The DoTerra Essential Oil Chemestry Handbook

Chapter 1: An Introduction to Essential Oils
THE dōTERRA ESSENTIAL OIL

CHEMISTRY HANDBOOK
Edited by Dr. David K. Hill, D.C.
3
Chapter 1: An Introduction to Essential Oils
TABLE OF CONTENTS
FOREWORD .............................................................................................................i
THE dōTERRA OIL CHEMISTRY WHEEL .....................................................ii
PART 1: THE BASICS OF ESSENTIAL OIL CHEMISTRY..........................2

1. An Introduction to Essential Oils ..............................................................3
1.1 What are essential oils? .............................................................................................. 3
Essential oils are called “essential” because they are the
“essence” of a plant ..................................................................................................... 3
Why do plants produce essential oils?......................................................... 3
1.2 Obtaining Essential oils from plant parts ....................................................... 3
Steam Distillation........................................................................................................... 3
Cold Press........................................................................................................................... 4
Solvent Extraction ......................................................................................................... 4
1.3 Essential Oils are complex mixtures of aromatic compounds ..... 4
Essential oils are made of volatile aromatic compounds ............... 4
Essential oils can be made up of anywhere between 1
and 1000 different compounds with different chemical
identities ............................................................................................................................... 5
2. Essential Organic Chemistry .................................................................... 6

2.1 Oil usage is linked to oil chemistry.....................................................................6
2.2 The carbon backbone .................................................................................................6
Terpenes.............................................................................................................................. 7
Monoterpenes .................................................................................................................8
Sesquiterpenes...............................................................................................................8
2.3 Introduction to Functional Groups .....................................................................9
3. The Functional Groups and their Functions .................................... 10

3.1 Alcohols .................................................................................................................................11
3.2 Aldehydes...........................................................................................................................12
3.3 Alkenes .................................................................................................................................13
Foreword
3.4 Esters .....................................................................................................................................13
FOREWORD
3.5 Ethers .....................................................................................................................................15
3.6 Ketones ................................................................................................................................16 Dear friends,
3.7 Phenols .................................................................................................................................17
3.8 Phenylpropenes ............................................................................................................18 I, like you, have a passion for essential oils. They have played a
3.9 Conclusion .........................................................................................................................19 significant role in both my professional and personal life for many
years. I remain convinced that the benefits of essential oils are
PART 2: OIL CHEMISTRY A-Z ........................................................................20 unique and almost universally applicable to all who choose to
Arborvitae – Blue Tansy ................................................................................................. 22 experience them.
Cardamom – Clary Sage ................................................................................................ 24
I am so pleased to be a part of dōTERRA and to participate in the
Clove - Dill ................................................................................................................................. 26
Douglas Fir – Ginger .......................................................................................................... 28 progress and discovery of essential oils. They have found their
Grapefruit – Lemon ............................................................................................................30 rightful place in science, healthcare, and most importantly, in
Lemongrass – Myrrh ......................................................................................................... 32 individualized approaches to health and wellness. Through my own
Oregano – Rose .................................................................................................................... 34
Rosemary – Spikenard ..................................................................................................... 36 experience, I have learned the importance of quality, and I think it
Tangerine – Ylang Ylang................................................................................................. 38 is significant that dōTERRA stands alone as the sole provider of the
highest quality essential oils in the world.
PART 3: CONSTITUENT CHEMISTRY ........................................................41 It is my pleasure to introduce to you the dōTERRA Essential Oil
Anethole - Bisabolene ..................................................................................................... 42 Chemistry Handbook. I am confident that it will help you expand
Bornyl Acetate - Carvone .............................................................................................. 44
your knowledge of essential oils and empower you to use them
beta-Caryophyllene - Cinnamaldehyde ............................................................46
Cinnamyl Acetate - Curcumene ............................................................................... 48 more effectively. It is my sincere desire that this chemistry
Curzerene - Farnesene....................................................................................................50 compendium will enhance your own experience, providing you
Fenchone - Guaiene .......................................................................................................... 52 with the basic framework from which you can develop your own
Guaiadene - Jatamansone............................................................................................ 54
personalized model of self-care and affording you the opportunity
Khusimol - Lindestrene ...................................................................................................56
Menthol - Myrcene .............................................................................................................58 to share dōTERRA essential oils with others more meaningfully and
Neral - Patchoulol................................................................................................................60 in a way that is scientifically correct.
Alpha-Phellandrene - Sabinene............................................................................... 62
gamma-Terpinene - Thujopsene ............................................................................64 With kindness,
Thymol - Zingiberene .......................................................................................................66
Dr. David Hill
i
The doTERRA Oil Chemistry Wheel
THE dōTERRA OIL Oil Chemistry Wheel

CHEMISTRY WHEEL RESTORIN
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Backbone Anethole
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The oils in the dōTERRA Chemistry Wheels are grouped according

to their shared key properties. The shared key properties provide a
starting point for understanding how to use the oils. The combina- Restoring: These are oils for emotional and physical support. They are
meant to help revive, strengthen, and rejuvenate the body and the senses.
tion of these different groupings enables individuals to begin to un-
Uplifting: These oils are meant to be inspiring. They encourage feelings of
derstand the characteristics and properties of dōTERRA’s amazing exhilaration, refreshment, and enlivening.
essential oils. Energizing: These oils are used to bring feelings of motivation and
activation. They tend to be brisk, naturally stimulating oils that help wake
up the mind and body.
ii iii
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Restoring: These are oils for emotional and physical support. They are Soothing: These are oils that help ease and alleviate issues, both emotional
meant to help revive, strengthen, and rejuvenate the body and the senses. and physical. They are meant to reassure and console as needed.
Clarifying: As the name implies, these are oils that help to “make clear.” Stabilizing: These are oils that help steady the nerves, helping you feel that
Topically they are used for improved skin tone and appearance, and you are on an even keel. By analogy, stabilizing oils encourage a person’s
aromatically they can be used to help settle and resolve ambiguous, feelings and emotions to go from a rocking boat to standing on solid ground.
uncertain feelings.
Calming: These are classic oils for feelings of relaxation, both physically
and mentally. These oils are typically used for stress relief, meditation, and
preparation for sleep.
iv v
Oil Chemistry Wheel
Essential Oil
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the chemical constituents in the oil. Usually the backbone type is either
monoterpene or sesquiterpene.
Functional Group: Indicates the presence of a specific arrangement of
atoms within the constituent molecule that has distinct chemical properties.
RED LINE=DIE CUT
Chemical Constituent Name: The chemical names for the main compounds
found in each oil.
Essential Oil: Gives the names of the dōTERRA oils with the backbone,
functional group, and constituent composition that fit into the chemical
categories explained above.
vi vii
Part 1: The Basics of Essential Oil Chemistry Chapter 1: An Introduction to Essential Oils
PART 1: THE BASICS OF CHAPTER 1: AN INTRODUCTION TO

