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Kari BoddyChem 1120Alvarez16 November 2012Chemistry in LifeAre Essential Oils Essential?That is the question I’ve been asking myself ever since I was “accidentally” invited to an essential oil “party” that occurred just as I was getting out of a massage. Maybe they’re not essential in the same way that essential fatty acids are essential – because the body needs them, but doesn’t make them. And maybe they are. With this paper, the intention is to find out how essential oils, in general, work; how they’re extracted, today and in the past; how method of application makes a difference in efficacy of the oils; and how their use compares with conventional medications, including side effects or contraindications. Finally, I hope to come to a conclusion on the uses of essential oils in conjunction with pharmaceuticals – or in place of some of them. Specific oils that will be included are: Cinnamon, Frankincense, Lavender, and Peppermint. To the first question – No, essential oils (EOs) are not essential, in that they don’t contain linoleic acid, or a-linolenic acid. They do have something in common with these essential fatty acids (EFAs) in that they are derived from plants and for the most part appear to be unsaturated, at first glance. So, why are they called essential? They are extracted from the “essence” of plants, which comes from plant metabolism, which will be explained later, along with distillation.PharmacologySimilarities among essential oils vary. According to Advanced Aromatherapy: The Science of Essential Oil Therapy, by Kurt Schnaubelt, Ph. D., the molecular components of EOs can be divided into two main groups: terpenes and higher monologues, and phenylpropane derivitaves. Monoterpenes have a backbone of ten carbon atoms and include alcohols, phenols, aldehydes, ketones, esters and oxides. All of which are found in various EAs. Sesquiterpenes, consisting of 15 carbon atoms, or three 5-carbon isoprenes, include Hydrocarbons, alcohols, and lactones. With phenylpropanes, we get closer to why therapy with EAs is called “aromatherapy” by some – they contain benzene rings, typical of compounds with pleasant aromas. Relevant to EOs, phenylpropanes are generally separated into “mild” molecules such as estragol, and anethol; and irritants such as cinnamic aldehyde and eugenol. How do EOs work, then? It depends on their composition. Cinnamon (Cinnamomum ceylanicum) contains cinnamic aldehyde (cinnamaldehyde, or (2E)-3-Phenylacrylaldehyde,) CinnamaldelhydeThe double bonds will be reactive and the aldehyde portion will be polar. Because the molecule (and other EO molecules) are small and, in the case of cinnamon, hydrophilic, they are easily absorbed into the skin, tissues, and capillaries. (Cinnamaldehyde should NOT be applied topically, as it is a sensitizer.) The best way to determine how an EO reacts is with Schnaubelt’s Structure-Effect Diagram. In the diagram EOs are placed according to whether they are more hydrophilic, or lipophilic, and also according to whether they are nucleophilic (less electronegative,) or electrophilic (more electronegative.) Cinnamaldehyde falls in the hydrophilic/electrophilic sector, where other phenylpropanes fall, though some are more lipophilic. Because Cinnamaldehyde is electronegative and hydrophilic it is a stimulant and antibacterial, as it stimulates ATP generation (which also makes it an anti-oxidant.) Frankincense (Boswellia carteri,) a resin from the Boswellia tree, is composed primarily of: terpenes, such as pinene (2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene); sesquiterpenes; and ketones, though it also contains o-Cresol, (2-Methylphenol.) That’s what makes essential oils unique from synthetically produced compounds with the same “active” ingredients – EOs are composed of a variety of molecules with different properties, just as natural vanilla contains more than just vanillin. An oil is not just an ingredient, it is a composition. a-Pinene o-CresolLavender (Lavandula angustifolia,) one of the most used and studied EOs, has as its main components: linalool (3,7-Dimethyl-1,6-octadien-3-ol,) a terpene; and linalyl acetate (3,7-Dimethyl-1,6-octadien-3-yl acetate,) an acetate ester of linalool. LinaloolLinalyl acetateLinalool is more electronegative and hydrophilic, while Linalyl acetate is less electronegative and more hydrophobic/lipophilic. Lavender is balanced and because of that can be used for a variety of symptoms. Peppermint (Mentha piperita) is mainly composed of menthol (2-Isopropyl-5-methylcyclohexanol,) a monoterpene alcohol, and menthone ((2S,5R)-2-Isopropyl-5-methylcyclohexanone,) a monoterpene ketone. MentholMenthoneAs such, peppermint oil is more hydrophilic and electronegative. Adding to the structures of some of the composites of the EOs above and their mechanisms of