Flavor Chemistry 820

The Ohio State University

Food Science and Technology

Instructor : Dr. David B. Min

 General Objective

The objective of this course is to teach students the

role of flavor chemistry in food quality. Chemical
structures and formation of flavor compounds,
organic, bio, and analytical chemistries involved
in flavor research, the effects of processing,
packaging and storage conditions on the flavor
quality and stability of foods, and current research
related to flavor are covered.
Upon completion of this course, students
should be able to:
1. Understand Chemical reactions involved in
flavor compounds formation in natural and
processed food.

2. Comprehend the effects of food components,

processing parameters and storage conditions on
flavor quality of foods.

3. Understand principles, techniques and

applications of analytical instruments involved in
flavor analysis.
4. Optimize ingredient concentration, processing
parameters, packing materials and storage
conditions for optimum quality and stability.

5. Develop simple research programs of flavor

chemistry.

6. Specify the flavor qualities of raw ingredients.

 Evaluation

Midterm Examinations (2) 40%

Final Examination 30%
Home Work and Class Participation 30%
 1. Introduction
I. Definition of Flavor
II. Classification of Food Flavor
III. Scope of Flavor Chemistry
1.Chemical compounds responsible for food flavor
2.Flavor of foods
3.Reconstitution of flavor compounds
4.Precursors of the flavor compounds
5.Mechanism for the formation of flavor compounds
and precursors in foods
6.Relationship between physical properties and its
flavor

IV. Objectives of Flavor Chemistry

2. Isolation and Separation of Flavor
Compounds
I. Objective
II. Prerequisites
III. Apparatus for Isolation
1.Headspace analysis
2.Continuous solvent extraction
3.Steam distillation and continuous
solvent extraction

IV. Extraction and Concentration

V. Preliminary and Final Fractionation
VI. Dynamic Headspace analyzer
V. Solid Phase Microextraction Analysis
3. Flavor Identification by Spectrometric
Methods
I. Introduction of Spectrometric Analyses
II. Ultra Violet Spectrometry
III. Infrared Spectrometry
IV. Nuclear Magnetic Resonance Spectrometry
V. Mass Spectrometry
1.Furans
2.Pyrroles
3.Thiophenes
4.Pyridines
5.Pyrazines
 4. Manufacture of Food Flavor

I. Natural or Imitation Flavor

II. Problems of Using Natural Flavor
III. Disadvantages of Using Imitation Flavor
IV. Advantages of Imitation Flavor
V. Methods in Synthetic Flavor Reconstitution
 5. Chemistry of Flavor Precursors

I. Flavor Compounds from Carbohydrates and

Proteins
II. Thermal Degradation of Vitamin B1
III. Lipid Oxidation
IV. Flavor Generated from Enzymatic Method,
Microbiological Reaction, and Biogenesis
 6. Dairy Products Flavor Chemistry
I. Milk Flavor
1.Oxidized flavor
2.Rancid flavor
3.Heated flavor
4.Microbiological flavor
5.Absorbed flavor
6.Sunlight flavor
II. Cheese Flavor
1.Isolation, separation and identification of cheese flavor
2.Biological pathways of fat in cheese flavor
3.Reaction products of methionine
4.Biochemical pathways of cheese flavor formation from protein
5.2-Butanone and 2-Butanol formation from diacetyl and acetone
6.Biochemical pathways of cheese flavor formation from lactose
7.Lactone formation
8.Mechanisms of methyl ketone formation
 7. Meat Flavor Chemistry

I. Introduction
II. Effect of Psychrotropic Bacteria on the
Volatile Compounds of Raw Beef
1.Introduction
2.Volatile compounds of aseptic raw ground beef
3.Effects of psychrotropic bacteria on the volatile
compounds of aseptic raw ground beef

III. Isolation, Separation, and Identification of

Roast Beef Flavor Simulated Meat Flavor Formation
8. Interaction of Flavor Compounds with Foods

I. Physical and Chemical Stability of Flavor

Compounds of Lipid Food
II. Effects and Interactions of Carbohydrates with
Flavor Compounds
III. Interactions of Proteins with Flavor Compounds
9. Packaging and Flavor Compounds Interaction

I. Effects of Packaging Materials on the

Flavor Quality of Food
II. Sorption of Orange Flavor Compounds by
Packaging Materials
10. Favor Compounds and Solvent Interaction

I. Commercial Cherry Flavor and Solvent Interaction

II. Acetal Formation
 1. INTRODUCTION
I. Definition of Flavor

1. Flavor is the sensation produced by a material taken

in the mouth, perceived principally by the senses of taste
and smell, and also by the general pain, tactile, and
temperature receptors in the mouth. Flavor also denotes
the sum of the characteristics of the material which
produces that sensation.

