Chapter 5.68 PEPPERMINT OIL the Scandinavian countries, Canada and the USA. The plant is cultivated in large parts of Europe, USA, Canada, DEFINITION Chile, Argentina, Australia, some African countries, Brazil Peppermint oil (essential oil of peppermint) is the essen- and Japan (GRIN Taxonomy for Plants; Mansfeld’s World tial oil obtained from the flowering aerial parts and Database of Agriculture and Horticultural Crops, http:// leaves of the peppermint, Mentha x piperita L. mansfeld.ipk-gatersleben.de). Mentha piperita is widely used as medicinal plant. The herb has a strong, pepper-like, pungent odor, hence INCI NOMENCLATURE the specific name ‘piperita’ (16). Peppermint is com- Description/definition: Mentha piperita oil is the vola- monly used to soothe or treat symptoms of the gastroin- tile oil obtained from the whole plant of the peppermint, testinal tract such as nausea, vomiting, abdominal pain, Mentha piperita (L.), Labiatae indigestion, irritable bowel, and bloating (1). The plant INCI name EU: Mentha piperita oil is described to have a wide range of properties includ- INCI name USA: Mentha piperita (peppermint) oil ing anti-oxidant, antitumor, anti-allergic, adstringent, CAS registry number(s): 8006-90-4; 84082-70-2 antiseptic, antipruritic, anti-catarrhal, carminative, anti- EINECS number(s): 282-015-4 inflammatory, anti-spasmodic, diaphoretic, anti-emetic, nervine, antimicrobial, analgesic, stimulant, stomachic ISO (INTERNATIONAL ORGANIZATION and rubefacient (1,2,16). Peppermint has a high FOR STANDARDIZATION) STANDARD content, and is often used as a flavoring agent in tea, ice ISO number: 856 cream, confectionery, chewing gum and toothpaste (1). ISO name: Essential oil of peppermint The essential oil of peppermint, obtained by steam- Botanical origin: Mentha x piperita L. distillation of the leaves, has many pharmaceutical appli- Parts of plant used: Aerial parts, leaf cations (2,24,49). It has vasoconstrictive and cooling ISO values: ISO values (minimum and maximum concen- properties and is one of the main oils used as an exter- trations) are shown in Table 5.68.1. nal application for relieving muscle spasms, pain, neural- gia, headache and tooth-ache (15,49). Furthermore, it is Other Mentha species from which mint oils are obtained often used orally for relieving stomach upset, nausea and and which are mentioned in CosIng include Mentha other intestinal disorders (2,15). Sometimes peppermint spicata L. (spearmint oil, Chapter 5.79), Mentha arven- oil may be used in steam inhalation or by other routes sis (corn mint), Mentha aquatica (water mint), Mentha to relieve the symptoms of a cold (2,24). The European viridis (synonym of Mentha spicata), Mentha pulegium Medicines Agency recently reviewed the pharmacologi- (pennyroyal) and Mentha citrata (bergamot mint). cal and clinical literature of peppermint oil and consid- ered two indications as proven and well established: THE PLANT, THE OIL, AND THEIR USES minor spasms of the gastrointestinal tract, flatulence Mentha x piperita L. is an herbaceous rhizomatous peren- and abdominal pain, especially in patients with irritable nial plant growing to 30-90 cm tall. It is a sterile hybrid bowel syndrome (oral use) and mild tension type head- cross between Mentha aquatica and Mentha spicata ache (cutaneous use) (23). Peppermint oil is also widely (1,15,24). The peppermint is naturalized in the Azores, employed for flavoring chewing gum, cough drops, Siberia, Australia, New Zealand, all across Europe except sweets, alcoholic drinks, toothpaste, mouth freshener and is also used for perfumes, other cosmetic products and in the tobacco industry (5,15,16,49). It is also a pop-

