NATURAL & FUNCTIONALNATURAL & FUNCTIONAL

FLAVOURSFLAVOURS

John MargettsJohn Margetts

UNGERER LIMITED UNGERER LIMITED ©©20042004

Ungerer Group

Functional Flavours

Ungerer Group

Natural Flavours

Summary

Ungerer GroupUngerer Group•• MultiMulti--million dollar international Flavour, Fragrance, Essential Oils million dollar international Flavour, Fragrance, Essential Oils and and

Aroma chemical companyAroma chemical company

•• Expanding international business with subsidiaries around worldExpanding international business with subsidiaries around world

•• Presence in over 27 countries Presence in over 27 countries

•• 110 years history of providing customer satisfaction110 years history of providing customer satisfaction

•• Worldwide production and technical support facilitiesWorldwide production and technical support facilities

•• Established reputation within the industryEstablished reputation within the industry

Product PortfolioProduct Portfolio

•• Natural & Nature Identical Flavourings Natural & Nature Identical Flavourings

•• Essential Oils, Aroma Chemicals & Natural ExtractsEssential Oils, Aroma Chemicals & Natural Extracts

•• Liquid Liquid –– water soluble, oil soluble, emulsionwater soluble, oil soluble, emulsion

•• Powder Powder –– dry blend, spray dry, encapsulatedry blend, spray dry, encapsulate

•• Concept Design & Market IntelligenceConcept Design & Market Intelligence

•• Regulatory SupportRegulatory Support

Ungerer NutraceuticalsUngerer Nutraceuticals

•• Utilisation of functional ingredients in food and beveragesUtilisation of functional ingredients in food and beverages

•• Using Ungerer flavour expertise to either enhance the flavour Using Ungerer flavour expertise to either enhance the flavour of the of the

functional ingredient or to mask itfunctional ingredient or to mask it

•• Functional ingredients such as Spirulina, Pycnogenol, CoFunctional ingredients such as Spirulina, Pycnogenol, Co--enzyme enzyme

Q10, Aloe Vera, Green BarleyQ10, Aloe Vera, Green Barley

• Natural, non-GMO, healthy foods• Nutraceuticals, cosmoceuticals• Nutritional enhancement – vitamins, calcium, omega 3• Well being, natural remedies – herbal extracts, echinacea, spirulina• Healthy or super foods – soy, green barley grass• Pre-biotic & now pro-biotic• Low salt, low fat, no MSG• Low carbohydrate (Glycemic Index)• Atkins, South Beach, Zone, Weight Watchers etc• Combinations of taste and functionality – layering• Good for you and tastes good!

TrendsTrends

Ungerer Group

Functional Flavours

Natural Flavours

Summary

Functional FlavoursFunctional Flavours

•• Flavour EnhancementFlavour Enhancement

• low fat, low salt, low carbohydrate, low alcohol, non-MSG

•• Flavour MaskingFlavour Masking

•• Soy, vitamins, omega 3/6, nutraceuticals, herbal extracts, Soy, vitamins, omega 3/6, nutraceuticals, herbal extracts, caffeine, taurine, artificial sweetenerscaffeine, taurine, artificial sweeteners

•• Enhancement or MaskingEnhancement or Masking

•• The key is to consider the total taste sensation.The key is to consider the total taste sensation.

Flavour MaskingFlavour Masking

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Flavour PerceptionFlavour Perception

•• TasteTaste

• non-volatile compounds

• 5 basic tastes – sweet, sour, salt, bitter, umami

•• SmellSmell

•• volatile, small moleculesvolatile, small molecules

•• 3600+ different identifiable compounds3600+ different identifiable compounds

TasteTaste•• Classical taste map is an over simplificationClassical taste map is an over simplification

•• Sensitivity to all tastes distributed across whole tongueSensitivity to all tastes distributed across whole tongue

•• Some areas more specific/more sensitiveSome areas more specific/more sensitive

•• Taste buds use a combination of different cellsTaste buds use a combination of different cells

•• Salt & sour Salt & sour -- ion channelion channel response

•• Sweet & bitter Sweet & bitter -- surface protein surface protein responseresponse

•• Mask by preventing responseMask by preventing response

•• Mask by competing responsesMask by competing responses

Taste Masking ComponentsTaste Masking ComponentsPreventing ResponsePreventing Response