ESSENTIAL OILS
ESSENTIAL OIL CHEMISTRY
1.1 WHAT ARE ESSENTIAL OILS?
Everything is chemistry. Every cell, organ, and tissue in the body
performs its function using enzymes, receptors, and other proteins, Essential oils are called “essential” because they are the “essence”
which work together to break down, build up, and rearrange the of a plant. In the Middle Ages, it was believed that essential oils were
chemical bonds in biological molecules. Essential oils also operate essential for life, giving them the moniker that has stuck even to the
under the principles of chemistry. In fact, the chemical makeup of present day. Modern references define an essential oil as the essence,
essential oils is what gives them the ability to affect the body’s sys- or extract, that is the source of a plant’s aroma and flavor. For example,
tems. Molecules in essential oils can selectively support the function peppermint plants smell like peppermint because of the essential
of subcellular structures that run the processes that keep us alive.
oil contained in their leaves and stems. Oranges smell like oranges
By understanding the fundamentals of oil chemistry, you can begin because of the essential oil contained in the peel.
to classify oils by their chemical properties. This will help you learn
which oils might have applications in different daily life contexts and Why do plants produce essential oils? Essential oils are a critical part
how they work. This portion of the Oil Chemistry Handbook will give of a plant’s immune system. Plants produce essential oils to protect
you the intellectual tools you need in order to understand how to use themselves against environmental threats. The parts of a plant with the
essential oils effectively and how to share them with others. greatest amount of essential oil are usually the parts with the greatest
In Part 1, generalizations are made based on chemistry to help de- risk for invasion by microorganisms: the bark, sap, leaves, seeds, and
velop a conceptual framework for grouping and categorizing oils. fruit rinds. The compounds found in essential oils have all sorts of
Because this framework is so compact and simple, there will, of biological activities. They are known to protect against environmental
course, be exceptions. Before using any of the oils mentioned in this
threats, soothe the body, and even calm the mind.
section, be sure to refer to Part 2 of this book for the suggested uses
and skin sensitivity associated with each specific oil.
This reference is designed for a general audience with basic knowl- 1.2 OBTAINING ESSENTIAL OILS FROM PLANT PARTS
edge of chemistry. The content in Part 1 provides background in-
While it is important to note that essential oil extraction is unique
formation on essential oils and the basics of general and organic
chemistry before delving into essential oil chemistry. The chemical to every plant, in general, dōTERRA essential oils are extracted
structure of essential oil molecules, the functional groups, and their using one of three methods: steam distillation, cold press, or solvent
uses are then outlined in detail. extraction.
Read through this section carefully; it will provide you with the back- Steam Distillation is the most common method for collecting
ground knowledge necessary to understand the detailed chemical essential oils. In steam distillation, water is boiled and the resulting
information on essential oils and their constituents contained in Parts steam passes through the plant material. The steam carries the
2 and 3.
essential oil from the plant into a collecting tube, where the steam
is cooled and condensed back into water. Because essential oils are
lipid soluble (meaning that they mix readily with other oils), they are
2 3
easily separated from the water. physical and chemical properties of volatile aromatic compounds
Cold Press is a method that doesn’t involve heat. Cold press allow them to quickly enter the gas state, move through the air, and
extraction is used exclusively with citrus fruits because it is a way of directly interact with olfactory sensors in the nose.
extracting oil from the outermost layer of the fruit’s peel. The fruit is Essential oils can be made up of anywhere between 1 and
passed across sharp rasping cylinders that abrade the surface of the 1000 different compounds with different chemical identities.
peel to break open small essential oil-containing sacs. Water is then For example, Birch oil is almost
sprayed over the fruit to collect the essential oil. The resulting watery entirely composed of one
mixture is then filtered and centrifuged to separate the essential oil compound: methyl salicylate.
from the water. Spikenard, on the other hand,
Solvent Extraction can be used on every type of plant material, but contains hundreds of compounds.
is most commonly used on flowers that are too fragile to endure Most oils fall somewhere in
the conditions required for steam distillation. The plant material is between these two extremes. For
washed with a solvent to dissolve out the fragrant compounds. The instance, Frankincense essential
resulting mixture is then filtered to remove the plant material, and oil contains over 65 distinct
then the solvent is removed using vacuum distillation. The yield chemical compounds in various
of this process is a thick, waxy material called a “concrete.” The quantities.
concrete is processed again in a similar fashion but with a different The different compounds in an
solvent. After another round of vacuum distillation to remove the essential oil are known as constituents. Each constituent has its own
second solvent, a pure mixture of only absolute remains. Common distinct structure, meaning that the shape, size, and arrangement of
absolutes extracted by this method are Jasmine and Vanilla. chemical bonds in that molecule is unique. The different constituents
in an essential oil determine both the oil’s aroma and the benefits it
offers.
1.3 ESSENTIAL OILS ARE COMPLEX MIXTURES OF
AROMATIC COMPOUNDS The exact composition of an essential oil varies between plant
species. When speaking of essential oils, the word “composition”
Essential oils are made of volatile aromatic compounds. Volatile
refers to the oil’s constituent makeup or, in other words, what chemical
aromatic compounds are small organic molecules that tend to
constituents it contains and how much of those constituents are
change from the liquid state to the gas state at room temperature.
present. For instance, Bergamot essential contains over 35 different
These molecules are so incredibly small that a single drop of essential
compounds, but it has especially high levels of two constituents
oil contains around 40,000,000,000,000,000,000 (40 million trillion)
called limonene and linalyl acetate. Blue Tansy essential oil, on
of them. The word “volatile” emphasizes their tendency to evaporate
the other hand, contains over 50 compounds, with the two most
quickly at room temperature. This property is what makes them smell
abundant constituents being chamazulene and sabinene.
so potent. When you first open a bottle of essential oil, you instantly
notice the aroma, and you can smell it even from a distance. The
4 5
Part 1: The Basics of Essential Oil Chemistry Chapter 2: Essential Oil Organic Chemistry
CHAPTER 2: ESSENTIAL OIL ORGANIC Chemists use special diagrams called Lewis structures to map
out the detailed structure of a molecule. For example, figure 2.1 is
CHEMISTRY a Lewis structure depicting the essential oil constituent limonene.
The letters in this diagram represent atoms. “C” stands for carbon,
2.1 OILS USAGE IS LINKED TO OIL CHEMISTRY and “H” stands
Again, everything is chemistry. Chemical structure influences how for hydrogen. The
substances are absorbed and metabolized, how they smell, and what lines represent
their biological activities are. By understanding the fundamentals chemical bonds
of oil chemistry, you can learn to categorize oils by their chemical between atoms
properties. This will help you understand how to use them effectively and the double
and how to share them with others. lines represent
Perhaps you want to enjoy the skin-supporting properties of double bonds.
Geranium, but you don’t particularly like its aroma. Maybe you just Notice how the
used your last few drops of Frankincense and you need to find molecule’s shape
is determined Figure 2.2: Carbon skeleton
something else for your daily support of healthy cellular function.* diagram of limonene. Note
Or maybe you are crafting your own blend to meet a specific by the carbon Figure 2.1: Lewis structure that H’s and C’s are not
of limonene. Note the shown, greatly simplifying
set of health needs or to create a specific aroma. If you have the backbone. You the diagram.
complexity of the diagram.
information about essential oils’ chemical composition and you may have also
know how to use it, you can skillfully do any of these tasks. In fact, noticed how complicated the diagram is. A more compact way
the more you understand chemistry, the more effectively you will be to depict the backbone structure is by using a carbon skeleton
able to use essential oils in general. In this section, we will describe diagram (figure 2.2). Because of their simplicity, carbon skeleton
two common ways of categorizing essential oils based on chemistry: diagrams are the most commonly used chemical diagrams for
carbon backbone and functional groups. depicting organic molecules.
Carbon skeleton diagrams show the structure of an organic
compound in a similar fashion to Lewis structures, but there are a few
2.2 THE CARBON BACKBONE
key differences. Take a moment to look at the differences between
Organic chemistry is the study of organic molecules. In chemistry, the figure 2.1 and figure 2.2. In the skeleton diagram, hydrogens are left
word “organic” means “carbon-based.” So organic chemistry literally out and the carbons are not labeled. Since the bonds are still shown,
means “the study of carbon-based molecules.” Understanding the you can tell where the carbons are because they exist at either end
basics of organic chemistry is essential for understanding essential of a line representing a bond.
oils because every aromatic molecule is made of carbon atoms joined
Terpenes are the class of aromatic molecules synthesized by
together by chemical bonds. The portion of a molecule comprised of
plants. Every plant has hundreds of special enzymes called terpene
a chain of carbon atoms is known as the carbon backbone.
synthases that work together to build these compounds out of smaller
6 7
Part 1: The Basics of Essential Oil Chemistry Chapter 2: Essential Oil Organic Chemistry
building blocks called isoprene units, which have five carbons. There Sesquiterpenes can have
are three main kinds of terpenes: monoterpenes, sesquiterpenes, a straight-chain backbone,
and diterpenes. Diterpenes are sometimes present in essential oils, one ring, or two rings (see
but only in very small amounts. Their large molecular weight keeps figure 2.4). Sesquiterpenes
them from evaporating during steam distillation. Monoterpenes and aren’t quite small enough
sesquiterpenes are the main compounds found in essential oils. to pass through the cell
Due to their differences in size and structure, monoterpenes and membrane as efficiently as
sesquiterpenes have different effects on the body. monoterpenes, but they have
Monoterpenes are found in unique shapes that allow
them to adhere to pockets Figure 2.4: Some common sesquiterpenes
some amount in almost all include germacrene (top left), guaiene
essential oils. They have a in three-dimensional protein (top right), and farnesene (bottom).
structure of 10 carbon atoms structures, affecting protein

derived from two isoprene activity. Sesquiterpenes are known to activate various cell surface
units and at least one double receptors.
bond. Monoterpenes can have
a straight-chain backbone or 2.3 INTRODUCTION TO FUNCTIONAL GROUPS
a single ring (see figure 2.3).
Another way to characterize essential oils is based on functional
Due to their smaller size, they
groups. Functional groups are easy to spot on a skeleton diagram
tend to react quickly to air Figure 2.3: Some common mono-
terpenes include limonene (top left), because they are spelled out, in contrast to the carbon and hydrogen
and heat, and they tend to be
gamma-terpinene (top middle), myrcene molecules, which are omitted. For instance,
broken down more quickly (right), and para-cymene (bottom).
the letters “O” and “H” (representing
than their more complex
oxygen and hydrogen) are spelled out in
sesquiterpene counterparts. Monoterpenes have strong effects on
the carbon skeleton diagram of an alcohol,
cell membranes because they are small enough to fit between the
which is one specific kind of functional
fatty molecules that make up the cell membrane. They are also small
group (see figure 2.5).
enough to completely pass through it and affect targets inside the cell.
There are believed to be well over 2,000 varieties of monoterpenes, Functional groups are distinct groups of
each with its own unique biological activity. atoms within a molecule, but they have
characteristic properties that manifest
Sesquiterpenes have a structure of 15 carbon atoms derived from
themselves regardless of the other
three isoprene units. Because of their higher molecular weights,
atoms contained within the molecule. For
sesquiterpenes are less volatile than monoterpenes and are
instance, menthone and carvone are both Figure 2.5: A monoterpene
therefore less prevalent in essential oils overall. It is believed that with an alcohol functional
ketones, meaning that somewhere in their group
there are over 10,000 different varieties of sesquiterpenes.
8 Part 1: The Basics of Essential Oil Chemistry 9