a ular oil in aromatherapy (2,81). Table 5.68.1 ISO values (%) for peppermint oil Peppermint has been thoroughly reviewed in refer- ences 18 and 19. The biological properties of menthol, Compound CAS Minimum Maximum the main component of peppermint oil, are discussed in Menthol 89-78-1 32.0 49.0 ref. 33. Menthone (p-) 89-80-5 13.0 28.0 1,8-Cineole 470-82-6 3.0 8.0 Isomenthone 491-07-6 2.0 8.0 CHEMICAL COMPOSITION Menthyl acetate 16409-45-3 2.0 8.0 Peppermint oil is a colorless to pale greenish-yellow, Menthofuran 494-90-6 1.0 8.0 clear mobile liquid which has a fresh, minty, cooling, Neomenthol 3623-51-6 2.0 6.0 β-Caryophyllene 87-44-5 1.0 3.5 green and sweetish odor, with variations depending on 138-86-3 1.0 3.0 its origin. The yield of essential oil from the flowering 89-82-7 0.5 3.0 aerial tops and leaves of Mentha x piperita L. gener- trans- 17699-16-0 0.5 2.3 ally varies from 0.3 to 0.9 per cent. The main producing hydrate countries of this oil are USA, India, Russia, China, France, 3-Octanol 589-98-0 0.1 0.5 Italy, Bulgaria, Japan, Spain, Morocco, England, Poland, Canada, Hungary and Australia. a ISO 856 Essential oil of peppermint ©ISO 2006; Geneva, Literature data (up to September 21, 2014) on the Switzerland, www.iso.org chemical composition of peppermint oils and unpublished

653

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Table 5.68.2 Constituents identified in peppermint oils

Constituent CAS Percentage and range A B (3) C (16) D (49) E Acetaldehyde 75-07-0 +b Acetic acid 64-19-7 +b Acetophenone 98-86-2 +b p-Acetylanisole 100-06-1 0.2y4 Amorphene 0.5l Amyl alcohol 71-41-0 +b Amyl isovalerate 25415-62-7 0.1-0.4 0.2w4 (E)-Anethole 4180-23-8 0-0.2 0.1h p-Anisaldehyde 123-11-5 +b Aromadendrene 489-39-4 0.1-0.2 0.2k; 0.7l; 1.8w; 10.2o allo-Aromadendrene 25246-27-9 +b,p Benzaldehyde 100-52-7 +b Benzyl alcohol 100-51-6 +b α-Bergamotene 17699-05-7 trw4 Bicycloelemene 32531-56-9 0.6w7 Bicyclogermacrene 24703-35-3 0-0.7 0-0.1 0.08p; 0.1w1,w3; 0.2c,m,y3; 1.3r epi-Bicyclosesqui- 54274-73-6 1.7w4 phellandrene β-Bisabolene 495-61-4 tr-0.7 Borneol 507-70-0 0.01y9; 0.05w2 Bornyl acetate 76-49-3 trw5; 0.02j; 1.1x5 endo-1-Bourbonalol +b α-Bourbonene 5208-58-2 0.1-0.4 0.5e 1,5-di-epi-α-Bourbonene 0.2c β-Bourbonene 5208-59-3 0.02-0.5 2.5 0.4r; 0.5z6; 0.6f,k; 0.7w7; 1.2y7; 1.8l; 2.6o β-Bourbonene isomer +b 2-Bromocyclohexanol 2425-33-4 0.08d Butanal 123-72-8 +b 2-Butanol 78-92-2 +b Butyl isovalerate 109-19-3 +b Butyl 2-methylbutyrate 15706-73-7 0-0.1 α-Cadinene 24406-05-1 0-tr 0.1z6; 0.3l γ-Cadinene 39029-41-9 tr-0.2 +b; trw4; 0.8z6; 3.7w5 δ-Cadinene 483-76-1 0.01-0.2 0.1 0-0.1 trw5; 0.1p; 0.2d,k; 0.5o,y4; 0.8r; 1.2l α-Cadinol 481-34-5 tr-0.1 tr-0.1 0.1f,w3; 0.2p; 0.3z6 epi-α-Cadinol 5937-11-1 0-0.2 0.2p; 0.5o,w5 δ-Cadinol 19435-97-3 tr-0.1 α-Calacorene 21391-99-1 0.08l trans-Calamenene 73209-42-4 0.2z7 Camphene 79-92-5 tr-0.6 0-tr 0-tr trh,k; 0.02w1; 0.3e; 1.1y9; 1.2y7 Camphor 76-22-2 0-tr 0-tr 0.4w2 4-Carene 29050-33-7 0.05l δ3-Carene 13466-78-9 0-0.06 0-0.3 trw4; 0.4e,y6 Carvacrol 499-75-2 0.1-0.2 Carveol 99-48-9 0.2e (E)-Carveol 1197-07-5 tr-0.1 tr-0.2 14.5y7 (Z)-Carveol 1197-06-4 0-tr tr-0.1 +b; 0.2l Carvone 99-49-0 0.03-0.9 0-0.2 0.5 0.8w3; 0.9l; 1.7t; 3.1z6; 5.0y4; 23.4v4 D-Carvone 2244-16-8 0.1c Carvone oxide 33204-74-9 0-0.2 Carvotanacetone 499-71-8 2.3z7 cis-Carvyl acetate 1205-42-1 0-0.1 0-0.1 (E)-Carvyl formate 29239-07-4 +b (Z)-Carvyl formate +b β-Caryophyllene 87-44-5 0.1-5.2 1.2-2.4 4.9 0.1-1.3 4.2x3; 4.3z6; 4.9v1; 6.6w7; 7.6y7; 19.2x Caryophyllene oxide 1139-30-6 0-0.2 0.1-0.2 0.3 tr-0.3 0.3d,w3; 0.5z6; 0.8f; 1.0l; 1.2x1; 1.7x5 α-Cedrol 77-53-2 0.2l Chromene 254-04-6 0.6o 1,8-Cineole 470-82-6 0.3-9.9 0-4.8 8.9 0.5-6.5 0-8.9v; 1.0-13.5q; 6.0n; 6.2x6; 6.4x1; 6.6c; 7.0u; 7.5s; 8.8z3; 9.6y5; 11.6m; 13.9v1

