Abstract
Essential oils are complex mixtures of volatile compounds produced by aromatic plants and extracted by distillation or expression. More than 3000 essential oils are known with about 300 being commercially relevant as perfume, cosmetic, cleaning, food, and pharmaceutical products. The main trade oils (over 1000 t/year) are those extracted from Citrus aurantifolia, Citrus limon, Citrus sinensis, Cymbopogon nardus, Cymbopogon winterianus, Eucalyptus citriodora, Eucalyptus globulus, Lavandula × intermedia, Mentha canadensis, Mentha × gracilis, Mentha × piperita, Ocotea odorifera, Pogostemon cablin, Sassafras albidum and Syzygium aromaticum. A remarkable progress in the development of analytical methods has contributed to a precise and more reliable characterization of essential oils. Volatile compounds of terpenoid origin, primarily monoterpenes and sesquiterpenes, have been identified as hydrocarbons and their oxygenated derivatives in the form of alcohols, aldehydes, ketones, esters, ethers, peroxydes, and phenols. Also, non-terpenoid compounds namely phenylpropanoids, fatty acids and their esters and, more rarely, nitrogen- and sulfur-containing compounds are also present. Numerous parameters (physiological, environmental, and genetic factors) influence essential oil composition and in order to ensure the best quality of commercialized oils, specific guidelines have been developed and should be considered.
This chapter attempts to shed light on essential oils chemistry by pointing out biosynthetic aspects, relevant compounds in essential oil composition, and the major global trade oils.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Abbasipour H, Mahmoudvand M, Rastegar F et al (2011) Fumigant toxicity and oviposition deterrency of the essential oil from cardamom, Elettaria cardamomum, against three stored-product insects. J Insect Sci 11:165
Andro A-R, Boz I, Zamfirache M–M et al (2013) Chemical composition of essential oils from Mentha aquatica L. at different moments of the ontogenetic cycle. J Med Plants Res 7(9):470–473
Asghari G, Mostageran A, Shebli M (2009) Essential oil components of turmeric leaves and rhizome cultivated in Iran. Planta Med 75:PI10
Avé DA, Gregory P, Tingey WM (1987) Aphid repellent sesquiterpenes in glandular trichomes of Solanum berthaultii and S. tuberosum. Exp Appl 44:131–138
Bakkali F, Averbeck S, Averbeck D et al (2008) Biological effects of essential oils—a review. Food Chem Toxicol 46:446–475
Barnard DR, Xue R (2004) Laboratory evaluation of mosquito repellents against Aedes albopictus, Culex nigripalpus, and Ochlerotatus triseriatus (Diptera: Culicidae). J Med Entomol 41(4):726–730
Baser KHC, Demirci F (2007) Chemistry of essential oils. In: Berger RG (ed) Flavours and fragrances—chemistry, bioprocessing and sustainability. Springer, Berlin, pp 43–86
Bauer K, Garbe D (2001) Common fragrance and flavour materials. Preparation, properties and uses. VCH Verlagsgesellschaft, Weinheim
Behr A, Johnen L (2009) Myrcene as a natural base chemical in sustainable chemistry: a critical review. ChemSusChem 2(12):1072–1095
Bouwmeester HJ (2006) Engineering the essence of plants. Nat Biotech 24:1359–1361
Bovill H (2010) 20-Trade of essential oils. In: Baser CKH, Buchbauer G (eds) Handbook of essential oils: science, technology, and applications. CRC Press, Taylor & Francis Group, Boca Raton, FL
Bowsher C, Steer M, Tobin A (2008) Plant biochemistry. Garland Science, New York
Breitmaier E (2006) Terpenes—flavors, fragrances, pharmaca, pheromones. Wiley-VCH Verlag GmbH & Co.kGaA, Germany
Buchbauer G (2000) The detailed analysis of essential oil leads to the understanding of their properties. Perfumer Flavorist 25:64–67
Carson CF, Hammer KA, Riley TV (2006) Melaleuca alternifolia (tea tree) oil: a review of antimicrobial and other medicinal properties. Clin Microbiol Rev 19(1):50–62
Chang C-T, Chang W-L, Hsu J-C et al (2013) Chemical composition and tyrosinase inhibitory activity of Cinnamomum cassia essential oil. Bot Stud 54:10–17
Chericoni S, Prieto JM, Iacopini P et al (2005) In vitro activity of the essential oil of Cinnamomum zeylanicum and eugenol in peroxynitrite-induced oxidative processes. J Agric Food Chem 53(12):4762–4765