action will be the effect that carrier oils have on the absorption of EOs. What is a carrier oil? A carrier oil would be used to dilute an oil that is too strong for direct (neat) topical application. It would also be used because it would be less expensive than a quality EO. Fractionated coconut oil is sometimes used as a carrier oil. “Fractionated” means that it is only a part of the whole oil, as some fatty acids that can be used elsewhere, such as Lauric Acid, are removed from the carrier coconut oil. Coconut oil is mostly saturated, so would not alter the EO as it helps to “carry” it through the tissues of the skin. In reality, “carrier” oils are sometimes themselves “carried” through the skin with the EO. (Schnaubelt, pg. 100.)ProcessingReturning for a moment to the raw materials of EOs – how, exactly do we get an oil out of a plant? Expression, or cold extraction was historically used to get the “essence” out of a plant. This method is still used for citrus peels, mostly. Today, we use the same method used for centuries: distillation, which takes advantage of the fact that oil and water do not mix, to separate out the oil of essence from a plant. The raw material is brought to a boil in water (or the whole plant is steamed through hydrodistillation.) The volatile oil will be extracted in the steam, which is cooled and condensed. Finally, the oil and water separate. There is no waste, as the water will contain plant components that are water soluble – the aromatic hydrosols. This “essential” water is then used by some who find them less irritating than the actual EOs. There are two other modern methods of extraction that can be used. The first is carbon dioxide extraction, where the CO2 is put into a “supercritical” state. In this state it has qualities of gases and liquids. This produces very pure EOs, but is a very expensive extraction method. The other modern method is called “phytonic” and gentler, still, than the CO2 process, using non-CFCs (non-chlorofluorocarbons) at a very low temperature. The fluorohydrocarbons used in place of non-CFCs may still be harmful, however. (Shnaubelt, pg. 13.) MetabolismOnce we have the end product, the EO, how does it circulate in the body? Similar to other compounds, it depends on the method we use, be it diffused into the air with a diffuser, ingested directly or in food, or applied topically. If we use a diffuser, the oil will enter the respiratory system, then the venous and lymphatic systems. The oil then reaches the heart and goes to various tissues via the arterial system. Metabolism in the digestive system puts an end to any beneficial constituents, except for the effect they can still have in the urinary system. Anything that’s left will be stored in adipose tissue, for the most part. (The Chemistry of Aromatherapeutic Oils, Bowles, E. Joy, pg. 128.) If we apply the oils directly, or diluted to the skin, the process will be the same, except the EO will bypass the respiratory system. If the oils are taken internally, it will only be to have an effect on the digestive system, before reaching the liver and eventually being eliminated (where the EO can once again have some effect on the kidneys and urinary tract.) But what, specifically do EOs do when they reach a target organ or tissue? Here again, it depends on the specific components. Since most of the compounds are at least partially lipophilic, they interact with the phospholipid membranes of cells, including bacterial cells. There are other methods of getting oils into the body, such as suppositories, but that will be discussed when we get to the issue of parison to PharmaceuticalsHow then, do EOs compare to “conventional” medicines? They fared very well, according to one study by Nicolette Perry and Elaine Perry, titled Aromatherapy in the Management of Psychiatric Disorders. (Retrieved from EBSCOhost 16 November 2012.) Based on admittedly limited studies, especially in treatment of psychiatric disorders, save “dementia,” the authors conclude that “aromatherapy” is a “potentially effective treatment for a range of psychiatric disorders. In addition, it appears to be without the adverse effects of many conventional psychotropic drugs.” (Perry and Perry, Abstract.) As evidence of this they presented the some clinical studies, most of which used lavender, or a mix of EOs including lavender. Their paper is an appetizer of sorts – a plea to do more controlled studies on more conditions. The trials are “teaser” trials, leading to a desire for more studies. In one:Ten patients with dementia were treated for 6 months with a range of essential oils (vaporized mixtures of orange, ylang ylang, patchouli, basil, rosemary, peppermint, rosewood, geranium, bergamot, chamomile and jasmine.) A marked decrease in disturbed behavior was observed in the majority of patients, leading to reductions in