Polytechnic University of the Philippines Sta.

Mesa Manila College of Nutrition and Food Science Department of food technology

Flavor and Aromatic compounds in Foods

Structure And Properties of Compounds in Aroma

Reported by: Roschell Agregado

Flavor
is the sensory impression of a food or other substance, and is determined mainly by the chemical senses of taste and smell. results from compounds:
1. Responsible for Aroma 2. Responsible for Taste

Aroma Compounds
Volatile. Recognized by receptor cells called Olfactory Cells . Can be classified in families based on their chemical structure and physicochemical sensory properties.

Non Enzymatic Reactions

observed only after prolonged storage of food. Lipid Peroxidation, Maillard Reaction, and Strecker degradation of Amino Acids. Furanones Caramel-like odor Meat broth, soya sauce, strawberry, coffee etc.

4-Hydroxy-5-methyl Norfuraneol

4-Methoxy-2,5-dimethyl Mesifuran

The hydroxy group in furanone II is methylated to form IV, the caramel-like aroma disappears.

Phenols
Smoke generated by burning of wood is used for cold or hot smoking of meat and fish products. Ferulic acid was identified as an important precursor in model experiments.

Thermal degradation of ferulic acid, 4-Vinyl-guaiacol (I), vanillin (II), and guaiacol (III).

Enzymatic Reactions
Esters
chemical compounds derived by reacting an oxoacid with a hydroxyl compound such as an alcohol or phenol. are ubiquitous. Nitrate esters, such as nitroglycerin, are known for their explosive properties, while polyesters are important plastics. Used as flavoring agents for its fruity aroma.

Lactones a cyclic ester it is characterized by a closed ring consisting of two or more carbon atoms and a single oxygen atom, with a ketone group =O in one of the carbons adjacent to the other oxygen.

4-Decanolide ( -decalactone)

Terpene
are a large and varied class of organic compounds, produced primarily by a wide variety of plants, particularly conifers. are also known as isoprenoids (isoprenes). primary constituents of the essential oils of many types of plants and flowers. Vitamin A is an example of a terpene.

Other Aroma Compounds

Sulfur Compounds Possess powerful and distinctive odours which contribute to both, pleasant and unpleasant. Brassica - cabbage, cauliflower, brussel sprouts, broccoli - milder than allium family.

Alliums
- onion, garlic - the flavor compound is formed from a precursor by the action of an enzyme. - the characteristic odour of garlic is due to allicin by the action of enzyme allinase

Carbonyl compounds, Alcohol

Obtained by degradation of carotene Fatty acids and amino acids are precursors of aldehydes. Carbohydrate degradation is the source of ethanal only. Aldehydes formed by Strecker degradation can also be obtained as metabolic by products of the enzymes.

Chemical compounds responsible for flavor and Thories on taste perception

1. Introduction i. Definition of flavors "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 produce that sensation." Flavor has been defined by Hall (1968). 2. Classification of food flavors Flavors can be classified by the general sensations that one feels when eating different foods. Flavor comes from three different sensations: taste, trigeminal and aroma (odor). It is generally agreed that taste sensations are divided into four major categories: saltiness, sweetness, sourness and bitterness. However, some Japanese scientists also include a fifth category called umami (savory) that can be represented by the flavor of glutamate.

Sweet Taste Sweet taste is produced by several different classes of compounds (Fig. 5), such as sugars, aldehydes, ketones, esters, amino acid, and synthetic sweeteners. Sour Taste Sour taste results from the presence of hydrogen ions on the tongue; however, sourness and acidity (pH) are not directly related, but there is some correlation. Sour taste produced by several different classes of compounds, such as esters, terpenoids, and organic acid (Citric, malic, tartaric) Salty Taste Salt taste is stimulated by most soluble salts having low molecular weights. Salty taste produced by several different classes of compounds, Maillard reaction. Bitter Taste Three major classes of organic compounds encountered in food materials are associated with bitterness: alkaloids, glycosides, and peptides.

Chemical compounds responsible for flavor and Thories on taste perception 1. Aldehydes (sweet taste) Is an organic compound containing a formyl group. This functional group, with the structure R-CHO, consists of a carbonyl centre bonded to hydrogen and an R group. The group without R is called the aldehydes group or formyl group. Acetaldehyde (systematically ethanal) is an organic chemical compound with the formula C2H4O or MeCHO. It occurs naturally in coffee, bread, and ripe fruit, and is produced by plants as part of their normal metabolism. Vanillin is a phenolic aldehyde, an organic compound with the molecular formula C8H8O3. It is the primary component of the extract of the vanilla bean. It is also found in roasted coffee.

2. Sugars (Sweet flavor) Sugar is a term for a class of edible crystalline carbohydrates, mainly sucrose, lactose, and fructose, characterized by a sweet flavor. In food, sugar almost exclusively refers to sucrose, which in its fully refined (or free sugar) form primarily comes from sugar cane and sugar beet, though is present in natural form in many carbohydrates.

