Chemical properties of essential oils

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Dale Nichols
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1 Chemical properties of essential oils Much of the information in this chapter is gathered from a variety of reference books I use every day in my office. Among these, I have found Aromatherapy with Chinese Medicine: Healing the Body/Mind/Spirit with by Dennis Willmont to be the most comprehensive and easy to understand for Acupuncturists and health-care practitioners with any Oriental Medical training. The Desk Reference by Essential Science Publishing is a must have for any holistic, health-care provider and perfect for massage therapists and consumers of essential oils. You can find many good books that go into greater detail on the chemical properties and suggested uses of essential oils; a few of these are included in the bibliography. Essential oils consist of small, volatile molecules called isoprenes. Isoprenes determine the basic healing attributes and physiological effects found in essential oils. Understanding the isoprene composition of individual essential oils provides a deeper understanding of its healing capacity. It also offers an additional method of choosing essential oils for testing. Specific safety precautions are recommended for each isoprene subgroup or family. Isoprenes absorb into skin, fat cells, brain matter and the bloodstream rapidly permeating the body while bypassing normal digestive pathways. There is a blood-brain barrier designed to protect the brain while allowing oxygen, glucose and hormones to enter. Chronic inflammation, food intolerances and stress will weaken the blood brain barrier allowing infections and toxins to penetrate. Essential oil isoprenes are the only botanical supplements 2018 Body-Feedback for Health, LLC All Rights Reserved 1

2 known to pass through this barrier easily to promote healing. My clients with viral infections that have passed into the brain or those with impaired cognitive function report feeling both healthier and stronger when applying the recommended essential oils using Body- Feedback testing methods to the spinal column, neck and head. Lists of essential oils with high percentages of particular isoprenes are provided below for quick reference. The oils listed are ranked from highest to lowest isoprene concentration within each list. Because some isoprenes are found in numerous oils, their lists are longer than those for less frequently occurring chemical properties. Oils on the shorter lists have a minimum of 35% of the particular chemical property and oils on the longer list start at 50%. Oils with significant multiple properties will appear on multiple lists. When testing a Body-Feedback reflex are or symptom, these lists can be helpful to identify essential oils with the needed healing attributes. For example, brain-based conditions respond favorably to essential oils high in sesquiterpene isoprenes such as vetiver, spikenard, black pepper, patchouli, myrrh, ginger and cedarwood. Anyone with memory issues, lack of focus, Parkinson s, mental illness, insomnia and other brain-based conditions usually respond favorably to a several of the sesquiterpene essential oils. To understand how compounds work, chemists strive to dissect each compound into the smallest possible molecule. This divide and conquer approach has its limits because it is the molecular synergies between these compounds that create a healing response in the body. As you read through the following lists, please keep in mind that the chemical properties of essential oils are only one aspect of their healing potential Body-Feedback for Health, LLC All Rights Reserved 2

3 In essential oils, a single isoprene contains five carbon atoms and eight hydrogen atoms (C 5H 8). A double isoprene contains ten carbon atoms and sixteen hydrogen atoms (C 10H 16). A triple isoprene contains fifteen carbon atoms and twenty-four hydrogen atoms (C 15H 24). Single isoprenes are the least stable and evaporate quickly. Triple isoprenes are the most stable and evaporate slowly. Double isoprenes are the most common and fall in the midrange in terms of stability and evaporation rate. Molecular bonds within the isoprene connect the carbon and hydrogen atoms. Essential oils are divided into three main groups based on the number of isoprene bonds they contain: phenylpropenes (one isoprene bond), monoterpenes (two isoprene bonds) and sesquiterpenes (three isoprene bonds). Oriental medicine classifies phenylpropenes as yang; hot, aggressive and stimulating. Sesquiterpenes are classified as yin; consolidating, receptive and nourishing. Monoterpenes are considered balancing and harmonizing. From these three groups, Willmont identifies thirteen subgroups based on their healing properties. I think of these subgroups as families of oils and like to test them together Body-Feedback for Health, LLC All Rights Reserved 3

4 Single isoprenes Double isoprenes Triple isoprenes Phenylpropenes Monoterpenes Sesquiterpenes C5H8 C10H16 C15H24 1. Hot Cinnamic Aldehydes 1. Hydrocarbons 1. Hydrocarbons 2. Mild Anetholes 2. Alcohols 2. Alcohols 3. Coumarins 3. Phenols 3. Lactones 4. Esters 5. Aldehydes 6. Keytones 7. Oxides Phenylpropenes C 5H 8 Phenylpropenes can be either hot or mild and have a spicy or warm aroma. They facilitate the proper transfer of intercellular messengers such as hormones, peptides, neurotransmitters and steroids by cleaning the receptor sites. Phenylpropenes contain one isoprene and are highly volatile and vaporize quickly. They are strong antivirals, antibacterials and antifungals. Phenylpropenes create an unfriendly environment for pathogens but can also become irritating to sensitive skin and digestive systems. I recommend testing often and dilution with Hot type Phenylpropenes 1. Clove 2. Cinnamon 3. Oregano vegetable oil when using hot 2018 Body-Feedback for Health, LLC All Rights Reserved 4

