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2D Structure
Also known as: 142-47-2, Sodium l-glutamate, Sodium glutamate, Ajinomoto, Glutacyl, L-glutamic acid, monosodium salt
Molecular Formula
C5H8NNaO4
Molecular Weight
169.11  g/mol
InChI Key
LPUQAYUQRXPFSQ-DFWYDOINSA-M

One of the FLAVORING AGENTS used to impart a meat-like flavor.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
sodium;(2S)-2-amino-5-hydroxy-5-oxopentanoate
2.1.2 InChI
InChI=1S/C5H9NO4.Na/c6-3(5(9)10)1-2-4(7)8;/h3H,1-2,6H2,(H,7,8)(H,9,10);/q;+1/p-1/t3-;/m0./s1
2.1.3 InChI Key
LPUQAYUQRXPFSQ-DFWYDOINSA-M
2.1.4 Canonical SMILES
C(CC(=O)O)C(C(=O)[O-])N.[Na+]
2.1.5 Isomeric SMILES
C(CC(=O)O)[C@@H](C(=O)[O-])N.[Na+]
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Accent

2. Glutamate, Sodium

3. Msg

4. Sodium Glutamate

5. Vestin

2.2.2 Depositor-Supplied Synonyms

1. 142-47-2

2. Sodium L-glutamate

3. Sodium Glutamate

4. Ajinomoto

5. Glutacyl

6. L-glutamic Acid, Monosodium Salt

7. Monosodium L-glutamate

8. Glutavene

9. Ancoma

10. L-monosodium Glutamate

11. Chinese Seasoning

12. L-glutamic Acid Monosodium Salt

13. 16177-21-2

14. L-glutamic Acid Sodium Salt

15. Glutamic Acid, Sodium Salt

16. L(+) Sodium Glutamate

17. Glutamate Monosodium Salt

18. Sodium Hydrogen Glutamate

19. Natriumglutaminat

20. Glutamate Sodium

21. Natrium L-hydrogenglutamat

22. Monosodioglutammato

23. Glutammato Monosodico

24. Fema No. 2756

25. Vetsin

26. Zest

27. Sodium (s)-2-amino-4-carboxybutanoate

28. Rl-50

29. Msg

30. Sodium;(2s)-2-amino-5-hydroxy-5-oxopentanoate

31. Monosodium Glutamate Anhydrous

32. Sodium (2s)-2-amino-4-carboxybutanoate

33. L-glutamic Acid Monosodium

34. Accent (food Additive)

35. Glutamat Sodny [czech]

36. Glutamat Sodny

37. Sodium Glutamate (van)

38. Natriumglutaminat [german]

39. C3c196l9fg

40. Sodium L-glutamate (van)

41. Monosodioglutammato [italian]

42. Ccris 3625

43. Hsdb 580

44. Glutammato Monosodico [italian]

45. Mono Sodium Glutamate

46. Glutamic Acid, L-, Sodium Salt

47. L-glutamic Acid, Sodium Salt (1:1)

48. Glutamate Sodium [jan]

49. Einecs 205-538-1

50. L-glutamic Acid, Sodium Salt (van)

51. Nsc 135529

52. Unii-c3c196l9fg

53. Ai3-18393

54. Einecs 240-313-1

55. Glutamic Acid, Monosodium Salt, L-

56. L-glutamic Acid, Sodiumsalt (1:1)

57. H-glu-oh.na

58. 6106-04-3

59. Ec 205-538-1

60. Schembl16336

61. Dtxsid9020906

62. Akos027257231

63. Sodium 2-amino-5-hydroxy-5-oxopentanoate

64. G0188

65. J-007661

2.3 Create Date
2008-02-05
3 Chemical and Physical Properties
Molecular Weight 169.11 g/mol
Molecular Formula C5H8NNaO4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count4
Exact Mass169.03510202 g/mol
Monoisotopic Mass169.03510202 g/mol
Topological Polar Surface Area103 Ų
Heavy Atom Count11
Formal Charge0
Complexity149
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Therapeutic Uses

One of the FLAVORING AGENTS used to impart a meat-like flavor. Medically it has been used to reduce blood ammonia levels in ammoniacal azotemia, therapy of hepatic coma, in psychosis, and mental retardation.

National Library of Medicine - Medical Subject Headings (2007)


4.2 Drug Warning

The large doses of sodium glutamate required for the treatment of hepatic encephalopathy may result in dangerous alkalosis and hypokalemia ... important to keep close control on the electrolyte balance during therapy.

Reynolds, J.E.F., Prasad, A.B. (eds.) Martindale-The Extra Pharmacopoeia. 28th ed. London: The Pharmaceutical Press, 1982., p. 59


Injections of sodium glutamate should be given with caution to patients with hepatic cirrhosis, impaired renal function, or liver disease not associated with hyperammonemia.

Reynolds, J.E.F., Prasad, A.B. (eds.) Martindale-The Extra Pharmacopoeia. 28th ed. London: The Pharmaceutical Press, 1982., p. 59


Food and Environmental Agents: Effect on Breast-Feeding: Monosodium glutamate: None. /from Table 7/

Report of the American Academy of Pediatrics Committee on Drugs in Pediatrics 93 (1): 142 (1994)


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Flavoring Agents

Substances added to foods and medicine to improve the taste. (See all compounds classified as Flavoring Agents.)