Part 1: The Basics of Essential Oil Chemistry Chapter 3: The Functional Groups and Their Functions
structure they both contain a special kind of double bond with an Before using any of the oils mentioned in this section, be sure to
oxygen atom. For instance, experimental research suggests that refer to Part 2 of this book for the suggested uses and skin sensitivity
essential oils rich in menthone or carvone (i.e., Peppermint and Dill) associated with each specific oil.
can be soothing to the tissues and also support digestive function.*
Although categorizing oils by functional group does not tell the entire
3.1 ALCOHOLS
story of use and efficacy, it is clear that it can provide a meaningful
framework for daily usage of essential oils. An alcohol is any molecule with an
alcohol functional group. An alcohol
group consists of an oxygen atom Figure 3.1: An alcohol group
CHAPTER 3: THE FUNCTIONAL GROUPS bound to both the carbon backbone
AND THEIR FUNCTIONS on one end and a hydrogen atom on the other end (see figures 3.1
and 3.2). In general, alcohol molecules have names ending with the
There are more than 20 different functional groups in organic suffix –ol. For instance, menthol, terpinen-4-ol, citronellol, geraniol,
chemistry, but there are only 8 main functional groups found in and linalool are examples
essential oil constituents. The functional groups in essential oils are of monoterpene alcohols.
alcohols, aldehydes, alkenes, ketones, esters, ethers, phenols, and Santalol, isovalencenol,
phenylpropenes. In this chapter, we’ll discuss the atomic structure of khusimol, cedrol (also
each of these functional groups, their properties and potential uses, known as eudesmol), and
and examples of oils and constituents that contain these functional patchoulol (also known
groups. as patchouli alcohol) are
sesquiterpene alcohols. One
It is important to realize that functional groups and carbon backbones
exception to this naming rule
are two separate features of aromatic compounds. This means that
is the compound eucalyptol, Figure 3.2: An example of an alcohol group
a molecule can be both a monoterpene and an alcohol at the same found in menthol, a monoterpene alcohol
which is actually an epoxide
time. Likewise, there are molecules that are sesquiterpene alcohols, found in peppermint oil
(a type of ether).
monoterpene aldehydes, sesquiterpene ketones, etc. Every possible
combination of terpene and functional group represents its own Properties and Uses of Alcohols
unique class of molecules. Aromatic: Relaxing aromas, helps soothe anxious feelings
In this section, generalizations are made based on chemistry to Topical: Repellant activity, cleansing properties, helps the skin
develop a conceptual framework for grouping and categorizing oils. look young and healthy
There will be exceptions to these generalizations. For example, while Internal: Supports the circulatory system, calms the nervous
many alcohols have health benefits when taken internally, some are system*
not recommended for internal use. Oils high in monoterpene alcohols: Melaleuca, Geranium,
Coriander, Basil, and Lavender
10 11
Oils high in sesquiterpene alcohols: Sandalwood, Vetiver, 3.3 ALKENES

Cedarwood, and Patchouli An alkene is a molecule with no functional groups present and at least
one double bond between any two of the carbons in its backbone.
3.2 ALDEHYDES Alkene molecules usually have names that end with the suffix –
ene. For instance, alpha-pinene, sabinene, limonene, and gamma-
An aldehyde is a molecule with
terpinene are examples of monoterpene alkenes. Germacrene D,
an aldehyde group. An aldehyde
caryophyllene, zingiberene, and alpha-cedrene are examples of
group is characterized by a carbon
sesquiterpene alkenes. Each of the molecules in figures 2.3 and
double bonded to an oxygen (see Figure 3.3: An aldehyde group
2.4 are alkenes: they have no other functional groups and at least
figures 3.3 and 3.4), where the
one double bond between carbons. In fact, most of these molecules
same carbon atom is also bonded to both a hydrogen (not shown) and
have many double bonds.
another carbon in the molecule’s main backbone. In general, aldehyde
molecules have names ending with the suffix –al or –aldehyde. For Monoterpene and sesquiterpene alkenes are well-known for their
instance, geranial, neral, antioxidant properties.* The large number of double bonds and the
cinnamaldehyde, cuminal, existence of ring structures in these molecules makes them excel-
and decenal are examples lent at accepting the lone electrons contained in free radicals.
of monoterpene aldehydes. Properties and Uses of Alkenes
Santalal, farnesal, and Aromatic: Many unique and pleasant fragrances
valeranal are examples of Topical: Antioxidant benefits for the skin and the tissues
sesquiterpene aldehydes. Internal: Antioxidant benefits for the internal organs, may also sup-
Figure 3.4: An example of an aldehyde group
Sesquiterpene aldehydes in the compound terpinen-7-al, a monoterpene port the nervous, immune, digestive, reproductive, integumentary,
are far less common than aldehyde found in cumin essential oil
and circulatory systems*
monoterpene aldehydes.
Oils high in monoterpene alkenes: Frankincense, Douglas Fir, Blue
Properties and Uses of Aldehydes Tansy, Lemon, and Wild Orange
Aromatic: Calming, relaxing, and protecting Oils high in sesquiterpene alkenes: Ylang Ylang, Black Pepper,
Topical: May reduce the appearance of blemishes, keep skin Copaiba, Melissa, and Ginger
looking healthy, support oral health and hygiene, and provide a
warming sensation to the skin
Internal: Supports the health of the cardiovascular, digestive, 3.4 ESTERS
immune, and nervous systems. Many essential oils high in An ester is a functional group that results from the reaction between
aldehydes are also known to support healthy metabolism.* an alcohol and an acid. Esters have a central carbon atom double
Oils high in monoterpene aldehydes: Cassia, Cinnamon, Melissa, bonded to an oxygen atom, single bonded to the backbone, and
Lemongrass, and Lime single bonded to a second oxygen atom (see figures 3.5 and 3.6). This
12 13
second oxygen is 3.5 ETHERS

bonded to a short An ether is a molecule with an
hydrocarbon oxygen atom bonded between
chain on the other two carbons (see figures 12 and
side. These short 13). In order to be an ether, the
chains are usually two flanking carbons must only Figure 12: An ether group
one, two, or three Figure 3.5: An ester group
have bonds with other carbons
carbons long. (or hydrogen). Ethers are sometimes found in the main carbon chain
Because there are two or in ring structures, appearing as if an oxygen had replaced a carbon
carbon chains in an ester in the backbone. They can also be found in the peripheral parts of
molecule, they usually some molecules. Ethers are not
have two-word names, very common in monoterpenes.
the second word ending The monoterpene ether eucalyptol,
with the suffix –ate. also known as 1,8-cineole, is the
Linalyl acetate, methyl- most common ether found in
amyl angelate, benzyl Figure 3.6: An example of an ester group in the
essential oils. Anisole is another
compound benzyl acetate, a main constituent of
acetate, bornyl acetate, Jasmine absolute. common monoterpene ether.
neryl acetate, methyl Sesquiterpenes, on the other hand,
thujate, and methyl salicylate are examples of monoterpene esters are more likely to contain ether
found in essential oils. Sesquiterpene esters are fairly uncommon in groups. For instance, curzerene and
essential oils. Figure 13: An example of an ether
furanoeudsema-1,3-diene are two group in the compound eucalyptol,
Properties and Uses of Esters sesquiterpene ethers. the main constituent of Eucalyptus oil
Aromatic: Relaxing, soothing, balancing Properties and Uses of Ethers