Coşge B, Kiralan M, Gürbüz B (2008) Characteristics of fatty acids and essential oil from sweet fennel (Foeniculum vulgare Mill. var. dulce) and bitter fennel fruits (F. vulgare Mill. var. vulgare) growing in Turkey. Nat Prod Res 22(12):1011–1106
Council of Europe (2004) European pharmacopoeia, 5th edn. Council of Europe, Strasbourg
Craveiro AA, Alencar JW, Matos FJA et al (1991) Essential oil of Zanthoxylum gardneri Engl. A new source of nerolidol. J Essent Oil Res 3:371–372
Davazdahemami S, Sefidkon F, Jahansooz MR (2011) Chemical composition of the essential oils from Foliages and seeds of Ajowan (Trachyspermum ammi (L.) Sprague) in two planting dates (spring and summer). J Essent Oil Bear Plants 14(5):639–642
Derwich E, Benziane Z, Taouil R (2010) Compounds of the essential oil of the leaves of Mentha pulegium growing in Morocco. Chem Bull “Politehnica” Univ Timisoara, Romaina. Ser Chem Environ Eng 55:103–106
Dewick PM (2002a) Chap. 4—The shikimate pathway: aromatic amino acids and phenylpropanoids. In: Medicinal natural products: a biosynthetic approach, 2nd edn. Wiley, United Kingdom, pp 121–164
Dewick PM (2002b) Chap. 5—The mevalonate and deoxyxylulose phosphate pathways: terpenoids and Steroids. In: Medicinal natural products: a biosynthetic approach, 2nd edn. Wiley, United Kingdom, pp 167–285
Eccles R (1994) Menthol and related cooling compounds. J Pharm Pharmacol 46(8):618–630
Fahn A (1979) Secretory tissues in plants. Academic Press, London
Figueiredo AC, Barroso JG, Pedro LG et al (2008a) Factors affecting secondary metabolite production in plants: volatile components and essential oils. Flavour Frag J 23:213–226
Figueiredo AC, Barroso JG, Pedro LG et al (2008b) Portuguese Thymbra and Thymus species volatiles: chemical composition and biological activities. Curr Pharm Des 14(29):3120–3140
Franz C, Novak J (2010) Chap. 3—Sources of essential oils. In: Baser CKH, Buchbauer G (eds) Handbook of essential oils: science, technology, and applications. CRC Press, Taylor & Francis Group, Boca Raton, FL
Ganjewala D (2009) Cymbopogon essential oils: chemical compositions and bioactivities. Int J Essen Oil Ther 3:56–65
Gomes da Silva MDR, Cardeal Z, Marriott PJ (2008) Comprehensive two-dimensional gas chromatography: application to aroma and essential oil analysis. In: Tamura H et al (eds). Food flavour. ACS Symposium Series, American Chemical society, Washington, DC
Gonny M, Cavaleiro C, Salgueiro L et al (2006) Analysis of Juniperus communis subsp. alpine needle, berry, wood and root oils by combination of GC, GC/MS and13C-NMR. Flavour Fragr J 21: 99–106
Gowda PJ, Ramakrishnaiah H, Krishna V et al (2012) Caryophyllene-rich essential oil of Didymocarpus tomentosa: chemical composition and cytotoxic activity. Nat Prod Commun 7(11):1535–1538
Harborne JB (1993) Introduction to ecological biochemistry, 4th edn. Academic Press, London
Harborne JB, Baxter H (2001) Chemical dictionary of economic plants: dictionary of useful plant products. Wiley, West Sussex
Hendriks H, Malingre T, Battermann S et al (1975) Mono- and sesquiterpene hydrocarbons of the essential oil of Cannabis sativa. Phytochemistry 14:814–815
Homer LE, Leach DN, Lea D et al (2000) Natural variation in the essential oil content of Melaleuca alternifolia Cheel (Myrtaceae). Biochem Syst Ecol 28(4):367–382
Huang Y, Zhao J, Zhou L et al (2010) Antifungal activity of the essential oil of Illicium verum fruit and its main component trans-anethole. Molecules 15(11):7558–7569
Hunter M (2009) Essential oils: art, agriculture, science, industry and entrepreneurship (a focus on the Asia-Pacific region). Agriculture issues and policies series. Nova Science Publishers, Inc, New York
Hussaina AI, Anwara F, Sherazib STH et al (2008) Chemical composition, antioxidant and antimicrobial activities of basil (Ocimum basilicum) essential oils depends on seasonal variations. Food Chem 108(3):986–995
ISO 9235:2013–Aromatic natural raw materials-vocabulary
ISO 19332:2007- Oil of blue chamomile (Chamomilla recutita (L.) Rauschert syn. Matricaria chamomilla auct.)
