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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?

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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