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56-86-0

Basic Information
CAS No.: 56-86-0
Name: L-Glutamic acid (alpha)
Article Data: 429
Molecular Structure:
Molecular Structure of 56-86-0 (L-Glutamic acid (alpha))
Formula: C5H9NO4
Molecular Weight: 147.131
Synonyms: 1-Aminopropane-1,3-dicarboxylic acid;2-Aminopentanedioic acid;2-Aminopentanedioic acid, (S)-;AI3-18472;Acide glutamique;Acido glutamico;Acidum glutamicum;Acidum glutaminicum;Aciglut;CCRIS 7314;D-Glutamiensuur;EPA Pesticide Chemical Code 374350;FEMA No. 3285;Glusate;Glutacid;Glutamate, L-;Glutamic acid (H-3);Glutamic acid (VAN);Glutamic acid, (S)-;Glutamicol;Glutamidex;Glutaminic acid;Glutaminic acid (VAN);Glutaminol;Glutaton;L-2-Aminoglutaric acid;L-Glutaminic acid;NSC 143503;Pentanedioic acid, 2-amino-, (S)-;UNII-3KX376GY7L;alpha-Aminoglutaric acid;alpha-Aminoglutaric acid (VAN);
EINECS: 200-293-7
Density: 1.41 g/cm3
Melting Point: 205 °C (dec.)(lit.)
Boiling Point: 333.783 °C at 760 mmHg
Flash Point: 155.667 °C
Solubility: 7.5 g/L (20 °C) in water
Appearance: White cryst. powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 24/25-36-26
PSA: 100.62000
LogP: -0.03660
Synthetic route

56-86-0

L-glutamic acid

Conditions
ConditionsYield
With dimethylsulfide; hydrogen fluoride; methoxybenzene at 0℃; for 1h; Product distribution; Rate constant; other concentration of reagents;100%
With dimethylsulfide; trifluorormethanesulfonic acid; 30 (v/v); trifluoroacetic acid at 0℃; for 4h; Yield given;
With trifluoroacetic acid In dichloromethane at 20℃; Rate constant;
With recombinant Pseudomonas nitroreducens IFO12694 γ-glutamyltranspeptidase at 30℃; for 0.0333333h; pH=10.5; aq. buffer; Enzymatic reaction;
With E. coli BL21 Star (DE3) S30 extract In aq. buffer at 37℃; for 6h; pH=7.5;
13574-13-5

Boc-Glu(OBzl)-OH

56-86-0

L-glutamic acid

Conditions
ConditionsYield
With Nafion H; dimethylsulfide; 3-methyl-phenol; trifluoroacetic acid for 3h;100%
With dimethylsulfide; hydrogen fluoride at 0℃; for 2h; Product distribution; Var.: HF in anisole;100%
23506-06-1

Z(OMe)-Glu(OBzl)-OH

56-86-0

L-glutamic acid

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate; diphenyl sulfide In trifluoroacetic acid at 0℃; for 0.5h; Product distribution; New peptide deprotection procedure: hard-soft acid-base concept; the role of soft bases (thioanisole, dimethylsulfide, diphenylsulfide) employed.;100%
73821-97-3

N-α-tert-butyloxycarbonyl-glutamic acid, γ-cyclohexyl ester

56-86-0

L-glutamic acid

Conditions
ConditionsYield
With phenylthiotrimethylsilane; pertrimethylsilylated Nafion; 3-methyl-phenol; trifluoroacetic acid for 3h;100%
91871-28-2

N-allyloxycarbonyl α-allyl-L-glutamate

56-86-0

L-glutamic acid

Conditions
ConditionsYield
With diethylamine; tetrakis(triphenylphosphine) palladium(0) In dichloromethane at 20℃; for 3h; deallylation;100%
5680-86-4

N-benzyloxycarbonyl-5-O-benzyl-L-glutamic acid

56-86-0

L-glutamic acid

Conditions
ConditionsYield
With hydrogen In ethanol for 1.33333h;98%
With hydrogen; hydroxyapatite-bound Pd In methanol at 40℃; for 12h;96%
With hydrogen In ethanol at 20℃; under 760.051 Torr; for 3h;95%
132316-96-2

(S)-(N-benzyl-N-benzyloxycarbonyl)glutamic acid

56-86-0

L-glutamic acid

Conditions
ConditionsYield
With hydrogen; palladium dihydroxide In water; acetic acid for 45h; Ambient temperature;97%
13726-84-6

Boc-Glu(OtBu)-OH

56-86-0

L-glutamic acid

Conditions
ConditionsYield
With triethylsilane; trifluoroacetic acid In dichloromethane for 1.08333h; Ambient temperature;96%
2419-94-5