K23588_Book.indb 654 4/15/16 9:39 AM Peppermint Oil 655

Table 5.68.2 Constituents identified in peppermint oils (continued)

Constituent CAS Percentage and range A B (3) C (16) D (49) E Citronellol 106-22-9 +b Citronellyl acetate 150-84-5 tr-1.7 +b α-Copaene 3856-25-5 0-0.1 +b; trw4; 0.1z6; 0.4l β-Copaene 18252-44-3 0.1f α-Cubebene 17699-14-8 tr 0-tr +b; trw5 β-Cubebene 13744-15-5 +b; trw4; 0.5w7; 0.6l; 1.1o Cubenol 21284-22-0 0.2e Cuparene 16982-00-6 0.2l m-Cymene 535-77-3 0.6y6 o-Cymene 527-84-4 0.6e p-Cymene 99-87-6 0-07-0.6 0.1 0.3 0.08-1.0v; 0.5l; 0.6k; 0.7d; 0.8v1; 0.9f p-Cymen-8-ol 1197-01-9 0.1e (E)-β-Damascenone 23726-93-4 +b 3,4-Didehydro-7,8- +b dihydro-γ-ionone 2,5-Diethyltetrahy- 41239-48-9 0-0.03 +b; trw4 drofuran Dihydrocarvone 5948-04-9 0.2z7 cis-Dihydrocarvone 3792-53-8 0.5-0.8 Dihydrocarvyl acetate 57287-13-5 0-0.1 Dihydroedulan 0.06p; 0.1c; 0.4w3 Dihydroedulan I 74006-61-4 0-0.1 +y1 trans-2,6-Dimethyl- 0.1 3,5,7-octatrien-2-ol Dimethyl sulfide 75-18-3 +b α-Elemene 5951-67-7 1.1w β-Elemene 33880-83-0 0.02-0.3 0.1-0.2 0.1-0.2 +p; trw5; 0.1h,y8; 0.2w6; 0.3w; 0.5z6; 1.0l γ-Elemene 29873-99-2 0.3-0.6 0.3w5 Elemol 639-99-6 0.06l Epiglobulol 88728-58-9 0.6-1.1 0.3d; 0.8e 1,5-Epoxysalvial- 88395-47-5 +b 4(14)-ene Ethanol 64-17-5 +b 2-Ethylfuran 3208-16-0 +b; trw4 Ethyl isovalerate 108-64-5 +b Ethyl-2-methyl butyrate 7452-79-1 +b β-Eudesmol 473-15-4 0.3 0.2l γ-Eudesmol (selinenol) 1209-71-8 0-0.1 Eugenol 97-53-0 +b; 0.1w4; 0.4y4 β-Farnesene 502-60-3 0.4w4; 0.9d (E)-β-Farnesene 18794-84-8 0.06-0.6 0.2-0.4 0.5 0.1p; 0.2h,w1; 0.3y3; 0.5y4; 1.2w7 (Z)-β-Farnesene 28973-97-9 0.2c; 0.4w6; 0.7r Furfural(dehyde) 98-01-1 +b Geranial 141-27-5 0-0.1 +b Geraniol 106-24-1 0-0.4 0.05w2; 3.2v5; Geranyl acetate 105-87-3 tr-0.1 0.1y7 Geranyl formate 105-86-2 0.6e Germacrene A 28387-44-2 0.4w6; 0.5r Germacrene B 15423-57-1 0.3z2; 0.4n Germacrene D 23986-74-5 tr-2.7 1.2-3.3 1.7 0-0.6 2.4z2; 2.5v1; 2.6n; 3.0u; 3.1z6; 6.2w7; 9.7o Germacrene D-4-ol 198991-79-6 6.3 Globulol 489-41-8 0-0.1 0.2c; 0.3f; 0.4z5 α-Gurjunene 489-40-7 +p; 0.1y7; 8.9x7 β-Gurjunene 73464-47-8 +b; 0.1w5 γ-Gurjunene 22567-17-5 1.4x7 Heneicosane (n-) 629-94-7 0-0.5 n-Heptadecane 629-78-7 0-0.1 Heptadecen-2-one 0-tr Heptanal 111-71-7 +b 1-Heptanol 111-70-6 0-0.1 0-tr 3-Heptanol 589-82-2 +b; trw4