5.2 Absorption, Distribution and Excretion

Glutamate is absorbed from the gut by an active transport system specific for amino acids. This process is saturable, can be competitively inhibited, and is dependent on sodium ion concentration... . During intestinal absorption, a large proportion of glutamic acid is transaminated and consequently alanine levels in portal blood are elevated. If large amounts of glutamate are ingested, portal glutamate levels increase ... . This elevation results in increased hepatic metabolism of glutamate, leading to release of glucose, lactate, glutamine, and other amino acids, into systemic circulation ... . The pharmacokinetics of glutamate depend on whether it is free or incorporated into protein, and on the presence of other food components. Digestion of protein in the intestinal lumen and at the brush border produces a mixture of small peptides and amino acids; di-and tri-peptides may enter the absorptive cells where intracellular hydrolysis may occur, liberating further amino acids. Defects are known in both amino acid and peptide transport ... .. Glutamic acid in dietary protein, together with endogenous protein secreted into the gut, is digested to free amino acids and small peptides, both of which are absorbed into mucosal cells where peptides are hydrolyzed to free amino acids and some of the glutamate is metabolized. Excess glutamate and other amino acids appear in portal blood. As a consequence of the rapid metabolism of glutamate in intestinal mucosal cells and in the liver, systemic plasma levels are low, even after ingestion of large amounts of dietary protein. /Glutamic acid/

WHO Food Additive Series 22; L-Glutamic Acid and its Ammonium, Calcium, Monosodium and Potassium Salts. Available from, as of March 20, 2007: https://www.inchem.org/documents/jecfa/jecmono/v22je12.htm


... Intestinal and hepatic metabolism results in elevation of levels in systemic circulation only after extremely high doses given by gavage (>30mg/kg body weight). Ingestion of monosodium glutamate (MSG) was not associated with elevated levels in maternal milk, and glutamate did not readily pass the placental barrier. Human infants metabolized glutamate similarly to adults.

PMID:10736380 Walker R and Lupien JR; J Nutr 130 (4S Suppl): 1049S-52S (2000)


Oral administration of pharmacologically high doses of glutamate results in elevated plasma levels. The peak plasma glutamate levels are both dose and concentration dependent ... . When the same dose (1 g/kg b.w.) of monosodium glutamate (MSG) was administered by gavage in aqueous solution to neonatal rats, increasing the concentration from 2% to 10% caused a five-fold increase in the plasma area under curve; similar results were observed in mice ... . Conversely, when MSG (1.5 g/kg b.w.) was administered to 43-day-old mice by gavage at varying concentrations of 2 to 20% w/v, no correlation could be established between plasma levels and concentration ...

WHO Food Additive Series 22; L-Glutamic Acid and its Ammonium, Calcium, Monosodium and Potassium Salts. Available from, as of March 20, 2007: https://www.inchem.org/documents/jecfa/jecmono/v22je12.htm


Administration of a standard dose of 1 g/kg b.w. MSG by gavage as a 10% w/v solution resulted in a marked increase of plasma glutamate in all species studied. Peak plasma glutamate levels were lowest in adult monkeys (6 times fasting levels) and highest in mice (12-35 times fasting levels). Age-related differences between neonates and adults were observed; in mice and rats, peak plasma levels and area under curve were higher in infants than in adults while in guinea pigs the converse was observed.

WHO Food Additive Series 22; L-Glutamic Acid and its Ammonium, Calcium, Monosodium and Potassium Salts. Available from, as of March 20, 2007: https://www.inchem.org/documents/jecfa/jecmono/v22je12.htm


For more Absorption, Distribution and Excretion (Complete) data for MONOSODIUM GLUTAMATE (7 total), please visit the HSDB record page.


5.3 Metabolism/Metabolites

Glutamic acid is metabolized in the tissues by oxidative deamination ... or by transamination with pyruvate to yield oxaloacetic acid ... which, via alpha-ketoglutarate, enters the citric acid cycle ... .. Quantitatively minor but physiologically important pathways of glutamate metabolism involve decarboxylation to gamma-aminobutyrate (GABA) and amidation to glutamine ... . Decarboxylation to GABA is dependent on pyridoxal phosphate, a coenzyme of glutamic acid decarboxylase ..., as is glutamate transaminase. Vitamin B6-deficient rats have elevated serum glutamate levels and delayed glutamate clearance ... . /Glutamic acid/

WHO Food Additive Series 22; L-Glutamic Acid and its Ammonium, Calcium, Monosodium and Potassium Salts. Available from, as of March 20, 2007: https://www.inchem.org/documents/jecfa/jecmono/v22je12.htm


Oral dose of 1 g/kg monosodium glutamate given to rats was followed by only a small rise in plasma pyroglutamate levels. No incr of pyroglutamate or glutamate brain levels was observed under these conditions.

PMID:7080082 CACCIA S ET AL; TOXICOL LETT 10 (2-3): 169 (1982)


5.4 Mechanism of Action

L-Glutamate and GABA supposedly act as excitatory and inhibitory transmitters, respectively, in the central nervous system. Glutamate is also involved in the synthesis of proteins. /Glutamate/

WHO Food Additive Series 22; L-Glutamic Acid and its Ammonium, Calcium, Monosodium and Potassium Salts. Available from, as of March 20, 2007: https://www.inchem.org/documents/jecfa/jecmono/v22je12.htm