psychotropic medications with overall cost savings. (Pg. 261.)It’s unfortunate that specific oils weren’t tested individually, but these results are encouraging nevertheless, since applications of individual oils overlap those of other oils. The “disturbed behavior” that was reduced included agitation, insomnia, wandering, “difficult” behavior and social withdrawal. Another study was done on100 patients with epilepsy who chose to complement their conventional anticonvulsants with aromatherapy. One-third were no longer taking their prescribed medications and were free of seizures after two years. (Perry & Perry, pg. 265.) Unfortunately, most of the studies are anectodal, and/or based on self-reports. Feeling like you’re feeling better doesn’t mean that you’re not actually feeling better, however. As Perry and Perry said, “The effects of an aroma can be instantaneous and include both direct and indirect psychological effects – even thinking about a smell may have a similar effect to the smell itself.” (Pg. 258.) The scientists have also been honest in concluding that aromatherapy isn’t effective for all conditions. For example, in patients with severe learning disability, lavender, lemongrass, and wild orange provided no benefit. (Perry, pg. 265.) Schaubelt points out that aromatherapy is best for treating conditions in the following order: infectious illnesses (95% potential success rate); psychiatric disorders, the nervous system, and hormonal imbalance (75%); inflammatory, allergic, or autoimmune conditions (50%); and metabolic or degenerative conditions (25%). (Pgs, 99, 101.)Just as with synthetic drugs an individual’s chemical makeup is bound to influence the outcomes of various treatments. There is also the matter of individual preferences of oils. The very aromas that can be soothing or stimulating to some, may be irritating to others, depending on the circumstances, or even in every circumstance. On a physiological response level, patients may simply respond differently – in the same way that some patients taking fluoxetine (Prozac) may get drowsy while others may experience insomnia. In the case of the Prozac, patients would need to adjust the time of their dosage accordingly. And if an individual found wild orange stimulating, rather than relaxing, that individual would not want to diffuse wild orange while attempting to get some sleep. Side Effects and ContraindicationsIt’s important in discussing the effectiveness of therapeutic oils compared to conventional medications, to consider the harmful side effects of each. Many problems with drugs of any kind, “natural,” or synthetic, occur when they are misused. Two cases concerning cinnamon oil were found on EBSCOhost where the cinnamon oil was used trans-dermally. In one case, an elderly woman had a mud bath with cinnamon oil at a spa. Within 24 hours, she exhibited contact dermatitis on her arms and legs, which were exposed. (Mud bath dermatitis due to cinnamon oil., Garcia-Abujeta, Jose` Luis.) The other was a case concerning a girl who used “galenic” vaginal suppositories containing cinnamon oil. She developed allergic dermatitis, eczematous eruptions, and her vulvitis [worsened.] (Allergic Contact Dermatitis due to Cinnamon Oil in Galenic Vaginal Suppositories., Lauriola, Maria Michela.) Peppermint oil contains methone, which may be damaging to the liver in high doses. In small doses it can help nausea and strengthen the liver. Ketones in Rue (Methyl nonyl ketone,) or Mugwort (Thujone) are highly toxic. Sage also contains thujone, but the oil as a whole is less toxic than the thujone would be on its own. Once again, how the oil is administered effects potential toxicity, with oral application being the most dangerous, followed by rectal, vaginal, percutaneous, and finally by inhalation being the least dangerous where EOs are concerned. (Schnaubelt, pg. 44-45.)Oils containing phenols, such as cinnamon, can also be damaging to the liver in high doses, or if used continuously for a long time. They do this by changing the number of liver enzymes. Kidney damage, on the other hand, can occur through overuse of terpene hydrocarbons, such as those found in Frankincense, because they are so lipophilic. Side effects of pharmaceuticals are legion. Almost every side effect – minor to serious - is possible when such a varied population take the same medications, sometimes in concert with conditions or other medications that are contraindicated. Let’s take a common antacid (in comparison to Peppermint,) used for heartburn – they can cause diarrhea or constipation with overuse. Levaquin, an antibiotic (in comparison to Cinnamon) is another medication that can cause diarrhea and joint paint and stiffness, among many other side effects. Fluoxetine, an anti-depressant SSRI, can cause restlessness and hives with normal use. With overdose, it can cause