5 phenylpropenes oils long-term. Hot phenylpropenes are the strongest antiseptics and antibacterials of the essential oils and can irritate the skin. As a precaution they should be used with carrier oils both internally and externally. Hot phenylpropenes help balance digestive flora. Mild type Phenylpropenes 1. Basil 2. Anise 3. Tarragon 4. Peppermint Mild phenylpropenes have a strong affinity for calming the autonomic nervous system. They are antispasmodic while relaxing and soothing to the digestive system. Coumarin phenylpropenes are emotionally grounding, calming and refreshing. They also support and strengthen the circulatory system and heart. Coumarin phenylpropenes are found in low concentrations, fewer than 4%, in citrus oils and dill-seed essential oil. I do not individually test the coumarin family of essential oils for any special symptoms. This coumarin information has little practical application, but is provided here for general knowledge. Monoterpenes C 10H Body-Feedback for Health, LLC All Rights Reserved 5

6 Monoterpenes are best known for their ability to remove damaged cellular coding and for their immune-modulating functions. Highest concentrations of Monoterpene Monoterpenes are best known for their ability to remove damaged cellular coding and for their immune-modulating functions. The monoterpene parent group contains two isoprenes and is the most 1. Orange abundant chemical group among essential oils. The molecular 2. Galbanum 3. Lemon structure of a monoterpene is 10 carbon atoms and 16 hydrogen 4. Hyssop 5. Angelica Root atoms. Monoterpenes modulate immune function and cellular 6. Lime 7. Peppermint communication within the plant. 8. Juniper 9. Frankincense 10. Spruce The chemical and healing properties of monoterpenes as a group include: stimulant, expectorant, purgative, decongestant, gallstone-dissolver, analgesic, antirheumatic, antihistaminic, antitumor, antiseptic, antiviral, antibacterial, antifungal, insecticide and hypotensive. Monoterpene hydrocarbons are a plant s natural defense. These oils are strong decongestants for the respiratory and lymph systems due to their drying effect. Monoterpene hydrocarbons are best known for their antitumor and antiviral properties. If you have a family history of cancer I recommend testing and daily use of ingesting citrus oils in your water. Monoterpene hydrocarbons are concentrated in citrus peels and evergreen needles, and these are their predominant aromas. They are Monoterpene Hydrocarbon 1. Grapefruit 2. Tangerine 3. Orange 4. Galbanum 5. Cypress 6. Eucalyptus Globulus 7. Angelica 8. Lime 9. Cumin 10. Celery Seed 11. Frankincense 12. Helichrysum 2018 Body-Feedback for Health, LLC All Rights Reserved 6

7 considered safe for long-term use, though I recommend testing monthly to monitor for any needed to rotation or discontinuation. Monoterpene Alcohol 1. Palmarosa 2. Rosewood 3. Coriander 4. Carrot Seed 5. Geranium 6. Ylang Ylang 7. Thyme 8. Tea Tree 9. Marjoram Monoterpenes alcohols are best known for their ability to treat intestinal irritation, chronic inflammation and chronic infections. Because monoterpene alcohols have a gentle affect on the body, they are well suited for long-term use at relatively higher doses. I recommend these oils often when blood or stool testing indicates infections. They strengthen and calm while also fighting infection and inflammation. The aroma of monoterpene alcohols is often floral. Monoterpene phenols are powerfully stimulating and warming. They are the most forceful antibacterial, antiinfectious and antiseptic of the molecules. Monoterpene phenols are highly irritating and can be slightly toxic because the liver has to work harder to process these molecules. Oils Monoterpene Phenols 1. Anise Seed 2. Clove Bud 3. Tarragon 4. Thyme 5. Tea Tree (melalecua) high in phenols are recommended in lower doses and should be monitored with long-term use by Body-Feedback testing frequently. I find these oils are better tolerated when combined with other mild essential oils, vegetable oils or applied externally. Clove heals ulcerations in the digestive system while fighting infections. Tea tree oil is often tests the best 2018 Body-Feedback for Health, LLC All Rights Reserved 7

8 tolerated among this group. Monoterpene phenols are highly aromatic and can cause the eyes to tear if applied too close. Monoterpene Ester 1. Birch 2. Wintergreen 3. Roman Chamomile 4. Helichrysum 5. Clary Sage 6. Fennel 7. Bergamot 8. Lavender 9. Cardamom 10. Geranium Monoterpene esters are unique in their ability to self-regulate, adjusting their healing action based on immediate cellular needs. They are balancing, regulating, strengthening, antispasmodic and sedating. Monoterpene esters have strong antifungal and antibacterial properties. These oils usually test well for a few months and require less rotation due to their ability to self-regulate. Except for the methyl salicylate found in wintergreen and birch, monoterpene esters are generally safe and gentle. Wintergreen and birch are strong blood-thinners and should be avoided with anticoagulants. Otherwise esters are safe for liberal, long-term use. The aroma of the most esters is fruity, floral and sweet. The aromas of the esters to be used with caution (wintergreen and birch) are sharper. Monoterpene keytones penetrate deep in the body and dissolve fats, loosen and eliminate mucus, and stimulate tissue regeneration. Monoterpene keytones properties are calming, antispasmodic and anticoagulant. Most essential oils, however, Monoterpene Keytone with minimal toxicity 1. Helichrysum 2. Eucalyptus Globulus 3. Vetiver 4. Cedarwood 5. Peppermint 6. Eucalyptus Dives have low levels of monoterpene keytones, making them safe. High Monoterpene Keytone with higher concentrations 1. Pennyroyal 2. Sage 3. Basil 4. Spearmint 5. Spike Lavender (lavandula latifolia) 2018 Body-Feedback for Health, LLC All Rights Reserved 8

