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Food Flavor

Flavor Chemistry
Flavor is a combination of taste and aroma Taste Sweet, sour, bitter, salty Sensed on the tongue (protein receptors) Nerves sense metallic and astringent flavors Aroma Volatiles released directly from the food Volatiles that are released in the mouth, then sensed in the nasal cavity (retro-nasal).

Flavor Chemistry

Flavor Chemistry

Sensory Impressions

Visual impression

Color, size, shape, luster


Volatile, odor-active compounds Sweet, sour, bitter, salty

Odor

Taste

Somato-sensory

Pain, burning, cold, warmth, astringent, fizzy

Trigeminal nerve response

Texture, resistance, elasticity Sounds

Taste Substances

Sweet attention because of interest in sugar alternatives and the desire to find suitable replacements for the low-calorie sweeteners saccharin and cyclamate Bitter appears to be closely related to sweetness from a molecular structure- receptor relationship Sour Salty reduction of sodium in diets have stimulated renewed interest in the mechanisms of the salty taste

Structural basis of the sweet modality

-OH groups Acree and Shallenberger AH/B concept

Acree and Shallenberger


(Shallenberger & Acree) published a paper entitled the "Molecular Theory of Sweet Taste" in Nature [1969]. The model developed in that paper for sweetness was based on a structure-activity relationship between the simplest sweet tasting compounds and their structural features of the stimulants and has become known as the AH-B theory. The theory described with considerable success the structural features necessary for sweetness, but it was not sufficient to predict sweetness. That is, not all compounds that satisfied the theory tasted sweet nor was the theory able to predict potency level especially for very high potency sweeteners. However, all sweet compounds seemed to have an identifiable AHB feature.

Sweet tasting compounds should have

covalently bound H-bonding proton (AH) an electronegative atom (B) lipophilic region (g)

THE AH/B THEORY OF SWEETNESS


The perception of sweetness is proposed to be due to a chemical interaction that takes place on the tongue Between a tastant molecule and tongue receptor protein A sweet tastant molecule (i.e. glucose) is called the AH+/Bglycophore. It binds to the receptor B-/AH+ site through mechanisms that include H-bonding.

AH+ / BB Glycophore

Hydrophobic interaction
AH

AH

Tongue receptor protein molecule For sweetness to be perceived, a molecule needs to have certain requirements. It must be soluble in the chemical environment of the receptor site on the tongue. It must also have a certain molecular shape that will allow it to bond to the receptor protein. Lastly, the sugar must have the proper electronic distribution. This electronic distribution is often referred to as the AH, B system. The present theory of sweetness is AH-B-X (or gamma). There are three basic components to a sweetener, and the three sites are often represented as a triangle.

Identifying the AH+ and Bregions of two sweet tastant molecules: glucose and saccharin.

Gamma () sites are relatively hydrophobic functional groups such as benzene rings, multiple CH2 groups, and CH3

Sucralose

Non-caloric sweetener produced by the selective chlorination of the sucrose molecule Splenda 1998, approved for table-top sweetener and use in various foods
Clean, sweet taste (600X sweeter than sucrose and no undesirable off-flavor

Sucralose

Sucralose exhibits a high degree of crystallinity, high water solubility, and very good stability at high temperatures, thus making it an excellent ingredient for bakery applications. It is also quite stable at the pH of carbonated soft drinks, and only limited hydrolysis to monosaccharide units occurs during usual storage of these products. Sucralose possesses a sweetness time intensity profile similar to sucrose, and exhibits no bitterness or other unpleasant aftertastes.

Saccharin

Sweetn Low, The 1st artificial sweetener Accidentally found in 1879 by Remsen and Fahlberg Saccharin use increased during wars due to sugar rationing By 1917, common table-top sweetener in America Banned in 1977 due to safety issue 1991, withdrew ban, but with warning label 2000, removed warning label Intensely sweet, but slight bitter aftertaste

Saccharin

Saccharin is about 300 times as sweet as sucrose in concentrations up to the equivalent of a 10% sucrose solution, but the range is from 200 to 700 times the sweetness of sucrose depending on the concentration and the food matrix Saccharin exhibits a bitter, metallic aftertaste, especially to some individuals, and this effect becomes more evident with increasing concentration

Aspartame

Nutrasweet, Equal Discovered in 1965 by J. Schlatter Composed of aspartic acid and phenylalanine 4 kcal/g, but 200 times sweeter Approved in 1981 for table-top sweetener and powdered mixes Safety debating 1996, approved for use in all foods and beverage Short shelf life, not stable at high temperature

Aspartame

A caloric sweetener because it is a dipeptide that is completely digested after consumption. However, its intense sweetness (about 200 times as sweet as sucrose) allows functionality to be achieved at very low levels that provide insignificant calories. It is noted for a clean, sweet taste that is similar to that of sucrose.

