Glutaminsure

GLU · H-GLU-OH · L-GLU · glutamic · L-Glutamate · L-Glu-OH · (S)-GLUTAMIC ACID · FEMA 3285

https://huagongshe.com/de/chemical/33032

Identifikatoren & physikalische Daten

CAS No.	56-86-0
Summenformel	C5H9NO4
Durchschnittliche Molmasse	147,13 g/mol
Monoisotopische Masse	147,05315777 g/mol
SMILES	N[C@@H](CCC(=O)O)C(=O)O
InChIKey	WHUUTDBJXJRKMK-VKHMYHEASA-N
PubChem CID	33032
ChEMBL	CHEMBL575060
ChEBI	CHEBI:16015
EC No.	200-293-7
DTXSID	DTXSID5020659
Lokaler Name	Glutaminsure

Chemische & physikalische Eigenschaften

XLogP	-3,7
Polarare Oberfläche (TPSA)	101
H-Brücken-Donoren	3
H-Brücken-Akzeptoren	5
Frei drehbare Bindungen	4
Schwere Atome	10
Formalladung	0
Komplexität	145
Stoffklassen	Biological Agents -> Amino Acids and Derivatives
Kosmetika	Cosmetic ingredients (Glutamic Acid) -> CIR (Cosmetic Ingredient Review)Hair conditioningHumectantAntistatic
pH	Between 3,0 and 3,5 (saturated solution)Aqueous solutions have pH values of approximately 23.0-3.5 (8.6g/l, H2O, 25℃)
LogP (Verteilungskoeffizient)	log Kow = -3.69 at pH 7.0
Geruch	Odorless
Geschmack	Umami sour tasteAcidic (glutamate-like) taste
Lebensmittelzusatzstoffe	FLAVORING AGENT OR ADJUVANT, NUTRIENT SUPPLEMENT, PH CONTROL AGENT -> FDA Substance added to food
Dichte	1.538 g/cu cm at 20 °C1.54 g/cm3 at 20 °C
Color/Form	Orthorhombic plates from dilute alcohol
Löslichkeit	Sparingly soluble in waterpractically insoluble in ethanol or etherIn water, 8570 mg/L at 25 °CInsoluble in methanol, ethanol, ether, acetone, cols glacial acetic acid and common neutral solvents.8.57 mg/mLSlight soluble in water and ether1 M HCl: 100 mg/mL7.5 g/L (20 ºC)
Animal Drugs	Pharmaceuticals -> UK Veterinary Medicines Directorate List
Siedepunkt	Sublimes at 175 °C267.21°C (rough estimate)
Schmelzpunkt	205 °C (dec.) (lit.)
Brechungsindex	1.4300 (estimate)
FEMA	3285 \| L-GLUTAMIC ACID
Lagerbedingungen	2-8°C
Aggregatzustand	powder
pKa (Säurekonstante)	2.13(at 25℃)
Farbe	White
Geruch	at 100.00 %. mild yeast baked bread
Geruchsart	yeasty
Biologische Quelle	non-animal source
Merck	14,4469
JECFA Number	1420
BRN	1723801
Hauptanwendungen	pharmaceutical (small molecule)
Kosmetik-Inhaltsstoffe Funktionen	HAIR CONDITIONINGANTISTATICHUMECTANT
InChI	1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1
InChIKey	WHUUTDBJXJRKMK-VKHMYHEASA-N
SMILES	N[C@@H](CCC(O)=O)C(O)=O
LogP (Verteilungskoeffizient)	-3.69
CAS Datenbank	56-86-0(CAS DataBase Reference)
NIST chemische Informationen	L-Glutamic acid(56-86-0)
EPA chemische Informationen	L-Glutamic acid (56-86-0)