•• Modify texture Modify texture –– e.g. hydrocolloidse.g. hydrocolloids

•• Coat taste buds Coat taste buds –– e.g. fats, emulsifierse.g. fats, emulsifiers

Competing ResponsesCompeting Responses

•• Sweeteners Sweeteners –– e.g. sucrose, glucose, fructosee.g. sucrose, glucose, fructose

•• High intensity sweeteners e.g. saccharin, aspartame, acesulfameHigh intensity sweeteners e.g. saccharin, aspartame, acesulfame K, K, Sucralose, thaumatin, NHDC, monoSucralose, thaumatin, NHDC, mono--ammonium glycyrrhizinateammonium glycyrrhizinate

• Salt – e.g. sodium chloride, sodium citrate

• Sour – e.g. citric acid, malic acid

Flavour Masking ComponentsFlavour Masking ComponentsMasking ComponentsMasking Components

•• Creamy, buttery, vanilla, milky notesCreamy, buttery, vanilla, milky notes

Competing ResponsesCompeting Responses

•• Sweet, fruity, citrus, minty notesSweet, fruity, citrus, minty notes

Flavour Enhancement ComponentsFlavour Enhancement ComponentsLow FatLow Fat

•• Creamy, buttery, vanilla, milky notesCreamy, buttery, vanilla, milky notes

Low CarbLow Carb

•• Sweet, fruity, citrus notesSweet, fruity, citrus notes

Low AlcoholLow Alcohol

•• Fermented notesFermented notes

Low Salt/NonLow Salt/Non--MSGMSG

•• No/low sodium, natural extracts with savoury enhancing characterNo/low sodium, natural extracts with savoury enhancing characteristicsistics

Enhancement & Masking Enhancement & Masking

•• Custom flavour solutionCustom flavour solution

•• Dependant on total product matrixDependant on total product matrix

•• High quality complex flavour deliveryHigh quality complex flavour delivery

•• The key is to consider the total taste sensationThe key is to consider the total taste sensation

Ungerer Group

Functional Flavours

Natural Flavours

Summary

Natural FlavoursNatural Flavours

US Definition of NaturalUS Definition of Natural

Code of Federal Regulations (CFR) 21, Part 101.22 (a) (3).Code of Federal Regulations (CFR) 21, Part 101.22 (a) (3).

‘the term natural flavor or natural flavoring means the essentialoil, oleoresin, essence or extractive, protein hydrolysate, distillate, or any product of roasting, heating or enzymolysis, which contains the flavoring constituents derived from a spice, fruit or fruit juice, vegetable or vegetable juice, edible yeast, herb, bark, bud, root, leaf or similar plant material, meat, seafood, poultry, eggs, dairy

products, or fermentation products thereof, whose significant function in food is flavoring rather than nutritional’

EU Definition of NaturalEU Definition of Natural

Community Directive 88/388/EEC as amended by 91/71/EECCommunity Directive 88/388/EEC as amended by 91/71/EEC

Broadly, natural ingredients used in flavourings must be obtained ‘by appropriate physical processes (including distillation and

solvent extraction) or enzymatic or microbiological processes from material of vegetable or animal origin either in the raw state or after processing for human consumption by traditional food-

preparation processes (including drying, torrefaction and fermentation)’

Accepted PrinciplesAccepted Principles

•• Source materials must occur in natureSource materials must occur in nature

•• Water and atmospheric air can be used during productionWater and atmospheric air can be used during production

•• When considering a process, the resultant material must be founWhen considering a process, the resultant material must be found in nature d in nature or as an artefact in traditional foodsor as an artefact in traditional foods

•• In biotechnological processes, the substrate must be natural, bIn biotechnological processes, the substrate must be natural, but the ut the nutrients can be used regardless of sourcenutrients can be used regardless of source

•• Processing conditions are allowed so long as they meet the critProcessing conditions are allowed so long as they meet the criteria of eria of traditional or intraditional or in--home preparation techniqueshome preparation techniques

ChiralityChirality

•• Different isomers of the same moleculeDifferent isomers of the same molecule

•• Sometimes referred to as mirror imagesSometimes referred to as mirror images

•• These are know as stereoThese are know as stereo--isomers or enantiomersisomers or enantiomers

•• Nature is very specific and selective, favouring one isomerNature is very specific and selective, favouring one isomer

