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Welcome to Fragrance 301
March 14, 2017
8:30 – 9:00 am Continental Breakfast
9:00 am Welcome & Introductions
Morning Session What Are Essential Oils?
Growing & Harvesting Essential Oils
How Do We Obtain Oils From Plants?
Adulteration of Essential Oils
12:00 – 1:00 pm Lunch
Afternoon Session Pricing & Supply
Restrictions & Allergens
Truth or Myth?
2:30 pm Hands on Blending of Essential Oils
Introducing our R&D Staff
Return to Agenda
Jim PowellSr. Perfumer & Technical Director
Cara RogersPerfumer
John LittlePerfumer
Almond Bitter
Amyris
Angelica Root
Anise Star
Armoise
Balsam Peru
Basil
Basil Indian
Bay
Bergamot Italian
Birch Tar
Black Pepper
Buchu Leaf
Cade
Cajeput
Calamus
Camphor White
Cananga
Caraway
Cardamom
Carrot Seed
Cassia
Cedarleaf
Cedarwood Texas
Cedarwood Virginia
Celery Seed
Chamomile
Cilantro
Cinnamon LeafCinnamon Bark
Citronella Ceylon
Citronella Java
Clove Bud
Clove Leaf
Cognac
Copaiba
Coriander
Cornmint
Cumin
Cypress
Davana
Dill Weed
Elemi
Eucalyptus 80/85
Fennel Sweet
Fir Needle Canadian
Fir Needle Siberian
Galbanum
Garlic
Geranium Bourbon
Geranium Egyptian
Ginger
Grapefruit
Guaiacwood
Jasmine
Juniper Berry
Labdanum
Laurel Leaf
Lavandin GrossoLavender
Lemon
Lemongrass
Lime
Lovage
Mace
Mandarin
Marjoram
Melissa
Myrrh
Myrtle
Neroli Bigarde
Nootka Tree
Nutmeg
Olibanum
Onion
Opoponax
Orange Bitter
Orange NavelOrange Valencia
Oregano
Palmarosa
Parsley Seed
Patchouli
Pennyroyal
Peppermint
Petitgrain
Pimento Berry
Pimento Leaf
PineRose
Rosemary
Sage Clary
Sage Dalmatian Sandalwood
Spearmint
Styrax
Sweet Birch
Tagette
Tangerine
Tarragon
Tea Tree
Thyme White
Valerian Root
Vetiver
Wintergreen
Wormseed
Ylang Ylang #1 & #3
Essential Oils
What Are Essential Oils?
Return to Agenda
Cara Rogers
Perfumer
• Highly concentrated, volatile
oils extracted from plants
• Give plants their distinctive smell
• Not fixed oils; Fixed oils don’t vaporize
• In the fragrance industry: EOs used in
fragrances for cosmetics, soaps,
detergents and perfumes
• Resins – Fir Balsam
What are Essential Oils?
• Mixture of aromatic organic compounds
– Alcohols, aldehydes, esters, ketones, lactones, phenols,
terpenes and sesquiterpenes
• Odor profile of EOs determined by delicate
ratio of constituents
– DNA or genetic footprint
– Example: Lavender vs. Lavandin
– Variation from species to species, even plant to plant
• Can change to adapt to the environment
Complexity of Essential Oils
Complexity of Rose Oil
GeraniolNerol
Citronellol
Linalool
PEA
Rose
Oxide
Citral
Complexity of Lavender 40/42
Linalool
Linalyl acetate
Camphor
Caryophellene
Geranyl
Acetate
Lavandulol
Rose oil extracted
from petals
Orange oil extracted
from peel and flesh
Lavender oil
extracted from flower
Jasmine oil extracted
from petals
Sandalwood extracted
from heartwood and roots
Cinnamon bark oil
extracted from bark
Where do Essential Oils come from?