K23588_Book.indb 655 4/15/16 9:39 AM 656 Essential Oils: Contact Allergy and Chemical Composition

Table 5.68.2 Constituents identified in peppermint oils (continued)

Constituent CAS Percentage and range A B (3) C (16) D (49) E Heptan-3-yl acetate +b Hexadecanal 629-80-1 0-0.1 Hexadecane 544-76-3 +y1 Hexadecanoic acid 57-10-3 0-0.1 cis-9-Hexadecenoic 373-49-9 0-0.1 acid Hexadecen-1-ol 37822-83-6 0-0.4 Hexadecyl acetate 629-70-9 0-0.1 Hexanal 66-25-1 +b Hexanol (1-; n-) 111-27-3 0-0.04 +b; trz5 3-Hexanol 623-37-0 +b (Z)-3-Hexanol 0-0.1 (E)-2-Hexenal 6728-26-3 +b; trw4 (Z)-2-Hexenal 16635-54-4 +b (E)-2-Hexen-1-ol 928-95-0 +b (Z)-3-Hexen-1-ol 928-96-1 tr-0.2 +b; trw4; 0.1z5; 0.2v1; 0.5t (Z)-3-Hexenyl acetate 3681-71-8 +b (Z)-3-Hexenyl 35154-45-1 tr-0.6 +b; 0.06w2; 0.1e iso-valerate (Z)-3-Hexenyl 53398-85-9 0.1w4 methyl-butyrate Hexyl isovalerate 10032-13-0 +b α-Humulene 6753-98-6 tr-0.1 0.1 0.1-1.4 0.08c; 0.1w3; 0.2w2; 0.4n; 0.7l; 1.5x7 Humulene epoxide II 19888-34-7 0-0.1 Isoamyl acetate 123-92-2 +b Isoamyl alcohol 123-51-3 +b Isoamyl isobutyrate 2050-01-3 +b Isoamyl isovalerate 659-70-1 +b; trw4; 0.1w3 Isoamyl 2-methylbu- 27625-35-0 0.1w3 tyrate Isoamyl methyl ketone 110-12-3 0-0.1 Isobornyl acetate 125-12-2 trk Isobutanal 78-84-2 +b Isobutyl alcohol 78-83-1 +b Isobutyl isovalerate 589-59-3 +b Isobutyl-2-methyl- +b butyrate Isocaryophyllene oxide 0.1p Isodihydrocarvyl acetate 0-tr Isoeugenol 97-54-1 0.3x5 Isoisopulegol 18674-65-2 0.8x7 Isomenthol 3623-52-7 0.1-3.0 0.2-0.7 1.0d; 1.7w5; 2.5w; 3.0g; 4.9v1; 6.4e; 6.5x6 Isomenthone 491-07-6 2.2-10.6 2.4-7.0 3.9 4.4-8.5 4.1w5; 4.8i; 5.3k; 5.4w2; 5.5z4; 5.8n; 6.5p; 7.4f; 7.6l; 9.0w3; 11.8y5; 14.8e; 15.5z6 Isomenthyl acetate 20777-45-1 0.01-0.3 0.1-0.2 0.8z2; 2.5w3; 3.1w8; 7.3y5; 10.3y7; 30.5j Isoneomenthol 0.02j Isopiperitenone 529-01-1 +b Isopiperitone 58615-39-7 tr-0.2 Isopropyl 66576-71-4 0.1w4 2-methyl-butyrate Isopulegol 89-79-2 0.09-0.8 0.6 0-5.1 0.1w3; 0.3d; 0.5y6; 0.6l; 1.3y6; 1.5v1; 3.0e Isopulegol acetate 57576-09-7 0-0.1 +b; 0.4l Isopulegone 29606-79-9 trh; 0.2y6; 0.3w4 Isothujone 59573-80-7 +b Isovaleraldehyde 590-86-3 +b Isovaleric acid 503-74-2 0.2d Italicene 94535-52-1 0.1w3 (E)-Jasmone 6261-18-3 +b (Z)-Jasmone 488-10-8 0.1 0-0.1 0.04w2; 1.0l Ledene oxide II 0.2k