•• Chemical synthesis tends to result in mixed isomers Chemical synthesis tends to result in mixed isomers -- racemicracemic

•• Individual isomers can have distinctive and characteristic aromIndividual isomers can have distinctive and characteristic aromaa

ChiralityChiralityMolecule Aroma

(R)-(+)-2-methyl butanol(S)-(-)-2-methyl butanol(1S,3S,4R)-(+)-menthol(1R,3R,4S)-(-)-menthol(R)-(+)-limonene(S)-(-)-limonene(4S)-(+)-carvone(4R)-(-)-carvone(1S,4R)-cis-p-menthan-8-thiol-3-one(1R,4S)-cis-p-menthan-8-thiol-3-one(+)-(E,S)-5-methyl-2-hepten-4-one(-)-(E,R)-5-methyl-2-hepten-4-one

fermented, fattyethereal, freshminty, musty, bittercooling, minty, freshcitrus, orangecitrus, harsh, turpentinecaraway, herbaceousspearmintblackcurrant leaf, tropical fruit, fruityrubber, burnt, sulphuroushazelnut, fatty, metallic, stronghazelnut, soft, butter, chocolate, weak

Flavouring PreparationsFlavouring Preparations

•• Essential OilsEssential Oils

•• ExtractsExtracts

•• OleoresinsOleoresins

•• TincturesTinctures

•• DistillatesDistillates

•• Juice ConcentratesJuice Concentrates

Methods of PreparationMethods of Preparation

•• ExpressionExpression

•• MacerationMaceration

•• DistillationDistillation

•• ExtractionExtraction

•• ConcentrationConcentration

Plant MaterialsPlant MaterialsCommon Name Botanical Name Parts Used

Allspice (Pimento)Almond, bitterBalsum ToluBlackcurrantCinnamonDavanaEucalyptusFennel, sweetGarlicGingerHopsJasmineLemonLemongrassLocustMintPeachPine, ScotchRoseVanilla

Pimento dioicaPrunus amygdalus var. amaraToluifera balsamumRibes nigrumCinnamomum zeylanicumArtemisia pallensEucalyptus globulusFoeniculum vulgare var. dulceAllium sativumZingiber officinaleHumulus lupulusJasminum officinaleCitrus limonCymbopogon citratus C. flexuosusCeratonia siliquaMentha spp.Prunus persicaPinus sylvestrisRosa albaVanilla planifolia

Berry, LeafNutGum ExudateBud, LeafBark, LeafHerbLeafSeed, HerbBulbRhizomeFemale flowerFlowerFruit, PeelGrassBeanFlowering top & leafLeaf, fruit, kernelNeedle, twigFlower, Hip, LeafFruit/pod

ExtractsExtracts•• Aqueous extractionAqueous extraction

•• water, water and organic solventwater, water and organic solvent

•• NonNon--aqueous/organic solventaqueous/organic solvent

•• polar polar -- ethanolethanol

•• nonnon--polar polar -- hexanehexane

•• critical fluid extraction critical fluid extraction -- COCO22

•• ConcentrationConcentration

•• distillation, reverse osmosis, column separationdistillation, reverse osmosis, column separation

Essential OilsEssential Oils•• Expressed OilsExpressed Oils

•• abrasion & pressingabrasion & pressing

•• Distilled OilsDistilled Oils

•• water, water & steam, steam distillationwater, water & steam, steam distillation

•• Essence OilsEssence Oils

•• water phase recovered from citrus processingwater phase recovered from citrus processing

•• Folded/Concentrated OilsFolded/Concentrated Oils

•• distillation, fractionationdistillation, fractionation

Essential Oil ComponentsEssential Oil ComponentsEssential Oil Principle ComponentsBergamot

Grapefruit

Lemon

Lime (distilled)

Lime (expressed)