• External Secretory Structures– Glandular trichomes found on surface of plant; responsible for the
production of EO chemicals
– Plants with glandular trichomes: Basil, Lavender, Marjoram, Melissa,
Oregano, Peppermint, Rosemary, and Spearmint
• Internal Secretory Structures– Secretory cavities and ducts consisting of large, intercellular spaces;
formed by separation of neighboring cell walls or by disintegration of cells
– Plants with secretory cavities: Grapefruit, Lemon, Eucalyptus, Orange
– Plants with secretory ducts: Caraway, Dill, Fennel, Fir, Cedar, Juniper
• Essential oil cells– Found within plant tissue throughout the plant
– EOs with cells: Black pepper, Cinnamon, Ginger, Lemongrass, Nutmeg
Where do plants make and store Essential Oils?
Trichomes on surface of leaf Oil droplets produced by Trichomes
External Storage of Essential Oils
Internal Storage of Essential Oils
Attract Pollinators
Why do plants produce Essential Oils?
Allelopathy
Why do plants produce Essential Oils?
Defense Mechanism
Why do plants produce Essential Oils?
Protection
Against Fungus
& Bacteria
Thymol Thyme
Eugenol Clove Leaf
Why do plants produce Essential Oils?
• Organic– Free of pesticides, fertilizers,
fungicides, herbicides
• Pure & Natural – Unadulterated
• Natural– Doctored with naturally derived
materials
• N & A– Doctored with synthetic chemicals
• Therapeutic Grade– Not a real standard
– Used to describe Pure & Natural
Essential Oil Terms
Questions?
Return to Agenda
John Little
Perfumer
Return to Agenda
Production Techniques and Differences in
Resulting Materials
How Do We Get Oil From Plants?
Methods of Essential Oil Production
• Expression
– Valencia orange oil
• Distillation
– Lavender oil
– Sandalwood oil
– Cinnamon bark oil
• Solvent Extraction
– Turkish rose absolute
– Jasmine absolute
Hydrodistillation Process
Citrus Oil Production
Solvent Extraction
Process in Flowers
Supercritical CO2
Extraction Process
Same Starting Material, Different Results
How does this?
End up like this?
But also this?
Processing Method Changes the Chemical
Composition
Lime Distilled Lime Expressed
Molecular Distillation Process
Molecular Distillation
Patchouli Oil Patchouli Oil MD
• Iconic powdery, woody, wet
earthy odor
• Not compatible in candles
• Powdery, wet earth, slightly
less rich woody
• Compatible in candles
But Wait, There’s More!
• Resinoid
– A special type of extraction involving plant resins (i.e. myrrh,
olibanum/frankincense, benzoin)
– Extracted using a hydrocarbon based solvent
• Resin “Absolute”
– Repeated washing, chilling, and filtering of a resin with ethyl
alcohol
– Better solubility and odor character than resinoid
• Resinoid “Absolute”
– Repeated washing, chilling, and filtration of resinoid with ethyl
alcohol
– Best character and solubility
Supercritical Fluid Extract (SFE)
Benzoin Resin
• Heavy, thick, amber color
• Incense/smoky character
• Not compatible in candles
• Prone to discoloration
• Lower impact
Benzoin SFE
• Sweeter, cleaner profile
• Reminiscent of hard candy
• Spicy floral
• No incense/smoky notes
Descriptors: butterscotch,
milk, candy, sweet, root beer
Orchidia Distillation Facility
Essential Oils Can Be Processed Again
Valencia Orange Oil
• Flashpoint: 110˚F
• Moderate orange color
• 90% monoterpenes
(ex. d-Limonene)
5-Fold Orange Oil
• Flashpoint: 130˚F
• Intense orange color
• More potent sweet orange
• Less zesty peel like
• Better for candles and
alcohol solubility
It’s All About the Process
• Why are there so many different
production methods?
• The type of processing method
changes chemical composition
• Small changes in composition can
have a big impact on the odor
• Perfumers use the different
production methods in creative ways
Questions?