9 levels of monoterpene keytones are potentially toxic to the nervous system and can damage the myelin sheath in high doses. Oils high in monoterpene keytones are best used externally and in low dosages. I recommend testing higher-concentration monoterpene keytones at least weekly to monitor their use closely. Monoterpene keytones have a wide variety of aromas, generally sharp. Monoterpene aldehydes are strengthening, calming, anti-inflammatory, fever-reducing, anti-infectious and antiviral. Taken internally, they help the body process sugars and carbohydrates while reducing excessive candida levels associated with insulin resistance. Aldehydes may irritate the skin and mucus membranes and are best diluted with carrier oils or used in small doses. Externally applied to the feet, they can easily Highest concentrations of Monoterpene Aldehyde 1. Coriander 2. Lemongrass 3. Cinnamon Bark 4. Cumin 5. Citronella penetrate the bloodstream and there is the least risk of skin irritation. The aromas of monoterpene aldehydes are strong, sharp and sweet. Monoterpene Oxide Monoterpene oxides are strongly antiviral and stimulate the respiratory system. These oils have a special oxygen atom 1. Eucalyptus Globulus 2. Thyme Cineole integrated into the terpene ring. The only monoterpene 3. Eucalyptus Radiata 4. Niaouli oxide compound commonly found in essential oils is called 5. Hyssop the 1.8 cineole molecule. Other monoterpene oxides are naturally found in food waste and manure. Because monoterpene oxides are irritating to the skin, diluting with other essential oils or carrier oils Body-Feedback for Health, LLC All Rights Reserved 9

10 Sesquiterpenes C 15H 24 Sesquiterpenes are known for their ability to oxygenate and erase damaged DNA in the brain. They are powerful anti-inflammatory agents, antiseptic, cooling, anti-allergic, analgesic, antispasmodic and slightly antibacterial. Because of their strong effect on the brain, these oils effectively calm and balance emotions. The sesquiterpene oils are my favorite to incorporate into treatment sessions because all imbalances affect the brain and these oils help to restore health in the brain. Sesquiterpenes Essential Oils 1. Vetiver 2. Spikenard 3. Sandalwood 4. Black Pepper 5. Patchouli 6. Myrrh 7. Ginger 8. Cedarwood 9. Celery Seed Sesquiterpenes are safe for long-term use, even in high doses. Except for cedarwood and sandalwood, the strong aromas of this group can be unappealing for external use by some (usually not the people using the oils). If the intense aroma of these oils is bothersome for you or your partner, try blending with appealing aromas such as lavender or ylang ylang. Or you can apply 30 minutes prior to showering which allows the hot water to penetrate the oils in deeper and wash off the top layer of aroma. Sesquiterpene Hydrocarbon 1. Ginger 2. Cedarwood 3. Blue Tansy 4. Helichrysum Sesquiterpenes are made up of three isoprenes, making them the most stable of the essential oils, meaning that they vaporize slowly. The molecular structure of a sesquiterpene is 15 carbon atoms and 24 hydrogen atoms. Sesquiterpene hydrocarbons protect tissue by eliminating free radicals. They are powerful anti-inflammatory and 2018 Body-Feedback for Health, LLC All Rights Reserved 10

11 anti-allergic agents. Sesquiterpene alcohols are regenerative for the heart, liver, endocrine glands, muscles and nerves. They decongest the lymphatic system and veins. Sesquiterpene alcohols are anti-allergic, anti-inflammatory, antimicrobial and non-irritating. While sandalwood is highly prized and Highest concentration of Sesquiterpene Alcohol 1. Sandalwood 2. Carrot Seed 3. Cedarwood very expense, cedarwood is a comparative bargain: I personally think cedarwood is the most versatile oil for the price. Plants containing high amounts of sesquiterpene lactones are not used in therapeuticgrade essential oils because they are potential toxicity. These include ragweed, mugwort and chrysanthemum Body-Feedback for Health, LLC All Rights Reserved 11

Aromatherapy Introduction & Chemistry

Slide 1 Aromatherapy Introduction & Chemistry Bethany Williamson Bastyr University Trained Aromatherapist Slide 2 What is Aromatherapy? Aromatherapy is the therapeutic use of plant derived, aromatic essential