Fragrances in Consumer Products Judy Kerschner International Flavor and Fragrances Bergen Academy April 21, 2006

Fragrance & Human Psychology “(Human beings) are avid smellers. We attract our mates through smell, identify our babies through smell, experience spirituality through smell and remember the experiences of our lives through smell. Smell is the muse of memory...” “Browning wrote of devouring violets to satiate himself with their scent. Walt Whitman was the epic poet of body odor. Colette was drunk on the smells of muskmelon, honeysuckle, blue lilac, tea rose and the sea - her heroines were too. Sappho described incense burning in an apple grove summoning Aphrodite. Without smell, there is no poetry of love. As Li Po wrote: ‘You left three years ago. Still your perfume haunts my solitude.’” My Generation March-April 2002

How We Smell - Odorants are volatile chemicals carried by inhaled air to the Regio olfactoria (olfactory epithelium) located in the roof of the two nasal cavities of the human nose, just below and between the eyes. The olfactory region of each of the two nasal passages in humans is a small area of about 2.5 square centimeters containing in total approximately 50 million primary sensory receptor cells.

History of Perfume – Greece Greek Perfume Urns By the 7th century BC, Athens had developed into a mercantile center in which hundreds of perfumers set up shop. Trade was heavy in fragrant herbs such as marjoram, lily, thyme, sage, anise, rose and iris, infused into olive, almond, castor and linseed oils to make thick unguents. These were sold in small, elaborately decorated ceramic pots, similar to the small jars still sold in Athens today.

History of Perfume– France 16th & 17th centuries - Southern France (Grasse) becomes a center of expertise for the growing, extraction and distillation of essential oils. France becomes the the Perfume center of the world. Large scale cultivation & processing of valuable plants for oils such as rose soon was centered there. And raw materials from around the world were imported for processing. Extraction & distillation techniques were refined.

History of Perfume – The Organic Chemist Mid-1800’s - From Germany came a new breed of Chemist that would revolutionize industry and bring an end to “Alchemy”. This type chemist used the scientific method to unravel chemical structures and create materials from coal, petroleum and other materials. 1855 – First synthesis of cinnamaldehyde 1868 – Commercial production of coumarin – the first synthetic fragrance chemical 1874 – Chemical structure of vanillin determined. 1876 – Synthetic vanillin production starts. 1850 to 1900 – Significant advances in elucidating major chemicals in Essential oils.

The Perfumer – An artist with a different palette

Example of a Simple Fragrance Ethyl Butyrate 10 ethyl w-methyl butyrate 155 isoampy acetate 5 ethyl pentanoate 25 prenyl acetate 15 methyl hexanoate 150 Benzaldehyde 10 alpha-Pinene 165 Camphene 50 beta-Pinene 130 Myrcene 110 cis-3-hexenyl acetate 110 hexyl acetate 45 methyl anisole 170 Limonene 250 Aldehyde AA-Triplal 15 Dihydromyrcenol 10 allyl hexanoate 5 Methyl Benzoate 2 Terpinolene 35 Linalool 3.5 Allyl s-methyhexanoate 12 methyl octanoate 5 Benzyl acetate 12 ethyl benzoate 4 Syrallyl acetate 3 ethyl linalool 100 myrtenal 25 citronellol 4 carvone 55 linalyl acetate 200 citronellyl formate 175 dihyrdolinalyl acetate 2 undecanone 12 verdox 45 galoxolide 35 dimethylbenzyl carbinyl acetate 2 methyl decanoate 125 delta damascone 5 geranyl acetate 200 alpha- damascone 5 mirascone 75 cyclacet 125 allylcyclohexyl propinonate 50 alpha ionone 10 dihydro beta-ionone 3 cyclamal 15 beta-ionone 10 bimethylbenzyl carbinyl butyrate 100 cyclabute 12 Delta-cadinene 25 tosetone 5 rose oxide 2 gamma-undecalactone 50 diethyl phthalate 250 Iso E Super 100 hexyl cinnamic aldehyde 50 isopropyl myristate 10 tonalide 55 zenolide 65 benzyl salicylate 25 habanolide 150 isoamyl salicylate 5 benzyl benzoate 20 rosetone 75 vertelilial 75 nex 150 ionone 2 allyl heptanoate 25

Character Visualizing a Fragrance Long lasting memory Seduction/Freshness TOP NOTE Character Cost MIDDLE NOTE Volatility Long lasting memory BACK (BASE) NOTE

Fine Fragrance Design BACK (BASE) NOTE TOP NOTE MIDDLE NOTE Give initial impact of fragrance Provide freshness Typically citrus, green notes Lasts 15-30 minutes on skin TOP NOTE Give fragrance its character and depth Typically spicy, leather, floral Lasts 3-4 hours on skin MIDDLE NOTE Fragrance foundation Substantivity Typically amber, musk Topnotes The most volatile of the fragrance raw materials. Typical notes are citrus, Herbal, Aldehydic, Green, Marine/Ozone, Fruit. Herbal notes are essentially used in masculine perfumery. Aldehydic notes give power, diffusion and uniqueness to a fragrance and are entirely synthetic. Fruit - generally extracted from the skin of the fruit. However, most fruit tend only to have a light skin and therefore the extraction of the oil from the skin has been replaced by a synthetic reproduction of the odours. Middle Notes Typical notes - floral, spice, wood, leather. Base Notes Typical Notes - animal, musk, amber, sweet/powdery. Typically the most expensive. An increase in the base notes of a fragrance will increase the cost of the fragrance. The base notes of a fragrance give the fragrance its substantivity/longevity. Only synthetic musks are now used, however they only reproduce the softness, sweetness and fixative properties of natural musk without its animalic notes. Amber notes - labdanum, incense. Sweet/powdery notes - often referred to as pastry notes. eg. Tonka bean, Benzoin, Vanilla. BACK (BASE) NOTE Lasts >4 hours

