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) Final Examination Home Work and Class Participation

40% 30% 30%

1. Introduction
I. II. III. Definition of Flavor Classification of Food Flavor 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 Objectives of Flavor Chemistry

IV.

2. Isolation and Separation of Flavor Compounds

I. II. III. Objective Prerequisites Apparatus for Isolation 1.Headspace analysis 2.Continuous solvent extraction 3.Steam distillation and continuous solvent extraction Extraction and Concentration Preliminary and Final Fractionation Dynamic Headspace analyzer Solid Phase Microextraction Analysis

IV. V. VI. V.

3. Flavor Identification by Spectrometric Methods

I. II. III. IV. V. Introduction of Spectrometric Analyses Ultra Violet Spectrometry Infrared Spectrometry Nuclear Magnetic Resonance Spectrometry Mass Spectrometry 1.Furans 2.Pyrroles 3.Thiophenes 4.Pyridines 5.Pyrazines

4. Manufacture of Food Flavor

I. II. III. IV. V. Natural or Imitation Flavor Problems of Using Natural Flavor Disadvantages of Using Imitation Flavor Advantages of Imitation Flavor Methods in Synthetic Flavor Reconstitution

5. Chemistry of Flavor Precursors

I. II. III. IV. Flavor Compounds from Carbohydrates and Proteins Thermal Degradation of Vitamin B1 Lipid Oxidation 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. II. Introduction 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 Isolation, Separation, and Identification of Roast Beef Flavor Simulated Meat Flavor Formation

III.

8. Interaction of Flavor Compounds with Foods

I. II. III.

Physical and Chemical Stability of Flavor Compounds of Lipid Food Effects and Interactions of Carbohydrates with Flavor Compounds 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. II.

Commercial Cherry Flavor and Solvent Interaction 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
Odor

Flavor

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 N

OCH3 CH2CH CH3 CH3

Vanilla: 4-Hydroxy-3-methoxy-benzolaldehyde

CHO

OCH3 OH

Cucumber: 2-Trans-6-cis-nonadienal

CH 2 CH CH 3 2 C C H H

CHO C C CH 2 H

Reversion Rancid Flavor of Soybean Oil: 2-Pentylfuran and 2-Pentenylfuran

(CH 2)4 CH 3

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 broil stew Amino acid + Sugar Water beef broth

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)
S H3 C
5 1

S
3

S
4

CH 3

3, 5-Dimethyl-1,2,4-trithiolane

Model Studies

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 H2O g/100 ml
20.0 4.0 0.5 insoluble

Sense of smell (ppm)

0.17 0.07 0.03 0.012

n-propanol n-butanol n-hexanal CH3-S-CH3

61.0 75.7 131.0 37.5

Odor Threshold (ppm) in Water

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

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 (200ppm) acetone 2-butanone 2-pentanone 2-hexanone 2-heptanone Water (peak area) 10 14 22 29 24 Corn oil (peak area) 47 11 5.7 2.7 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 offflavors 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 CH 3 C CH 3 CH CH 2 CH 2 C CH3 CH CH 2

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

II. Classification of Food Flavors

Flavor Class
Fruit flavor

Subdivision

Representative Example

citrus-type flavors (terpeny) grapefruit, orange berry-type flavors (non-terpeny) apple, raspberry, banana lettuce, celery aromatic lachrymogenic hot unfermented flavors fermented flavors compounded flavors cinnamon, peppermint onion, garlic pepper, ginger juices, milk wine, beer, tea soft drinks

Vegetable flavors Spice flavors

Beverage flavors

Flavor Class
Meat flavors Fat flavors Cooked flavors

Subdivision
mammal flavors sea food flavors

Representative Example

Processed flavors

Stench flavors

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