Mandarin Petitgrain

Orange Peel (Sweet)

linalyl acetate, limonene, linalool, beta pinene, gamma terpinene, geranial, neral, geraniol, neryl acetate, geranyl acetate, bergaptene

limonene, myrcene, octanal, decanal, linalool, nootkatone, citronellal, neral, geranial, beta sinensal

limonene, beta pinene, gamma terpinene, geranial, neral, neryl acetate, geranyl acetate, citronellal, linalool, nonanal

limonene, gamma terpinene, alpha terpinolene, alpha terpineol, alpha terpinene, 1,4 – cineole, beta pinene, myrcene, beta bisabolene, gamma terpineol

limonene, beta pinene, gamma terpinene, sabinene, alpha pinene, beta bisabolene, geranial, myrcene, alpha bergamotene, farnesene, neral

limonene, dimethyl anthranilate, geraniol, citral, citronellal

limonene, myrcene, decanal, octanal, linalool, citronellal, neral, geranial, valencene, beta sinensal, alpha sinensal

Essential Oil ComponentsEssential Oil ComponentsEssential Oil Principle ComponentsBitter Almond

Cassia

Cinnamon Leaf

Caraway

Fusel

Ho Wood

Litsea Cubeba

Spearmint Oil

benzaldehyde

cinnamaldehyde, ortho-methoxy cinnamaldehyde, cinnamyl acetate, benzaldehyde, ethyl cinnamate, salicaldehyde

eugenol, caryophyllene, cinnamaldehyde, iso eugenol, linalool, cinnamyl acetate

d-carvone, limonene, myrcene, alpha phellandrene, alpha pinene, beta pinene

iso amyl alcohol (3-methyl butanol & 2-methyl butanol), butanol, ethanol, iso butanol, propanol, pyrazines

Linalool

geranial, neral, limonene, 6-methyl hept-5-en-2-one, myrcene, linalyl acetate, linalool, geraniol, nerol, caryophyllene, citronellal

l-carvone, limonene, myrcene, 1,8-cineole, carvyl acetate, dihydrocarvyl acetate, dihydrocarveol, octan-3-ol, cis-jasmone

More Naturals NeededMore Naturals Needed

•• Wide range of natural extracts, essential oils, distillates & tWide range of natural extracts, essential oils, distillates & tincturesinctures

•• Global demand for natural continues to riseGlobal demand for natural continues to rise

•• Demand exceeds supply or cost is prohibitiveDemand exceeds supply or cost is prohibitive

•• New technologies required for natural flavour molecules (naturaNew technologies required for natural flavour molecules (natural substances)l substances)

•• IsolationIsolation

•• BiotechnologyBiotechnology

•• Soft ChemistrySoft Chemistry

Isolation Isolation

•• Exclusively physical techniquesExclusively physical techniques

•• Distillation Distillation -- steam, water, fractional, molecular, pervaporationsteam, water, fractional, molecular, pervaporation

•• Solvent extraction Solvent extraction -- including subincluding sub--critical and supercritical and super--critical solvents)critical solvents)

•• Membrane technologies Membrane technologies -- ultraultra--filtration and reverse osmosisfiltration and reverse osmosis

•• Preparative chromatographyPreparative chromatography

•• Columns Columns -- adsorption and exclusionadsorption and exclusion

Natural IsolatesNatural IsolatesNatural isolate SourceAcetaldehydeIso amyl alcoholBenzaldehydeIso butanolCinnamaldehydeCitralDimethyl AnthranilateDimethyl SulphideEthyl ButyrateEugenolCis-3-hexenolGeraniolGeranyl acetateAlpha ironeLimoneneLinaloolLinalyl acetatel-mentholMethyl cinnamateNootkatonePhenyl Ethyl AlcoholPyrazinesValenceneVanillin

OrangeFuselBitter Almond, Apricot, PeachFuselCassia, cinnamon barkLitsea Cubeba, lemongrass, lemonMandarin PetitgrainMintOrangeClove, bay, cinnamon leafMintCitronellaLitsea Cubeba, lemongrassOrrisCitrusHo wood, rosewood, corianderMentha citrata, petitgrainMintSweet basil, ocimum canumGrapefruitRose, Geranium RoseFuselOrangeVanilla

BiotechnologyBiotechnology

•• Book of Genesis Book of Genesis -- reference to wine makingreference to wine making

•• 6000 BC 6000 BC –– beer brewing by Babylonians beer brewing by Babylonians

•• 3000 BC 3000 BC –– bread making by Egyptiansbread making by Egyptians

•• 2500 BC 2500 BC –– butter & cheese making by Syriansbutter & cheese making by Syrians

•• 2000 BC 2000 BC –– vinegar making by Sumeriansvinegar making by Sumerians

•• 1850 AD 1850 AD –– beginnings of scientific understandingbeginnings of scientific understanding