Individual Fragrance Ingredients Chemical structure does not always indicate odor type Aldehyde C8 CH3(CH2)6CHO Orange Aldehyde C9 CH3(CH2)7CHO Rose Aldehyde C10 CH3(CH2)8CHO Citrus Aldehyde C11 CH3(CH2)9CHO Citrus-floral Aldehyde C12 CH3(CH2)10CHO Soapy Aldehyde C13 CH3(CH2)11CHO Waxy-citrus Aldehyde C14 CH3(CH2)12CHO Fatty-citrus

Individual Fragrance Ingredients Geranium (Rose-like, Citrus, Wood, Green) Fragrance Categories: Floral Fruity Woody Herbal Balsam and Vanilla Spice Animal Marine Aldehyde Bergamot (Citrus, Lemon, Earl Grey Tea) Cedarwood (Sawdust, Pencil Shavings, Dry) Cis-3-Hexenol (Wet, Green, Cut Grass) Clove (Spicy, Creamy) Musk (Soft, Warm, Fluffy Clouds) Calone (Watery, Dewy, Fresh)

Perfumed Products Fine Fragrance (Happy, Chanel No. 5, etc) Air Care (Candles, Electricals, etc) Fabric Care (Detergents, Conditioners, etc) Personal Care (Shampoos, AP/DEOs, etc) Personal Wash (Bar Soaps, Liquid Body or Hand Wash, etc) Home Care (Dish Wash, All Purpose Cleaners, etc)

Fragrance Predominate Deciding Factor! “People tell you they buy cleaning products based on performance,” said Dr. Pamela Dalton, a cognitive psychologist at the Monell Chemical Senses Center in Philadelphia. “But the deciding factor in blind tests is always fragrance.” New York Times March 6, 2002

Typical Consumer Products are difficult to perfume For Fine Fragrances, the perfumer has availble circ.4000+ ingredients and a simple solvent base (alcohol). For Functional Perfumery, the perfumer has only <400 ingredients depending on the type of base (pH, solvent, color, etc). Because; Many ingredients are not stable in acid or alkaline bases Many ingredients are broken down by bleach (TAED / Percarbonate) Many ingredients will react with the base to cause base instability (color, rheology, phase separation) and Limitations of product production process Limitations of packaging used Limitations of way the product is used

Fragrances in Consumer Products The Impact threshold of each perfume ingredient The mix of ingredients chosen The level used in the product The odour quality of the base The degree of interaction with the base The effect of processing the product The stability of the perfume during storage The interaction with the packaging The amount of product used by the consumer The wash conditions chosen by the consumer The amount of perfume deposited The amount of perfume retained after the wash The rate of release of the perfume over time Need to understand and control Need new technical routes and innovative approaches ....and the ability to measure their value

Measure Fragrance Performance Combine analytical and sensory studies to understand fragrance performance - Fine Fragrance – Diffusivity, Long-lasting - Personal Wash – POP, Bloom, Deposition, Substantivity - Laundry – POP, Deposition, Substantivity - Home/Air Care – Diffusivity, Fragrance Release, Coverage of Mal-odors - AP/Deo – POP, Long-lasting, Coverage of Body Odor

Applied Fragrance Technology Most important drivers of technical performance Ingredient Chemical and Physical Properties: Vapor pressure POP/Soap Log p Bloom (Shower/Wash) Water Solubility Deposition Odor Threshold Substantivity (Long lasting) Odor Intensity

Applied Fragrance Technology Physical characteristics of ingredients that influence performance Model Accord Neat Oil – Wt% in Oil Model Accord Neat Oil – Vapor Phase Limonene Bornafix Meth Ionone Nebulone Phen Eth Acet Ald C11 Linalool Oxide Rose Oxide Yara Yara Hexenyl iso butyl Iso Eugenol Meth Anth Patch alc Damascone Delta Limonene Bornafix Meth Ionone Nebulone Phen Eth Acet Ald C11 Linalool Oxide Rose Oxide Yara Yara Hexenyl iso butyl Iso Eugenol Meth Anth Patch alc Damascone Delta Vapor Pressure = >1000 100-1000 <100

Sensory Dose/Response Curve 1: Extremely Weak 2: Moderately Weak 3: Weak to Moderate 4: Moderate 5: Slightly Strong 6: Moderately Strong 7: Strong Solution Concentration (in ppm) Threshold (50% Population) Saturation Rate of intensity increase Intensity

Applied Fragrance Technology Sensory Dose Response

Design of High Performing Fragrances Marketing Research & Development Consumer Insight Creative Fragrance Development Technical Fragrance Development Perfumers