Sucrose C12H22O11 Combustible, white crystals soluble in water, decomposes at 160 to 186C; derived from sugarcane or sugar beet; used as a sweetener in drinks and foods and to make syrups, preserves, and jams. Also known a saccharose; table sugar.

Guanidines Derivatives of guanidino acetic acid are among the sweetest compounds known until now. Guanidine Strongly alkaline member of the organic nitrogen compounds, commonly used in the hydrochloride form for the denaturation of proteins.

Sourness is always assumed to be a property of solutions of low pH, but it appears that the hydrogen ion H+* is much less important for taste than the undissociated forms of the organic acids that occur in acidic foodstuffs. Organic acid - is an organic compound with acidic properties. Citric acid is a weak organic acid. It is a natural preservative/conservative and is also used to add an acidic, or sour, taste to foods and soft drinks. Commercially important, versatile organic acid, widely used, along with its salts (citrates), in the food and beverage industries. Highly soluble in water and used in acidulants, antioxidants, flavourings, antimicrobial compounds and chelating agents. Usually obtained commercially by extraction from citrus fruits (it is the predominant acid in lemons, oranges and limes). Phosphoric Acid With its salts account for 25% of all the acids used in food industries. Main field of use is in the soft drink industry Used in fruit jellies, processed cheese and baking powder Active buffering agent in fermentation process.

Bitterness is exhibited by alkaloids such as quinine, picric acid, and heavy metal salts. Quinine is permitted as an additive in beverages, such as soft drinks, that also have tart-sweet attributes. Caffeine C8H10O2N4H2O An alkaloid found in a large number of plants, such as tea, coffee, cola, and mate. occurs in coffee, tea, and cola nuts

Theories of taste perception

Flavor antagonism - when one or more compounds are mixed together and interfere with flavor detection, i.e., the response (actual) is less than the arithmetic sum (theory).

Flavor synergism - when one or more compounds are mixed together and enhance the ability to detect the flavor, i.e., the response (actual) is greater than the arithmetic sum (theory).

 Shallenberger and Acree first proposed the AH/B theory for the saporous (taste eliciting) unit of all compounds that cause sweetness. The saporous unit is a combination of a covalently bound H-bonding proton and electronegative orbital positioned at a distance from the proton One of the atoms must also posses a hydrogen bonding atom. Oxygen, Nitrogen and Chlorine atoms frequently fulfill these roles.

FLAVOR ENHANCERS

FLAVOR ENHANCERS
Flavor enhancers are used in savory foods to enhance the existing flavor in the food.

COMMON FOOD FLAVOR ENHANCERS

Monosodium glutamate, MSG Monosodium glutamate is one of the chief flavor enhancers that are used as a flavor in protein rich food. Monosodium glutamate is a natural flavor that is used as a food additive under the category of food flavor enhancers.

Monopotassium glutamate Monopotassium glutamate is a potassium and acid salt of glutamic acid. It is one of the non-sodium food flavor enhancers. Calcium diglutamate This flavor enhancer is also called calcium glutamate or CDG.

Monosodium Glutamate (MSG) C5H8NNaO4 H2O

Monosodium glutamate is the sodium salt of glutamic acid. Glutamate is a naturally occurring amino acid that is found in nearly all foods, especially high protein foods such as dairy products, meat and fish and in many vegetables. It acts as a flavor enhancer and adds a fifth taste, called UMAMI .

5 -NUCLEOTIDES
5 -Inosine monophosphate (IMP) and 5 -guanosine monophosphate (GMP) Their mixture are white crystals or crystalline powder. Their flavor enhancing ability at 75 500 ppm is good in all food. some other specific effects, besides the MSG effect , have been described for nucleotides.

MALTOL
White crystalline powder having a characteristic caramel butterscotch odor. Maltol's sweetness adds to the odor of freshly baked bread. Sparingly soluble in water, soluble in ethanol and in propylene glycol. Maltose is produced from plant starch during the process of saccharification.

Control of Flavor and Aroma in Processed food

 Control of flavor and Aroma in processed food is the utmost importance in determining the quality and selling price of the finished product.

Factors must be considered:

The quality of the ingredients Conditions of processing must be carefully controlled Avoidance of contamination by flavorful compounds during processing or storage must be watched Foods must also be protected from contamination by bacteria and molds and stored under conditions where these microorganisms cannot grow rapidly

 Good flavor in a food product is desired by everyone who works in food production whether a housewife or the director of a nation-wide industry.

Caul has analyzed pattern of good flavor as the ff. sensations:

1. An early impact of appropriate flavor 2. Rapid development of an impression of highly blended and usually full-bodied 3. Pleasant mouth sensations 4. Absence of isolated unpleasant notes 5. Anticipation of next mouthful

Measurement of Flavor
>Since the flavor of food products is so important in determining their commercial value, many methods for measuring flavor have developed.

 Expert taster
through interest and opportunity he has developed a discriminating palate for the food of his company.

Panel of tasters
the panel may indicate its preference or judgment of quality by scoring a food on some well defined qualities.