Past 150 yearsPast 150 years

•• Understanding of yeast, mould & bacteriaUnderstanding of yeast, mould & bacteria

•• Development of Penicillin Development of Penicillin

•• Isolation & purification of enzymesIsolation & purification of enzymes

•• Discovery of the structure of DNADiscovery of the structure of DNA

•• Recombinant DNA technologyRecombinant DNA technology

•• Genetic engineeringGenetic engineering

•• BiotechnologyBiotechnology

Flavour BiotechnologyFlavour Biotechnology

•• Intact/whole organisms Intact/whole organisms -- fermentationfermentation

•• Crude enzyme preparations Crude enzyme preparations –– complex transformationcomplex transformation

•• Isolated enzymes Isolated enzymes –– transformation or transesterificationtransformation or transesterification

•• Plant cell tissue cultures Plant cell tissue cultures –– not commercialisednot commercialised

•• Genetic engineering Genetic engineering –– not acceptable!not acceptable!

•• Total flavour enhancementTotal flavour enhancement

•• Specific moleculesSpecific molecules

Total Flavour EnhancementTotal Flavour Enhancement

•• Enzyme modified cheese/natural butter flavoursEnzyme modified cheese/natural butter flavours

•• Fatty acid release from triglycerides by hydrolysis using lipasFatty acid release from triglycerides by hydrolysis using lipases. es. Selectivity can be modified depending on the source of lipase e.Selectivity can be modified depending on the source of lipase e.g. g. Mucor Mucor mieheimiehei is known to exhibit a high selectivity towards short chain fattis known to exhibit a high selectivity towards short chain fatty y acidsacids

•• Concentrated blue cheese notesConcentrated blue cheese notes

•• Methyl ketone generation by microbial fermentation using e.g. Methyl ketone generation by microbial fermentation using e.g. Penicillium roquefortiPenicillium roqueforti. Lipolytic enzymes produce free fatty acids that are . Lipolytic enzymes produce free fatty acids that are then oxidised to the equivalent then oxidised to the equivalent αα--keto acids and then decarboxylated to keto acids and then decarboxylated to form methyl ketonesform methyl ketones

AlcoholsAlcohols•• Short chain alcoholsShort chain alcohols

•• Either products or byEither products or by--products of spirit and/or ethanol production. Fusel Oil products of spirit and/or ethanol production. Fusel Oil contains many primary & secondary alcoholscontains many primary & secondary alcohols

•• Phenyl ethyl alcoholPhenyl ethyl alcohol

•• Fermentation using e.g. Fermentation using e.g. Aspergillus nigerAspergillus niger strains or strains or Hansenula anomalaHansenula anomala

CH2 CH2

CH2OH

deaminase decarboxylase

-CO2

reductase

-NADH

L-phenylalanine phenylacetaldehyde phenylethyl alcoholphenylpyruvic acid

-NH3

CNH2 COOH

H

CH2

C COOHO CH O

CH2

CarbonylsCarbonyls•• AcetaldehydeAcetaldehyde

•• Ethanol conversion using alcohol dehydrogenase enzyme. Poor proEthanol conversion using alcohol dehydrogenase enzyme. Poor process due to cocess due to co--factor factor reliance. An easier approach is to find microorganisms with the reliance. An easier approach is to find microorganisms with the appropriate metabolic appropriate metabolic pathways and/or that will produce the required enzymes in situ. pathways and/or that will produce the required enzymes in situ. Ethanol may be oxidised by Ethanol may be oxidised by the production in situ of methanol oxidase and catalase using mithe production in situ of methanol oxidase and catalase using microorganisms such as yeast croorganisms such as yeast of the genera of the genera PichiaPichia, , CandidaCandida, , HansenulaHansenula and and TorulopsisTorulopsis

•• DiacetylDiacetyl

•• Principle component in dairy Principle component in dairy ““starter culturestarter culture””. Industrial production reported from citric acid . Industrial production reported from citric acid using using Streptococcus cremorisStreptococcus cremoris and and Streptococcus diacetylactisStreptococcus diacetylactis