Return to Agenda
Growing & Harvesting
Essential Oils
Return to Agenda
Steve Schuh
Sr. Director of Perfumery
Outline of Topics
• Habitat
• INCI Name
• Source
• Harvest
• Treatment
• Yield
Orange
Habitat: Florida, Brazil, California
South Africa, Portugal, Spain
INCI Name: Citrus Aurantinum Dulcis
(Orange) Peel Oil
Source: Outer Rind of Fruit
Harvest: November - May
Treatment: Expression
Yield: 0.3 – 0.5% of Oil
Cinnamon Bark
Habitat: Sri Lanka, Madagascar
INCI Name: Cinnamomum Zeylanicum
(Cinnamon) Bark Oil
Source: Inner Bark
Harvest: Year Round
Treatment: Steam Distillation
Yield: 0.5 – 1% of Oil
Lavender
Habitat: France, Bulgaria
INCI Name: Lavandula Angustifolia
(Lavender) Oil
Source: Flowers and Stalks
Harvest: June - August
Treatment: Steam Distillation
Yield: 0.5 – 1.6% of Oil
Rose
Habitat: Bulgaria, Turkey, France,
Morocco, Russia
INCI Name: Rosa Damascena (Rose)
Flower Extract
Source: Freshly Gathered Flowers
Harvest: May - June
Treatment: Solvent Extraction
Yield: 0.25% of Absolute
Jasmine
Habitat: Egypt, India, France, Morocco
INCI Name: Jasminum Grandiflorum
(Jasmine) Flower Extract
Source: Freshly Picked Flowers
Harvest: August - November
Treatment: Solvent Extraction
Yield: 0.3% of Absolute
Sandalwood
Habitat: Australia, East Indes
INCI Name: Santalum Spicatum
(Sandalwood) Oil
Source: Heartwood
Harvest: Year Round
Treatment: Steam Distillation
Yield: 5% of Oil
Many Contributing Factors
• Soil Texture / Moisture
• Weather Dependent
• Nature Dependent
• Environmental Impact
• Cultivation Methods
• Harvesting Techniques
Do you have a
favorite
Essential Oil?
Return to Agenda
Essential Oils: Methods and Ethics
of Adulteration
Jim Powell
R&D Director / Sr. Perfumer
Return to Agenda
A Close Look at Rose and Lavender
Refractive Index• A number that describes how light propagates through that medium.
• Defined as n = c/v where c is the speed of light in a vacuum and v is
the phase velocity of light in the medium.
• For example, the refractive index of water is 1.333, meaning that light
travels 1.333 times faster in a vacuum than it does in water.
Optical Rotation• The rotation of the plane of polarization of linearly polarized light as it
travels through certain materials
• Optical activity occurs only in chiral materials, those lacking
microscopic mirror symmetry.
• The rotation of the plane of polarization may be either clockwise, to
the right (dextrorotary — d-rotary), or left (levorotary — l-rotary)
depending on which stereoisomer is present (or dominant).
• Optical activity is measured using a polarized source and polarimeter.
Specific Gravity• The ratio of the density of a substance to the density of a reference
substance (usually water)
• Equivalently, it is the ratio of the mass of a substance to the mass of a
reference substance for the same given volume
Definitions
Lavender Oil PropertiesSpecific Gravity @ 25C 0.880 - 0.896
Refractive Index 1.4588 to 1.4600
Optical Rotation -6o37’ to -8o50’
Lavandin Oil PropertiesSpecific Gravity @ 25C 0.888 - 0.896
Refractive Index 1.4616 to 1.4640
Optical Rotation -2o50’ to -5o25’
Linalool PropertiesSpecific Gravity @ 25C 0.859 - 0.867
Refractive Index 1.4610 to 1.4640
Linalyl Acetate PropertiesSpecific Gravity @ 25C 0.895 - 0.914
Refractive Index 1.4480 to 1.4570
Lavender Oil
Lavender Oil 40/42 Pure & Natural