Topical: Rejuvenate the skin, soothe the tissues, protect against Aromatic: Soothing to the emotions, promote feelings of clear
certain kinds of environmental threats airways
Internal: Varies on a case-by-case basis. Some esters can Topical: Surface cleaning properties, help improve the appearance of
support the health of the cardiovascular, immune, nervous, and skin
digestive systems. Other esters are not recommended for internal Internal: Varies on a case-by-case basis. Some ethers provide
consumption.* antioxidant support and can also support proper immune system
Oils high in monoterpene esters: Lavender, Roman Chamomile, function.* Other ethers are not recommended for internal
Helichrysum, Arborvitae, and Wintergreen consumption.
Oils high in monoterpene ethers: Cardamom, Eucalyptus,
14 15
Rosemary, Melaleuca, and Peppermint tion and health.* Sesquiterpene ketones are generally not recom-
Oils high in sesquiterpene ethers: Myrrh and Vetiver mended for internal use.
Oils high in monoterpene ketones: Spearmint, Dill, Peppermint,
Geranium, and Caraway
3.6 KETONES
Oils high in sesquiterpene ketones: Spikenard, Frankincense
A ketone is a molecule with a
carbon atom double bonded to
an oxygen atom (see figures 3.7 3.7 PHENOLS
and 3.8). The two carbons flanking Phenols are a special subtype of
this carbon must not be bonded alcohols. A phenol is an alcohol group (an
to any atoms other than carbon oxygen and a hydrogen) attached to a
(or hydrogen). Ketone molecules benzene ring (see figures 3.9 and 3.10).
Figure 3.7: An ketone group
usually have names that end A benzene ring has six carbon atoms
with the suffix –one. For instance, arranged in a hexagon pattern and must
menthone and carvone are have exactly three double bonds inside
ketones. Camphor is also the ring. Because phenols are alcohols,
a notable ketone whose their names also end with the suffix
name doesn’t follow the Figure 3.9: An phenol group
–ol. Thymol, carvacrol, and eugenol
normal pattern. Many are the most common
sesquiterpenes contain monoterpene phenols.
ketones. Jatamansone, Sesquiterpene phenols are
rotundone, mustakone, fairly uncommon.
faurinone, davanone,
Properties and Uses of
and leptospermone Figure 3.8: An example of a ketone group
found in Menthone, a constituent of Phenols
are the names of a few
Peppermint oil.
sesquiterpene ketones. Aromatic: Invigorating
aroma
Properties and Uses of Ketones
Topical: Powerful cleans- Figure 3.10: An example of a phenol group in
Aromatic: Some are energizing and uplifting, others are stabilizing properties on skin and the compound carvacrol, the primary
ing and grounding. Certain ketones can support feelings of open constituent of Oregano oil
surfaces
airways. Internal: Antioxidant proper-
Topical: repellant properties, may help keep the skin looking clean ties, support the proper function of cardiovascular, circulatory, di-
Internal: Varies on a case-by-case basis. Most monoterpene ke- gestive, gastrointestinal, immune, nervous, and respiratory systems*
tones support digestive, gastrointestinal, and nervous system func-
16 17
Oils high in monoterpene phenols: Thyme, Oregano, Clove, Cinna- 3.9 CONCLUSION
mon Bark, and Basil Now that you’ve learned about functional groups and the terpene
backbone, you are ready to move on to Parts 2 and 3 of this book. Part
3.8 PHENYLPROPENES 2 contains the most detailed chemical information publicly available
on every single oil currently offered by dōTERRA. Each oil’s func-
A phenylpropene group is
tional group content, terpene content, and constituent composition
characterized by a carbon in
is listed to help you characterize, compare, contrast, and categorize
a benzene ring bonded to a
oils at your convenience. Part 3 contains detailed information on the
second carbon that is then
chemical constituents mentioned in part 2. Part 3 details the usage
bonded to a third carbon with
and benefits of nearly a hundred different constituents and explains
a double bond (see figures
Figure 3.11: A phenylpropene group which oils those constituents can be found in, and in what quantities.
3.11 and 3.12). The third carbon
While Part 1 was primarily focused on the general concepts under-
is single bonded to a fourth
lying essential oil chemistry, the rest of this book contains detailed
carbon at the end of the
information on every dōTERRA oil and its chemical constituents.
chain. Phenylpropenes
are usually found
in monoterpene
compounds, but they
are not common
in most essential
oils. Anethole and
chavicol (also known Figure 3.8: An example of a phenylpropene group in
as estragole) are the the compound anethole, the primary constituent of
Fennel oil. Note that anethole also has an ether
two most common group.
phenylpropenes.
Properties and Uses of Phenylpropenes
Aromatic: Energizing aroma
Topical: Support overall skin health and appearance
Internal: May support the cardiovascular system and promote
healthy blood flow*
Oils high in monoterpene phenylpropenes: Fennel, Myrtle, Anise,
Star Anise, and Basil
18 19
PART 2: A-Z OIL CHEMISTRY
This part of the Oil Chemistry Handbook contains the most detailed Another limitation is the ecological variance of oil composition.
chemical information publicly available on each of dōTERRA’s The exact percent of constituent composition in an essential oil
single oils. The oil name and botanical name are both included in depends on the geographical location, time of year, and even the
the header of each entry, with the suggested uses (Aromatic, Topi- time of day the plants are harvested. The composition of an es-
cal, and Internal) and skin sensitivity (Neat, Sensitive, or Dilute) on sential oil isn’t always identical to the percentages presented in
the right side of the header. The middle section of each entry con- this booklet. However, the percentages given here are considered
tains information about the potential uses of each oil and the body standard, meaning that they represent the most likely composi-
systems it may support. tion for each oil. In fact, dōTERRA’s staff of analytical chemists work
Below the uses and body systems are two pie graphs represent- hard to ensure that every batch of oil matches these standards
ing the chemical composition of each oil, one characterizing its within a reasonable margin.
functional group and the other giving information on the backbone
composition. To the right of these pie charts is a list of the main We hope that you will enjoy having this valuable information at your
constituents that consistently appear at levels at or above 5%. A fingertips as you browse this reference on essential oil chemistry.
percentage range indicates the possible values for the percent
composition of constituent depending on the oil batch. Note that
the percent composition of the main constituents often does not
add up to 100%. This is because there are many additional com-
pounds present in smaller amounts.
One limitation of the information given here is that it doesn’t ad-
dress the topic of chemical diversity. Unfortunately, this aspect of
chemistry is impossible to convey in the form of a simple pie chart
or a short list of constituents. For example, Spikenard and Myrrh are
two incredibly diverse oils, each with potentially hundreds of differ-
ent compounds. It would require many pages to list the names of
all of their constituents. It is important to realize that the presence
of these minor constituents can often give an oil additional benefits
that are not associated with its main constituents. Because of syn-
ergy and the interaction between oil constituents, the benefits of
the oils listed in this section may different than a simple sum of the
benefits of their constituents taken from Part 3.
20 21
Part 2: A-Z Oil Chemistry Arborvitae – Blue Tansy
Arborvitae Thuja Plicata Birch Betula lenta

Uses: Protects against environmental and seasonal threats. Powerful Uses: Provides a soothing massage and cooling sensation after exercise.
cleansing and purifying agent. Natural insect repellent and wood Promotes healthy-looking skin. Apply topically to reduce appearance
preservative. of blemishes.
Body Systems: Immune, Skin
Body Systems: Nervous, Skin, Musculoskeletal
Carbon backbone Functional groups Main Constituents Carbon backbone Functional groups Main Constituents
50–70% Methyl > 98% Methyl
thujate salicylate
Basil Ocimum Basilicum Black Pepper Piper nigrum

Uses: Apply topically to help keep the skin looking clean, clear, and Uses: Provides antioxidant support, supports healthy circulation,
healthy. Diffuse to promote mental alertness and lessen anxious and aids digestion. Enhances food flavor. Diffuse to soothe
feelings. Take internally to help to ease monthly feminine discomfort.* anxious feelings.
Body Systems: Nervous, Reproductive, Skin Body Systems: Nervous, Cardiovascular, Digestive
40-80% Linalool 8–46% Beta-
caryophyllene
1–15% 1,8-Cineole 9–25% Limonene
(eucalyptol) 0.1–23% Sabinene
1–7% Bergamotene 2–20% beta-Pinene
1–20% alpha-Pinene
0.01–21% delta-3-Carene
Bergamot Citrus Bergamia Blue Tansy Tanacetum Anuum

Uses: Diffuse for a calming and soothing aroma. Provides skin purifying Uses: Helps reduce the appearance of blemishes. Provides a
benefits. Frequently used in massage therapy for its calming benefits. soothing sensation when applied to the skin.
Body Systems: Nervous, Skin
Body Systems: Skin
20–55% Limonene 2–15% Chamazulene
10–45% Linalyl 10–30% Sabinene
acetate
3–12% gamma- 5–20% Camphor
Terpinene 2–10% beta-Pinene
3–20% Linalool
3–12% beta-Pinene
Monoterpene Alcohol Ester Phenol *These statements have not been evaluated by Monoterpene Alcohol Ester Phenol *These statements have not been evaluated by
the Food and Drug Administration. This product the Food and Drug Administration. This product
Legend: Sesquiterpene Aldehyde Ketone Ether is not intended to diagnose, treat, cure, or prevent Legend: Sesquiterpene Aldehyde Ketone Ether is not intended to diagnose, treat, cure, or prevent
Other Alkene Phenylpropene any disease. Other Alkene Phenylpropene any disease.
22 *Statements marked with asterisks refer to internal use only. Some essential oils containing the compounds presented are not recommended for internal use. *Statements marked with asterisks refer to internal use only. Some essential oils containing the compounds presented are not recommended for internal use. 23
Part 2: A-Z Oil Chemistry Cardamom – Clary Sage
Cardamom Eletarria cardamomum Cilantro Coriandrum sativum