CH2 COOH

CHO COOH

CH2 COOH

CH3 C COOH

OCH2 COOH

CO COOH

citric acid oxaloacetic acid pyruvic acid

CH3 C C CH3

H

OHO

CH3 C C CH3

O O

acetoindiacetyl

CH3 C C CH3

OHO

COOH

α-acetolactic acid

CarbonylsCarbonyls•• Raspberry Ketone Raspberry Ketone -- 44--hydroxyhydroxy--phenylphenyl--butanbutan--22--one one

•• Betuloside may be extracted from birch bark (also from rhododenBetuloside may be extracted from birch bark (also from rhododendron dron and maple) and hydrolysed with, for example, a and maple) and hydrolysed with, for example, a ββ--glucosidase from glucosidase from Aspergillus nigerAspergillus niger to form betuligenol. This may then be converted with a to form betuligenol. This may then be converted with a microorganism containing a secondary alcohol dehydrogenase, suchmicroorganism containing a secondary alcohol dehydrogenase, such as as the yeast the yeast Candida boidiniiCandida boidinii, into Raspberry Ketone, into Raspberry Ketone

OH

β-glucosidase

OH

Candida boidinii

betuloside betuligenol raspberry ketone

C

CH3

O GlucoseH

(CH2)2

C

CH3

O

OH

CH3

OHCH

(CH2)2 (CH2)2

AcidsAcids•• Conversion from alcoholsConversion from alcohols

•• Fusel oil or other natural alcohol sources can be converted by Fusel oil or other natural alcohol sources can be converted by ““vinegarvinegar””microbial fermentation using microbial fermentation using AcetobacterAcetobacter and and PropionibacterPropionibacter speciesspecies

•• Hydrolysis of triglyceridesHydrolysis of triglycerides

•• Vegetable oils, nut oils and animal fats can be converted througVegetable oils, nut oils and animal fats can be converted through the action h the action of lipases which catalyse the hydrolysis of lipids to fatty acidof lipases which catalyse the hydrolysis of lipids to fatty acids and glycerols and glycerol

R-CH2-OH R-COOH

O2

Acetobacter species

LactonesLactonesCH3 (CH2)5 (CH2)7 COOH

OH

12-hydroxy-9-octadecenoic acid (ricinoleic acid )

(CH2)5

OH

COOHCH3 (CH2)5 10-hydroxy-7-hexadecenoic acid

CH3 (CH2)5

OH

4-hydroxydecanoic acid

CH3 (CH2)5O O

γ-decalactone

COOH

Example of lactone production is the microbial conversion of ricinoleic acid (from castor oil) via partial β-oxidation into γ-decalactone, which has a peach like aroma, by yeast such asSporidiobolus salmonicolor and Yarrowia lipolytica

EstersEsters•• Lipase catalysed reactionLipase catalysed reaction

•• Reverse reaction to the release of fatty acids from triglycerideReverse reaction to the release of fatty acids from triglycerides. Major s. Major requirement is to removal of water to drive the reaction forwardrequirement is to removal of water to drive the reaction forward. Well . Well documented and principle method for combining an acid and alcohodocumented and principle method for combining an acid and alcohol to form l to form an esteran ester

R1 - CH2 - OH + O

CHO

R

alcohol acid

Lipase esterase

-H2O

R1 - C - O - C - R

ester

O

Sulphur CompoundsSulphur Compounds•• Methional/olMethional/ol

•• The biofermentation of methional/ol from natural L-methionine. Under conditions of nitrogen limitation growing yeast will deaminate L-methionine to produce 2-oxo-4-(methylthio)-butyric acid. This α-keto acid is then decarboxylated to form methional, which in turn is rapidly reduced to methionol

S COH

NH2

O

deamination S COH

O

O

L-methionine 2-oxo-4(m ethylthio)-butyric acid

decarboxylation SC

O

Hreduction S

CH2OH

m ethional m ethionol

VanillinVanillin

OH

OCH3

CH

CH

C

OH

CH

CH

CH3

OCH3

OH

CH2

CH

CH2

OCH2

OH

OH

OCH3

C HH

OH

OH

OCH3

COH

OH

OCH3

COHO

ferulic acid isoeugenol eugenol

vanillyl alcohol vanillin vanillic acid

Soft ChemistrySoft Chemistry

•• Does not use biocatalystsDoes not use biocatalysts

•• Does not use hard or aggressive chemicalsDoes not use hard or aggressive chemicals