$78.00/lbLinalool 35%-50%Linalyl Acetate 35%-55%Camphor 0.1%-0.4%Ocimene cis & trans 2.0%-4.0%Caryophellene 3%-7%1,8 Cineole 1%-3%
Lavender Oil 40/42 Natural Commercial
$37.65/lbLinalool 30%-45%Linalyl Acetate 30%-45%Camphor 3%-7%Ocimene cis & trans 2.0%-4.0%Caryophellene 3%-7%1,8 Cineole 3%-8%
Lavender Oil 40/42 Nat & Art
$24.50/lbLinalool 30%-40%Linalyl Acetate 30%-40%Camphor 3%-7%Ocimene cis & trans 0%-2.0%Caryophellene 2%-5%1,8 Cineole 3%-8%
Lavandin Oil Grosso Natural
$19.00/lbLinalool 25%-35%Linalyl Acetate 25%-40%Camphor 5%-10%Caryophellene 0.75%-2.5%1,8 Cineole 4%-7%
Lavender Oil
Rose Oil
Rose Oil PropertiesSpecific Gravity @ 15C 0.8485-0.8605
Refractive Index 1.4530 to 1.4640
Optical Rotation -2o18’ to -4o24’
Geranium Oil Bourbon PropertiesSpecific Gravity @ 15C 0.888-0.896
Refractive Index 1.461 to 1.468
Optical Rotation -7o40’ to -13o50’
Palmarosa Oil PropertiesSpecific Gravity @ 15C 0.887-0.900
Refractive Index 1.472 to 1.477
Optical Rotation -1o34’ to +2o45’
Rose Oil Bulgarian $10,000/lbl-Citronellol 30%-35%
Geraniol 15%-20%
Nerol 5%-7%
Nonadecane 13%-16%
Linalool 1.5%-3.0%
Geranium Oil Bourbon $105/lbl-Citronellol 20%-25%
Geraniol 15%-20%
Citronellyl Formate 7%-12%
Geranyl Formate 5%-9%
Linalool 10%-15%
Palmarosa Oil $42.50/lbGeraniol 70%-80%
Geranyl Acetate 5%-20%
Linalool 2%-4%
Natural l-Citronellol $59.50/lb
Natural Geraniol $37.00/lb
Natural Linalool $50.00/lb
Rose Oil
Rose Oil $10000 x 100% = $10000
Rose Oil $10000 x 90% = $9000l-Citronellol $59.50 x 5% = $2.98Geraniol $37.00 x 3% = $1.11Linalool $50.00 x 2% = $1.00Total (Adulterated) $9005.09
Lavender Oil 40/42 $78.00 x 100% = $78.00
Lavender Oil 40/42 $78.00 x 90% = $70.20Lavandin Grosso $19.00 x 10% = $1.90Total (Adulterated) $72.10
4000 lbs x $78.00 = $312,0004000 lbs x $72.10 = $288,400Total Saved = $23,600
Adulteration Costs
Questions?
Return to Agenda
Pricing & Supply
Cara Rogers
Perfumer
Return to Agenda
Essential oils are priced based
on the following factors:
• Yield from crops
• Labor
• Extraction Techniques
• Availability and demand
Pricing of Essential Oils
• Certain oils require more plant material
to generate a substantial amount of oil
• It takes about 4 tons (1,600,000) rose
petals to make 1 kg of oil
• It takes about 0.055 tons of eucalyptus
leaves to make 1 kg of oil
• Rose oil is far more expensive than
eucalyptus oil
• Market price for Bulgarian Rose Oil is $5,126/lb (25 lb pricing)
• Market price for eucalyptus oil is $9.50/lb
(drum pricing)
Yield From Crops
Harvesting procedure affects pricing of essential oils
Cost of Labor
Oranges Jasmine
• Harvested in bulk at any time of
the day
• Gently picked no later than
10am on the day of harvest
• Mechanically harvested • Hand picked, labor intensive
• Market price is $8/lb (drum) • Market price is $2,600/lb (drum)
• Most citrus oils are extracted via
cold press
• Most essential oils are extracted
by distillation
• Essential Oils produced by supercritical fluid extraction (SFE)
tend to be more expensive than other extraction methods
• SFE equipment costs hundreds of thousands of dollars
• Ginger oil from SFE is $865/lb compared to $37/lb from distillation
Extraction Techniques
• A shortage or limited supply in any essential oil
will drive up the price.
• On the other hand, an overflow of any essential
oil in the market might drive prices down.
• A strong demand of an essential oil will push
prices up.
