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laevo-glutamic acid

Chemical Structure

General Material Information

Preferred name laevo-glutamic acid
Trivial Name L-Glutamic acid
Short Description (2S)-2-aminopentanedioic acid
Formula C5 H9 N O4
CAS Number 56-86-0
FEMA Number 3285
ECHA Number 200-293-7
FDA UNII 3KX376GY7L
Nikkaji Number J9.171E
Beilstein Number 1723801
MDL MFCD00002634
COE Number 10100
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 1420 L-glutamic acid
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 56-86-0 ; L-GLUTAMIC ACID
Synonyms
  • (2S)-2-aminopentanedioic acid
  • (S)-(+)-glutamic acid
  • (S)-2-aminoglutaric acid
  • (S)-2-aminopentanedioic acid
  • glutamic acid, (S)-
  • glutamic acid, L-
  • L-glutamic acid
  • L-glutamic acid fcc base
  • L-glutamic acid FCC, natural
  • L-(+)-glutamic acid
  • Aciglut
  • Glusate
  • Glutacid
  • α-Glutamic acid
  • l-Glutaminic acid
  • Glutaminol
  • Glutaminic acid
  • Glutaton
  • Pentanedioic acid, 2-amino-, (S)-
  • α-Aminoglutaric acid
  • 1-Aminopropane-1,3-dicarboxylic acid
  • Glutamic acid
  • Glutamicol
  • Glutamidex
  • (S)-Glutamic acid
  • 2-Aminoglutaric acid
  • L-α-Aminoglutaric acid
  • E 620
  • NSC 143503
  • (S)-2-Amino-1,5-pentanedioic acid
  • (+)-L-Glutamic acid
  • Sortem
  • (2S)-2-Azaniumyl-5-hydroxy-5-oxopentanoate
  • 9: PN: WO2023056433 PAGE: 60 claimed sequence
  • MeSH ID: D018698

