Scent chemistry blaženka čiško anić eng

Author: Blaženka Ćiško-AnićAuthor: Blaženka Ćiško-Anić
Saponija d.d. Osijek, CroatiaSaponija d.d. Osijek, Croatia
SCENTSCENT
CHEMISTRYCHEMISTRY
ModifiedModified byby MscMsc Miro MeleMiro Mele dipl.ing.dipl.ing.
Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 11

History of scentHistory of scent
 Awareness of scent is so old as human race.Awareness of scent is so old as human race.
 Knowledge about scented materials is known from allKnowledge about scented materials is known from all
written history from 5000 years as before troughwritten history from 5000 years as before trough
unwritten communication.unwritten communication.
 Our ancestors noticed a pleasent odour of flowers ndOur ancestors noticed a pleasent odour of flowers nd
also other plant and animal materials. That was a pointalso other plant and animal materials. That was a point
for aromatizing everyday food.for aromatizing everyday food.
 A word perfume comes from latin “per fumum” meaninA word perfume comes from latin “per fumum” meanin
“with help of smoke”“with help of smoke”
Modified by Miro MeleModified by Miro Mele

History of scentHistory of scent
 Picture 1.Picture 1. One of oldest found stone wessels (height 7,4 cm), where use for scented oilOne of oldest found stone wessels (height 7,4 cm), where use for scented oil
storage is pressumptied. Found in Iranian mountains Presumption taht is from era 2750-2350storage is pressumptied. Found in Iranian mountains Presumption taht is from era 2750-2350
b.C. (Source:: Edwin T. Morris,b.C. (Source:: Edwin T. Morris, Scents of TimeScents of Time, The Metropolitan Museum, The Metropolitan Museum of Art, New York,of Art, New York,
1999, str.16)1999, str.16)

Origin of scent industryOrigin of scent industry
 Flourishing of chemistry in 19 century inFlourishing of chemistry in 19 century in
Germany and United Kingdom madeGermany and United Kingdom made
foundation for development of scent andfoundation for development of scent and
aroma industry we know today.aroma industry we know today.
 Globally scent and aroma industry isGlobally scent and aroma industry is
grown to business at more than 20 billiongrown to business at more than 20 billion
dollars annually.dollars annually.

Scent raw materialsScent raw materials
 Natural (essential oils andNatural (essential oils and
extracts)extracts)
 Synthetic moleculesSynthetic molecules

Production of natural scentProduction of natural scent
ngredients:ngredients:
 ExpressionExpression
 DistillationDistillation
• dry distillationdry distillation
• steam distillationsteam distillation
• waterdiffusionwaterdiffusion
 Extraction (different solvents and CO2)Extraction (different solvents and CO2)

NATURAL SOURCE
CONCRETECONCRETE
(REZINOID)(REZINOID)
Ethanol
extraction
Solvent
extraction
Enfleurage
POMMADEPOMMADE
TINKTURETINKTURE
ABSOLUTEABSOLUTEESSENTIAL OILESSENTIAL OIL
Terpeneless oilTerpeneless oil
Ethanol
exstryctionEthanol
extraction
Deterpening
DISTILLATION

Proces of natural scenting raw materials
vary widely, then they are dependent on
seasonal variations. Variations can be
Compensated by long term contracts and
on site organization of growing.
For production of 1 kg jasmine extract
about 7 000 000 flowers picked by hand in
early morning are needed.

Synthetic scent ingredientsSynthetic scent ingredients
Chemistry of scent compounds is alsoChemistry of scent compounds is also
Interesting for ability of synthesis chemistInteresting for ability of synthesis chemist
to investignate realtion between structure ofto investignate realtion between structure of
molecule and its activitymolecule and its activity (structure – activity(structure – activity
relaationships)relaationships); just smelling is enough for; just smelling is enough for
Estimation of new substance.Estimation of new substance.

Ernest Beaux, creator of historically famous perfumeErnest Beaux, creator of historically famous perfume
Chanel No. 5 said:Chanel No. 5 said:
«We'll have to count on chemists to find new substances, if«We'll have to count on chemists to find new substances, if
we are to make new and original notes. Yes, the future ofwe are to make new and original notes. Yes, the future of
perfumery is in the hand of chemistry.»*perfumery is in the hand of chemistry.»*
*Classification des Parfums et Terminologie, Comité Française du Parfum,
Paris, (1998) str. 36-37

CoumarinCoumarin
• synthetized year 1868, available onsynthetized year 1868, available on
market from 1876 was a turning pointmarket from 1876 was a turning point
and is looked as milestone of modernand is looked as milestone of modern
perfumeryperfumery
• Jean-François Houbigant createdJean-François Houbigant created
perfumeperfume Fougère RoyaleFougère Royale 1882.1882.
O O

Historically relevant molecules for
creating trends in creation of scents
O O CHO
HO
CH3O
CHO
4
O
OHHO
OCH3
O
O O
3
Kumarin (1868.) Vanilin (1876.)
γ-undekalakton(1908.)Evernyl®
(1898.)α-ionon(1898.)
Aldehid C12 (1880.)