Availability and Demand
Price fluctuations are based
on various factors:
• Weather Conditions
• Crop Issues
• Geographical Location
• Politics
Fluctuation in Pricing
• Heavy rains/storms during growing and
harvesting periods may delay crop
collection and processing.
• This could lead to temporary shortages
and price hikes.
• Haiti is the world’s leading producer of
vetiver oil—constantly suffers from severe
heavy rains and tropical storms.
• Consequently, vetiver oil production is
reduced due to a decrease in root yield.
• Shortage caused fluctuation in vetiver
prices from $170/lb to $230/lb
Weather Conditions
• Delays and reduction in new crop
growth also causes shortages and
may increase price.
• If new crops have better yields than
previous years, there’s a possibility
prices could drop.
• Florida is a leading producer for
grapefruit production.
• Recently grapefruit trees have been
suffering from HLB virus
– Major reduction in grapefruit yield
– Resulted in price hikes; price of
grapefruit EO continues to rise
Crop Issues
• Crops from various geographical locations
tend to vary in quality and price.
• Traditional sandalwood oil is from India
and is very rare to obtain.
• Indian sandalwood is a higher grade and
better quality than sandalwood from other
regions.
• Australian sandalwood is the most widely
purchased sandalwood today.
• Even though Australian sandalwood is not
the same genus as Indian sandalwood, it’s
price is still high due to investment in
agricultural techniques.
Geographic Location
• Indian sandalwood is the most known source of
sandalwood oil.
• Government restriction of private ownership of
sandalwood plantations has led to a shortage and hence continuous price increases of sandalwood oil.
• As local currencies in Indonesia and Brazil weaken
against the US dollar, prices for products in these
countries have declined.
• If currency in these countries appreciate, this will be
reflected through an increase in the US dollar price.
Politics
Essential Oil Pricing (Year to Year)
Essential Oil Pricing (Year to Year)
Grapefruit Oil
2002
2004
2006
2008
2010
2012
2014
2016
2018
487.85
531.9
531.9
532
532
517.75
542.45
542.45
580.5
681.05
829.05
681.05
953.2
1056.65
1059.9
Sandalwood Oil
Farmer
Manufacturer
Broker/Distributor
Fragrance House
Essential Oil Supply Chain
Questions?
Return to Agenda
Jim Powell
R&D Director / Sr. Perfumer
Return to Agenda
Restrictions & Allergens
Regulatory Agencies
Natural & Organic Certification Agency Standards
EcocertVery first certification company to develop
standards for natural and organic cosmetics
• Imposes 95% minimum of total ingredients derived from natural origin
• Natural and Organic Label: 95%
minimum of all plant-based ingredients in formula and 10% minimum of all ingredients by weight must come from organic farming
• Natural Cosmetic Label: 50% minimum of
all plant-based ingredients in formula and 5% minimum of all ingredients by weight must come from organic farming
Natural Product Association (NPA)Most widely used natural certification program for personal care products
• Products must be made up of only natural ingredients
• For each ingredient, substance must be listed as “generally recognized as safe” (GRAS) by the FDA when used in accordance with good manufacturing practices (GMPs)
• Fragrances must be 100% natural
International Fragrance Association (IFRA)
• Self-regulating system of the fragrance industry
• Based on risk assessments carried out by an independent
expert panel
• GOAL: Safe use of fragrance ingredients
• Globally accepted and recognized risk management system
Research Institute for Fragrance Materials (RIFM)
• Scientific arm of IFRA
• Expert panel that instructs IFRA to issue a standard
• Comprehensive dossiers on the fragrance materials
• Dermatology, toxicology, pathology, and environmental science experts
• 174 substances that are either banned, have specifications or are restricted in their use in fragrance products
IFRA Standards
• Prohibited: cannot use at all (0.1% is acceptable as
“unavoidable impurities” in raw materials such as essential oils)
– Verbena Oil (Phototoxicity and Sensitizing)
• Restricted: can use the material but only below a certain
concentration in the finished product
– Bergamot Oil (Phototoxicity) Nutmeg(Safrole content < 0.01%)
• Specification: adhere to specific purity criteria
– Cade Oil (Rectified) limited PAH
Linalool and natural products to be rich in linalool, such as bois de rose, should only
be used when the level of peroxides is kept to the lowest practical level. It is recommended
to add antioxidants at the time of production of the raw material. The addition of
0.1% BHT or alpha-tocopherol has shown great efficiency.
