl-glutamine supplementation on plasma and tissue glutamine concentrations in rats submitted to exhaustive exercise
PubMed:[The dipeptide L-alanyl-L-glutamine--its preparation and therapeutic use]
PubMed:Effects of diazepam on neutrophil (PMN) free amino acid profiles and immune functions in vitro. Metabolical and immunological consequences of L-alanyl-L-glutamine supplementation
PubMed:[Expression, purification, characterization and application of -amino acid ester acyltransferase from recombinant Escherichia coli]
PubMed:Effects of supplementation with free glutamine and the dipeptide alanyl-glutamine on parameters of muscle damage and inflammation in rats submitted to prolonged exercise
PubMed:Metabolic engineering for L-glutamine overproduction by using DNA gyrase mutations in Escherichia coli
PubMed:Glutamine-containing dipeptides in parenteral nutrition
PubMed:Early Administration of Glutamine Protects Cardiomyocytes from Post-Cardiac Arrest Acidosis
PubMed:Synthesis and application of dipeptides; current status and perspectives
PubMed:Enteral Glutamine Administration in Critically Ill Nonseptic Patients Does Not Trigger Arginine Synthesis
PubMed:[Administration of glutamine and its dipeptides in parenteral nutrition. Which patients are candidates?]
PubMed:Endogenous glutamine production in critically ill patients: the effect of exogenous glutamine supplementation
PubMed:Oral supplementations with free and dipeptide forms of L-glutamine in endotoxemic mice: effects on muscle glutamine-glutathione axis and heat shock proteins
PubMed:Oral glutamine supplementation attenuates inflammation and oxidative stress-mediated skeletal muscle protein content degradation in immobilized rats: Role of 70?kDa heat shock protein
PubMed:Effects of glutamine and alanine supplementation on muscle fatigue parameters of rats submitted to resistance training
PubMed:Effects of Glutamine and Alanine Supplementation on Adiposity, Plasma Lipid Profile, and Adipokines of Rats Submitted to Resistance Training
PubMed:Effect of alanyl-glutamine on leucine and protein metabolism in endotoxemic rats
PubMed:Availability of glutamine supplied intravenously as alanylglutamine
PubMed:Glutamine and alanine-induced differential expression of intracellular IL-6, IL-8, and TNF- in LPS-stimulated monocytes in human whole-blood
PubMed:Quantitative high-performance liquid chromatography-tandem mass spectrometry impurity profiling methods for the analysis of parenteral infusion solutions for amino acid supplementation con
PubMed:Highly active nanobiocatalysis in deep eutectic solvents via metal-driven enzyme-surfactant nanocomposite
PubMed:A novel and efficient enzymatic method for the production of peptides from unprotected starting materials
PubMed:Effect of free glutamine and alanyl-glutamine dipeptide on mucosal proliferation of the human ileum and colon
PubMed:Oral free and dipeptide forms of glutamine supplementation attenuate oxidative stress and inflammation induced by endotoxemia
PubMed:Availability of glutamine from peptides and acetylglutamine for human tumor-cell cultures
PubMed:Current topics in the biotechnological production of essential amino acids, functional amino acids, and dipeptides
PubMed:Effects of parenteral nutrition supplemented with alanyl-glutamine on nutrition status in rats
PubMed:Effect of stable glutamine compounds on porcine islet culture
PubMed:Improving culture conditions for temporomandibular joint disc tissue engineering
PubMed:A randomized trial of intravenous glutamine supplementation in trauma ICU patients
PubMed:Targeted Metabolomic Profiling of Peritoneal Dialysis Effluents Shows Anti-oxidative Capacity of Alanyl-Glutamine
PubMed:Total parenteral nutrition supplemented with L-alanyl-L-glutamine and gut structure and protein metabolism in septic rats
PubMed:Is alpha-ketoisocaproyl-glutamine a suitable glutamine precursor to sustain fibroblast growth?
PubMed:Peritoneal Dialysis Fluid Supplementation with Alanyl-Glutamine Attenuates Conventional Dialysis Fluid-Mediated Endothelial Cell Injury by Restoring Perturbed Cytoprotective Responses
PubMed:Glycemia recovery with oral amino acid administration during experimental short-term insulin-induced hypoglycemia
PubMed:The Reaction between Furfuryl Alcohol and Model Compound of Protein
PubMed:A controlled trial of glutamine effects on bone healing
PubMed:[Efficacy of parenteral glutamine in patients undergoing bone marrow transplantation]
PubMed:Intravenous glutamine supplementation to head trauma patients leaves cerebral glutamate concentration unaffected
PubMed:[Effects of glutamine on antioxidants systems and hepatic detoxification in rats: influence of formulation]
PubMed:Scandinavian glutamine trial: a pragmatic multi-centre randomised clinical trial of intensive care unit patients
PubMed:Does glutamine promote benefits for patients with diabetes mellitus scheduled for cardiac surgery?