Uses: May help ease indigestion and maintain overall gastrointestinal Uses: Supports healthy digestion when taken internally.*
health.* Promotes clear breathing and respiratory health. Flavorful Powerful cleanser and detoxifier.* Gives food a fresh and tasty flavor.
spice for cooking and baking.
Body Systems: Digestive
Body Systems: Digestive, Respiratory
25–50% Terpinyl 15–45% 2-Decenal
acetate
5–25% 2-Decenol
25–50% 1,8-Cineole
10–35% Linalool
(eucalyptol)
Cassia Cinnamomum cassia Cinnamon Bark Cinnamomum zeylanicum

Uses: Promotes healthy digestion when taken internally.* Ingest to Uses: Supports healthy metabolic function.* Maintains a healthy
support healthy cardiovascular, metabolic, and immune function.* immune system.* Naturally repels insects. Long used to flavor food
Possesses a warming, uplifting aroma. and for its internal health benefits.
Body Systems: Cardiovascular, Digestive, Endocrine, Immune Body Systems: Endocrine, Immune
75-97% 45-80%
Cinnamaldehyde Cinnamaldehyde
1-8% 2-15%
Cinnamyl acetate Cinnamyl acetate
1-10% Eugenol
Cedarwood Juniperus virginiana Clary Sage Salvia sclarea

Uses: Naturally repels insects. Promotes relaxation. Helps to keep Uses: Promotes healthy-looking hair and scalp. Promotes a
skin looking healthy. restful night’s sleep. Calming and soothing to the skin.
Body Systems: Nervous, Skin Body Systems: Nervous, Skin
10–47% alpha- 40–75% Linalyl
Cedrene acetate
9–40% Cedrol 8–40% Linalool
7–30% Thujopsene
Part 2: A-Z Oil Chemistry Clove – Dill
Clove Eugenia caryophyllata Cumin Cuminum cyminum
Uses: Powerful antioxidant properties.* Supports cardiovascular Uses: Supports digestive health and helps to relieve
health.* Helps clean teeth and gums. occasional digestive discomfort.* Purifying to the body’s systems.*
Body Systems: Cardiovascular Body Systems: Digestive, Cardiovascular, Skin
63–95% Eugenol 10–40% Cuminal
1–35% Terpinen-7-al
0.6–20% beta-
3–35% gamma-
Caryophyllene
Terpinene
4–35% beta-Pinene
3–20% p-Cymene
Copaiba Copaifera spp. Cypress Cupressus sempervirens
Uses: Supports the health of the cardiovascular, immune, digestive and Uses: Promotes vitality and energy. Helps improve the
respiratory systems.* Powerful antioxidant.* Helps calm and soothe the nervous appearance of oily skin.
system.* Promotes clear skin and reduces the appearance of blemishes.
Body Systems: Cardiovascular, Digestive, Immune, Nervous, Respiratory, Skin
45–65% beta- 20–65% alpha-
Caryophyllene Pinene
2–12% Bergamotene 7–30% delta-
3-Carene
2–12% Copaene
Coriander Coriandrum sativum Dill Anethum graveolens
Uses: Promotes digestion.* Helps maintain a clear complexion. Uses: Supports digestion and overall gastrointestinal health.*
Promotes relaxation. Provides powerful antioxidant protection.* Purifying to the body’s
systems.* Promotes restful sleep.*
Body Systems: Digestive, Nervous, Skin
Body Systems: Digestive, Nervous
60–75% Linalool 40–65% Carvone
5–20% alpha-Pinene 30–55% Limonene
2–8% Camphor 0.5–6% alpha-Phel-
landrene
0.1-10% gamma-
Terpinene
Part 2: A-Z Oil Chemistry Douglas Fir – Ginger
Douglas Fir Pseudotsuga menziesii Frankincense Boswellia spp.

Uses: Promotes feelings of clear airways and easy breathing. Uses: Ingest to support healthy cellular function.* Aroma promotes
Cleansing and purifying to the skin. Promotes a positive mood feelings of relaxation. Helps reduce the appearance of skin
and sense of focus. imperfections when applied topically. Supports healthy immune,
nervous, and digestive function when taken internally.*
Body Systems: Nervous, Respiratory, Skin Body Systems: Nervous, Digestive, Immune, Skin
20–40% beta-Pinene 25–65% alpha-
Pinene
5–25% Sabinene
5–20% Limonene
5–25% Terpinolene 0.1–10% beta-
Caryophyllene
0.1-10 % alpha-
Thujene
Eucalyptus Eucalyptus radiata Geranium Pelargonium graveolens

Uses: Helps to clear the mind. Promotes feelings of relaxation. Uses: Promotes the appearance of clear, healthy skin.
Promotes feelings of clear breathing. Naturally repels insects. Gives hair a vibrant, healthy glow.
Body Systems: Nervous, Respiratory Body Systems: Immune, Skin
55–85% 1,8-cineole 30–45% Citronellol
(eucalyptol) 1–15% Citronellyl
1–15% Terpineol formate
0.5–10% Guaiadene
5–25% Geraniol
Fennel Foeniculum vulgare Ginger Zingiber officinale

Uses: Promotes healthy digestion.* Supports a healthy respiratory Uses: May help to support healthy digestion.* May help to reduce
system.* May help promote healthy metabolism, liver function, bloating, gas, and occasional indigestion.* May help reduce
and circulation.* occasional nausea.*
Body Systems: Cardiovascular, Digestive, Endocrine, Respiratory Body Systems: Digestive

