The Cropwatch Series

Cropwatch 10

   

 

 

Tagetes Extracts & Oils – Cropwatch Objection to SCCP Opinion

(SCCP/0869/05; June 2005).

 

 

Copyright Ó Cropwatch Aug 2005

 

 

 

 Preamble.

Once again, we see a negative Opinion against yet another natural aromatic material from the SCCP – this time against tagete extracts & oils from three named Tagetes spp. The perfumery & essential oil trades cannot afford to loose the freedom to use of any more of these vital natural aromatic ingredients at the rate at which the SCCP is discriminating against them - often on dubious safety grounds. Many of these materials have been employed in perfume formulae for centuries, and the social cost of destroying the craft-base of an industry with hundreds of years of history is at stake here; an industry which does nothing more harmless than give pleasure and benefit to millions.

Opinion on Tagetes erecta, T. minuta and T. patula Extracts and Oils (Phototoxicity Only)” can be viewed at http://europa.eu.int/comm/health/ph_risk/committees/04_sccp/docs/sccp_o_025d.pdf

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 The SCCP Opinion.

The Opinion concludes that as “no safe limit of use in cosmetic products has been demonstrated, it is recommended that Tagetes erecta, Tagetes minuta and Tagetes patula extracts and oils should not form part of cosmetic products.” This seems to be at variance with IFRA’s previous Code Of Practice April 17th 2001, whose voluntary code for members recommended a concentration limit of 0.01% in fragrances applied to, but not washed off the skin, and subsequently exposed to sunshine. Even more pointedly, the IFRA recommendation above was based on exactly the same evidence from the 16 RIFM studies cited & described in the SCCP report, and the article by Letizia & Api (2000). Other authors concerned with safety advice had previously noted that the earlier RIFM studies on tagete oil photo-toxicity were unpublished (Tisserand & Balacs 1995).

 

* defined as “tinctures, concretes, resinoids, pomades, absolutes, rectified extracts etc.”

** “obtained either by dry-distillation or by steam-distillation, flash pasteurization (- we don’t think so here at Cropwatch! – perhaps they mean molecular distillation?) etc”.

 

Briefest Summary of the Uses of Tagete Commodities.

The Tagetes genus (Fam. Compositae) contains some fifty strongly scented herbs, four of which are well-known garden ornamentals (Schultes & Raffauf 1990). Tagete infusions, tinctures and juice from the leaves of Tagetes spp. have been globally used as traditional herbal medicines for many years, tagete oil itself being used for it’s anti-microbial, biocidal and other properties (Leung & Foster 1996, Vasudevan et al. 1997). Biocidal uses include tropical uses as a blowfly dressing for livestock (Jacobsen 1983) and as a mosquito larvicide (Arnason et al. 1981). Tagete oil is extensively used as a flavour component of foodstuffs, at a usage level in condiments and relishes not exceeding 0.003% (Leung & Foster 1996).

 

Tagete oil has unique place in perfumery being used in men's perfumes, and for general use to support floral themes, where it bends well with many absolutes. More importantly, tagete oil, with its radiant power and diffusiveness, and the ability to impart lift to perfumery creations, is used in small amounts in many perfumery situations to impart green and fruity top notes (e.g. for white floral fragrances, etc.). Often the usage level here is well below 0.1% in perfume concentrate (= below 0.02% in final product) (Burfield 2005).

 

Tagete Oil Production and Chemistry of the Different Oils.

