FLAVORS AND

FRAGRANCES

Chapter 7.1

Definition

Fragrance & flavors substances

Strong smelling organic compound with

pleasant odor

Uses in : perfume & perfumed product

Food flavoring

beverages

Fragrance & flavor are chemical

messengers with the receptor are

olfactory cells in the nose and in the

tongue

Physiological importance

Chemical signals are very important for organisms for the following:

to hunt for and inspect food to detect enemies and harmful object to find members of the opposite sex to find the way For human the important of flavor and

fragrance substances are not as drastic as for other mammals The use of fragrance for human is for

invoking pleasurable sensation For flavor example added for food is

enhancing the enjoyment of food

Natural, Nature Identical, Artificial Product

• Natural Products are obtained

from plant or animal. • Nature Identical Products are

produced synthetically but are chemically identical to their natural counterparts

• Artificial Products are

compounds that have not been identified in plant or animal product

Problems of Using Natural Flavors

• 1) Many natural flavor have low intensity,

and hence it is used at a high dosage which results in an unsatisfactory texture and poor stability.

• 2) Concentration of natural flavors is usually

accompanied by significant changes in the

flavor profile.

• 3) Natural flavors exhibit variations in

strength and quality.

Problems of using Natural Flavors

• 4)The supply of natural materials is becoming uncertain.

• 5) Most natural flavors are unstable and undergo changes during postharvest handling, processing

or storage.

• 6) Many natural products contain enzyme systems which may result in the formation of off-notes.

• 7) The toxicity of many natural products has yet to be

established.

Disadvantage using Imitation Flavors

1) Original natural flavor more subtle, imitation flavor maybe described as “chemical”

2) Difficulties in “labeling”

3) Many natural flavors have a built in reservoir of flavor precursors which can result in the generation of additional flavor, imitation flavors are not.

4) Imitation flavor generally require the use of either a

solvent or a carrier

5) Restriction by legislation

6) Problems with texture in the end product

Advantage of Imitation Flavor

• 1) Cheaper than natural flavor

• 2) Stable

• 3) Can be designed to withstand severe processing condition

• 4) Can be produced in a variety of forms (e.g., alcohol-

based, oil-based, or encapsulated powders )

• 5) Generally readily available

• 6) Consistency of quality

Aromatics Sources

• Plants have long been used in

perfumery as a source of essential oils and aroma compounds. A plant can offer more than one source of aromatics, for instance the aerial portions and seeds of coriander have remarkably different odors from each other. Orange leaves, blossoms, and fruit zest are the respective sources of petitgrain, neroli, and orange oils.

Plant Source

• Bark: eg cinnamon, cascarilla, sassafras , safrole.

• Leaves and twigs: lavender , patchouli, sage, violets, rosemary, and citrus, hay and tomato leaf.

Plant Source

Flowers and blossoms:

rose, jasmine, as well as

osmanthus, plumeria,

mimosa, tuberose,

narcissus, scented

geranium, cassie, ambrette

as well as the blossoms of

citrus and ylang-ylang, clove

, vanilla.

Plant Source

Fruits:

• Fresh fruits such as apples, strawberries, cherries, litsea cubeba, vanilla, and juniper berry. The most commonly used fruits yield their aromatics from the rind; they include citrus such as oranges, lemons, and limes, grapefruit.

Plant Source

• Resins:

Valued since antiquity, resins have been widely used in incense and perfumery. Commonly used resins in perfumery include labdanum, frankincense/olibanum, myrrh, Peru balsam, gum benzoin. Pine and fir resins and fossil conifers.

Plant Source

• Roots, rhizomes and bulbs: Commonly used terrestrial portions in perfumery include iris rhizomes, vetiver roots, various rhizomes of the ginger family.

• Seeds: Commonly used seeds include tonka bean, carrot seed, coriander, caraway, cocoa, nutmeg, mace, cardamom, and anise.

• Woods: Commonly used woods include sandalwood, rosewood, agarwood, birch, cedar, juniper, and pine.

Different Oils from different Parts of plant

SOURCES OF ESSENTIAL OILS

EXTRACTION-

ORANGE FLOWER

ABSOLUTE

DISTILLATION

NEROLI OIL

FLOWER

EXPRESSION-

BITTER ORANGE OIL

FRUIT

EXTRACTION-

PETITGRAIN

ABSOLUTE

DISTILLATION-

PETIGRAIN OIL

LEAVES AND

TWIGS

BITTER ORANGE TREE

Distillation

Fractionation

Acetylation

Isomerisation

Methylation

Hydrogenation

Oxidation

Mild Acid Reaction

Benzylation

Clove Oil Derivatives

O

HO

O

OO

HO

O

O

O

O

O

O

HO

O

O

OO

O

OH

O

HO

O

O

CH3

CH3

CH2

H3CHH

H HH3C

CH2

CH3

OH3C

Animal Sources

• Civet: Also called Civet Musk,

this is obtained from the odorous sacs of the civets, animals in the family Viverridae, related to the mongoose.

• Hyraceum: Commonly known

as "Africa Stone", is the petrified excrement of the Rock Hyrax. [13]

Animal Source

• Honeycomb: From the honeycomb of the

honeybee. Both beeswax and honey can be solvent extracted to produce an absolute. Beeswax is extracted with ethanol and the ethanol evaporated to produce beeswax absolute.

• Deer musk: Originally derived from the musk sacs from the Asian musk deer, it has now been replaced by the use of synthetic musks sometimes known as "white musk".

Animal Source

• Ambergris: Lumps of oxidized fatty

compounds, whose precursors were secreted and expelled by the sperm whale. Ambergris should not be confused with yellow amber.

