6 Flavor
6 Flavor
Intermolecular Copigmentation
OH
OH
HO
+
O HO O OH O
OH
HO
+
O HO O OH
OH
OH O OH O O OH
OH OH OH
Cyanidin-3--D-glucoside
Cyanidin-3-(6-O-p-coumaroyl-D-glucoside
Copigment Stacking
Co-Factor
Pigment
Co-Factor
Anthocyanin Color
The
poor stability of anthocyanins creates the need to modify stability or find new sources
Increase
Abs
Result:
More red color at higher pH levels Greater application range in foods Enhanced antioxidant capacity; health benefits
l nm
Flavor Chemistry
Flavor is a combination of taste and aroma Taste - sweet, sour, bitter, salty - only what can be sensed on the tongue - nerve sensations for metallic and astringent Aroma - volatiles are released in mouth and then sensed in the nasal cavity
Sensory Impressions
Visual impression
Color, size, shape, luster Volatile, odor-active compounds Sweet, sour, bitter, salty Pain, burning, cold, warmth, astringent, fizzy
Odor
Taste
Somato-sensory
Savory
Diary
Fruit
Beverages
Sweet
AH/B Model
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
THE AH/B THEORY OF SWEETNESS 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. Intermolecular, anti-parallel hydrogen-bonding interaction
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
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
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
Sucralose
Splenda 1998, approved for table-top sweetener and use in various foods Approved already in UK, Canada before US Only one made from sugar
There was a law suit last year of this claim Splenda lost.not a natural compound.a bit of a deceptive marketing.
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
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
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
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
Flavor Houses
Givaudan IFF Bell Flavors Wild Sensus Flavors Virginia Dare Blue Pacific
Natural flavors can also be enzymatically or chemically produced - Fermentation reactions - Microbial enzymes Saccharomyces Sp. Lactobacillus Sp. Bacillus Sp. Molds Maillard flavor compounds Glucose Glucose Glucose Glucose + + + + Glutamic acid = chicken Lysine = burnt or fried potato Methionine = cabbage Phenylalanine = caramel + + + + Glutamic acid Lysine Methionine Phenylalanine = = = = chicken fried potato bean soup 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
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 Oxalacetic acid acetyl lactic acid
Acetaldehyde
Citric acid
Flavor stabalization
- Need to protect from light, heat, oxygen, water
Flavor interactions
pH, tartness of acids dependent on acid
- 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
- 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
- Sulfides - dimethyl, butyl, dimethyl sulfides -Aliphatic esters - butyrates, laurates, valerates - Di-keytones - diacetyl, acetylpropionyl - Lactones - undecalactone (C11) = peach/ sweet - octalactone (C8) = cooked coconut/ sweet
Gamma-Octalactone http://www.iff.com/Ingredients.nsf/FragIngredients!OpenForm
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
N-glycosylamine or N-fructosylamine
1-Amino-1-deoxy-2-ketose (Amadori intermediate) or 2-Amino-2-deoxy-1-aldose (Heynes intermediate) H2S NH3
Furans Thiophenes Pyrroles
Heterocyclizaion
Thiazoles Pyrroles
- 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
Sour
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
Bitter
KI CsCl MgSO4
Certain amino acids and peptides (dipeptide leucine-leucine) Alkaloids derived from pyridine (N-containing 6-membered ring) and purines
GYCOSIDES are sugars that have been added to a natural compound. Grapefruits generally have a bitter taste to them. This is due to the flavonoid compound Naringin.
Salty
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
Trigeminal Response
HOTNESS (pungency) is characteristic of piperine in black pepper and capsicum in red pepper and gingerols in ginger
HO OMe eugenol
Spicy is a characteristic of eugenol Clove, nutmeg, cinnamon, bay leaf
OH
menthol
Aromas
flavors
flavors
Browning
flavors
Allium sp.
(onions, garlic, shallots, leeks)
S-(1-propenyl)-L-cysteine sulfoxide Allinase 1-propenyl sulfenic acid
Chemical rearrangement Chemical Rearrangement w/heat
B O2 lipoxygenase
green
COH hexenal
melon, cucumber
COH
nonadienal
Sunlight Flavor
Sunlight will induce oxidized flavor and sunlight flavor and hay-like flavor. Oxidized flavor Sunlight flavor: burnt and / or cabbage
sunlight flavor
2) Riboflavin increase in milk will increase the sunlight flavor 3) Riboflavin removal prevent the sunlight flavor
Studies at the Silliker Laboratories in Illinois, the University of Michigan, and other leading labs and universities concluded that both sunlight and the fluorescent lighting in stores could decrease the freshness and flavor of milk and the potency of vital vitamins in it. But this research also showed that the majority of natural and artificial light could be blocked by containers that were yellow instead of white.
sunlight flavor
2) Riboflavin increase in milk will increase the sunlight flavor 3) Riboflavin removal prevent the sunlight flavor