50–90% Anethole 20–40% Zingiberene
5–20% Sesquiphel-
1-20% Fenchone landrene
1-15% alpha-Pinene 1–10% Camphene
0.1–10% Curcumene
0.1–10% Bisabolene
0.1–10% Farnesene
Part 2: A-Z Oil Chemistry Grapefruit – Lemon
Grapefruit Citrus X paradisi Juniper Berry Juniperus communis
Uses: Improves the appearance of blemishes. Supports healthy Uses: Supports healthy kidney and urinary tract function.*Acts as a
metabolism.* Uplifts mood. natural skin toner and a natural cleansing and detoxifying agent.*
Has a calming, grounding effect.
Body Systems: Endocrine, Nervous, Skin
Body Systems: Skin, Urinary
90–97% Limonene 24–55% alpha-
Pinene
0.0–25% Myrcene
0.0–30% Sabinene
Helichrysum Helichrysum italicum Lavender Lavandula angustifolia
Uses: Helps skin look young and healthy. May help promote a Uses: Soothes occasional skin irritations. When taken internally,
healthy metabolism.* Lavender reduces anxious feelings and promotes peaceful sleep.*
Helps ease feelings of tension.*
Body Systems: Endocrine, Skin
25–50% Neryl 25–45% Linalyl
acetate acetate
2–20% Curcumene 20–47% Linalool
5–20% alpha-Pinene 0.3–10% Ocimene
Jasmine Jasminum grandiflorum Lemon Citrus limon
Uses: Promotes a healthy-looking, glowing complexion. Nourishes Uses: Cleanses and purifies the air and surfaces. Naturally
and protects the skin and scalp. cleanses the body and aids in digestion.* Supports healthy
respiratory function.* Promotes a positive mood.
Body Systems: Skin
Body Systems: Digestive, Respiratory, Immune, Skin
3–50% Phytol 55–75% Limonene
5–25% Phytol 6–18% beta-Pinene
acetate
5–25% Benzyl 3–16% gamma-
acetate Terpinene
0.1-10% Benzyl
benzoate
Part 2: A-Z Oil Chemistry Lemongrass – Myrrh
Lemongrass Cymbopogon flexuosus Melaleuca Melaleuca alternifolia
Uses: Supports healthy digestion when taken in a capsule.* Uses: Renowned for its cleansing and rejuvenating effect on the
Natural insect repellent. Protects against certain environmental skin. Promotes healthy immune function when used internally.*
threats. Ingest to protect against environmental and seasonal threats.*
Body Systems: Digestive, Immune Body Systems: Immune, Skin
25–50% Neral 20–60% Terpinen-4-ol
25–50% Geranial 10–55% Terpinene
(alpha and gamma)
1–15% Geraniol
1–10% alpha-Pinene
Lime Citrus aurantifolia Melissa Melissa officinalis
Uses: Supports healthy immune function.* Used as an aromatic, Uses: May help to support a healthy immune system.* Calms tension
topical, and internal cleanser.* Natural degreaser and surface and nerves. Promotes feelings of relaxation.
cleanser.
Body Systems: Immune, Nervous
Body Systems: Digestive, Immune
40–70% Limonene 10–47% Geranial
5–20% gamma- 1–32% Neral
Terpinene
1–22% beta-
10–25% beta-Pinene Caryophyllene
1-25% Germacrene D
Marjoram Origanum majorana Myrrh Commiphora myrrha
Uses: Valued for its calming properties and positive effect on the Uses: Powerful cleansing properties, especially for the mouth
nervous system when taken internally.* Supports a healthy immune and throat. Soothing to the skin; promotes a smooth, youthful-
system when consumed.* May promote a healthy cardiovascular looking complexion. Promotes emotional balance and well-being
system when ingested.* when diffused.
Body Systems: Cardiovascular, Immune, Nervous Body Systems: Digestive, Nervous, Skin*
0.1–55% Terpinene- 15–45% Curzerene
4-ol 15–45% Fura-
0.5–20% gamma- noeudesma-1,3-
Terpinene diene
0.4–33% Sabinene-
hydrate 1–20% Lindestrene
0.1 -20% Sabinene
Part 2: A-Z Oil Chemistry Oregano – Rose
Oregano Origanum vulgare Petitgrain Citrus aurantium
Uses: Used as a powerful cleansing and purifying agent. Uses: May help support healthy cardiovascular function.*
Supports a healthy immune system, healthy digestion, and May provide antioxidant support* Supports healthy immune
respiratory function when used internally.* Offers powerful function.* May help promote a restful sleep*
antioxidants when ingested.*
Body Systems: Cardiovascular, Immune, Nervous
Body Systems: Digestive, Immune, Respiratory
60–80% Carvacrol 40–65% Linalyl
acetate
0.5–10% Thymol
15–30% Linalool
1–12% Terpineol
Patchouli Pogostemon cablin Roman Chamomile Anthemis nobilis
Uses: Grounding, balancing effect on emotions. Promotes a Uses: Has a calming effect on the skin, mind, and body.* May help
smooth, glowing complexion. Reduces the appearance of support healthy immune system function.*
wrinkles, blemishes, and skin imperfections.
Body Systems: Immune, Nervous, Skin
Body Systems: Skin, Nervous
20–40% Patchoulol 5–40% 4-Methylamyl
angelate
1–20% Bulnesene
5–40% Isoamyl tiglate
2–25% Aromaden-
drene 5–40% Isobutyl
angelate
2-25% Guiaene
Peppermint Mentha piperita Rose Rosa damascena
Uses: When ingested, promotes healthy respiratory function and Uses: Helps balance moisture levels in the skin. Reduces the
clear breathing.* Promotes digestive health when taken internally.* appearance of skin imperfections. Promotes an even skin tone and
Repels bugs naturally. Apply topically for a cooling sensation. healthy complexion. Emotionally uplifting aroma.
Body Systems: Digestive, Respiratory Body Systems: Nervous, Skin
10–30% Menthone 20–40% Citronellol
20–60% Menthol 10–30% Geraniol
1-10% 1,8-Cineole 5–15% Nerol
(eucalyptol)
Part 2: A-Z Oil Chemistry Rosemary – Spikenard
Rosemary Rosmarinus officinalis Siberian Fir Abies sibirica
Uses: Supports healthy digestion.* Supports healthy respiratory Uses: Helps balance emotions and soothe anxious feelings.
function.* Helps reduce nervous tension and occasional fatigue.* Diffuse for a relaxing aroma. Provides a soothing effect when
used in massage.
Body Systems: Digestive, Nervous, Respiratory
Body Systems: Musculoskeletal, Nervous, Skin
30–60% 1,8-Cineole 20–40% Bornyl
(eucalyptol) acetate
10–30% delta-
5–15% Camphor
3-Carene
5–20% alpha-Pinene 5–20% alpha-Pinene
Sandalwood (Hawaiian) Santalum paniculatum Spearmint Mentha spicata
Uses: Promotes healthy looking, smooth skin. Reduces the Uses: Promotes digestion and helps reduce occasional stomach
appearance of skin imperfections. Enhances mood. Frequently upset.* Promotes a sense of focus and uplifts mood. Cleanses
used in meditation for its grounding and uplifting properties. the mouth and promotes fresh breath.
Body Systems: Nervous, Skin Body Systems: Digestive, Nervous
Carbon backbone Functional groups Main Constituents Carbon backbones Functional groups Main Constituents
10–60% Santalol 20–80% Carvone
(alpha and beta) 5–30% alpha-Pinene
2–16% Lanceol 0.1-10% 1,8-Cineole
(eucalyptol)
Sandalwood (Indian) Santalum album Spikenard Nardostachys jatamansi
Uses: Promotes healthy looking, smooth skin. Reduces the appearance Uses: Uplifting aroma. Promotes feelings of calmness and relaxation.
of scars and skin imperfections. Enhances mood. Frequently used in Frequently used in aromatherapy and meditation for its grounding
meditation for its grounding and uplifting properties. properties. Purifying to the skin.
Body Systems: Nervous, Skin Body Systems: Nervous, Skin
10–60% Santalol 3–13% Gurjunene
(alpha and beta) 3–20% Jatamansone
2–15% Spirojatamol
Part 2: A-Z Oil Chemistry Tangerine – Ylang Ylang
Tangerine Citrus reticulata Wild Orange Citrus sinensis
Uses: Skin clearing agent, promote mental alertness, Uses: Powerful cleanser and purifying agent. Supports healthy
soothe anxious feelings.* immune function.* Uplifting to the mind and body.
Body Systems: Cardiovascular, Immune, Nervous, Skin* Body Systems: Immune, Nervous
80–99% Limonene 80–97% Limonene
0.5–8% Myrcene 0.5–5% Myrcene
Thyme Thymus vulagris Wintergreen Gaultheria fragrantissima
Uses: Provides powerful antioxidants.* Supports a healthy immune Uses: Great for a warming soothing massage after exercise. Has a
system.* Naturally repels insects. refreshing aroma that’s uplifting and stimulating. Frequently used in
gum, candy, and toothpaste for flavoring.
Body Systems: Immune
Body Systems: Musculoskeletal, Nervous, Skin
30–66% Thymol >98% Methyl
3–35% p-Cymene salicylate
0.2–16% Carvacrol
0.1–15% beta-
Caryophyllene
Vetiver Vetivera zizanioides Ylang Ylang Cananga odorata
Uses: Calming, grounding effect on emotions. Immune-supporting Uses: Provides antioxidant support.* Promotes appearance of
properties.* healthy skin and hair. Lifts mood while having a calming effect.
Body Systems: Immune, Nervous Body Systems: Nervous, Skin
5–15% Khusimol 10–30% Germacrene
D
5–20% Isovalencenol
5–25% beta-
caryophyllene
5–15% Farnesene
PART 3: ESSENTIAL OIL
CONSTITUENTS
This portion of the Oil Chemistry Handbook presents the chemical
properties of around 80 of the main chemical constituents found
in dōTERRA oils. The name, structure, chemical classification, uses,
and benefits of each compound are listed along with the oils in
which these compounds can be found, and in what percent com-
position. This section is designed to serve as an expansion of the
constituent details provided in the dōTERRA Oil Chemistry Wheel.
It is important to realize that this section of the handbook only
highlights the most abundant essential oil constituents. In reality,
there are hundreds of different monoterpene compounds and over
10,000 different kinds of sesquiterpenes. While most oils are mainly
composed of just a few of the compounds listed in Part 3, many
oils contain close to a hundred other minor constituents present in
small quantities. Interestingly, these minor constituents can make
a major contribution to an oil’s properties. Synergistic effects be-
tween minor constituents can also play an important role in how
the oil interacts with the body and other substances. The scientific
consensus from the current research is that an oil is much more
than the sum of its main compounds. This means that the benefits
of an essential oil may be different than the simple sum of the ben-
efits of its constituents.
Knowing the main constituents in an oil can help you determine
how it fits into a daily usage model and how it can be compared to
other oils. An oil with high levels of a certain constituent will likely
have the properties of that constituent. If a given constituent is use-
ful in a certain context, another oil also containing that constituent
would probably be useful in the same context. These principles are
the basis of the framework that we hope you can take from the in-
formation contained in this section of the Oil Chemistry Handbook.
40 41
Part 3: Essential Oil Constituents Anethole - Bisabolene
Chemical Percent Composition in

Constituent Structure Benefits
Classification dōTERRA oils
• Supports digestive system*

• Helps maintain healthy cellular function*
Anethole O Phenylpropene
• Supports healthy blood flow *
Fennel 50-90%
• Soothing to the tissues.
• Surface cleansing properties