K23588_Book.indb 656 4/15/16 9:39 AM Peppermint Oil 657

Table 5.68.2 Constituents identified in peppermint oils (continued)

Constituent CAS Percentage and range A B (3) C (16) D (49) E Limonene 138-86-3 0.3-18.5 2.8-9.8 2.9 0.1-0.7 0-4.5v; 0.2-6.8q; 4.2u; 5.2x5; 5.8y6; 6.0p; 6.2v1; 6.9r; 7.7l; 9.6s; 10.0m; 10.6e; 10.8x Limonene-1,2-epoxide +b isomer Limonene oxide 1195-92-2 0.1e Linalool 78-70-6 0.03-0.7 0.6 tr-1.1 0.4d; 0.5f; 0.7z; 0.9n; 1.5l; 4.8x3; 7.3y5 12.3v3; 51.0v4; 60.7v5 Linalool oxide 1365-19-1 trk; 0.03j cis-Linalool oxide 11063-77-7 0-tr trans-Linalool oxide 11063-78-8 0.02j Linalyl acetate 115-95-7 0.08-0.6 0.03y9; 0.2w5; 20.7v5; 62.7o; 72.0v3 Linalyl butyrate 78-36-4 +y1 Linalyl isobutyrate 78-35-3 0.1j Linalyl propionate 144-39-8 0-0.2 Longifolene (junipene) 475-20-7 0.5l p-Mentha-1(7),8-di- 499-97-8 +b ene Menthalactone 13341-72-5 0-0.2 cis-p-Mentha-2,8- 3886-78-0 0-0.1 +b dienol trans-p-Mentha-2,8- 4017-77-0 +b dienol p-Menthane-3,8-diol 42822-86-6 0.2y7 3-Menthene 500-00-5 +y1; 0.3k p-Menth-1-en-9-ol 18479-68-0 0.2y7 p-Menth-2-en-1-ol 619-62-5 0.1w5; 0.6k; 1.6n,z2 cis-p-Menth-2-en-1-ol 29803-82-5 tr 0.1 +b; 0.05p; 0.1w3 trans-p-Menth-2- 29803-81-4 tr-0.5 tr-0.1 0.04c en-1-ol p-Menth-1-en-9-yl 28839-13-6 +b acetate Menthofuran 494-90-6 0.07-7.0 3.3-4.5 14.6 0-0.8 0.3-13.7q; 4-7.3v; 11.2y3; 11.8x4; 14.9x2; 17.9v1; 19.5u; 21.3z2; 27.2z3; 46.8z4 Menthofurolactone +y Menthofurolactone +b isomer Menthol 89-78-1 23.0-47.9 26.4- 47.8 29.8-37.3 27.1-60.6q; 41.5v2; 51.8w; 51.9n; 52.4w; 54.2y4; 47.7 55.3y3; 56.9t; 59.2x5; 76.7x Mentholactone 68330-67-6 0.2z5 Menthone 89-80-5 10.6-38.5 13.6- 48.6 24.4-33.0 2-31.9v; 2-44.5q; 28.2n; 29.8i; 31.8y5; 32.5o; 31.9 32.8p; 33.874.6s; 55.0t; 74.6s p-Menthone-1,2,3-triol 0.05j Menthyl acetate 16409-45-3 0.5-7.7 0.6-0.9 9.5 1.6-4.3 0.5-10.3v; 0.8-23.6q; 12.4t; 15.1y3; 16.8z3; 17.2x; 17.4r; 29.5o; 32.8v1 cis-Menthyl acetate 0.6w5 trans-Menthyl acetate 13.3w5 Menthyl formate 2230-90-2 +b 2-Methylbutanal 96-17-3 +b; trw4 2-Methyl-3-buten-2-ol 115-18-4 +b 3-Methyl-3-butenol 763-32-6 +b 2-Methylbutyl acetate 624-41-9 +b 2-Methylbutyl 2445-69-4 +b iso-butyrate 2-Methylbutyl 2-me- 2445-78-5 0.06p,w2 thylbutyrate 2-Methylbutyl 3- 2445-77-4 +b,p; 0.08w2 methylbutyrate Methyl chavicol 140-67-0 0-0.1 +b; 0.7y4 Methyl cinnamate 103-26-4 0.3x5 3-Methylcyclohexanol 591-23-1 +b 3-Methylcyclohexanone 591-24-2 +b; trw4