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Literature & References

(2S)-2-aminopentanedioic acid
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:56-86-0
Pubchem (cid):33032
Pubchem (sid):134972924
Publications by PubMed
Umami evaluation in taste epithelium on microelectrode array by extracellular electrophysiological recording.
Production and optimization of L-glutaminase enzyme from Hypocrea jecorina pure culture.
Kokumi-active glutamyl peptides in cheeses and their biogeneration by Penicillium roquefortii.
II. Glutamine and glutamate.
Glutamate and the flavor of foods.
Improved Production of Poly-gamma-Glutamic Acid by Bacillus subtilis D7 Isolated from Doenjang, a Korean Traditional Fermented Food, and Its Antioxidant Activity.
Enzymatic production of alpha-ketoglutaric acid from l-glutamic acid via l-glutamate oxidase.
Identifying key non-volatile compounds in ready-to-drink green tea and their impact on taste profile.
The effects of glycine, L-threonine, and L-cystine supplementation to a 9% casein diet on the conversions of L-tryptophan to nicotinamide and to serotonin in rats.
CuInS(2) quantum dots/poly((L)-glutamic acid)-drug conjugates for drug delivery and cell imaging.
pH-Sensitive nano-systems for drug delivery in cancer therapy.
Ingestion of bacterial lipopolysaccharide inhibits peripheral taste responses to sucrose in mice.
Specific amino acids inhibit food intake via the area postrema or vagal afferents.
Umami evaluation in taste epithelium on microelectrode array by extracellular electrophysiological recording.
Effect of metformin on the urinary metabolites of diet-induced-obese mice studied by ultra performance liquid chromatography coupled to time-of-flight mass spectrometry (UPLC-TOF/MS).
Recombinant expression, purification and characterisation of the native glutamate racemase from Lactobacillus plantarum NC8.
Effects of L-theanine or caffeine intake on changes in blood pressure under physical and psychological stresses.
Novel synthesis of steryl esters from phytosterols and amino Acid.
Folate analysis in foods by UPLC-MS/MS: development and validation of a novel, high throughput quantitative assay; folate levels determined in Australian fortified breads.
Antiadhesion as a functional concept for prevention of pathogens: N-Phenylpropenoyl-L-amino acid amides as inhibitors of the Helicobacter pylori BabA outer membrane protein.
Twofold pH and temperature stimuli-responsive behaviour in block copolypeptide-decorated single wall carbon nanotubes.
The influence of monoacylglycerol and L-glutamic acid on the viscoelastic properties of wheat flour dough and sensory characteristics of French loaf product.
Comparison of genotypes of Salmonella enterica serovar Enteritidis phage type 30 and 9c strains isolated during three outbreaks associated with raw almonds.
Enzymatic synthesis of theanine from glutamic acid γ-methyl ester and ethylamine by immobilized Escherichia coli cells with γ-glutamyltranspeptidase activity.
Directed assembly of carbon nanotubes on soft substrates for use as a flexible biosensor array.
Sensory-directed identification of beta-alanyl dipeptides as contributors to the thick-sour and white-meaty orosensation induced by chicken broth.
History of glutamate production.
Kokumi-active glutamyl peptides in cheeses and their biogeneration by Penicillium roquefortii.
Odor detection thresholds and enantiomeric distributions of several 4-alkyl substituted gamma-lactones in Australian red wine.
Enhanced production of poly (gamma-glutamic acid) from Bacillus licheniformis NCIM 2324 by using metabolic precursors.
Effects of cultivation conditions on the production of gamma-PGA with Bacillus subtilis ZJU-7.
Absorption of N-phenylpropenoyl-L-amino acids in healthy humans by oral administration of cocoa (Theobroma cacao).
Mechanism of the suppression against D-galactosamine-induced hepatic injury by dietary amino acids in rats.
Microstructure of poly(gamma-glutamic acid) produced by Bacillus subtilis consisting of clusters of D- and L-glutamic acid repeating units.
Luteimonas composti sp. nov., a moderately thermophilic bacterium isolated from food waste.
High-throughput microplate enzymatic assays for fast sugar and acid quantification in apple and tomato.
The influence of extrusion on loss and racemization of amino acids.
Antimicrobial polypeptide multilayer nanocoatings.
Characterization of gamma-glutamyl hydrolase produced by Bacillus sp. isolated from Thai Thua-nao.
Terminal nerve-derived neuropeptide y modulates physiological responses in the olfactory epithelium of hungry axolotls (Ambystoma mexicanum).
Efficient production of poly-gamma-glutamic acid by Bacillus subtilis ZJU-7.
Quantitative studies, taste reconstitution, and omission experiments on the key taste compounds in morel mushrooms (Morchella deliciosa Fr.).
Synergistic interactions between commonly used food additives in a developmental neurotoxicity test.
[Media optimization for the novel antimicrobial peptide by Bacillus sp. fmbJ224].
Atopococcus tabaci gen. nov., sp. nov., a novel Gram-positive, catalase-negative, coccus-shaped bacterium isolated from tobacco.
Isolation, structure determination, synthesis, and sensory activity of N-phenylpropenoyl-L-amino acids from cocoa (Theobroma cacao).
Sensory-guided decomposition of roasted cocoa nibs (Theobroma cacao) and structure determination of taste-active polyphenols.
Activity-guided identification of (S)-malic acid 1-O-D-glucopyranoside (morelid) and gamma-aminobutyric acid as contributors to umami taste and mouth-drying oral sensation of morel mushrooms (Morchella deliciosa Fr.).
Glutathione: a review on biotechnological production.
Bioprocess monitoring using near-infrared spectroscopy.
Low molecular weight compounds responsible for savory taste of Indonesian soy sauce.
Application of stepwise discriminant analysis to classify commercial orange juices using chiral micellar electrokinetic chromatography-laser induced fluorescence data of amino acids.
Effect of the shear rate on pullulan production from beet molasses by Aureobasidium pullulans in an airlift reactor.
Monohydroxamates of aspartic acid and glutamic acid exhibit antioxidant and angiotensin converting enzyme inhibitory activities.
Discrimination between arabica and robusta coffee species on the basis of their amino acid enantiomers.
Industrial production of amino acids by coryneform bacteria.
Synthesis and sensory characterization of novel umami-tasting glutamate glycoconjugates.
Reaction of folic acid with reducing sugars and sugar degradation products.
Changes in nitrogen compounds in must and wine during fermentation and biological aging by flor yeasts.
Long-term zinc deficiency decreases taste sensitivity in rats.
Formation of Pentylpyridines in an Oil Medium.
Glutamate and the flavor of foods.
Metabolism of theanine, gamma-glutamylethylamide, in rats.
Pullulan production from deproteinized whey by Aureobasidium pullulans.
High-throughput flow-injection analysis of glucose and glutamate in food and biological samples by using enzyme/polyion complex-bilayer membrane-based electrodes as the detectors.
Aspartate dehydrogenase in vitamin B12-producing Klebsiella pneumoniae IFO 13541.
Effect of glutamic acid on broilers given submarginal crude protein with adequate essential amino acids using feeds high and low in potassium.
Mitigating the effects of halofuginone on skin strength by feeding L-proline to broiler chickens.
The addition of glutamic acid or protein to a threonine-deficient diet differentially affects growth performance and threonine dehydrogenase activity in fattening pigs.
The significance of apical K+ channels in mudpuppy feeding behavior.
Nutritional profile and antimicrobial spectrum of the spice Aframomum danielli K. Schum.
Interactive effects of dietary levels of tryptophan and protein on voluntary feed intake and growth performance in pigs, in relation to plasma free amino acids and hypothalamic serotonin.
Enzymatic determination of free glutamic acid in dried soups and in minced sausages: NMKL collaborative study.
Glutamic acid-induced shoot differentiation in tobacco callus tissues and changes in nicotine content and in activities of aminotransferases, ornithine transcarbamylase, and arginase.
Effects of l-glutamic acid diethyl ester on discrimination learning in rats.
Two proglumide analogues are equipotent antagonists of the inhibition of food intake by CCK-8.
[Toxicological characteristics of disodium salt of N-lauroyl-L-glutamic acid--a surface-active agent used in the food processing industry].
Effect of diets supplemented with amino acids on intestinal sucrase and leucine aminopeptidase activities in rats.