Boc-Glu

56-86-0

L-glutamic acid

Conditions
ConditionsYield
With tetradecyl(trihexyl)phosphonium bistriflamide; trifluoroacetic acid at 130℃; for 0.166667h; Ionic liquid;96%
98-79-3

L-Pyroglutamic acid

56-86-0

L-glutamic acid

Conditions
ConditionsYield
With sodium hydroxide; zinc(II) sulfate In water at 105℃; for 50h; Product distribution; Mechanism; Heating; at pH 6.5; variation of amount of substrate and added salts, reaction time and temperature; further metal salts;93.1%
Rate constant;
Multi-step reaction with 7 steps
1.1: 100 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH2Cl2 / 0 - 20 °C
2.1: 100 percent / 3-chloroperoxybenzoic acid / CH2Cl2 / 4 h / 0 °C
3.1: bis(cyclopentadienyl)zirconium dichloride; silver(I) perchlorate / CH2Cl2 / 48 h
4.1: 9.40 g / 4-(dimethylamino)pyridine / acetonitrile / 1.5 h / 20 °C
5.1: sodium bis(trimethylsilyl)amide; N,N'-dimethylpropyleneurea / tetrahydrofuran / 0.5 h / -78 °C
5.2: tetrahydrofuran / 2 h
6.1: 6.48 g / hydrogen peroxide / tetrahydrofuran / 2 h / 20 °C
7.1: hydrogen / palladium on carbon / methanol
7.2: 77 percent / hydrochloric acid / Heating
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

1. Introduction of L-Glutamic acid

L-Glutamic acid, with the IUPAC Name of (2S)-2-Aminopentanedioic acid, is one kind of white cryst. powder. This chemical belongs to the Product Categories which include Food & Feed ADDITIVES; chiral; Glutamic acid [Glu, E]; Amino Acids and Derivatives; alpha-Amino Acids; Amino Acids; Biochemistry; for Resolution of Bases; Optical Resolution; Synthetic Organic Chemistry; Nutritional Supplements; Amino Acids; Chiral Compound; Glutamate receptor; Glutamate; fine chemicals; glutamic acid; amino acid; bio-chemical; chemicals; food additive; food additives; nutritional supplement; organic acids; pharmaceutical intermediate.

2. Properties of L-Glutamic acid

L-Glutamic acid has the following property datas: (1)Melting point: 205 °C; (2)Index of Refraction: 1.522; (3)Molar Refractivity: 31.83 cm3; (4)Molar Volume: 104.3 cm3; (5)Surface Tension: 69.2 dyne/cm; (6)Density: 1.409 g/cm3; (7)Flash Point: 155.7 °C; (8)Enthalpy of Vaporization: 63.39 kJ/mol; (9)Boiling Point: 333.8 °C at 760 mmHg; (10)Vapour Pressure: 2.55E-05 mmHg at 25 °C; (11)storage temp.: Store at RT.; (12)solubility: 1 M HCl: 100 mg/mL; (13)Water Solubility: 7.5 g/L (20 °C).

3. Structure Descriptors of L-Glutamic acid

You could convert the following datas into the molecular structure:
InChI: 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: InChIKey=WHUUTDBJXJRKMK-VKHMYHEASA-N 
Smiles: [C@H](CCC(=O)O)(C(=O)O)N

4. Toxicity of L-Glutamic acid

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo intravenous 117mg/kg (117mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING American Journal of the Medical Sciences. Vol. 214, Pg. 281, 1947.
human TDLo oral 71mg/kg (71mg/kg) BEHAVIORAL: HEADACHE Science. Vol. 163, Pg. 826, 1969.
 
rabbit LD50 oral > 2300mg/kg (2300mg/kg)   FAO Nutrition Meetings Report Series. Vol. 48A, Pg. 42, 1970.
rat LD50 oral > 30gm/kg (30000mg/kg)   FAO Nutrition Meetings Report Series. Vol. 48A, Pg. 42, 1970.

5. Safety Information of L-Glutamic acid
Hazard Codes of L-Glutamic acid (CAS NO.56-86-0): IrritantXi
Risk Statements: 36/37/38 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 24/25-36-26 
S24/25: Avoid contact with skin and eyes. 
S36: Wear suitable protective clothing. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 2
RTECS: LZ9700000
F: 10
Human systemic effects by ingestion and intravenous routes: headache and nausea or vomiting. When heated to decomposition it emits toxic fumes of NOx.

6. Production of L-Glutamic acid

L-Glutamic acid can be obtained directly from fermentation of carbohydrates with Micrococcus glutarnicus or Brevihacterium divaricatum.

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