Tagete oil is produced in India, Egypt, Madagascar, Mexican, South America (Brazil) & South Africa & some other parts of Africa (e.g. Botswana), and Lawrence (1999) estimates the annual world production of tagetes oil at 12 tons/annum. There seems to be some difference of account with respect to the part(s) of the plant used for essential oil production. According to some authorities Tagete oils are usually hydrodistilled or steam distilled from the terminal leaves, stems and flowering parts / whole flowering plant of Tagetes minuta (e.g. Burfield 2001; Hélthelyi et al. 1986; Lawrence et al. 1986; Bauer & Garbe 1997), which would make the term ‘flower oils’ as described in the SCCP document incorrect. However Shiva et al. (2002) describe the picking of fresh Tagetes erecta L. flowers in India, and maintains that flowers are mainly used to prepare the oil. According to the authors, flowers are steam distilled 3-4 hrs, oil being is produced on a 40-50Kg scale per annum alone in the Kannauj district of Uttah Pradesh. The authors further quote the following yields of essential oil from different plant parts of T. erecta:

 

Flowers:  0.017-0.018%

Leaves :  0.05-0.07%

Stems  :  0.009%

 

Lawrence (1985) has reviewed the essential oils of the Tagetes genus, describing some forty Tagetes oils, and in a further article (Lawrence et al. 1985b) describes the composition of a steam distilled N. American T. minuta oil from the whole plant in bloom.

 

Since photo-toxicity may be connected with the presence of sulphur compounds in Tagetes oil (especially a-terthienyl), it might be interesting to note that some workers report on sulphur compounds that are mainly found in the roots of the plant (Vaudevan et al. 1998, Gil et al. 2002 ). However Weaver et al. (1994) noted the presence of 2.30% 5-methyl-2’,2’,5’,2’’-tertthiophene and 0.40% 2.2’,5’,2’’-tertthiophene (= a-terthienyl) in the leaf oil distilled from T. minuta. Bicchi et al. (1992) had earlier discussed the presence of further acetylenic thiophenes compounds in the oil of T. patula cv. Nana, and it is probable that these acetylenic thiophenes degrade to thiophenes within the plant. Biosynthesis studies of 5-(3-buten-1-ynyl)-2,2′-bithiophene in T. patula root cultures have been carried out by Margl et al. (2001). Perhaps most importantly, Roberts & Schuler (1997) have indicated that thiophene production in T. patula may be controlled by the available sulphate level.

 

           

 

 

Cutaneous application of a low concentration of a-terthienyl (0.1%) in a non-sensitising vehicle has been investigated by Rampone (1986) who showed photo-toxicity was induced when the skin was exposed to an ultra-violet ‘A’ source. A mechanism for a-terthienyl photosensitisation in aqueous media involving the superoxide ion has been put forward (Kagan et al. 1989).

 

Tagete oils polymerize readily in the presence of air, changing from pale yellow mobile liquids to deep red viscous semi-solids. Hélthelyi et al. (1985) noted the remarks of other authors, that polymerization was especially associated with the ability of tagetone, dihydrotagetone and (Z)- and (E)-ocimenone to form polymers.

 

The case against the SCCP Opinion on Tagete Extracts & Oils.

1. It is possibly quite true that some or all tagete qualities, from some or all geographic origins, and from some or all Tagetes spp., are indeed photo-toxic. Its just that the SCCP Opinion hasn’t provided convincing evidence that this is the case for the three Tagetes oils & extracts cited, and needs to explain why it is at variance with the previous IFRA recommendation, which essentially maintained that Tagete oil at levels of 0.01% were safe, based on a NOEL level of 0.05% (see Appendix 1). There is a difference between a recommendation for voluntary code of practice restricting tagete use, based on available evidence, which seemed to work satisfactorily, and an outright ban. A ban would seem the inevitable outcome from the SCCP conclusion that no concentration is safe (which essentially remains unproven across the broad spectrum of commercial Tagete products).

 

The RIFM Expert Panel Opinion on Essential Oils (Rexpan 2002) had suggested previously:

 

“For dermal effects, in order to treat the essential oils as distinct materials, it is necessary to examine a complete description of the essential oil including full chemical characteristics with quantitative data on the components and data on the possible variability in concentrations of the components. The essential oils need to be reviewed on a case by-case basis. There will be cases in which the Panel feels that the differences in effect of the pure chemical components and the oils containing that component must be verified by additional testing of the oils.”