O
H
H O
CO2CH3
OH
O
O
O
O
OH
α-damaskon (1969.)Galaxolide ®
(1967.)
Dihidromircenol (1960.)Hedione ®
(1960.)Ambrox®
(1950.)
Etilmaltol (1969.)

Classification of scents according to type of scent:Classification of scents according to type of scent:
 citrus (lemon, orange, bergamot, grapefruit)citrus (lemon, orange, bergamot, grapefruit)
 greengreen
 aldehydealdehyde
 plantplant
 green (bluebell, jasmin, lilly of the valley,green (bluebell, jasmin, lilly of the valley,
orange flower, iris, violet, rose, tuberose, freesia)orange flower, iris, violet, rose, tuberose, freesia)
 fruitfruit
 amberamber
 food likefood like
 woodywoody
 moshusmoshus

Ingredient Scent Approx. usage
(ton/year)
Ambrox®
Ambric 6
L-Karvon Spearmint 600
Citronelol and its esters Rose 6000
Dihidromyrcenol Lemon, flower 2000
Geraniol/nerol and their
esters
Rose 6000
Hidroksicitronellal Lilly of the valley 1000
Borneol/izoborneol and
acetates
Conifera 2000
Linalool Flower woody 4000
Linalil-acetat Flower fruity 3000
Mentol Like Mentha Piperita 5000
(Metil)iononi Violet 2000
α-Terpineol i acetati Conifera 3000
Acetilated ceddar oil woody 500
Table 1. Mayor terpene derived scent inredients.

Classification of scents according to funktionalClassification of scents according to funktional
groups:groups:
1.1.Compounds only with C, H, OCompounds only with C, H, O
• AlcoholesAlcoholes
• EstersEsters
• AldehydesAldehydes
• KetonsKetons
• CarbohydratesCarbohydrates
2.2.Heterocyclic compoundsHeterocyclic compounds
1.1.Compounds with sulphurCompounds with sulphur

AlcoholsAlcohols
• etanol, dipropyilene-glycoletanol, dipropyilene-glycol
• cis-3-heksenol (scent of fresh mawned grass)cis-3-heksenol (scent of fresh mawned grass)
• geraniol, linalool, dihidromyrcenol, citronellolgeraniol, linalool, dihidromyrcenol, citronellol
• menthol, terpineolmenthol, terpineol
• benzyl alcohol, 2-feniletanol (fenil-etil-alcohol)benzyl alcohol, 2-feniletanol (fenil-etil-alcohol)

EstersEsters
• ethyl esters – ethyl-acetate, triethyil-citratethyl esters – ethyl-acetate, triethyil-citrat
• allyil-cikloheksilpropanoat – scnet of ananasaallyil-cikloheksilpropanoat – scnet of ananasa
• benzyl-acetate, fenilethyl-acetate, benzyl-benzoatebenzyl-acetate, fenilethyl-acetate, benzyl-benzoate
• methyl-salicilate, heksyl-salicilate, benzyl-salicilatemethyl-salicilate, heksyl-salicilate, benzyl-salicilate
• lactones –lactones – γγ-undecalactone (Peach aldehyde),-undecalactone (Peach aldehyde), γγ-nona--nona-
lakton (Coconut aldehyde)lakton (Coconut aldehyde)
• metil-dihydrojasmonatmetil-dihydrojasmonatModified by Miro MeleModified by Miro Mele

AldehydesAldehydes
• lauril aldehid (Aldehid C12),lauril aldehid (Aldehid C12),
2-metilundecanal (Aldehid C12 MNA )2-metilundecanal (Aldehid C12 MNA )
• 3-(4-3-(4-terttert-butylfenil)-2-methylbutanal (Lilial-butylfenil)-2-methylbutanal (Lilial®®
),),
3-(4-isopropilfenyl)-2-methylbutanal (Cyclamen3-(4-isopropilfenyl)-2-methylbutanal (Cyclamen
aldehid)aldehid)
• vannilin, etil-vannilinvannilin, etil-vannilin

KetonesKetones
• 4-hidroksiphenyl-2-butanon (Raspberry Ketone)4-hidroksiphenyl-2-butanon (Raspberry Ketone)
• cis-3-metil-2-(2-pentenil)-2-ciklopenten-1-oncis-3-metil-2-(2-pentenil)-2-ciklopenten-1-on
(cis-Jasmone)(cis-Jasmone)
• iononi (iononi (αα--ionon,ionon, ββ--ionon)ionon)
• damasconesdamascones

Carbon hidratesCarbon hidrates
• d-limonene,d-limonene, αα-pinene,-pinene, ββ-pinene-pinene

Heterocyclic compoundsHeterocyclic compounds
• maltol
• coumarine
• indol

Compounds with moshus like scentCompounds with moshus like scent
CH3H3C
NO2O2N
C(CH3)3
NO2 CH3
NO2O2N
OMe
C(CH3)3
CH3H3C
NO2O2N
C(CH3)3
CH3O
Musk xylol Musk ketone Musk ambrette
Nitro-moshus