• Acceptable usage level of fragrance in your product
– Currently 11 categories and subcategories
IFRA Statements: What this tells our customer
EU Allergen List
• Established 26 materials that must be listed on cosmetic
labels within the European Union citing “A well-recognized
potential to cause allergy…”
• Labeling required for material present above 0.001% in leave-on product and 0.010% in rinse-off
• Does not restrict or prohibit use of fragrance materials
• High probability of expansion
• Not all allergens are synthetic
List A Allergens
• Fragrance chemicals that are most frequently reported
• Well-recognized consumer allergens
Amyl cinnamic aldehyde
Amyl cinnamic alcohol
Benzyl alcohol
Benzyl salicylate
Cinnamic alcohol
Cinnamic aldehyde
Citral
Coumarin
Eugenol
Geraniol
Hydroxycitronellal
Lyral
Isoeugenol
List B Allergens
• Fragrance chemicals that are less frequently reported
• Less documented consumer allergensAnisyl Alcohol
Benzyl Benzoate
Benzyl Cinnamate
Citronellol
Farnesol
Hexyl Cinnamic Aldehyde
Lilial
d-Limonene
Linalool
Methyl Heptine Carbonate
Methyl Ionone gamma
Oakmoss
Treemoss
Cinnamon Bark Oil Sandalwood Oil
Examples of EU Allergen Statements
Are Essential Oils Safe?
• Yes, essential oils are safe when used properly.
• Most are free of adverse side effects when used
properly.
• However, as with any substance you are
introducing to your body, it is important to use them properly.
Natural vs. Synthetic
• Natural does not mean it is safer
• Some Essential Oils do not contain any allergens
• Most Essential Oils contain one or more allergens
– Orange Oil has d-Limonene
– Lavender Oil has Linalool
– Sandalwood Oil has None
– Rose Oil has Geraniol
– Cinnamon Bark Oil has Cinnamic Aldehyde
– Jasmine Oil has Benzyl Benzoate
Questions?
Return to Agenda
John Little
Perfumer
Return to Agenda
Truth or Myth?
Facts and Misconceptions of Essential Oils
EOs are the foundation of perfumery…
It Starts with the Basics
• Essential oils are the OG fragrance materials
– Biblical references to EOs
– Egyptian use for embalming
• Learning addition and subtraction comes before
multiplication
• Popularity of these types has continued despite the
increase in options from new odor molecules
EOs can cost a lot of money…
A Rough Guide to Cost
• Orange Oil $
• Lavender Oil = $$
• Ginger SFE = $$$
• Rose Oil = $$$$$$
• Orris Absolute = If you have to ask then you
can’t afford it
EOs have irreplaceable character…
Time, Cost, Quality
• Plants are master perfumers in their own rite and
EOs should be considered plant derived fragrance
formulas
• It’s cheaper to use EOs than a perfumer trying to
recreate that character
• Perfumers consistently look to essential oils when the
price allows it
• Perfumer will also remove costly synthetics to use
more EOs
EOs are single materials…
EOs are always natural…
EOs are regulated by the FDA under
the Food and Cosmetic Act…
Highly Sought, Poorly Understood
• The FDA has a limited scope
• Same goes for USDA
• Understanding the precise wording on how
suppliers define EOs is important
• Ask about "pure & natural" when in doubt
The FDA does not define the terms “organic,”
“natural,” nor “essential oil” in cosmetics…
The characteristic smell of an EO
is what makes it an EO…
EOs smell better than fragrances
made from synthetic materials…
Essential Oils Can be Limiting
• Specific fragrance characters with well
established appeal for consumers cannot
be achieved with EOs alone
• The most popular fragrances achieve their
character from the creative blending of
naturals AND synthetics
Perfumers really, really like EOs…
…we adore them!
We Smell Them With Our Pets
We Take Them on Walks Along the Beach
We Read Them Bedtime Stories