Sesquiterpene
Aromadendrene Alkene • Synergizes with1,8-cineole (eucalyptol) to create Patchouli 2-25%
a potent cleanser
O
Benzyl acetate Ester Sweet aroma reminiscent of apple or pear Jasmine 5-25%
O
O
• Insect repellent
Benzyl benzoate Ester Jasmine 0.1-15%
O • May promote feelings of open airways
Sesquiterpene • Copaiba 2-12%

Bergamotene Alkene
Antioxidant*
• Basil 1-7%
Sesquiterpene • Supports healthy cellular function *

Bisabolene Alkene
Ginger 0.1-10%
• Posesses a balsamic odor.
*These statements have not been evaluated by the Food and Drug Administration. This product is not intended *Statements marked with asterisks refer to internal use only. Some essential oils containing the compounds
42 to diagnose, treat, cure, or prevent any disease. presented are not recommended for internal use. 43
Part 3: Essential Oil Constituents Bornyl Acetate - Carvone
• Supports feelings of moist airways
• Soothes the tissues
O
• Posesses a calming aroma that soothes
Bornyl acetate Monoterpene Ester Siberian Fir 20-40%
anxious feelings
O • Supports cellular function and the immune
system*
Sesquiterpene
Bulnesene Alkene
May support healthy blood flow* Patchouli 1-20%
Monoterpene • Siberian Fir 10-30%
Camphene Alkene
Antioxidant*
• Ginger 1-10%
• Blue Tansy 5-20%
Monoterpene
Camphor Ketone
Can help in a soothing massage for muscle aches • Rosemary 5-15%
• Coriander 2-8%
O
• Powerful surface cleansing properties
• Soothes the skin; Provides antioxidants*
Monoterpene • Supports liver function and the digestive, • Oregano 60-80%
Carvacrol Phenol • Thyme 0.2-16%
nervous, cardiovascular, and musculoskeletal
systems*
O H • Supports cellular health *
Monoterpene Soothing effect on the tissues and on the entire • Spearmint 20-80%
Carvone ketone body* • Dill 40-65%
O
Part 3: Essential Oil Constituents beta-Caryophyllene - Cinnamaldehyde
• Copaiba 45-65%
• Soothing to the skin and tissues
• Black Pepper 8-46%
• May reduce the appearance of blemishes • Ylang Ylang 5-25%
beta- Sesquiterpene
• Supports a healthy inflammatory response* • Melissa 1-22%
Caryophyllene Alkene
• Strong antioxidant* • Clove 0.6-20%
• Thyme 0.1-15%
• Supports the digestive and circulatory systems*
• Frankincense 0.1-10%
Sesquiterpene
alpha-Cedrene Alkene
Surface cleansing properties Cedarwood 10-47%
H
O
Sesquiterpene
Cedrol Alcohol
Calming and relaxing aroma Cedarwood 9-40%
• Soothing to the tissues; Supports cellular
health*
Chamazulene Alkene Blue Tansy 2-15%
• Supports immune and nervous system
health*
• Eucalyptus 55-85%
• Rosemary 30-60%
O
1,8-Cineole Monoterpene • Cardamom 25-50%
Ether • May support healthy respiratory system • Basil 1-15%
(eucalyptol) function*
• Peppermint 1-10%
• Spearmint 0.1-10%
O • Powerful antioxidant*
• Supports cellular, liver, brain, and kidney
Cinnamal- • Cassia 75-97%
Aldehyde health*
dehyde • Cinnamon 45-80%
• Promotes the functions of the digestive,
nervous, and circulatory systems *
Part 3: Essential Oil Constituents Cinnamyl Acetate - Curcumene
O
Cinnamyl O May help maintain health of the colon and • Cinnamon 2-15%
Ester
acetate gastrointestinal tract * • Cassia 1-8%
• Supports cellular function and response*
O • Promotes healthy blood flow *
Citronellol H Monoterpene
• Topical application may help the skin and
• Geranium 30-45%
Alcohol • Rose 20-40%
scalp look clean and healthy; Can keep
pesky insects at bay
O O
Citronellyl
Monoterpene Ester Surface cleansing properties Geranium 1-15%
formate
Sesquiterpene
Copaene Alkene
Antioxidant* Copaiba 2-12%
May help support and maintain healthy blood
Cuminal Aldehyde
glucose levels already in the normal range*
Cumin 10-40%
O
Sesquiterpene • Helichrysum 2-20%
Curcumene Alkene
Internally cleansing*
• Ginger 0.1-10%
Part 3: Essential Oil Constituents Curzerene - Farnesene
Sesquiterpene • Surface cleansing properties
Curzerene Ether
Myrrh 15-35%
• May support healthy cellular function *
O
• Cypress 7-30%
Monoterpene
delta-3-Carene Alkene
Surface cleansing properties • Siberian Fir 5-20%
• Black Pepper 0.01-21%
2-Decenal O Aldehyde Surface cleansing properties Cilantro 15-45%
2-Decenol O Alcohol Fragrant aroma Cilantro 5-25%
H
O • May help keep mouth and teeth clean
Phenol/ • May provide antioxidant properties* • Clove 63-95%
Eugenol Phenylpropanoid • Cinnamon Bark 1-10%
• May promote healthy immune response*
O • Supports cellular and cardiovascular health*
H
Sesquiterpene • Ylang Ylang 5-15%
Farnesene Alkene
May support cellular health *
• Ginger 0.1-10%
Part 3: Essential Oil Constituents Fenchone - Guaiene
Monoterpene
Fenchone Ketone
May support skin health* Fennel 1-20%
O
Furanoeud- Sesquiterpene
• May support calming and relaxation due to Myrrh 15-45%
esma 1,3-diene Ether
O effects on central nervous system*
• Surface cleansing properites
• May support healthy cellular function
O • Promotes healthy cholesterol levels already
Monoterpene • Lemongrass 25-50%
Geranial Aldehyde
in the normal range and hormonal balance*
• Melissa 10-47%
• Calms and soothe muscles*
• Supports healthy cognitive and immune
system function*
O • Rose 10-30%
H Monoterpene • Supports cellular health*
Geraniol Alcohol
• Geranium 5-25%
• Supports nervous system and digestive tract • Lemongrass 1-15%
health *
Sesquiterpene • May provide antioxidant support* • Ylang Ylang 10-30%
Germacrene D Alkene • Melissa 1-25%
• Supports healthy cellular function*
Sesquiterpene • Soothing properties
Guaiene Alkene
Patchouli 2-25%
Part 3: Essential Oil Constituents Guaiadene - Jatamansone
Sesquiterpene
Guaiadene Alkene
Surface cleansing properties Geranium 0.5-10%
Sesquiterpene • Surface cleansing properties
Gurjunene Alkene
Spikenard 3-13%
• May provide antioxidant support*
Sesquiterpene
Isovalencenol H Alcohol
Fragrant aroma Vetiver 5-20%
O
O
Isoamyl tiglate Ester Fragrant aroma Roman Chamomile 5-40%
O
Isobutyl O
Ester Fragrant aroma Roman Chamomile 5-40%
angelate
O
Sesquiterpene
Jatamansone Ketone
Calming and relaxing aroma Spikenard 3-20%
O
Part 3: Essential Oil Constituents Khusimol - Lindestrene
H Sesquiterpene
Khusimol O
Alcohol
May support lung and respiratory health * Vetiver 5-15%
H O
Sesquiterpene
Lanceol Alcohol
Fragrant aroma Hawaiian Sandalwood 2-16%
• Uplifting, energizing aroma • Tangerine 80-99%
• Grapefruit 90-97%
• Surface, teeth, and skin cleansing properties • Wild Orange 80-97%
• May help reduce appearance of skin blemishes • Lemon 55-75%
Monoterpene • Lime 40-70%
Limonene Alkene • Posesses internal cleansing properties* • Dill 30-55%
• Supports healthy metabolism* • Bergamot 20-55%
• Spearmint 5-30%
• Supports immune, respiratory, gastrointestinal, • Black Pepper 9-25%
and nervous system function * • Frankincense 5-20%
• Coriander 60-75%
• Calming and relaxing aroma • Basil 40-80%
surface cleansing properties • Lavender 20-47%
Monoterpene
Linalool Alcohol
• May support healthy immune system function • Petitgrain 15-30%
and gastrointestinal health* • Clary Sage 8-40%
H
O • Soothes and calms nervous system* • Cilantro 10-35%
• Bergamot 3-20%
• Calming aroma
• May support relaxation of smooth muscles*
• Clary Sage 40-75%
Linalyl acetate
O Monoterpene Ester • Supports heart and cardiovascular health
• Petitgrain 40-65%
• Lavender 25-45%
• Promotes gastrointestinal health and immune • Bergamot 10-45%
function*
O • Soothing and calming effects on the nervous system*
Sesquiterpene
Lindestrene Ether
Internally cleansing* Myrrh 1-20%
O
Part 3: Essential Oil Constituents Menthol - Myrcene
• Aromatically uplifting and energizing
• Supports feelings of clear breathing
• Surface and skin cleansing properties
Monoterpene • Cooling and soothing effect on the skin
Menthol Alcohol
Peppermint 20-60%
• Helps maintain a clean and fresh-smelling mouth
• Insect repellant
• May support healthy cellular function and
digestive health *
• Energizing and uplifting aroma
• Surface and skin cleansing
Monoterpene
Menthone ketone
• Has a cooling effect on skin Peppermint 10-30%
• Can help soothe the tissues
O • May provide antioxidant support *
O
O • Soothing to the skin
Methyl • Birch >98%
Ester • May help reduce appearance of blemishes
salicylate • Wintergreen >98%
O • May help protect against environmental threats*
H
4-Methylamyl O
Ester Fragrant aroma Roman Chamomile 5-40%
angelate
O
Methyl thujate O Monoterpene Ester Woody aroma Arborvitae 50-70%
O
• Supports skin health* • Juniper Berry 0.0-25%
Monoterpene
Myrcene Alkene
• Tangerine 0.5-8%
• May support immune system function* • Wild Orange 0.5-5%
Part 3: Essential Oil Constituents Neral - Patchoulol
O
• May support cellular health*
• May promote healthy cholesterol levels already
Monoterpene • Lemongrass 25-50%
Neral Aldehyde
in the normal range*
• Melissa 1-32%
• Calming and relaxing aroma; Supports cognitive
function*
• Supports immune system function *
H
O
Monoterpene
Nerol Alcohol
Fragrant aroma used in perfumery Rose 5-15%
O
O
Neryl acetate Monoterpene Ester Surface cleansing properties Helichrysum 25-50%
Monoterpene
Ocimene Alkene
Surface cleansing properties Lavender 0.3-10%
Monoterpene • Thyme 3-35%
p-Cymene Alkene
May promote healthy cellular function *
• Cumin 3-20%
• Cleansing and supportive of immune and
Sesquiterpene respiratory systems*
Patchoulol Alcohol
Patchouli 20-40%
• Promotes gastrointestinal health *
O
H
Part 3: Essential Oil Constituents alpha-Phellandrene - Sabinene
• Uplifting and soothing aroma
alpha- Monoterpene • Supports immune system and cellular health*
Dill 0.5-6%
Phellandrene Alkene • Protects against environmental threats*
• Provides antioxidants *
O
Phytol H Alcohol Surface and skin cleansing properties Jasmine 3-50%
O
Phytol acetate Ester Fragrant compound used in perfumery Jasmine 5-25%
O
• Frankincense 25-65%
• Supports cardiovascular, nervous, and
• Cypress 20-65%
digestive systems*
• Juniper Berry 24-55%
• Supports cellular function* • Coriander 5-20%
Monterpene
alpha-Pinene Alkene
• Helps gums, teeth, and skin look clean and • Helichrysum 5-20%
healthy • Rosemary 5-20%
• Soothing to the tissues • Siberian Fir 5-20%
• Aroma has powerful relaxing effects
• Fennel 1-15%
• Douglas Fir 20-40%
• Supports immune function and response* • Cumin 4-35%
• Lime 10-25%
Monoterpene • May help maintain healthy blood glucose
beta-Pinene Alkene levels already in the normal range*
• Lemon 6-18%
• Supports healthy respiratory system* • Bergamot 3-12%
• Douglas Fir 5-25%
Monoterpene
Sabinene Alkene
Skin cleansing properties • Marjoram 0.4-33%
• Juniper Berry 0.0-30%
• Black Pepper 0.1-23%
Part 3: Essential Oil Constituents Sabinene Hydrate - Terpinen-7-al
H
O
Sabinene Monoterpene
May posess antioxidant properties* Marjoram 0.4-33%
Hydrate Alcohol
• Uplifting aroma
• Soothes and promotes healthy-looking skin
Santalol (alpha Sesquiterpene when used topically • Hawaiian Sandalwood 10-60%
and beta) Alcohol • Indian Sandalwood 10-60%
• Promotes cellular health*
• Supports the digestive and immune systems *
O H
• May provide antioxidant support*
Sesquiphell- Sesquiterpene
• Promotes healthy cellular function* Ginger 5-20%
andrene Alkene
• Supports the immune and respiratory systems*
O H
Sesquiterpene
Spriojatamol Alcohol
Earthy aroma Spikenard 0.1-15%
• Surface and teeth cleansing properties
• Soothing and cleansing to skin
• Reduces appearance of skin blemishes
Monoterpene • Melaleuca 20-60%
Terpinen-4-ol Alcohol • Protects against environmental threats* • Marjoram 0.1-55%
• Soothes muscles and joints*
• May support healthy cellular and immune
H O
system function *
O
Monoterpene
Terpinen-7-al aldehyde
Surface cleansing Cumin 1-35%
Part 3: Essential Oil Constituents gamma-Terpinene - Thujopsene
• Melaleuca 10-55%
• Cumin 3-35%
• Lime 5-20%
gamma- Monoterpene • Surface cleansing properties
• Marjoram 0.5-20%
Terpinene Alkene • Protects against environmental threats* • Lemon 3-16%
• Bergamot 3-12%
• Coriander 0.1-10%
Monoterpene • Eucalyptus 1-15%
Terpineol O Alcohol
Calming and relaxing aroma
• Petitgrain 1-12%
H
• Promotes feelings of calmness and relaxation
Monoterpene when used aromatically
Terpinolene Alkene
Douglas Fir 5-25%
• May promote cellular health and immune
system function*
• Surface and skin cleansing properties
O
Terpinyl acetate Monoterpene Ester • May support cellular and digestive health* Cardamom 25-50%
• Supports a healthy metabolism *
O
Monoterpene
alpha-Thujene Alkene
Herbaceous aroma Frankincense 0.1-10%
Sesquiterpene
Thujopsene Alkene
Woody Aroma Cedarwood 7-30%
Part 1: The Basics of Essential Oil Chemistry Thymol - Zingiberene
• Invigorating aroma
• Cleansing and soothing to skin
Monoterpene • Promotes oral health when used in a mouth • Thyme 30-66%
Thymol Phenol rinse • Oregano 0.5-10%
• May provide antioxidant benefits*
• Supports immune, circulatory, respiratory,
H O cardiovascular, nervous system, and bone
health*
• Promotes cellular health*
Sesquiterpene
Zingiberene Alkene • Supports the health of stomach and digestive Ginger 20-40%
tract*
70 71
Part 1: The Basics of Essential Oil Chemistry