Jager W (2010) Metabolism of terpenoids in animal models and humans. In: Baser KHC, Buchbauer G (eds) Handbook of essential oils, science, technology and applications. CRC Press, United States of America, pp 209–234
Jamali CA, Bouzidi L E, Bekkouche K et al (2012) Chemical composition and antioxidant and anticandidal activities of essential oils from different wild Moroccan Thymus species. Chem Biodivers 9(6):1188–1197
Jayaprakasha GK, Jagan Mohan Rao L, Sakariah KK (2003) Volatile constituents from Cinnamomum zeylanicum fruit stalks and their antioxidant activities. J Agric Food Chem 51:4344–4348
Jeena K, Liju VB, Kuttan R (2013) Antioxidant, anti-inflammatory and antinociceptive activities of essential oil from ginger. Indian J Physiol Pharmacol 57(1):51–62
Jirovetz L, Buchbauer G, Stoilova I et al (2006) Chemical composition and antioxidant properties of clove leaf essential oil. J Agric Food Chem 54(17):6303–6307
Joshi R, Sharma P, Sharma V et al (2012) Analysis of the essential oil of large cardamom (Amomum subulatum Roxb.) growing in different agro-climatic zones of Himachal Pradesh, India. J Sci Food Agric 93(6):1303–1309
Juan LW, Lucia A, Zerba EN et al (2011) Chemical composition and fumigant toxicity of the essential oils from 16 species of Eucalyptus against Haematobia irritans (Diptera: Muscidae) adults. J Econ Entomol 104(3):1087–1092
Kamatou GP, Vermaak I, Viljoen AM et al (2013) Menthol: a simple monoterpene with remarkable biological properties. Phytochemistry 96:15–25
Katsiotis ST, Langezaal CR, Schefferj JJC (1990) Composition of the essential oils from leaves of various Humulus lupulus L. cultivars. Flavour Frag J 5:97–100
Kim J-K, Kang C-S, Lee J-K et al (2005) Evaluation of repellency effect of two natural aroma mosquito repellent compounds, citronella and citronellal. Ent Res 35(2):117–120
Kim S, Jung E, Kim JH, Park YH, Lee J, Park D (2011) Inhibitory effects of (−)-α-bisabolol on LPS-induced inflammatory response in RAW 264.7 macrophages. Food Chem Toxicol 49(10):2580–2585
Kim YW, Kimm MJ, Chung BY et al (2013) Safety evaluation and risk assessment of d-limonene. J Toxicol Environ Health Sci Part B Crit Rev 16:17–38
Kose EO, Deniz IG, Sarikurkcu C et al (2010) Chemical composition, antimicrobial and antioxidant activities of the essential oils of Sideritis erythrantha Boiss. and Heldr. (var. erythrantha and var. cedretorum P.H. Davis) endemic in Turkey. Food Chem Toxicol 48:2960–2965
Krüger H, Hammer K (1999) Chemotypes of fennel (Foeniculum vulgare Mill.). J Essent Oil Res 11:79–82
Litchenthaler HK (1999) The 1-deoxy-D-xylulose-5-phosphate pathway of isoprenoid biosynthesis in plants. Annu Rev Plant Physiol Plant Mol Biol 50:47–65
Little DB, Croteau RB (1999) Biochemistry of essential oil terpenes. In: Teranishi R, Wick EL, Hornstein I (eds) Flavor chemistry. Thirty years of progress. Kluwer Academic/Plenum Publishers, New York, pp 239–253
Lohani H, Haider SZ, Chauhan NK et al (2013) Aroma profile of two Juniperus species from Alpine region in Uttarakhand. J Nat Prod 6:38–43
Marongiu B, Piras A, Porcedda S et al (2013) Isolation of the volatile fraction from Apium graveolens L. (Apiaceae) by supercritical carbon dioxide extraction and hydrodistillation: chemical composition and antifungal activity. Nat Prod Res 27(17):1521–1527