Acesulfame K

Sunette, Sweet One Discovered in 1967 by Hoechst 1992, approved for gum and dry foods 1998, approved for liquid use Blending with Aspartame due to synergistic effect Stable at high temperature and long shelf life (34 years) Bitter aftertaste

Acesulfame K

Acesulfame K is about 200 times as sweet as sucrose at a 3% concentration in solution it exhibits a sweetness quality between that of cyclamates and saccharin. Acesulfame K possesses some metallic and bitter taste notes at higher concentrations it is especially useful when blended with other low-calorie sweeteners, such as aspartame

Acesulfame K

Acesulfame K is exceptionally stable at elevated temperatures encountered in baking, and it is also stable in acidic products, such as carbonated soft drinks. Acesulfame K is not metabolized in the body, thus providing no calories, and is excreted by the kidneys unchanged. Extensive testing has shown no toxic effects in animals, and exceptional stability in food applications.

Neotame

Brand new approved sweetener (Jan. 2000) 7,000 ~ 13,000 times sweeter than sugar Dipeptide methyl ester derivative; structurally similar to Aspartame Enhance sweetness and flavor Baked goods, non-alcoholic beverages (including soft drinks), chewing gum, confections and frostings, frozen desserts, processed fruits and fruit juices, toppings and syrups. Safe for human consumption

Polyhydric Alcohol Texturizers and Reduced-Calorie Sweeteners

Polyhydric alcohols are carbohydrate derivatives that contain only hydroxyl groups as functional groups they are generally water-soluble, hygroscopic materials that exhibit moderate viscosities at high concentrations in water. Usage of some polyhydric alcohols is growing because of demands for their reduced-calorie sweetener properties

Polyhydric Alcohol Texturizers and Reduced-Calorie Sweeteners

This class of substances includes

synthetic propylene glycol (CH2OH-CHOHCH3) naturally produced glycerol (CH2OHCHOHCH2OH) xylitol (CH2-OH-CHOHCHOH-CHOH-CH2OH) from xylose sorbitol, and mannitol

Polyhydric Alcohol Texturizers and ReducedCalorie Sweeteners

The polyhydroxy structures of these compounds provide water-binding properties that have been exploited in foods. Specific functions of polyhydric alcohols include control of viscosity and texture retention of moisture reduction of water activity control of crystallization improvement or retention of softness improvement of rehydration properties of dehydrated foods use as a solvent for flavor compounds

Bitter Taste Modality

BITTERNESS can be attributed to several inorganics and organics o KI CsCl MgSO4 o Certain amino acids and peptides (dipeptide leucine-leucine) o Alkaloids derived from pyridine (N-containing 6-membered ring)and purines

A = caffeine (1, 3, 7 trimethylxanthine)

B = theobromine (from cacao)

Bitter Taste Modality


Alpha Acids

Hop cones Humulus lupulus o Beer flavor (essential oils) and stability (anti-micro) o Beer bitterness (lupulone, colupulone, adlupulone) o Alpha-acids isomerize during boiling, increasing bitterness.

Bitter Taste Modality


GYCOSIDES are sugars that have been added to a natural compound. Citrus fruits generally have a bitter taste to them.
o o o

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This is due to the flavonoid compound Naringin. Naringin actually has 2 sugars (both glucose) as part of its structure. Compound is still intensely bitter. Removal of these sugars with naringinase, will render the compound tasteless. Naringin is then converted to Naringinin. The de-bittering of grapefruit juice can be done, if desired.

Salty Taste Modality


SALTY depends on the nature of the cation and anion in the ionic salt crystal structure; high molecular weight salts may be bitter; some salts may even exhibit sweetness Examples: NaCl NaBr NaI KCl LiBr NaNO3 = salty KBr = salty + bitter Lead acetate (toxic) = sweet

Sour Taste Modality


SOURNESS and sour taste is often thought of as acid However there is not a simple relationship between acid concentration (pH) and sourness Organic acids differ in sourness:
CITRIC ACID (0.05 N solution): fresh taste sensation LACTIC ACID (0.05 N solution): sour, tart PROPIONIC ACID (0.05 N solution): sour, cheesy ACETIC ACID (0.05 N solution): vinegar

PHOSPHORIC ACID (0.05 N solution): intense


MALIC ACID (0.05 N solution): green TARTARIC ACID (0.05 N solution): hard

Trigeminal Response
HOTNESS (pungency) is characteristic of piperine in black pepper and capsicum in red pepper and gingerols in ginger

