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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
Odor
Taste
Somato-sensory
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
(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.
covalently bound H-bonding proton (AH) an electronegative atom (B) lipophilic region (g)
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 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
synthetic propylene glycol (CH2OH-CHOHCH3) naturally produced glycerol (CH2OHCHOHCH2OH) xylitol (CH2-OH-CHOHCHOH-CHOH-CH2OH) from xylose sorbitol, and mannitol
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
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
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.
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.
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
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.
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
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)
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
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
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
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
The precursor of the sulfur compounds that are responsible for the flavor and aroma of this vegetable is S-(1-propenyl)-L-cysteine sulfoxide
Rapid hydrolysis of the S-(1-propenyl)-L-cysteine sulfoxide by allinase yields a hypothetical sulfenic acid intermediate along with ammonia and pyruvate
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
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
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
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.
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