2. Flavor is one of the three main sensory properties

which are decisive in the selection, acceptance, and
ingestion of a food.
Stimulus Senses Sensory Response

Taste
Food Flavor

Odor
 II. Scope of Flavor Chemistry

1. Chemical compounds responsible for food flavor

1) Even distribution: Brandy

2) Star compound: A star compound can not be identical

to the total true flavor but is close and can not
produce the true flavor without the star compound.
Almond: Benzoaldehyde

CHO
Green pepper: 2-Methoxy-3-isobutyl-pyrazine

N OCH3

CH3
N CH2CH
CH3
Vanilla: 4-Hydroxy-3-methoxy-benzolaldehyde

CHO

OCH3
OH
Cucumber: 2-Trans-6-cis-nonadienal

H CHO
C C
CH2 CH2 H
CH3 CH2 C C
H H
Reversion Rancid Flavor of Soybean Oil:
2-Pentylfuran and 2-Pentenylfuran

O (CH2)4 CH3
 2. Flavor of Foods
1) Desirable flavor
orange juice
potato chip
roast beef

2) Undesirable flavor (off-flavor)

oxidized
stale
rancid
warmed-over
 3. Precursors of Flavor Compounds

Linoleate 2-pentylfuran
1) Non-enzymatic reaction

Precursor of beef flavor can be isolated as a white fluffy powder.

White fluffy powder

Oil Water

broil stew beef broth

Amino acid + Sugar

Maillard reaction
2) Enzymatic reaction

Processed banana no fresh banana flavor

enzyme extracted from banana peel

Fresh banana flavor

4. Mechanisms for Flavor Compounds Formation
and Precursors in Foods
1) Volatile flavors developed in most food plants mainly at
the ripening stage - the result of plant metabolism through
enzymatic reaction.

2) Raw meat must be heated before it develops any

organoleptically acceptable flavor.
meat flavor (boiled beef)
1 2
S S
3
H3 C 5 S CH
3
4

3, 5-Dimethyl-1,2,4-trithiolane
 Model Studies
S S
CH 3 CHO + H S
2
S

(S)
H2S + CH3CHO CH3 CH S CH CH 3
SH SH

(O)

H3C S CH 3

S S
 Therefore,CH3CHO, H2S are precursors

HS C C COOH Beef flavor (reaction flavor)

NH2

Apply the knowledge we gained from the mechanism

and precursor studies to processed food.
a. Enhance the desirable food flavor.
b. Elimination of the undesirable food flavor.
c. Application of heated model system to processed
foods.
 5. Relationship between Physical Properties
of Compound and Flavor
B.P.(0C) Solubility in Sense of smell
H2O g/100 ml (ppm)

n-propanol 61.0 20.0 0.17

n-butanol 75.7 4.0 0.07
n-hexanal 131.0 0.5 0.03

CH3-S-CH3 37.5 insoluble 0.012

 Odor Threshold (ppm) in Water

2-t-pentenal 2.3
2-t-hexanal 10.0
2-t-heptanal 14.0
2-t-octenal 7.0
2-t-nonenal 3.2
2-t-decenal 33.8
2-t-undecenal 150.0

The series has an increase b.p. and decreased solubility in H2O

 Effect of Medium on the
Vapor Compositions of Flavor Compounds

Headspace Analysis

Compound Water Corn oil

(200ppm) (peak area) (peak area)

acetone 10 47
2-butanone 14 11
2-pentanone 22 5.7
2-hexanone 29 2.7
2-heptanone 24 0.7
 IV. Objectives of Flavor Chemistry

1. To understand the chemical composition of natural flavors and

the mechanism of their formation.

2. To retard or prevent the development of the off-

flavors in foods.

Reversion rancid flavor in soybean oil: hexenal, 2-pentyl furan

3. To restore the fresh flavor to a processed food

4. To improve the flavor of food by the addition of

synthetic flavor.

5. To produce new foods with special flavor such as

potato chip flavor.
6. To improve flavor by the acceleration of reactions which
produce desirable flavor compound (onion flavor: pH 5~7).

7. To assist geneticist to breed food raw material with

improved flavor compounds or flavor precursors.

8. To specify raw material and to control quality of food

products.

The price of tea can be correlated with GLC peak of linalool.

OH
CH3 C CH CH2 CH2 C CH CH2
CH3 CH3

Ceylon tea contains cis-hexenol, India tea doesnt contain cis-

hexenol
 II. Classification of Food Flavors

Flavor Class Subdivision Representative Example

Fruit flavor citrus-type flavors (terpeny) grapefruit, orange

berry-type flavors (non-terpeny) apple, raspberry, banana

Vegetable flavors lettuce, celery

Spice flavors aromatic cinnamon, peppermint

lachrymogenic onion, garlic
hot pepper, ginger

Beverage flavors unfermented flavors juices, milk

fermented flavors wine, beer, tea
compounded flavors soft drinks
Flavor Class Subdivision Representative Example

Meat flavors mammal flavors lean beef

sea food flavors fish, clams
Fat flavors olive oil, coconut fat, pork
at, butter fat
Cooked flavors broth beef bouillon
vegetable legume, potatoes
fruit marmalade
Processed flavors smoky flavors ham
broiled, fried flavors processed meat products
roasted, toasted, baked flavors coffee, snack foods,
processed cereals
Stench flavors cheese