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Detecting Traces of Methyl Eugenol in Essential Oils

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Detecting Traces of Methyl Eugenol in Essential Oils Detecting traces of methyl eugenol in essential oils Ian Southwella,Mike Russellband Noel Daviesc Introduction Regulatory authorities are becoming more concerned about even low levels of suspected toxins in fl avour, fragrance and medicinal applications1. For example, allyl alkoxybenzenes (eg safrole, estragole (methyl chavicol), methyl eugenol), common constituents of many essential oils2,3, are of concern because high doses have caused cancer in rodents4-6. This concern is often exaggerated considering that: ► safety threshold doses some 1000 times less than the offending concentration recommended (eg IFRA Standards5) ► carcinogenesis is not always considered a threshold phenomenon7-9 ► the validity of dose extrapolation from rodents to humans is uncertain10-11 ► many complete essential oils also contain anti-carcinogenic congeners12-14 Hence reliable methods for the determination of trace quantities of allyl alkoxybenzenes in essential oils and formulated products are essential. Determinations Gas Chromatography using FID and MS detection Because of the absence of competing mass spectral ions illustrated the complexity of these essential oils and the from Melaleuca oil components, GCMS in SIM mode using diffi culties encountered in locating trace constituents. the m/z 178 ion (Varian Factor-Four VF-5ms, 30m x 0.25mm id, 0.25 μm fi lm) facilitated the determination of methyl Using tea tree oil, “Oil of Melaleuca, terpinen-4-ol type” as eugenol (Figure 2). a model, careful column selection for GC-FID (DB 1701 Length 60 m x 0.25 mm Dia x 0.25 μm fi lm (mid polarity) ) Such SIM traces, although excellent for determining analytes facilitated the separation and determination of methyl like methyl eugenol, give a false impression of the complexity eugenol to the ppm level (Figure 1). of such oils. Fig.1 Fig.2 methyl eugenol m/z 178 methyl eugenol methyl isoeugenol GCMS SIM (m/z 178) trace of methyl eugenol in tea tree oil. Table: Interlaboratory comparison of methyl eugenol determinations (ppm) using two different methods methyl eugenol Sample No GC-FID GCMS-SIM 1 665 604 2 538 589 3 626 612 4 439 411 The FID analysis of 100 randomly selected commercial tea tree oils gave methyl eugenol determinations ranging from 0 to 554 ppm (mean 209 ppm). Comparison of four exhaustively, laboratory-distilled tea tree oils determined by both FID and GCMS-SIM gave close agreement (Table) using two different methods in two different laboratories. Discussion Both GC-FID and GCMS-SIM methods were found suitable for determining 100 Fig.3 trace quantities of methyl eugenol in essential oils. 90 80 These GC methods confi rmed that, in Melaleuca alternifolia essential oil, 70 methyl eugenol does not exceed 600 ppm (mean 209 ppm) for 60 commercial distillations and 700ppm for exhaustive laboratory distillations. 50 This result quantifi es previous reports of trace amounts15 and is 20 times 16 40 less than reports in a recently published SCCP opinion which must have 30 17 used non-commercial Melaleuca data from other species . When plotted 20 100 mg/day application 8 of neat tea tree oil against published results , the dangers presented by methyl eugenol in tea 10 tree oil are negligible because calculated absorption* from recommended 0 use is 106 times less than the level known to cause tumours in rodents8.9 Percent of rats with tumors (Figure 3). Molecules of methyl eugenol/kg/day Methyl eugenol dosage for 100mg/day application of tea tree oil compared to *100 mg neat oil applied per day = 1.25 mg/kg for 80 kg use = 1,250 μg/kg = 0.25 μg/kg methyl eugenol (@200ppm me eug in oil) = fl avour,food and pesto use of methyl eugenol (based on Fig.8 in Waddell 20028). 0.0014 μmoles/kg me eug = 1.4 x 10-9 moles/kg me eug = 1.4 x 10-9 x 6 x 1023 molecules me eug/kg = 8.4 x 1014 molecules methyl eugenol/kg applied = 4.2 x 1014 molecules methyl eugenol/kg absorbed (assuming 50% absorption). References [1] Robison, S.; Barr, D., Environ Health Perspect., 2006, 114(11): 1797–1801. [2] Burfi eld, T.(Ed) Cropwatch Opinion: Methyl eugenol-containing essential oils, Cropwatch 2004, 3b. [3] Burfi eld, T.(Ed) Cropwatch Opinion: Safrole: Human Carcinogenicity Risk Over-Stated? Cropwatch, 2009, Sept. [4] Phillips, D.H., Reddy, M.V., and Kurt Randerath, K. Carcinogenesis, 1984, 5, 1623 - 1628. [5] IFRA Standard – Safrole, Isosafrole, The authors would like to thank Claude Cassegrain from Cassegrain Tea Tree Oil for funding much of the methyl Dihydrosafrole; Estragole; Methyl eugenol, 2009, October 14. [6] Liikanen, E. Offi cial Journal of the European Communities. Cosmetic products. 18.4.2002, L102/19-20. [7] Waddell, W. Thresholds in chemical carcinogenesis: What are animal experiments telling us? Toxicol. Pathol. 2003, eugenol determination work and the Rural Industries Research and Development Corporation for funding 31, 260–262. [8] Waddell, W. (2002).Thresholds of Carcinogenicity of Flavors. Toxicol. Sci. 2002, 68, 275–279 .[9] Waddell, W. (2003). Thresh- olds of Carcinogenicity in the ED01 study. Toxicol. Sci. 2003, 72, 158–163. [10] Battershill, JM, Fielder, RJ. (1998) Mouse-specifi c carcinogens: participation in this symposium and Warwick Press, Industry & Investment NSW for preparing this poster. an assessment of hazard and signifi cance for validation of short-term carcinogenicity bioassays in transgenic mice. Human and Environmental Toxicology 17: 193-205. [11] Toth, B. 2001 Species susceptibilities to chemical carcinogens: a critical appraisal of the roles of genetic and viral a agents. In Vivo 15:467-478. [12] Tisserand, R. (2007). Challenges facing essential oil therapy: Proof of Safety. Presented to the Alliance of Inter- Phytoquest, 4 Sunset Place, Alstonville, NSW [email protected] national Aromatherapists Conference, Denver, Colorado, Oct. 2007. [13] Manosroi J, Dhumtanom P, Manosroi A 2005 Anti-proliferative activity b of essential oil extracted from Thai medicinal plants on KB and P388 cell lines. Cancer Letters 235:114-120 [14] Aruna K, Sivaramakrishnan VM Industry & Investment NSW, 1243 Bruxner Highway, Wollongbar, NSW [email protected] Anticarcinogenic effects of the essential oils from cumin, poppy and basil. Phytotherapy Research 10:577-580 [15] Southwell, I., in: Southwell, c I.A.; Lowe., R.F. (Eds) Tea Tree, the Genus Melaleuca, Harwood, Amsterdam, 1999, p 37. [16] Scientifi c Committee on Consumer Products, Central Science Laboratory, University of Tasmania, Private Bag 74, Hobart, Tasmania [email protected] Opinion on tea tree oil. Adopted 16.12.2008, p 34. [17] Brophy, J.J. and Doran, J.C. Essential Oils of Tropical Asteromyrtus, Callistemon and Melaleuca Species. ACIAR Monograph No. 40. 144pp (1996) W.
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