164-Perfumery As A Science (Illustrated Guide To Compose A Perfume by Mixing Chemistry With Art)

Perfumery as a Science
Steve Herman
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FRAGRANCE CREATION
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VOLATILITY
For a molecule To have odor, MW<300 for appreciable vapor pressure at RT

BASIC COMPOSITION
FRAGRANCE TRIANGLE
25%
TOP
25% 50%
MIDDLE BOTTOM
Jean Carles: Evaluate volatility Construct accords Build from bottom up
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CARLES BASE ACCORD

Oakmoss Ambergris 9 8 7 6 5 1 2 3 4 5
Selects 6:4, needed musk for chypre character: 6 Oakmoss 4 Ambergris 1 Musk Ketone
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ADD MIDDLE
Adds floral and animal notes: 3 1 6 4 1 Absolute Rose Absolute Civit 10% Oakmoss Ambergris Musk Ketone
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TOP ADDED
Pleasant, highly volatile notes for sparkle: 4 Sweet Orange Oil 1 Bergamot 3 Absolute Rose 1 Absolute Civit 10% 6 Oakmoss 4 Ambergris 1 Musk Ketone
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FRAGRANCE CHEMICALS
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CHEMICAL TYPES
Alcohols Aldehydes & Ketones Aliphatic & Aromatic Esters Nitriles Ethers Lactones Heterocyclics Terpenes
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ALCOHOLS
R-OH Aliphatic OH
Aromatic
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ALDEHYDES & KETONES H C=O R R C=O R Ketone

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Aldehyde
TERPENES #1
Isoprene Units Joined Head To Tail
(C5H8)n C I C=C-C=C
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TERPENES #2
n 2 3 4 6 8 Name Monoterpene Sesquiterpene Diterpene Triterpene Tetraterpene Formula C10H16 C15H24 C20H32 C30H48 C40H64
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ACYCLIC TERPENES
-Myrcene
MONOCYCLIC TERPENES
Limonene
BICYCLIC TERPENES
Pinene
SESQUITERPENE
-Bisabolene
NITRILES
R-C=N C=N Aliphatic
Aromatic
BASIC HETEROCYCLIC STRUCTURES
O +
S +
N H
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HETEROCYCLICS
N H
Indole
LACTONE
A Cyclic Ester
or Hydroxy Acid forms 5 or 6 member ring by intramolecular esterfication -Na+ RCHCH2CH2COO
I OH
LACTONES
Coumarin
NITROMUSKS
C((CH)3)3 NO2 NO2 CH3 NO2 NO2 C((CH)3)3 NO2 NO2
CH3
CH3 C=O I CH3
CH3
Musk Xylene
Musk Ketone
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POLYCYCLIC MUSKS
Galaxalide
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FRAGRANCE DILUENTS 1
CH3CHCH2-O-CH2CHCH 3 I I OH 0H
Dipropylene Glycol (DPG)

CH3CHCH2OH I OH
Propylene Glycol (PG)
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FRAGRANCE DILUENTS 2
HOCH2CH2CHCH3 I OH CH3 I CH3CCH2CHCH3 I I OH OH Butylene Glycol
Hexylene Glycol
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SCHIFF BASE #1
Aldehyde + Amine
H 2N CHO + OH COOCH3
HydroxyCitronellal
Methyl Anthranilate
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SCHIFF BASE #2
COOCH3 CH=N OH + H 2O
Aurantiol
CHEMICAL REACTIONS
HELPFUL REACTIONS Part of the natural maturing process HARMFUL REACTIONS Occur in isolated perfume oils or in reaction with base environment
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STORAGE EFFECTS
Elevated Temperatures UV Radiation Moisture Oxidation Accelerate change or deterioration
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AUTOOXIDATION
CHO COOH
Benzaldehyde
Benzoic Acid
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POLYMERIZATION
Aldehydes can Solidify OH I CH2CH-CHCHO
CH2CHO 2
Phenylacetaldehyde
HEMIACETALS
Aldehyde/Ketone + Alcohol
O II I C +- C- OH
Loose, reversible aging hydroalcoholics
OH I C O C
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ESTER HYDROLYSIS
O OH -OH
Benzyl Acetate
Benzyl Alcohol
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LACTONE HYDROLYSIS
O -OH O O HO OH
Epsilon Hexalactone
6-Hydroxy Hexanoic Acid
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FRAGRANCE APPLICATIONSPERSONAL CARE
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CHEMICAL EXAMPLES 1
PEA
.
CH2CH2OH
-Pinene
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CHEMICAL EXAMPLES 2
Hydroxycitronellal OH CH3
I I
CH3CCH2CH2CH2CHCH2CH I II CH3 O
CH3 HOCH2CH2CH CH3 Amyl Alcohol