Policylic moshus
O
CH3
H3C
CH3
H3C
CH3H3C
O
H3C
CH3
CH3H3C
H3C
CH3H3C
CH3H3C
CH3
CH3
O
Galaxolide®
Cashmeran®
Versalide®

Nirvanolide® Exaltolide®
Makrocyclic moshus
OH3C O O O
Nirvanolide®
Exaltolide®

Compounds with flower scent:Compounds with flower scent:
FlorhidralFlorhidral®®
H3C CH3
H
OCH3
H3C CH3
H
OCH3
R S
Enantiomers of Florhidrala®
Flower, watery green scent Fresh flower green scent of
Lilly of the valley

O CH3
COOMe
O CH3
COOMe
(1(1RR, 2, 2RR)-methyl-jasmonat)-methyl-jasmonat
IUPAC: metil-{(1R,2R)-3-okso-
2-[(2Z)-pent-2-en-1-il]-ciklopentil}
-acetat
(1(1RR, 2, 2SS)-methyl-jasmonat)-methyl-jasmonat
IUPAC: metil-{(1R,2S)-3-okso-
2-[(2Z)-pent-2-en-1-il]-ciklopentil}
-acetat
Compounds with flower scentCompounds with flower scent
- metil-jasmonat: gives character to jasmine scent (- metil-jasmonat: gives character to jasmine scent (Jasminum grandiflorum L.Jasminum grandiflorum L.))

Compunds with amber woody scentCompunds with amber woody scent
H3CCH3H
CH3CH2CH3OHCH3
OHCrO3AcOHH3CCH3H
CH3
CH3
OO
H3CCH3H
CH3
CH3
OO
+LiAlH4
H3CCH3H
CH3CH3OHOH
H3CC H3H
CH3CH3O
H3CCH3H
CH3CH3O+
(-)-A mbrox
TsOH
MeNO2,30°C
H3C CH3
H
CH3
CH2
CH3
OH
CH3
OH CrO3
AcOH
H3C CH3
H
CH3
CH3
O
O
H3C CH3
H
CH3
CH3
O
O
+
LiAlH4
H3C CH3
H
CH3
CH3
OH
OH
H3C CH3
H
CH3
CH3
O
H3C CH3
H
CH3
CH3
O
+
(-)-Ambrox
TsOH
MeNO2, 30 °C

Iso E SuperIso E Super®®
- main woody component
H3C CH3
CH2
CH2
H3C
H3C
CH3
O H3C CH3
CH3
CH3
O
H3C CH3
CH3
CH3
O
H3C CH3
CH3
CH3
O
CH3
H
(AlCl3)
H2SO4
+ ca. 5 %
500 ng/L 5 pg/L
prag osjetljivosti prag osjetljivosti

Process of smelling – chiralic identification ofProcess of smelling – chiralic identification of
compoundscompounds
CH3
O
C H
CH3H2C
O
CH3
H C
CH2H3C
L-karvon
spearmint
D-karvon
Caraway, cumine

Ohloff, 1961: first reults about enentioselectivity of chiralOhloff, 1961: first reults about enentioselectivity of chiral
scent substancesscent substances
OH
H3C CH3
(S)-(-)-citronelol
CH3
(R)-(+)-citronelol
OH
H3C CH3
CH3

Differences in scent of some enantiomeres ofDifferences in scent of some enantiomeres of
chiral substanceschiral substances
MATERAL
DESCRIPTION OF SCENT
(+)-ENANTIOMER (-)-ENANTIOMER
Hidroksicitronelal Lilly of the valley green
peppermint
Sweet lilly of the valley
Linalool Sweet petitgraine Woody lavandin
Karvon Scent of caraway Scent of spearmint
Nootkaton Scent of grapefruit Woody spicy scent
Nerol oksid Green flower scent Green spicy sccent with
geranium note
Mentol Fresh peppermint
Strong cold effect
Plant less peppermint
Weak cold effect
Limonen Orange Turpentine

You don’t taste with your mouth or your nose;
you taste with your brain.
Mark Friedman, Monell Chemical Senses Center,
SAD

 many aspects are still unexplained
 scent forms together with taste
chemical sensorial apparatus –
CHEMORECEPTION (ability of perception of
chemical signals)
 Chemoreception is probably a first
sensorial signal of living organisms
Present achievments about olfaction
process

Theory of olfaction
 Dominating is a thesys that molecules of
scenting inghredient are coming into contact with
receptors and they transmite electricalsignal trough
nervs.
 Contact between receptor and scented molecule
is realized trough olfactory epitel licated on top od
nose hole.

Results of scent perception
research
 By inhalation of pleasent scents gtested
persons gave
better notes about look of people on photos.
Casino visitors spent to 45% more in pleasent
odoured environment
 Hair shampoo initially graded as worst in effect
of hair washing efficiency, was graded much
higher after correction of scent

Thank You!

Scent chemistry blaženka čiško anić eng

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