 

So it is curious considering the above, that:

 

(a) That the compositional data for the samples used in the RIFM tests - if it exists - is not provided in the SCCP Opinion. Instead we are informed that T. minuta, T. patula and T. erecta ‘flower oils’ contain mainly “- limonene, ocimene, 2,6-dimethyl-7-octen-4-one (: possibly 2,6-dimethyl 5,7-octadien-4-one or tagetone? – Cropwatch)” a description which appears to be at variance with the published literature for distilled oils from both over-ground and flower plant parts (see Appendix II). No compositional data is provided for any of the three Tagetes extracts.

 

(b) Héthelyi et al. (1985) previously suggested oils of T. patula L., T. erecta , T. tenuifolia Cav. (syn. T. signata Bartl.; not considered in the SCCP Opinion), T. lucida (not considered in the SCCP Opinion) and T. minuta varied considerably in composition. They further considered that although T. minuta is considered synonymous with T. glandulifera by many authorities, the differing composition of the oils confirms the opinion of other authors that the taxonomic situation is more complicated than previously thought. Lawrence (1999) suggested that the variability in composition of commercial tagete oils is huge and provides concentration figures for major components that vary widely (see Appendix II).

 

2. A thorough literature search on adverse photo-toxic reactions to tagete oil is being conducted by Cropwatch, and an end-user survey of products containing tagete oil is planned, so that real data on any adverse photo-toxic reactions can be provided, where only speculation currently exists.

 

***

 

Conclusions.

1. Cropwatch considers that the SCCP Opinion SCCP/0869/05 is technically sloppy, incomplete, and presents no new data (although it does make public, previous unpublished RIFM studies). The Opinion fails either to clearly establish the individual qualities, species and geographic origins of Tagetes commodities that may be causing photo-toxicity problems, or fails to establish if they all have inherent problems. Further the Opinion fails to prove that the in-house work by RIFM on photo-toxicity of Tagetes qualities actually translates into problems at the user end, where adverse reactions from products containing Tagetes products can be proven to have occurred. An initial literature search conducted by Cropwatch (August 2005) does not indicate any end-user problems in fragranced retail products containing tagete qualities, possibly because the concentration of tagete oil / absolute etc. in these cosmetic products are typically used in at concentrations below the NOEL, as indicated by Letizia & Api (2000). Cropwatch recommends therefore, that we stick with the existing IFRA recommendations for Tagetes extracts & oil restrictions (see Appendix I).

 

2. Cropwatch asks that the EU Commission officials return the Opinion to the SCCP for re-working, so that the above points can be researched and eventually answered. In particular the point that Tagete oils produced from overground plants in bloom may not be specifically covered by the Opinion, and may provide a technical loophole for non-enforcement of any subsequent EU legislation.

 

3. Further Cropwatch asks the EU Commission if it intends (by consecutive adoption of SCCP Opinions against natural aromatic products) to deny the European public their rights to purchase perfumes composed or entirely composed of natural ingredients? – because this is the on-the-ground reality of what is happening. Many prospective fragrance buyers are of the persuasion that they do not necessarily wish to buy fragrances constructed of synthetic aromatic chemicals, but it seems increasing apparent that the SCCP are carrying out a vendetta against natural perfumes by biasing the EU legislature against natural ingredients.

 

****

 

Appendix I: IFRA Code of Practice April 17th 2001: For applications on areas of skin exposed to sunshine, excluding bath preparations, soaps and other products which are washed off the skin, oils and absolute obtained from Tagetes minuta L., syn. Tagetes glandulifera Schrank and Tagetes patula L. should not be used such that the level in the consumer product exceeds 0.01% (see remark on phototoxic ingredients in the introduction to the IFRA Code of Practice).