unconsciousness, delirium, and much more. It can even cause depression, while taking it, and after stopping. Compare that to Lavender, a calming oil which is very benign unless one doesn’t like the scent. Even Lavender, though, can cause skin dryness over long periods of use, due to its acids and esters. There has also been some evidence that Lavender impairs memory performance (Bowles, pg. 154) and arithmetic reasoning (Perry & Perry, pg. 261) – so it would not be good to use before a test. Lavender and tea tree oil were also blamed for breast development in young boys:Most cases of male prepubertal gynecomastia are classified as idiopathic. We investigated possible causes of gynecomastia in three prepubertal boys who were otherwise healthy and had normal serum concentrations of endogenous steroids. In all three boys, gynecomastia coincided with the topical application of products that contained lavender and tea tree oils. Gynecomastia resolved in each patient shortly after the use of products containing these oils was discontinued. Furthermore, studies in human cell lines indicated that the two oils had estrogenic and antiandrogenic activities. We conclude that repeated topical exposure to lavender and tea tree oils probably caused prepubertal gynecomastia in these boys. (Preburtal Gynecomastia Linked to Lavender and Tea Tree Oils.)Frankincense, which may also be used for depression along with Lavender, has no contraindications with normal use. In addition Frankincense oil can be useful as an anti-inflammatory if the oil is extracted with supercritical CO2, so that enough Boswellic acids (triterpenoids) will be in the oil to be effective. (Bowles, pg. 140-141.) EffectivenessAs mentioned above, therapeutic oils (at least when used to treat psychiatric symptoms) seemed as equally effective, if not more so, than prescribed medication - with fewer side effects and less cost. It should be noted that should the FDA begin regulating therapeutic oils as they do drug companies, then the cost of therapeutic oils would surely increase to the level of generic label drugs, if not those still under patent. The closest thing to the FDA for CAM (Complementary and Alternative Medicine, which oils would fall under,) seems to be the NCCAM, but as yet the aromatherapeutic oil industry is self-regulated. The NCCAM was established, under the National Institutes of Health (NIH,) to “foster research into CAM and make the findings available to the public,” according to the Mayoclinic website. Speaking of government, if the establishment of the NCCAM doesn’t quite establish CAM and/or EOs as legitimate in some way, then surely the fact that the George E. Wahlen Department of Veterans Affairs Medical Center has CAM clinics should. Though the VA hospital does not have clinics specifically for aromatherapy, it does include massage therapy and acupuncture and the therapists and practitioners of those often recommend the use of some therapeutic oils, including Lavender and Peppermint oils.Despite that, there still have not been enough random blind trials (how do you substitute a placebo with a scent for a scented oil?) to determine the efficacy of using oils alone or in conjunction with mainstream medical therapies. For some, EOs ARE the placebo. If a placebo causes ones condition to improve, then perhaps it’s not a placebo at all. For others, they could be a nocebo, producing unwanted effects due to a patients belief that the oil will harm them. Again, this could have something to do with the scent – and it is difficult, if not impossible to separate the psyche from the body. Physical illnesses influence ones emotions and vice versa, to a certain extent. Sometimes to a great extent, such as a case where someone dies of fright because they had a heart attack. (Scared to Death: How Fright Can Kill. Childs, Dan.)As with all chemical compounds, including EOs, one should read the directions and be cautious when using EOs – whether using them with or without mainstream medications. It makes sense, considering that mainstream medications are often derived or copied from chemicals found in nature. For example, Aspirin was first derived from salicin found in Willow Bark. And Coumadin, an anti-coagulant, is derived from Coumarins, which have a lactone ring attached to a benzene ring. Coumarins can be found in Tonka beans and Cassia, and in trace amounts in Lavender. (With this in mind, one may wish to use Lavender in conjunction with birth control pills, since birth control pills can contribute to the development of blood clots.)In conclusion, I think that with moderate use and in consultation with a doctor you trust, that EOs can complement the use of mainstream medications. If nothing else, they smell pleasant and that is a good thing when used sparingly. ................
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