Trigeminal Response
Cool is a characteristic of menthol, peppermint or mint oils

Food Flavors
Food flavors Mixtures of natural and/or artificial aromatic compounds designed to impart a flavor, modify a flavor, or mask an undesirable flavor Natural versus Artificial Natural - concentrated flavoring constituents derived from plant or animal sources Artificial - substances used to impart flavor that are not derived from plant or animal sources

Food Flavors
Most natural flavors are concentrated from botanicals -plants, trees, fruits, and vegetables Most artificial flavors are synthesized with high purity - pharmaceutical flavors

Isolation techniques - Steam distillation - mint and herbal oils - Solvent extraction - vanilla & oleoresins - Expression - citrus oils - Supercritical fluid extraction targeted extractions

Food Flavors
Natural flavors can also be enzymatically or chemically produced

- Fermentation reactions - Microbial enzymes


Saccharomyces Sp. Lactobacillus Sp. Bacillus Sp. Molds

Maillard flavor compounds Glucose + Glutamic acid = chicken Glucose + Lysine = burnt or fried potato Glucose + Methionine = cabbage Glucose + Phenylalanine = caramel Fructose + Glutamic acid = chicken Fructose + Lysine = fried potato Fructose + Methionine = bean soup Fructose + Phenylalanine = wet dog

Artificial Flavors
Typically are esters
Esters have pleasant fruity aromas, derived from acids a condensation reaction ACID + ALCOHOL --> ESTER + WATER Most artificial flavors are simple mixtures of esters i.e.

Isobutyl formate + isobutyl acetate = raspberry

Food Flavors
FERMENTATION and FLAVOR O O Diacetyl (CH3 C - C CH3 ) is a compound produced by Yeasts via fermentation of carbohydrates Major compound in the flavor of cultured dairy products Butter and butter-like flavor Compounds potentially used for diacetyl formation
Lactic acid Pyruvic acid Acetaldehyde Oxalacetic acid acetyl lactic acid Citric acid

Flavors complex mixtures of many compounds


-Amyl, butyl, ethyl esters - Amyl acetate = sweet fruity/ banana/ pear - Amyl caproate = sharp fruity/ pineapple - Amyl formate = sweet/ fruity -Organic acids containing aldehydes , aromatic esters, alcohols, ketones - Acetic acid = vinegary - Propionic acid = sour milk - Butyric acid = buttery

Flavors complex mixtures of many compounds


- Green flavors
- cis 3-hexenol = green leafy - trans 2-hexenal = green apple - Citrus flavors are mixtures of: - Aldehydes - Aromatic esters - Terpenes - Alcohols - Terpenes - Limonene = sweet citrus/ orange peel - Alpha pinene = warm resinous/ pine-like - Dipentene = fresh citrus/ lemon like

Flavors complex mixtures of many compounds


- Floral aldehydes - Citral = floral/ sweet/ lemon (Pledge) - Octanol = floral/ fatty/ orange-like - Dairy flavors - chemical and enzymatic -Short chain fatty acids Aliphatic alcohols - propyl, butyl, octyl -Lactonones - large chain delta lactones -Aliphatic aldehydes -acetyldehyde, butyraldehyde

Flavors complex mixtures of many compounds


Brown flavors - Caramelized, roasted or burnt character - Bread-yeast, caramel, chocolate, coffee, maple, peanut - Sweet brown compounds Vanillin = sweet/ chocolate-like Maltol = sweet/ malty/ brown (flavor enhancer) Di-hydrocoumarin = sweet/ caramel/ nutlike - Non-sweet brown compounds - Dimethyl pyrazine = nutty/roasted - 2,3,5 trimethyl pyrazine = chocolate/ roasted

Flavors complex mixtures of many compounds


- Woody compounds Alpha lonone = woody/balsamic/violet/red raspberry Beta lonone = woody/balsamic/black raspberry - Spicy compounds Cinnamic aldehyde = cinnamon Eugenol = cloves Thymol = thyme Zingerone = ginger oil Capsicum = peppers - Sulfur compounds - Diallyl disulfide = garlic onion - Methyl mercaptan = natural gas - Methyl thio butyrate = sour milk

Pungency
Cause characteristic hot, sharp, and stinging sensations Two kinds of pungent principles

non volatile and exert their effects on oral tissues (e.g. chili peppers, black pepper, and ginger) volatile (e.g. mustard, horseradish, radishes, onions, garlic, watercress, and clove)

Pungency of Chile Pepper


Chili peppers (Capsicum sp.) contain a group of substances known as capsaicinoids Capsaicinoids are vanillylamides of monocarboxylic acids with varying chain length (C8C11) and unsaturation Capsaicin is representative of these pungent principles

Pungency of Black and White Pepper

Black and white pepper are made from the berries of Piper nigrum Black pepper is prepared from immature green berries White pepper is made from more mature berries usually harvested at the time they are changing from green to yellow in color, but before they become red Principal pungent compound in pepper is piperine an amide