Marzouki H, Khaldi A, Falconieri D et al (2010) Essential oils of Daucus carota subsp. carota of Tunisia obtained by supercritical carbon dioxide extraction. Nat Prod Commun 5(12):1955–1958
Miguel MG, Dandlen S, Figueiredo AC et al (2008) Essential oils of flowers of Citrus sinensis and Citrus clementina cultivated in Algarve, Portugal. Acta Hort 773:89–94
Mockute D, Bernotiene G, Judzentiene A (2001) The essential oil of Origanum vulgare L. ssp. vulgare growing wild in vilnius district (Lithuania). Phytochemistry 57:65–69
Mota KSL, Pereira FO, Oliveira W A et al (2012) Antifungal activity of Thymus vulgaris L. essential oil and its constituent phytochemicals against Rhizopus oryzae: interaction with ergosterol. Molecules 17:14418–14433
Nabiha B, Abdelfatteh EO, Faten K (2010) Chemical composition of bergamot (Citrus bergamia Risso) essential oil obtained by hydrodistillation. J Chem Chem Eng 4:60–62
Ooi LS, Li Y, Kam SL et al (2006) Antimicrobial activities of cinnamon oil and cinnamaldehyde from the Chinese medicinal herb Cinnamomum cassia Blume. Am J Chin Med 34(3):511–522
Orav A, Stulova I, Kailas T et al (2004) Effect of storage on the essential oil composition of Piper nigrum L. fruits of different ripening states. J Agric Food Chem 52:2582–2586
Ottavioli J, Gonny M, Casanova J et al (2009) Chemical variability of the needle oil of Juniperus communis ssp. alpina from Corsica. Chem Biodivers 6(12):2192–2199
Ozcan MM, Pedro LG, Figueiredo AC et al (2006) Constituents of the essential oil of sea fennel (Crithmum maritimum L.) growing wild in Turkey. J Med Food 9(1):128–130
Ozek G, Demirci F, Ozek T et al (2010) Gas chromatographic-mass spectrometric analysis of volatiles obtained by four different techniques from Salvia rosifolia Sm., and evaluation for biological activity. J Chromatog 1217:741–748
Pereira SI, Santos PA, Barroso JG et al (2000) Chemical polymorphism of the essential oils from populations of Thymus caespititius grown on the island S. Jorge (Azores). Phytochemistry 55(3):241–246
Perrina A, Colsona M (1991) Timing of the harvest date for Mentha × piperita based on observations of the floral development. J Essent Oil Res 3:17–25
Pichersky E, Gershenzon J (2002) The formation and function of plant volatiles: perfumes for pollinator attraction and defense. Curr Opin Plant Biol 5:237–243
Pinto E, Salgueiro LR, Cavaleiro C et al (2007) In vitro susceptibility of some species of yeasts and filamentous fungi to essential oils of Salvia officinalis. Ind Crop Prod 26:135–114
Prashar A, Locke IC, Evans CS (2004) Cytotoxicity of lavender oil and its major components to human skin cells. Cell Prolif 37(3):221–229
Raal A, Paaver U, Arak E, Orav A (2004) Content and composition of the essential oil of Thymus serpyllum L. growing wild in Estonia. Medicina (Kaunas) 40(8):795–800
Raal A, Orav A, Arak E (2007) Composition of the essential oil of Salvia officinalis L. from various European countries. Nat Prod Res 21(5):406–411
Raina VK, Kumar A, Srivastava SK et al (2004) Essential oil composition of ‘kewda’ (Pandanus odoratissimus) from India. Flavour Frag J 19(5):434–436
Rubiolo P, Matteodo M, Riccio G et al (2006) Analytical discrimination of poisonous and nonpoisonous chemotypes of giant fennel (Ferula communis L.) through their biologically active and volatile fractions. J Agric Food Chem 54(20):7556–7563