Panel of tasters use:

Numerical scale is used so that the scoring of the individuals can be added readily to give a composite score. Difference tests are sometimes used in an attempt to get a more precise and reproducible test in flavor foods. Dilution test is a type of difference testing. A sample is presented to the judges and then other samples that may or may not contain the unknown at a definite level of dilution are offered.

 Ranking a series of samples are supplied to each member of the panel and he arranges them in order to increasing or decreasing quality of the characteristics. Flavor profile is a method for evaluating a flavor by describing it either as a whole or by characteristics. the reactions are broken down into (1)character notes,(2)order of appearance,(3)aftertaste, and (4)amplitude.

o Character notes are the protruding sensations, often exceedingly difficult to distinguish in a blend. o The Order of appearance may appear at first sight to be little importance or even absent. o Aftertaste is particularly common with foods that leave a residue in the mouth after swallowing. o Amplitude is the term used to express the total effect of flavor >it is rated by very low ,low, medium or high

 Consumer acceptance or preference If a new food is introduced, only one sample is offered to a large panel consumer panel, but if a food is modified, then two samples are submitted and a preference requested.

Flavor Intensifier: Monosodium Glutamate

It is claimed by some authors that this compound has little or no flavor itself but intensifies the flavor of meats and vegetables through a rounding or blending effect. It is widely used in stews, canned meats, soups, chowders, etc. They also reported that the effect is noticeable in the pH range 3.5 to 7.2, the range in which most foods are eaten.

FLAVORING EXTRACTS

Flavoring extracts
The Food and Drug Administration defines an extract as a solution in ethyl alcohol of proper strength of sapid and odorous principles derived from an aromatic plant, or parts of the plant, with or without its coloring matter, conforming in name to the plant used in its preparation. Flavoring extracts are made by adding the essential oil to alcohol or to water and alcohol, or by percolating the chopped plant or plant part with a mixture of water and alcohol.

 Vanilla extract is prepared by percolating macerated vanilla beans with alcohol, frequently in the presence of glycerol or sucrose. The flavorful compounds extracted are numerous but the most abundant is vanillin.

Synthetic Flavoring Substances

A synthetic banana flavouring. The concentrations in the final product of even the most abundant of these components will still be of the order of parts per million.
Major components Amyl acetate Amyl butyrate Ethyl butyrate Isoamyl acetate Isoamyl butyrate Linalool Minor components Amyl valerate Benzyl propionate Cyclohexyl propionate Ethyl caproate Geranyl propionate Heliotropin Vanillin Trace components Acetaldehyde Butyl acetate 2-Hexenal Isoamyl alcohol Lemon oil a-Ionone Methyl heptanone Orange oil

Non sugar sweeteners

Aspartame
A non-saccahride sweetener used as a sugar substitute in some foods and beverages White, odorless, crystalline powder approximately 200 times sweeter than sucrose, or table sugar. It is a methyl ester of a dipeptide. Aspartic acid and phenylalanine Slightly soluble in water and sparingly soluble in alcohols. Not soluble in fats and oils

Alitame
Formed from the amino acids and an amide High quality sweetness without an aftertaste Exhibit synergy Very soluble in water Used in hard candies and heat pasteurized foods

Acesulfame-K
Calorie free artificial sweetener dihydrooxathiazinone dioxides Approximately 200 times sweeter than sucrose but has slight bitter aftertaste The shelf-life of pure solid acesulfame K seems to be almost unlimited at room temperature Acesulfame K does not show a definitive melting point Soluble in water but slightly soluble in alcohols Exhibits synergism with other sweeteners pH stable Used in yogurts, soft drinks, candies and other confectionaries

Saccharin
a noncaloric substance produced from methyl anthranilate, a substance naturally found in grapes White, odorless, crystalline powder 300 times sweeter than sucrose but has a bitter or metallic aftertaste Taste is maintained over a long shelf life High stability in aqueous solution over a wide pH range

Cyclamate
the sodium or calcium salt of cyclamic acid 30 50 times sweeter than sugar Stable under heating

Sucralose
Sucralose is derived from sucrose in a process that substitutes chlorine atoms for hydroxyl group It has a pleasant sweet taste similar to sucrose and has no unpleasant aftertaste. The sweetener is highly soluble in water, ethanol, and methanol and has negligible effect on the pH of solutions. Soluble in water and ethanol

Monellin
From the pulp of Dioscoreophyllum cumminsii Sweet protein

Thaumatins
From the fruit Thaumatococcus daniellii Synergestic effect

Curculin and Miraculin

From the fruit Curculigo latifolia and Synsepalum dulcificum tasteless

REFERENCE BELITZ, H. D. ET AL. 2009. FOOD CHEMISTRY, 4TH ED..pdf Fisher C., Scott T.R. Food Flavors - Biology and Chemistry (RSC, 1997)(0854045384).pdf Food - The Chemistry of its Components.pdf deMAN, J. M. 1999. PRINCIPLES OF FOOD CHEMISTRY. 3RD ED..pdf