The aroma properties

of individual compounds
• Aroma compounds are volatile molecules
• As such they can enter the gas phase and pass to the
olfactory epithelium where they are sensed.
• The term flavour can be used instead of aroma, but,
taste is an oral sensation (salty, sweet, bitter, sour).
• 5,000 to 10,000 different molecules are though to
contribute towards aroma, sensed by ca. 350 different
types of aroma receptors
• Many of the most odiferous compounds contain nitrogen,
oxygen or sulfur – why are these elements important?
• Many flavours such as coffee are made of many
compounds that combine to produce the overall aroma –
some aromas such as spearmint are predominantly due
to one compound
 Mint
• We are familiar with mint through experience and use
• Mint flavours are associated with a few key compounds
• That is our association through use, just as we associate
the complex blend of compounds in coffee with coffee
• Mint is harvested and the aroma steam distilled from the
crop
• Some farms have trailers (with a close top) which load
the mint through a hatch in the front. When full the trailer
is connected to steam pipes at one end and outlet pipes
at the other
• The steam passing through the crop strips the mint oil
and carries it through to a condenser. The mint oil floats
on the water, it is collected and further refined before use
• Then the trailer goes out to the field, tips up, the back
opens and the spent mint falls out. The trailer lowers and
the process begins again
Mint aroma

(-) menthone

O
 (-) menthol

OH
 (-) carvone
O
The plant smells of this molecule
hence we associate this
molecule with this plant. This
only happens because the plant
produces one predominant
molecule. If it produced several
molecules that contributed to the
aroma it may not be so simple.
O
(+) carvone
 3D (+) carvone and
“space filling” menthol

Although shown as “stick diagrams”

Your nose senses the 3D arrangement of atoms
Which occupy space
Effect of chain length on aroma: the ketones

3 Carbons:

acetone
O or,
2-propanone
 Ketones are produced in blue

O cheese by the action of

Penicillium roqueforti this
mold (in conjunction with other
microorganisms) breaks down
4 Carbons: lipids to make ketones. Which
ketones are most blue cheese
like?
2-butanone
O 5 Carbons:

2-pentanone
 6 Carbons:
O
The carbon chain is not 2-hexanone
rigid but can rotate
around each bond
resulting in many 3D
shapes
O
7 Carbons:

2-heptanone
O
8 Carbons:

2-octanone
O
9 Carbons:

2-nonanone
O
10 Carbons:

2-decanone
Other compounds of biological origin

thymol

Essential oils often

occur in glands within
the plant tissue, when
these are ruptured the
OH oil comes out.
limonene

Try bending orange peel

backwards so that the glands on
the surface rupture, sometimes
the oil can be seen to spurt out
and can be wiped off the
surface.

Orange oil is produced by

distillation during orange juice
concentration, effectively steam
striped off and condensed
 Rancidity

O
hexanal Oxygen attacks the double bonds in the fatty-
acid chains of fat. This produces
hydroperoxides. These may degrade into
secondary oxidation products - aldehydes,
ketones, free-fatty acids etc. resulting in off-
flavours and odours.
Since double bonds (unsaturated fats) induce
faster oxidation, stability is reduced with
increased unsaturation. Palm oil, has a low
percentage of unsaturated fatty acids, it is
therefore more stable than polyunsaturated
oils such as corn oil.
 O

2,4-decadienal

Another product of oxidative

rancidity with and odour threshold
of 0.07 compared to hexanal 4.5,
so much more odiferous
 Rancid and sulfurous aromas
• Why do we detect rancidity
– Foraging? Lots of animals are attracted to
decay. Corpse = Food!
– Have we learnt to avoid (food hygiene is now
more important than food supply) what we
may have once loved?
• Sulfur – the smell of decaying protein?
– Foraging tool?
Sulfur

S S
Dimethyl disulfide
 Thermally generated aromas

O CHO
2-furaldehyde,
or A caramelisation
reaction product
furfural
 Caramelisation and Maillard
• Both chemical changes that happen during
cooking – heating food
• Heat supplies the energy to stimulate chemical
reactions – lots of chemical rearrangements
multiplies diversity of products.
• Caramelisation – heated sugars. Sugars have
carbon, hydrogen, oxygen – limits chemistry.
Toffee, caramel, burnt sugar aromas.
• Maillard is the reaction of sugars and an amino
source (protein or amino acids). Sulfur and
nitrogen also present – many more potential
products and aromas. Nutty, roasted, meaty.
N

A Maillard
N reaction product

2,3-dimethyl pyrazine