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SOLUBILITY PARAMETER
Measure of all the cohesive forces in a molecule Refinement of polar nonpolar division
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CLOG P
Calculated LOGarithm of the octanol/water Partition Coefficient
Trinh et al 5,783,544, 1998
SMILES SIMPLIFIED MOLECULAR INPUT LINE ENTRY SYSTEM

Allows entry of chemical structures into computer programs to predict properties
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EXAMPLE SMILES
Case ImportantAliphatic Upper Case Aromatic Lower Case Hydrogen Not Included SINGLE BOND C-C DOUBLE BOND C=C TRIPLE BOND C#C Rings- # at start and end e.g. c1ccccc1Br is Bromobenzene
CLOG P VANILLIN
SMILES: COc1cc(C=O)ccc1O
HO
H3C
CH O
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CONSEQUENCE
Fragrance will partition in phases of finished product
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FUNCTIONAL FRAGRANCE
Economics Stability Translation
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TEA-STEARATE EMULSION
Air
CH2CH2OH
PEA
O
Stearyl alcohol
Amyl alcohol
TEA-Stearate
O
Hydroxycitronellal Pinene
SURFACTANTS
More stable than emulsions, but viscosity more important, often color problems
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MICELLE EFFECTS
Water-Micelle Interface Between Surfactant Molecules Core of Micelle
SURFACTANT VISCOSITY
Water Sodium Laureth Sulfate (A) Cocamidopropyl Betaine (B) 1. Unperfumed 2. 2% Hydroxycitronellal 3. 2% Phenylethyl Alcohol A. Standapol ES-2 (COGNIS) B. Velvetex BK-35 (COGNIS)
67.0 18.0 15.0
VISCOSITY
1,000 800
600
400
200
3
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FRAGRANCE APPLICATIONSHOUSEHOLD PRODUCTS
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EVAPORATION CURVE
Wt Loss Days Typical Fragrance Evaporation Curve

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FREE EVAPORATION
Weight 1
2 Time
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LINEAR FRAGRANCE
4 3 2 1 Time
Weight
BLEACH
Bleach unstable, affected by fragrance, solubilizer, oxygen, temperaturemust test chlorine and fragrance.
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DECOMPOSITION AT 100F
5.6 5.4 5.2 5.0 4.8 4.6 4.4 4.2 4.0 3.8 3.6 3.4 3.2 3.0 2.8
0 10 20 30
% NaOCl
Days
40
50 60
70
80
90 100 110 120 130 140 150
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DOWFAX STRUCTURE
SO3-X+ O R SO3-X+
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TITRATION
0.1 N Sodium Thiosulfate
Titrate until clear Stirring Bar Magnetic Stirrer

Bleach Test Mixture
MASKING/MALODOR
Foul odors from bacterial decomposition or unpleasant molecules
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FAMOUS MALODORS
putrescine cadaverine spermidine
spermine
SKUNK ODOR
H C=C CH3 H CH2SH E-2-buten-1-thiol 38-44%
CH3 I CH3CHCH2CH2SH
3-methyl-1-butanethiol 18-26%
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ALDEHYDE ACTION
3-mercapto-3-methyl-1-butanol
OH
aldehyde
+
SH R
R-CHO
Alkylated 1,3-oxathiane
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METAZENE
H C=C-C H CH3
O-R
R=mixture from C 8H17 to C14H29

GRILLOCIN
O II C O C7H14 C6H13 I C-C2H3= CH O C 7H14
H Zn H O O C II O
CH=C2H3 -C I C6H13
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CYCLODEXTRIN
A B
a ? A 0.57nm 0.78nm 0.95mn B 1.37nm 1.53nm 1.69nm
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FRAGRANCE & COLOR