Sicherheit & Vorschriften

GHS-Einstufung	This chemical does not meet GHS hazard criteria for 95.4% (293 of 307) of all reports.Not ClassifiedAggregated GHS information provided per 307 reports by companies from 5 notifications to the ECHA C&L Inventory.DangerH314: Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P363, P405, and P501 (click each P-code to see the statement)
Regulatorische Informationen	Chemical: L-Glutamic acidRegulation (EC) No 1333/2008 (amended)L-Glutamic acid is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of L-Glutamic acid are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 31-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/12560L-Glutamic acid: Does not have an individual approval but may be used under an appropriate group standardGlutamic acid: Does not have an individual approval but may be used under an appropriate group standard
Weitere Sicherheitsinformationen	IMAP assessments - L-Glutamic acid: Environment tier I assessment
Gefahrenübersicht	Causes mild eye irritation in rabbits (classified by the EC as not irritating)Not a skin sensitizer in guinea pigs[IUCLID] Safe when used as a flavoring agent in food[JECFA] May cause irritation[Sigma-Aldrich MSDS] See DL-Glutamic acid.
FDA-Anforderungen	L-Glutamic acid is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity of the substance added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) any substance intended for use in or on food is of appropriate food grade and is prepared and handled as a food ingredient.This substance is generally recognized as safe when used as a salt substitute in accordance with good manufacturing practice.

Anwendungen & Verwendung

Beschreibung

L-Glutamic acid, or L-2-aminopentanedioic acid, is a naturally occurring amino acid of plant and animal proteins. It has a very faint odor reminiscent of yeast or freshly baked bread. It has a mild, somewhat sweet, meat-like taste.The average glutamic acid content of food proteins is 20 percent. Expressed as glutamic acid per 100 g of the edible portions, medium fat beef contains about 2.65 g of glutamic acid; whole liquid cow milk, 0.82 g; lean pork, 2.16 g; haddock, 2.32 g; peas, 5.58 g; soybeans, 7.01 g; commeal, 1.62 g; and whole grain wheat flour, 4.16 g. In addition, free glutamic acid is present in many vegetables, fish, and meats in small amounts (0. 005 to 0.23 g per 100 g) and as high as 2 g per 100 g in some varieties of cheese. Recent estimates of free amino acids in the milk of various species indicated that the free glutamic acid in human milk is about 0.22 g per 100 mL.Glutamic acid and its salts are prepared commercially by hydrolysis of gluten (wheat, corn, soybean, sugarbeet protein); by fermentation from glucose-containing raw materials; the racemic acid may be resolved into the d- and ι-isomer by fractional crystallization; from 2 -cyclopentenylamine; by microbial conversion of aketoglutaric acid; or by an alternative method, using Bacillus megatherium-cereus; from fumaric acid using B. pumilus; from starch.Glutamic acid and the hydrochloride as well as the mono-sodium, -potassium, and -ammonium salts of L-glutamic acid share similar physical properties: they are nearly odorless, white, free-flowing crystalline powders, and except for glutamic acid and glutamic acid hydrochloride, are freely soluble in water. Glutamic acid is slightly soluble and glutamic acid hydrochloride moderately soluble in water. The pH of a saturated solution is about 3.2.

Occurrence

Reported as occurring in many vegetable proteins, in beef fbrin, in the chrysalis of silkworm, in the hydro- lysate of crystalline insulin Also present in other important peptides, such as glutathione, tyrocidin, folic acid, β-lactoglobulin, secretin and bacitracin, and in growth hormone

Verwenden

L-glutamic acid or its salt, monosodium glutamate (MSG), is used as an additive to human food to enhance the taste. Although seaweed had been used in Asia to enhance food flavor for over 1000 years, it was not until 1908 that the essential component responsible for the flavor phenomenon was identified as glutamic acid. From 1910 until 1956, monosodium glutamate was extracted from sea weed, a slow and costly method. In 1956, Ajinomoto, a Japanese company, succeeded in producing glutamic acid by means of fermentation. Today, L-glutamic acid or MSG is generally made by microbial fermentation using genetically modified bacteria.

Herstellung & Synthese

synthetische

By hydrolysis of gluten (wheat, corn or other vegetable sources); by fermentation from glucose-containing raw materials; the racemic acid may be resolved into the d- and l-isomer by fractional crystallization; from 2-cyclopentenylamine; by microbial conversion of α-ketoglutaric acid; or by an alternative method, using Bacillus megatherium-cereus; from fumaric acid, using B pumilus; from starch.