 

This recommendation is based on test results of RIFM on the phototoxicity of oils and absolutes obtained from Tagetes minuta and Tagetes patula from Egypt and South Africa indicating similar phototoxic potential. A no-effect level of 0.05% for phototoxicity was determined on humans using Egyptian Tagetes minuta absolute (C.S. Letizia, A.M. Api (2000), The Toxicologist, 54 (1), 397).

 

Appendix II: Major Components of Tagetes Oils.

The major components of commercial Tagetes oils from T. minuta L. are in fact  b-ocimene, dihydrotagetone, tagetone, (Z)-ocimenone, (E)-ocimenone, piperitone and b-caryophyllene, and sometimes limonene (Chalcutt et al. 1994, Lawrence et al. 1985b & Burfield 2005). Chalcutt et al. (1994) presented results showing how flower oils and leaf oils differed in composition one against the other, and across varying ontological stages. In contrast a wild gathered Indian T. patula L. oil was found to have piperitenone (22.93%) and piperitone (24.74%) as major components (Romagnoli et al. 2005). Mookherjee & Patel (1983) suggested that increasing amounts of isopiperitenone are formed from the isomerisation of ocimenone during aging of the oil.

 

Garg & Mehta (1998) describe an Indian oil distilled from the flowers of Tagetes minuta (as opposed to the usual commercial oil from over-ground parts) which contained three unreported monocyclic ketones 3,7-dimethyloct-1-en-6-one, 3,7-dimethyl-5-hydroxyoct-1-en-6-one and 3,7-dimethyloct-1,7-dien-6-one, as well as the major compounds (Z)-β-ocimene (38.77%), dihydrotagetone (9.07%), (Z)-tagetone (7%), (Z)-ocimenone and (E)-ocimenone (20%).

 

Finally Lawrence (1999) presented the variations of major components of commercial tagete oil as:

 

Component

Variation

Limonene:                          

0.1 to 8.3%

(Z)-beta-ocimene:              

0.1 to 51.5%

Dihydrotagetone                 

0.1 to 99.0%

(E)-tagetone                        

0.1 to16.6%

(Z)-tagetone                       

0.1 to 19.5%

(Z)-tagetenone                   

0.1 to 33.4%

(E)-tagetenone                      

0.1 to 67.8%

Table 1: Variation in %-age of Major Components

 of T. minuta Oil (Lawrence 1999)

 

These results paint a very complex picture regarding the composition of tagete commodities.

 

 

 

 

 

 

 

 

 

 

 

 

 

Tagetes erecta, T. patula and T. minuta

 

References:

Arnason T., Swain T., Wat C.-K., Graham E.A., Partington S., & Towers G.H.N. (1981) Biochem. Syst. Ecol. 9, 63.

 

Bauer K. & Garbe D. (1997) Common Fragrance & Flavour Materials Wiley-VCH 3rd edn. 1997.

 

Bicchi C., Frattini C., Pellegrino G., Rubiolo P., Raverdino V. & Tsoupras G. (1992) “Determination of sulphurated compounds in Tagetes patula cv. nana essential oil by gas chromatography with mass spectrometric, Fourier transform infrared and atomic emission spectrometric detection” J. Chromatography A 606(1-2), 305-313.

 

Burfield T. (2005) from the forthcoming Natural Aromatic Materials – Odours & Origins (2nd edn. in prepn.) – 1st edn. pub. AIA, Tampa 2001 (= Burfield 2001).

 

Chalcutt J.C., Garry R.-P. Mahuyiama A. (1995) “Essential oil of Tagetes minuta from Rwanda & France: Chemical Composition According to Harvesting Location, Growth Stage and Part of Plant Extracted.” J. Essent. Oil Res. 7, 375-386.

Garg S.N. & Mehta V.K. (1998). “Acyclic monoterpenes from the essential oil of Tagetes minuta flowers.” Phytochem 48(2), 395-396.