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Chapter 1: An Introduction to Essential Oils

THE dōTERRA ESSENTIAL OIL

PART 1: THE BASICS OF ESSENTIAL OIL CHEMISTRY..........................2

2. Essential Organic Chemistry .................................................................... 6

3. The Functional Groups and their Functions .................................... 10

Dr. David Hill

THE dōTERRA OIL Oil Chemistry Wheel

The oils in the dōTERRA Chemistry Wheels are grouped according

eole late llene

PART 1: THE BASICS OF CHAPTER 1: AN INTRODUCTION TO

structure of 10 carbon atoms structures, affecting protein

8 Part 1: The Basics of Essential Oil Chemistry 9

Oils high in sesquiterpene alcohols: Sandalwood, Vetiver, 3.3 ALKENES

second oxygen is 3.5 ETHERS

Aromatic: Relaxing, soothing, balancing Properties and Uses of Ethers

Arborvitae Thuja Plicata Birch Betula lenta

Basil Ocimum Basilicum Black Pepper Piper nigrum

Bergamot Citrus Bergamia Blue Tansy Tanacetum Anuum

Cardamom Eletarria cardamomum Cilantro Coriandrum sativum

Cassia Cinnamomum cassia Cinnamon Bark Cinnamomum zeylanicum

Cedarwood Juniperus virginiana Clary Sage Salvia sclarea

Body Systems: Nervous, Skin Body Systems: Nervous, Skin

Douglas Fir Pseudotsuga menziesii Frankincense Boswellia spp.

Eucalyptus Eucalyptus radiata Geranium Pelargonium graveolens

Body Systems: Nervous, Respiratory Body Systems: Immune, Skin

Fennel Foeniculum vulgare Ginger Zingiber officinale

Body Systems: Cardiovascular, Digestive, Endocrine, Respiratory Body Systems: Digestive

Chemical Percent Composition in

• Supports digestive system*

• Soothing to the tissues.

• Surface cleansing properties

Sesquiterpene • Copaiba 2-12%

Sesquiterpene • Supports healthy cellular function *

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