PubMed:Intravenous glutamine administration reduces lung and distal organ injury in malnourished rats with sepsis
PubMed:Intravenous free and dipeptide-bound glutamine maintains intestinal microcirculation in experimental endotoxemia
PubMed:Evidence for a nutritional need for glutamine in catabolic patients
PubMed:Effect of amino acids and dipeptides on the acrosome reaction and accumulation of ammonia in porcine spermatozoa
PubMed:Retinoic acid receptor gamma is targeted by microRNA-124 and inhibits neurite outgrowth
PubMed:Reduction of liver ischemia-reperfusion injury via glutamine pretreatment
PubMed:Separation and determination of peptide metabolite of Bacillus licheniformis in a microbial fuel cell by high-speed capillary micellar electrokinetic chromatography
PubMed:ywfE in Bacillus subtilis codes for a novel enzyme, L-amino acid ligase
PubMed:Application of protein N-terminal amidase in enzymatic synthesis of dipeptides containing acidic amino acids specifically at the N-terminus
PubMed:Stress-induced intracellular glutamine depletion. The potential use of glutamine-containing peptides in parenteral nutrition
PubMed:Glutamine is cardioprotective in patients with ischemic heart disease following cardiopulmonary bypass
PubMed:Perioperative GLY-GLN infusion diminishes the surgery-induced period of immunosuppression: accelerated restoration of the lipopolysaccharide-stimulated tumor necrosis factor-alpha response
PubMed:Effect of parenteral glutamine peptide supplements on muscle glutamine loss and nitrogen balance after major surgery
PubMed:Study on the Soy Protein-Based Wood Adhesive Modified by Hydroxymethyl Phenol
PubMed:Effect of glutamine dipeptide on hepatic regeneration in partially hepatectomized malnourished rats
PubMed:Effect of multidrug-efflux transporter genes on dipeptide resistance and overproduction in Escherichia coli
PubMed:Glutamine dipeptide-supplemented parenteral nutrition maintains intestinal function in the critically ill
PubMed:Availability of amino acids supplied by constant intravenous infusion of synthetic dipeptides in healthy man
PubMed:Effects of Ala-Gln feeding strategies on growth, metabolism, and crowding stress resistance of juvenile Cyprinus carpio var. Jian
PubMed:Glutamine peptide does not improve gut barrier function and mucosal immunity in total parenteral nutrition
PubMed:[Need-related availability of short-chain peptides--a prerequisite for their use in artificial feeding]
PubMed:Parenteral glutamine dipeptide supplementation does not ameliorate chemotherapy-induced toxicity
PubMed:Gene cloning and characterization of -amino acid ester acyl transferase in Empedobacter brevis ATCC14234 and Sphingobacterium siyangensis AJ2458
PubMed:Effect of Dipeptides on In vitro Maturation, Fertilization and Subsequent Embryonic Development of Porcine Oocytes
PubMed:Brief Glutamine Pretreatment Increases Alveolar Macrophage CD163/Heme Oxygenase-1/p38-MAPK Dephosphorylation Pathway and Decreases Capillary Damage but Not Neutrophil Recruitment in IL-1/L
PubMed:Influence of molecular structure and plasma hydrolysis on the metabolism of glutamine-containing dipeptides in humans
PubMed:[Effect of glutamine on apoptosis of the small intestine in young rats with endotoxemia and its mechanism]
PubMed:Effects of in ovo injecting disaccharides and alanyl-glutamine dipeptide on the energy status in duck embryos and neonates
PubMed:Total parenteral nutrition with glutamine dipeptide after major abdominal surgery: a randomized, double-blind, controlled study
PubMed:The effect of glutamine-supplemented total parenteral nutrition on nitrogen economy depends on severity of diseases in surgical patients
PubMed:Advantages of AlaGln as an additive to cell culture medium: use with anti-CD20 chimeric antibody-producing POTELLIGENT? CHO cell lines
PubMed:Effect of amino acids and dipeptides on accumulation of ammonia in the medium during in vitro maturation and fertilization of porcine oocytes
PubMed:Glutamine-supplemented total parenteral nutrition attenuates plasma interleukin-6 in surgical patients with lower disease severity
PubMed:Importance of liver and kidney for the utilization of glutamine-containing dipeptides in man
PubMed:Discrimination of Enantiomers of Dipeptide Derivatives with Two Chiral Centers by Tetraaza Macrocyclic Chiral Solvating Agents Using (1)H NMR Spectroscopy
PubMed:[Immunomodulation after parenteral glutamine administration in colorectal surgery]
PubMed:Capillary electrophoresis with a diamine EOF modifier as an approach for glutamine dipeptide containing formulations
dipeptiven is for parenteral use.
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