Rudbäck J, Bergström MA, Börje A et al (2012) a-Terpinene, an antioxidant in tea tree oil, autoxidizes rapidly to skin allergens on air exposure. Chem Res Toxicol 25:713–721
Rude MA, Schirmer A (2009) New microbial fuels: a biotech perspective. Curr Opin Microbiol 12:274–281
Russo EB (2011) Taming THC: potential cannabis synergy and phytocannabinoid-terpenoid entourage effects. Br J Pharmacol 163(7):1344–1364
Saab AM, Tundis R, Loizzo MR (2012) Antioxidant and antiproliferative activity of Laurus nobilis L. (Lauraceae) leaves and seeds essential oils against K562 human chronic myelogenous leukaemia cells. Nat Prod Res 26(18):1741–1745
Safayhi H, Sabieraj J, Sailer ER et al (1994) Chamazulene: an antioxidant-type inhibitor of leukotriene B4 formation. Planta Med 60(5):410–413
Saharkhiz MJ, Motamedi M, Zomorodian K et al (2012) Chemical composition, antifungal and antibiofilm activities of the essential oil of Mentha piperita L. ISRN Pharm 718645. doi: 10.5402/2012/718645
Salgueiro L, Vila R, Tomi F et al (1997) Variability of the essential oils of Thymus caespititius from Portugal. Phytochemistry 45(2): 307–311
Salgueiro LR, Cavaleiro C, Pinto E et al (2003) Chemical composition and antifungal activity of the essential oil of Origanum virens on Candida species. Planta Medv 69(9):871–874
Salgueiro L, Martins AP, Correia H (2010) Raw materials: the importance of quality and safety. A review. Flavour Frag J 25:253–271
Sangwan NS, Farooqi AHA, Shabih F et al (2001) Regulation of essential oil production in plants. Plant Growth Regul 34:3–21
Sardashti A, Adhami Y (2013) Chemical composition of the essential oil of Mentha pulegium L. from Taftan area by means of gas chromatography/mass spectrometry (GC/MS). J Med Plant Res 7:3003–3007
Sarrou E, Chatzopoulou P, Dimassi-Theriou K et al (2013) Volatile constituents and antioxidant activity of peel, flowers and leaf oils of Citrus aurantium L. growing in Greece. Molecules 18:10639–10647
Schmidt E (2010) Chap. 4. Production of essential oils. In: Baser KHC, Buchbauer G (eds) Handbook of essential oils, science, technology and applications. CRC Press, United States of America, pp 83–120
Sell C (2010) Chap. 5—The chemistry of essential oils. In: Baser CKH, Buchbauer G (eds) Handbook of essential oils: science, technology, and applications. CRC Press, Taylor & Francis Group, Boca Raton, pp 121–150
Sharif R, Kiani H, Farzaneh M et al (2008) Chemical composition of essential oils of Iranian Pimpinella anisum L. and Foeniculum vulgare Miller and their antifungal activity against postharvest pathogens. Jeobp 11(5):514–522
Skold M, Karlberg AT, Matura M et al (2006) The fragrance chemical beta-caryophyllene-air oxidation and skin sensitization. Food Chem Toxicol 44(4):538–545
Svoboda KP, Svoboda TG (2000) Secretory structures of aromatic and medicinal plants. Microscopix Publications, Middle Travelly
Taiz L, Zeiger E (2010) Plant physiology, 5th edn. Sinauer Associates Inc. Publishers, Sunderland
Teixeira B, Marques A, Ramos C et al (2013) Chemical composition and bioactivity of different oregano (Origanum vulgare) extracts and essential oil. J Sci Food Agric. doi: 10.1002/jsfa.6089
Tisserand R, Balacs T (1995) Essential oil safety. Churchill Livingstone, London