Product is formulated, fragrance is chosen, color is added, time is short
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CHROMOPHORES
Configurations which can alter the energy of delocalized systems Benzene absorbs around 200 nm We see between 400-700 nm
VISIBLE STRUCTURES
Conjugated double bonds
-C=C-C=CAZO chromophore
-N=NN=N
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BENZALDEHYDE + UV
HC=0 -C=0
UV
Free radical
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SYNESTHESIA
Relation of two senses, such as smell and color
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Name _______________________
A ____ B ____ C ____ D ____ E ____ F ____ G ____ H ____ I ____ J ____ K ____ L ____ M ____ N ____
6 9 11
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8 10
CINNAMIC ALDEHYDE
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RIFM/IFRA
For thirty years, the fragrance industry has had a continuous program of safety testing, and the process has no end in sight.
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PHYSIOLOGICAL CONSIDERATIONS
Skin irritation Phototoxicity Carcinogens Allergens
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NON-SKIN CONTACT
Solid air fresheners Plug-in air fresheners Insecticides Toilet blocks Incense sticks Candles Plastic articles
SKIN CONTACT
Aerosols Detergents Potpourri Carpet powders Household cleaning products Liquid refills for air fresheners
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Hydroxycitronellal (Laurine, Hydronal, Phixia, Laurinal)

Last Amendment First Issued April 28, 2000 March 01, 1987
CAS # Recommendation Skin Contact Non-Skin Contact 107-75-5 Restricted 1% 10%

Hydroxycitronellal should not be used such that the level in consumer products exceeds 1%. This is equivalent to 5% in a fragrance compound used at 20% in the consumer product. This recommendation is based on a no-effect level of 10% in diethyl phthalate and on a no-effect level of 2.5% in ethanol/diethyl phthalate in standard Human Repeated Insult Patch Tests (R.A. Ford and A.M. Api, Fd. Chem. Toxic. Vol. 26, p. 921-926, 1988). The RIFM Expert Panel reviewed these data in September 1999 and concluded that no further actions were required.
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CHEMICAL GROUPINGS
A means to defend structurally related materials, without having to test every material in the group ~ 2,000 chemically defined fragrance ingredients 22 Groups (e.g. Acids, Acetals, Alcohols) > 60 Subgroups (e.g. Straight chain saturated, straight chain unsaturated etc.)
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RESPIRATORY SAFETY
Selected fragrance ingredients Benzyl acetate Eugenol -Hexyl cinnamic aldehyde (HCA) HHCB Hydroxycitronellal -ionone d-limonene Linalool Methyl dihydrojasmonate
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CHANDLER BURR
2002
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www.stephen-herman.com
Questions or Comments?
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164-Perfumery As A Science (Illustrated Guide To Compose A Perfume by Mixing Chemistry With Art)

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Perfumery as a Science

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

For a molecule To have odor, MW<300 for appreciable vapor pressure at RT

Jean Carles: Evaluate volatility Construct accords Build from bottom up

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

CARLES BASE ACCORD

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

ALDEHYDES & KETONES H C=O R R C=O R Ketone

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

BASIC HETEROCYCLIC STRUCTURES

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

CH3 C=O I CH3

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SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

Dipropylene Glycol (DPG)

Propylene Glycol (PG)

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

6-Hydroxy Hexanoic Acid

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

FRAGRANCE APPLICATIONSPERSONAL CARE

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

CH3 HOCH2CH2CH CH3 Amyl Alcohol

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

SMILES SIMPLIFIED MOLECULAR INPUT LINE ENTRY SYSTEM

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

Fragrance will partition in phases of finished product

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

67.0 18.0 15.0

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

FRAGRANCE APPLICATIONSHOUSEHOLD PRODUCTS

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

Wt Loss Days Typical Fragrance Evaporation Curve

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

90 100 110 120 130 140 150

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

Titrate until clear Stirring Bar Magnetic Stirrer

Bleach Test Mixture

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SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

SOFTbank E-Book Center Tehran, Phone: 66403879,66493070 For Educational Use.

R=mixture from C 8H17 to C14H29