•• US US -- ‘‘any product of roasting, heatingany product of roasting, heating’’

•• EU EU -- ‘‘traditional foodtraditional food--preparation processespreparation processes’’

•• Known as Known as ‘‘softsoft’’ or or ‘‘cookingcooking’’ chemistrychemistry

•• Lead by US, Europe slower to adoptLead by US, Europe slower to adopt

Accepted PrinciplesAccepted Principles

•• Source materials must occur in natureSource materials must occur in nature

•• Water and atmospheric air can be used during productionWater and atmospheric air can be used during production

•• When considering a process, the resultant material must be founWhen considering a process, the resultant material must be found in d in nature or as an artefact in traditional foodsnature or as an artefact in traditional foods

•• In biotechnological processes, the substrate must be natural, bIn biotechnological processes, the substrate must be natural, but the ut the nutrients can be used regardless of sourcenutrients can be used regardless of source

•• Processing conditions are allowed so long as they meet the critProcessing conditions are allowed so long as they meet the criteria eria of traditional or inof traditional or in--home preparation techniqueshome preparation techniques

BenzaldehydeBenzaldehyde•• Cinnamon bark, cinnamon leaf and cassia oil contain large amountCinnamon bark, cinnamon leaf and cassia oil contain large amounts of s of cinnamaldehyde. Under mild basic conditions with heating the thcinnamaldehyde. Under mild basic conditions with heating the this breaks is breaks down to form benzaldehyde and acetaldehyde in a retrodown to form benzaldehyde and acetaldehyde in a retro--aldol reactionaldol reaction

H O

H

O

cis,trans cinnamaldehyde

+ OH H

O

+ H

O

benzaldehyde acetaldehyde

FuraneolFuraneol®®

•• 2,52,5--dimethyldimethyl--44--hydroxyhydroxy--2H2H--furanfuran--33--one (Furaneolone (Furaneol®®) can be formed by can be formed by soft chemistry in the reaction between Lsoft chemistry in the reaction between L--Rhamnose and LRhamnose and L--prolineproline

+

NH

COOH O

HOO

CH3

5

4 3

2 1

L-rhamone L-proline 2,5-dim ethyl-3-hydroxy-3(2H)-furanone

H3C6

H

C

C

C

C

C

CH3

O

OH

OH

H

H

H

H

HO

HO

1

2

3

4

5

6

VanillinVanillin•• Turmeric root, extracts of turmeric root or purified curcumin isTurmeric root, extracts of turmeric root or purified curcumin is hydrolysed hydrolysed by the action of heat and pressure in the presence of water, to by the action of heat and pressure in the presence of water, to form form vanillin. The ratio of vanillin and other products was controllvanillin. The ratio of vanillin and other products was controlled by ed by adjusting the pHadjusting the pH

HO

CH3O

CH CH C CH2 C CH CH

OO

OH

OCH3

curcumin

heat +pressure

Vanillin

COH

OH

OCH3

Natural FlavoursNatural Flavours

•• Flavouring preparationsFlavouring preparations

• Essential oils, extracts, tinctures, distillates, juice concentrates

•• Natural flavouring substancesNatural flavouring substances

•• Isolates, biotechnology, soft chemistryIsolates, biotechnology, soft chemistry

•• Flavour solvents/carriersFlavour solvents/carriers

•• Ethanol, propylene glycol, maltodextrin, gum arabicEthanol, propylene glycol, maltodextrin, gum arabic

•• Other factorsOther factors

•• Customer requirements, labelling requirements, legislationCustomer requirements, labelling requirements, legislation

Ungerer Group

Functional Flavours

Natural Flavours

Summary

SummarySummary

•• Functional Flavours Functional Flavours –– Masking & EnhancementMasking & Enhancement

•• Natural Flavours Natural Flavours –– Isolates, Biotechnology & Isolates, Biotechnology & Soft ChemistrySoft Chemistry

•• Discussion & TastingDiscussion & Tasting

•• Thank youThank you

An international familyAn international family--owned flavour and owned flavour and fragrance business with an ever growing fragrance business with an ever growing

reputation for innovation, responsiveness and a reputation for innovation, responsiveness and a competitive approachcompetitive approach

Ungerer GroupUngerer Group

UNGERER LIMITED UNGERER LIMITED ©©20042004