Tomi F, Bradesi P, Bighelli A, Casanova J (1995) Computer aided identification of individual components of essential oils using carbon-13 NMR spectroscopy. J Magn Res 1:25–34
Tsai S-Y, Huang S-J, Chyau C–C et al (2011) Composition and antioxidant properties of essential oils from Curcuma rhizome. AJAS 2(1):57–66
Tyler VE, Brady LR, Robbers JE (1988) Pharmacognosy. Lea & Febiger, Philadelphia
Tzakou O, Bazos I, Yannitsaros A (2006) Essential oil composition and enantiomeric distribution of fenchone and camphor of Lavandula cariensis and L. stoechas subsp. stoechas grown in Greece. Nat Prod Commun 4(8):1103–1106
Valente J, Zuzarte M, Liberal J (2013) Margotia gummifera essential oil as a source of anti-inflammatory drugs. Ind Crops Prod 47:86–91
Vázquez-Araújo L, Rodríguez-Solana R, Cortés-Diéguez SM et al (2013) Use of hydrodistillation and headspace solid-phase microextraction to characterize the volatile composition of different hop cultivars. J Sci Food Agric 93(10):2568–2574
Vekiari SA, Protopapadakis EE, Papadopoulou P et al (2002) Composition and seasonal variation of the essential oil from leaves and peel of a Cretan lemon variety. J Agric Food Chem 50(1):147–153
Wagner H, Bladt S (2009) Plant drug analysis. A thin layer chromatography atlas, 2nd edn. Springer, Berlin
Wang W, Li N, Luo M et al (2012a) Antibacterial activity and anticancer activity of Rosmarinus officinalis L. essential oil compared to that of its main components. Molecules 17(3):2704–2713
Wang B, Peng XX, Sun R et al (2012b) Systematic review of β-elemene injection as adjunctive treatment for lung cancer. Chin J Integr Med 18:813–882
Yang D, Michel L, Chaumont JP et al (1999) Use of caryophyllene oxide as an antifungal agent in an in vitro experimental model of onychomycosis. Mycopathologia 148(2):79–82
Yannai S (2004) Dictionary of food compounds with CD-ROM: additives, flavors, and ingredients. Chapman & Hall/CRC, Florida
Yao S–S, Guo W–F, Lu Y et al (2005) Flavour characteristics of lapsang souchong and smoked lapsang souchong, a special Chinese black tea with pine smoking process. J Agric Food Chem 53(22):8688–8993
Zhang H, Liu Q, Cao Y et al (2014) Microbial production of sabinene—a new terpene-based precursor of advanced biofuel. Microb Cell Fact 13(1):20
Zuzarte M, Gonçalves MJ, Cavaleiro C et al (2009) Chemical composition and antifungal activity of the essential oils of Lavandula pedunculata (Miller) Cav. Chem Biodivers 6:1283–1292
Zuzarte M, Gonçalves MJ, Cruz MT (2012a) Lavandula luisieri essential oil as a source of antifungal drugs. Food Chem 135:1505–1510
Zuzarte M, Vale-Silva L, Gonçalves MJ et al (2012b) Antifungal activity of phenolic-rich Lavandula multifida L. essential oil. EJCMID 3:1359–1366
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2015 Springer International Publishing Switzerland
About this chapter
Cite this chapter
Zuzarte, M., Salgueiro, L. (2015). Essential Oils Chemistry. In: de Sousa, D. (eds) Bioactive Essential Oils and Cancer. Springer, Cham. https://doi.org/10.1007/978-3-319-19144-7_2
Download citation
DOI: https://doi.org/10.1007/978-3-319-19144-7_2
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-19143-0
Online ISBN: 978-3-319-19144-7
eBook Packages: Biomedical and Life SciencesBiomedical and Life Sciences (R0)