• Castoreum: Obtained from the odorous sacs of the North American beaver.

Synthetic Sources

• Many modern perfumes

contain synthesized odorants.

• Synthetics can provide

fragrances which are not found in nature. For instance, Calone, linalool and coumarin

Methods in synthetic

Flavor/Fragrance Reconstitution

Isolation of flavor concentrate

• Separation of components

• Identification

• Synthesis

• Scientifically reconstituted formulation

(match with GC)

• Organoleptically adjusted formulation

• Process and product development

• Manufacture and end use in consumer

product

Limitations

a. Some compounds decompose or do not come out of GC

b. Wide variety of flavor threshold (Some compounds can not be identified.

ODOR AND STRUCTURE

• Different

compound may have similar odor

• But small changes

in structure may change the intensity of an odor by several order of magnitude

Volatility

• Fragrances must be volatile, so therefore the molecular mass of the fragrance molecule is an important factor.

• Perfume consists of mixture of fragrance compounds which are different in volatility

• Perfume is devided into the Top note, Middle note and the End note.

• Sometime substances are added to perfume to prevent the more volatile component for evaporating too rapidly

FRAGRANCE NOTES

• Top notes: The scents that are perceived

immediately on application of a perfume. Top notes consist of small, light molecules that evaporate quickly. They form a person's initial impression of a perfume and thus are very important in the selling of a perfume. Also called the head notes.

FRAGRANCE NOTES

• Middle notes or Heart Notes : The scent of a perfume that emerges just prior to when the top

notes dissipate. The middle note compounds form the "heart" or main body of a perfume and act to mask the often unpleasant initial impression of base notes, which become more pleasant with time. They are also called the heart notes.

FRAGRANCE NOTES

• Base notes: The scent of a perfume that

appears close to the departure of the middle notes. The base and middle notes together are the main theme of a perfume. Base notes bring depth and solidity to a perfume. Compounds of this class of scents are typically rich and "deep" and are usually not perceived until 30 minutes after application.

FRAGRANCE NOTES

• The scents in the top and

middle notes are influenced by the base notes, as well the scents of the base notes will be altered by the type of fragrance materials used as middle notes.

• Manufacturers of perfumes usually publish perfume notes and typically they present it as fragrance pyramid, with the components listed in imaginative and abstract terms.

Odor description An odor can be described by adjectives which relate them

to other products with similar odor

woody General for odor or food e.g sandalwood

waxy Smell like candle wax

spicy General for odor of spices

resinous

Aromatic odor of tree exudate

powdery

Smell associated with talcum

mossy Smell of forest and seaweed

minty Peppermint / like odor

metallic Smell like metal surface

herbaceous

Smell like green herbs

green Typical odor of freshly cutgrass and leaf

Odor Description

fruity General for odor of food

floral General for odor of flowers

fatty Odor resemble animal fat and tallow

citrus Fresh odor of citrus fruits

balsamic Heavy sweet odor e.g cocoa, vanilla, cinnamon

earthty Humus like, of humid earth

Isolation of natural fragrance and

flavor concentrate

Three main methods use to obtain concentrates of plan flavor and fragrance substances :

1.Distillation

2.Mechanical separation (pressing)

3.Solvent extraction

DISTILLATION

• Distillation: A common technique for obtaining aromatic

compounds from plants, such as orange blossoms and roses. The raw material is heated and the fragrant compounds are re-collected through condensation of the distilled vapour.

• Steam distillation: Steam from boiling water is passed through the raw

material, which drives out their volatile fragrant compounds. The water collected from the condensate, which retains some of the fragrant compounds and oils from the raw material is called hydrosol and sometimes sold. This is most commonly used for fresh plant materials such as flowers, leaves, and stems.

DISTILLATION

• Dry/destructive distillation: The raw materials are directly

heated in a still. Fragrant compounds that are released from the raw material by the high heat often undergo anhydrous pyrolysis, which results in the formation of different fragrant compounds.

This method is used to obtain fragrant compounds from fossil amber and fragrant woods.

DISTILLATION

– Fractionation: Through the use of a

fractionation column, different fractions can be selectively excluded to modify the scent of the final product. This is sometimes performed to remove unpleasant scents of a material with certain purpose.

EXTRACTION

• Maceration/Solvent extraction: The most used and economically

important technique with raw materials are submerged in a solvent. Maceration lasts anywhere from hours to months. Fragrant compounds for woody and fibrous plant materials are often obtained in this manner as are all aromatics from animal sources. The technique can also be used to extract odorants that are too volatile for distillation or easily denatured by heat. Commonly used solvents for maceration/solvent extraction include hexane, and dimethyl ether.

The product of this process is called a

"concrete".

EXTRACTION

• Supercritical fluid extraction: A technique for extracting fragrant

compounds from a raw material, which often employs Supercritical CO2 with low heat of process and the relatively nonreactive solvent used in the extraction.

Ethanol extraction: Used to extract fragrant compounds

directly from dry raw materials, as well as the impure oily compounds materials resulting enfleurage.

Not used to extract fragrance from fresh plant materials .

EXTRACTION

• Enfleurage:

Absorption of aroma materials into

solid fat or wax and then extracting the odorous oil with ethyl alcohol. Extraction by enfleurage was commonly used when distillation was not possible because some fragrant compounds denature through high heat. This technique is not commonly used in the present day industry due to its prohibitive cost and the existence of more efficient and effective extraction methods. [9]

Expression

• Expression: Raw material is

compressed to obtain the oil.

The only fragrant oil from the peels of fruits is in the citrus family extracted in this manner .