Pungency of Black and White Pepper

The structure of piperine

Trans geometry of the alkyl unsaturation is necessary for strong pungency Loss of pungency during exposure to light and storage is attributed mainly to isomerizations of these double bonds

Pungency of Ginger
Ginger is a spice derived from the rhizome of a tuberous perennial, Zingiber officinale Pungency of fresh ginger is caused by a group of phenylalkyl ketones called gingerols

Pungency of Ginger

Ginger is a spice derived from the rhizome of a tuberous perennial, Zingiber officinale Pungency of fresh ginger is caused by a group of phenylalkyl ketones called gingerols Exposure of gingerol to an elevated temperature leads to cleavage of the alkyl chain external to the keto group, yielding a methyl ketone, zingerone, which exhibits only mild pungency

Cooling

Cooling sensations occur when certain chemicals contact the nasal or oral tissues and stimulate a specific saporous receptor Cooling sensations are often associated with mint-like flavors, including peppermint, spearmint, and wintergreen. Most commonly used flavour is menthol

Vegetable, Fruit, and Spice Flavors

Sulfur-Containing Volatiles in Allium sp.


Plants in the genus Allium are characterized by strong, penetrating aromas Important members are onions, garlic, leek, chives, and shallots These plants lack the strong characterizing aroma unless the tissue is damaged and enzymes are decompartmentalized so that flavor precursors can be converted to odorous volatile

Reactions involved in the formation of onion flavour

The precursor of the sulfur compounds that are responsible for the flavor and aroma of this vegetable is S-(1-propenyl)-L-cysteine sulfoxide

Reactions involved in the formation of onion flavour

Rapid hydrolysis of the S-(1-propenyl)-L-cysteine sulfoxide by allinase yields a hypothetical sulfenic acid intermediate along with ammonia and pyruvate

Reactions involved in the formation of onion flavour

The sulfenic acid undergoes further rearrangements to yield the lachrymator, thiopropanal S-oxide Part of the unstable sulfenic acid also rearranges and decomposes to mercaptans, disulfides, trisulfides, and thiophenes

Vegetable, Fruit, and Spice Flavors

Sulfur-Containing Volatiles in the Cruciferae

The Cruciferae family contains Brassica plants such as cabbage, brussel sprouts, turnips, brown mustard, watercress, radishes and horseradish The active pungent principles in the Cruciferae are also volatile and therefore contribute to characteristic aromas The pungency sensation frequently involves irritation sensations, particularly in the nasal cavity The flavor compounds in these plants are formed through enzymic processes in disrupted tissues and through cooking

Reactions involved in the formation of Cruciferae flavors

Pungency in certain raw vegetables [mustards, (horse)radish, cabbages etc.] are due to thiosugar derivatives - glucosinolates

When cells are damaged, such as in cutting or chewing, the action of myrosinase triggers the breakdown of glucosinolates into isothiocyanates

Reactions involved in the formation of Cruciferae flavors

Processing at temperatures well above ambient (cooking and dehydrating) tends to destroy the isothiocyanates and enhance the amount of nitriles and other sulfur-containing degradation and rearrangement compounds.

Lipoxygenase-Derived Flavors in Plants

In plant tissues, enzymeinduced oxidative breakdown of unsaturated fatty acids occurs extensively yielding to characteristic aromas associated with some ripening fruits and disrupted tissues

Hexenal gives the green flavor while nonadienal gives the inherent cucumber and melon flavours

Sunlight Flavor

Riboflavin is a catalyst for production of the sunlight flavor. sunlight 1) Milk protein and riboflavin sunlight flavor 2) Riboflavin increase in milk will increase the sunlight flavor 3) Riboflavin removal prevent the sunlight flavor Sunlight and the fluorescent lighting in stores could decrease the freshness and flavor of milk and the potency of vital vitamins in it the majority of natural and artificial light could be blocked by containers that were yellow instead of white

Interactions of Flavours with Other Food Constituents


Aroma interactions with lipids, proteins and carbohydrates affect the retention of volatiles within the food The interactions affect the intensity and quality of food aroma. Proteins are known to bind flavour compounds through hydrophobic interactions with the volatiles

Interactions of Flavors with Protein


Retentions of volatiles by protein is lower than that by fat In emulsions the presence of protein in the oil/water interface induces a significant effect on flavour release and flavour perception of hydrophobic flavour compounds

Interactions of Flavors with Carbohydrates


Amylose form complexes with aromatic compound Hydrocolloids limit diffusion of aromatic compounds due to change in viscosity

Interactions of Flavors with Lipids


Addition of fat induces the significant retention of hydrophobic flavor compounds Melting point of fats influences the solubility of the aromatic compounds and thus the flavor release