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
CHEBI:View
CHEMBL:View
Golm Metabolome Database:Search
Metabolomics Database:Search
KEGG (GenomeNet):C00025
HMDB (The Human Metabolome Database):HMDB00148
FooDB:FDB012535
YMDB (Yeast Metabolome Database):YMDB00271
Export Tariff Code:2922.42.5000
FDA Listing of Food Additive Status:View
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex Yes
Molecular weight 147.13052368164
Melting Point 247 to 249°C @ 760 mm Hg
Flash Point TCC Value 110 °C TCC
logP (o/w) -0.969 est
Solubility
water, 9.416e+005 mg/L @ 25 °C (est) Yes
water, 8570 mg/L @ 25 °C (exp) Yes
alcohol No

Organoleptic Properties

Odor Type: Yeasty
yeasty, bread baked
Odor strength low
General comment At 100.00 %. mild yeast baked bread

Occurrences

Potential Uses

Applications
Flavoring purposes Bread white bread , Yeast
Other purposes Antistatic agents , Hair conditioning , Humectants
Cosmetic purposes Antistatic agents , Hair conditioning , Humectants

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
None - None found.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
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
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50 > 30000 mg/kg
FAO Nutrition Meetings Report Series. Vol. 48A, Pg. 42, 1970.

oral-rabbit LD50 > 2300 mg/kg
FAO Nutrition Meetings Report Series. Vol. 48A, Pg. 42, 1970.

intravenous-human TDLo 117 mg/kg
GASTROINTESTINAL: NAUSEA OR VOMITING
American Journal of the Medical Sciences. Vol. 214, Pg. 281, 1947.

oral-human TDLo 71 mg/kg
BEHAVIORAL: HEADACHE
Science. Vol. 163, Pg. 826, 1969.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor enhancers, salt substitute
Recommendation for laevo-glutamic acid 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: 5. Update in publication number(s): 25
Click here to view publication 5
average usual ppmaverage maximum ppm
baked goods: 1400.000003000.00000
beverages(nonalcoholic): 400.00000600.00000
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: 60.00000300.00000
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

European Food Safety Authority (EFSA) reference(s):

Scientific Report of EFSA on the risk assessment of salts of authorised acids, phenols or alcohols for use in food contact materials [1]
View page or View pdf

Scientific Opinion on the safety and efficacy of the use of amino acids (chemical group 34) when used as flavourings for all animal species
View page or View pdf

Scientific Opinion on the safety of the change in the production method of L-glutamic acid (E620), monosodium L-glutamate (E621), monopotassium L-glutamate (E622), calcium di-L-glutamate (E623), monoammonium L-glutamate (E624) and magnesium di-L-glutamate (E625)
View page or View pdf

Re-evaluation of glutamic acid (E 620), sodium glutamate (E 621), potassium glutamate (E 622), calcium glutamate (E 623), ammonium glutamate (E 624) and magnesium glutamate (E 625) as food additives
View page or View pdf

EPI System: View
ClinicalTrials.gov:search
Daily Med:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
Carcinogenic Potency Database:Search
EPA Substance Registry Services (TSCA):56-86-0
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :33032
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
(2S)-2-aminopentanedioic acid
Chemidplus:0000056860
RTECS:LZ9700000 for cas# 56-86-0