Molecule of the week

MSG, glutamic acid and glutamate ions

The glutamates are an interesting group of molecules
which are important as components of proteins as well
as through their influence on the taste of foods.
Glutamates occur in quite a number of forms and the
first important distinction is between free and bound
forms. Free glutamates are those that are not linked
covalently to any other molecule and these do occur
naturally to varying extents in foods. Bound glutamates
are those linked to one or more other molecules and
most of the bound form is present in the many different
proteins found in our foods [1, 2].

Structure The two

Glutamate occurs naturally in foods Free

forms occur in many common foods including
tomatoes, meats and some cheeses [3]. These cannot be
distinguished chemically from molecules that have
been incorporated as an additive.
Bound glutamate occurs in all of the many different
protein molecules in foods (and living cells). Here it
can be a large proportion of the amino acids. For
example in wheat flour it is approx 33% of the total
weight of the proteins [4]. Less well known is that all
active forms of folate also contain at least one
glutamate unit as part of their structure [1, 2].

Forms of glutamate in food In reality, in most

foods glutamate does not occur in the acid form shown.
Regardless of the source or form of the molecule added,
it is the acidity (pH) of the food which determines the
extent of ionisation. This is shown in the equilibrium
reactions below. The pKa values indicate the pH at
which half of the molecules in the equilibrium are in
each of the two forms shown.

Use as an additive Glutamate is approved as an

additive around the world and can be incorporated in
one of six forms [5]: MSG (E621) (monosodium
glutamate), monopotassium (E622), calcium (E623),
monoammonium (E624) or magnesium (E625) as well
as glutamic acid (E620). The function of added
glutamate is as a flavour enhancer the taste provided
is known as umami [1-3]. Under the ANZFSC these
additives can only be added to particular foods and the
addition must be declared on the label [5] so that
consumers can make informed choices when selecting
foods to eat.

As an example of how this works, in very acidic

conditions the equlibria will shift strongly towards the
left. From this we can calculate that glutamate has no
overall charge at pH 3.32 (its isoelectric point, pI).
Therefore, as with many amino acids glutamate often
occurs as the double ion which as referred to as a
zwitterion.

References and further reading

[1] Fennema and [2] Coultate both have sections on
folates, amino acids and MSG as a flavour enhancer.
[3] Food Reviews International 18(1):23-38.
[4] NUTTAB has amino acid data.
[5] ANZFSC standards 1.2.4 and 1.3.1.

Functions and safety As well as being a

component of all proteins., glutamate functions in the
transmission of nerve impulses particularly in our
brains. Although some people may have adverse
reactions to glutamate, for most it is very safe [1-3].
O
H 3 +N

CH

O
H 3 +N

OH

CH2

OH

H 3 +N

CH2

CH2
C

CH

CH

H2 N

CH2

CH2

pKa
2.23

diagrams represent
glutamic acid and are
H2N
CH
C
OH
different depictions of
the same molecule.
CH2
The shading in the
upper structure shows
CH2
the part of the
molecule which is
C
O
common to all amino
OH
acids. This becomes
involved in the peptide
O
O
bonds when proteins
are biosynthesised.
HO
OH
The lower depiction
attempts to show the
NH2
actual 3D arrangement
of bonds around the carbon atoms, while omitting the
hydrogens that are present.

OH
+

+H

Prepared by Assoc Prof Darryl Small (v4 July 2012)

CH2

C
O

CH2

CH2

pKa
4.42

CH

pKa
9.95

C
O

+2H

+3H

questions/feedback to <darryl.small@rmit.edu.au>