Gil A., Ghersa G.M. & Perelman S. (2002) “Root thiophenes in Tagetes minuta L. accessions from Argentina: genetic and environmental contribution to changes in concentration and composition.” Biochemical Systematics & Ecology 30(1), 1-13.

Hélthelyi É., Dános B., Tétényi P. & Koczka I. (1985) “GC/MC Analysis of Essential Oils of Some Tagetes Species” in Progress In Essential Oil Research Walter de Gruyter (1986).

Kagan J., Bazin M. & Santus R. (1989) “Photosensitization with α-terthienyl: The formation of superoxide ion in aqueous media” J. Photochem & Photobiol B: Photobiol 3(2), 165-174.

Jacobsen M. (1983) – In Plants- The Potential for Extracting Protein, Medicines, and Other Useful Chemicals: Workshop Proceedings pp138-146. Congressional Office of Technology Assessment, Washington DC.

Lawrence B.D. (1985) “Essential Oils of the Tagetes Genus”. Perfumer & Flavorist Oct/Nov 10, 73-82.

Lawrence B.D., Powell R.H, Smith T.W. & Kramer S. (1985b) “Chemical Composition of Tagetes Oil” Perfumer & Flavorist (Dec 85/Jan 86) 10(6), 56-58.

Lawrence B.D. (1999) “Chemical Components of Less Commonly Used Oils in Aromatherapy” - paper presented at 2nd Symposium International d’Aromatherapie Scientifique «Finalité Thérapeutiques des Végétaux Aromatiques» Grasse 19-21 Mars 1999.

Letizia C.S. & Api A.M.  (2000), The Toxicologist, 54 (1), 397

Leung AY. & Foster S. (1996) Encyclopaedia of Common Natural Ingredients Used in Food, Drugs, and Cosmetics 2nd edn ed. A. Y. Leung & Steven Foster publ. John Wiley & Sons Inc.

Margl L., Eisenreich W., Adam P., Bacher A. & ZenkM.H. (2001) “Biosynthesis of thiophenes in Tagetes patulaPhytochem 58(6), 875-881.

Mookerjee B. & Patel R. (1983: unpublished results) through Verghese J. On Essential Oils pub. Synthite Ltd. Kolenchery, India 1986  p303.

Rampone W.M., McCullouch J.L., Weinstein G.D., Towers G.H., Berns M.W. & Abeysekera B. (1986) “Characterization of cutaneous phototoxicity induced by topical alpha-terthienyl and ultraviolet A radiation.” J Invest Dermatol. 87(3), 354-7.

Rexpan (2002) “RIFM Expert Panel Opinion on Essential Oils” Rexpan Final Oct 4th 2002.

Roberts S.C. & Schuler M.L. “Large Scale Plant Culture” Current Opinion in Biotechnology, Apr 1997.

Romagnoli C., Bruni R., Andreotti E., Rai M.K., Vincentini C.B. & Mares D. (2005) “Chemical characterization and antifungal activity of essential oil of capitula from wild Indian Tagetes patula L.” Protoplasma 225(1-2) 57-65.

Schultes R.E. & Raffauf R.F.  (1990) The Healing Forest Dioscorides Press, Portland, Oregon 1990.

Tisserand & Balacs (1995) Essential Oil Safety: a Guide for Health Care Professionals Churchill Livingstone 1995.

Vasudevan P., Kashyap S. & Sharma S. “Tagetes, a multipurpose plant” Bioresource Tech. 62(1-2), 29-35.

Weaver D.K. et al. (1994) “Insecticidal Activity of Floral, Foliar and Root Extracts of Tagetes minuta (Asterales: Asteracea) against adult Mexican Bean weevils (Colcoptea: B).” J. Econ. Entomol. 87, 1718-1

 

The information supplied in this bulletin is believed to be accurate, but views, comments, criticisms, corrections or additional material can be forwarded to info@cropwatch.org for consideration in future communiqués in the Cropwatch series.