Glutamic acid

Glutamic acid

Skeletal formula of L-glutamic acid
Space-filling model
Names
IUPAC name
Glutamic acid
Systematic IUPAC name
2-Aminopentanedioic acid
Other names
  • 2-Aminoglutaric acid
Identifiers
  • l isomer: 56-86-0 Y
  • racemate: 617-65-2 Y
  • d isomer: 6893-26-1 Y
3D model (JSmol)
3DMet
1723801 (L) 1723799 (rac) 1723800 (D)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.009.567
EC Number
  • l isomer: 200-293-7
E number E620 (flavour enhancer)
3502 (L) 101971 (rac) 201189 (D)
KEGG
PubChem CID
UNII
  • InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10) Y
    Key: WHUUTDBJXJRKMK-UHFFFAOYSA-N Y
  • l isomer: InChI=1/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)
    Key: WHUUTDBJXJRKMK-UHFFFAOYAD
SMILES
  • l isomer: C(CC(=O)O)[C@@H](C(=O)O)N
  • d isomer: C(CC(=O)O)[C@H](C(=O)O)N
  • Zwitterion: C(CC(=O)O)C(C(=O)[O-])[NH3+]
  • Deprotonated zwitterion: C(CC(=O)[O-])C(C(=O)[O-])[NH3+]
Properties
C5H9NO4
Molar mass 147.130 g·mol−1
Appearance White crystalline powder
Density 1.4601 (20 °C)
Melting point 199 °C (390 °F; 472 K) decomposes
8.57 g/L
Solubility Ethanol: 350 μg/100 g (25 °C)
Acidity (pKa) 2.10, 4.07, 9.47
Magnetic susceptibility (χ)
 −78.5·10−6 cm3/mol
Hazards
GHS labelling:
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)
2
1
0
Supplementary data page
Glutamic acid (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Not to be confused with Glutamine or Glutaric acid.
For the anion in its role as a neurotransmitter, see Glutamate (neurotransmitter).

Glutamic acid (symbol Glu or E; the anionic form is known as glutamate) is an α-amino acid that is used by almost all living beings in the biosynthesis of proteins. It is a non-essential nutrient for humans, meaning that the human body can synthesize enough for its use. It is also the most abundant excitatory neurotransmitter in the vertebrate nervous system. It serves as the precursor for the synthesis of the inhibitory gamma-aminobutyric acid (GABA) in GABAergic neurons.

Its molecular formula is C
5H
9NO
4. Glutamic acid exists in two optically isomeric forms; the dextrorotatory L-form is usually obtained by hydrolysis of gluten or from the waste waters of beet-sugar manufacture or by fermentation. Its molecular structure could be idealized as HOOC−CH(NH
2)−(CH
2)2−COOH, with two carboxyl groups −COOH and one amino group −NH
2. However, in the solid state and mildly acidic water solutions, the molecule assumes an electrically neutral zwitterion structure −OOC−CH(NH+
3)−(CH
2)2−COOH. It is encoded by the codons GAA or GAG.

The acid can lose one proton from its second carboxyl group to form the conjugate base, the singly-negative anion glutamate −OOC−CH(NH+
3)−(CH
2)2−COO−. This form of the compound is prevalent in neutral solutions. The glutamate neurotransmitter plays the principal role in neural activation. This anion creates the savory umami flavor of foods and is found in glutamate flavorings such as MSG. In Europe, it is classified as food additive E620. In highly alkaline solutions the doubly negative anion −OOC−CH(NH
2)−(CH
2)2−COO− prevails. The radical corresponding to glutamate is called glutamyl.

The one-letter symbol E for glutamate was assigned in alphabatical sequence to D for aspartate, being larger by one methylene –CH2– group.

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