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Table 5.68.2 Constituents identified in peppermint oils (continued)

Constituent CAS Percentage and range A B (3) C (16) D (49) E

(E)-4-Methylcyclohexyl +b acetate (E)-4-Methylcyclohex- +b yl isovalerate Methylcyclopentane 96-37-7 4.9y6 3-Methylcyclopen- 1757-42-2 +b tanone 2-Methylfuran 534-22-5 +b Methyl 1076-56-8 +b Mint furanone 0.06j; 0.3d Mintsulfide 72445-42-2 +b cis-Muurola-3,5-diene 157374-44-2 0-0.1 cis-Muurola-4(14),5- 157477-72-0 0.1 diene trans-Muurola-4(14), 262352-87-4 0.1 5-diene Muurolene 69671-15-4 0.1e α-Muurolene 10208-80-7 0.8l; 0.9z6; 3.7o γ-Muurolene 30021-74-0 0-1.6 tr +b; 0.2w5; 0.3n; 1.0l τ-Muurolene 152287-43-9 1.3o τ-Muurolol (epi-α-) 19912-62-0 +p; 0.1w5 Myrcene 123-35-3 0.05-3.1 0.3-0.4 3.0 0-0.9 1.0c; 1.1y9; 1.3e; 4.1m; 4.4z6; 4.9z3; 15.5v1 Myrtenal 564-94-3 0.3-0.5 Myrtenol 515-00-4 0.1 +b; 0.08p; 0.1w4; 0.2e Myrtenyl acetate 1079-01-2 +b; trw4 Neoisoisopulegol 21290-09-5 tr-0.4 Neoisoisopulegol 256332-34-0 0.1w3 acetate Neoisomenthol 491-02-1 0.08-3.0 0.5g; 0.6f; 1.1x7; 1.5e; 2.9w9; 6.5l Neoisomenthyl acetate 0-0.3 0.2z5; 0.4y2 Neoisopulegol 29141-10-4 0.2-1.0 0.3c Neoisopulegyl acetate 57576-10-0 0.05p Neomenthol 3623-51-6 0.2-7.4 2.0-2.7 4.9 1.9-4.4 5.2z4; 6.0w1; 6.3y4; 6.5x7; 6.9x9; 7.1t Neomenthyl acetate 2230-87-7 0.1-0.2 0.6c; 0.7w4; 0.9f; 1.0y5; 1.1w3; 1.5z6 Nerol 106-25-2 +b Nerolidol 7212-44-4 4.3d (E)-Nerolidol 40716-66-3 tr-0.1 +b (Z)-Nerolidol 3790-78-1 0.06w2 Neryl acetate 141-12-8 0.1e; 0.4e Nonadecane 629-92-5 0-0.1 Nonanal 124-19-6 +b 1-Nonen-3-ol 21964-44-3 +b (E)-Ocimene 27400-72-2 0.2r (Z)-Ocimene 27400-71-1 0.04y9; 0.1r β-Ocimene 13877-91-3 0.3x5 (E)-β-Ocimene 3779-61-1 tr-0.2 0.1-0.2 trh,n; 0.06i,p; 0.1w1; 0.7u; 1.7v1; (Z)-β-Ocimene 3338-55-4 tr-0.3 0.4-0.7 0.5 0-0.1 0.1w3; 0.2i,p; 0.3n; 0.9u; 1.8z6 Octadecanal 638-66-4 0-0.1 Octadecane 593-45-3 0-0.1 trw5 (Z)-1,5-Octadien-3-ol 50306-18-8 +b Octanoic acid 124-07-2 0-0.3 3-Octanol 589-98-0 0.05-2.4 0.2-0.4 0.3 0.2c; 0.3m; 0.4d; 0.8y6; 1.2v1; 3.5e; 10.1v4 n-Octanol (1-) 111-87-5 0.02-0.4 3-Octanone 106-68-3 0.2e Octan-3-yl acetate 103-09-3 +b; trk; 0.04j 1-Octen-3-ol 3391-86-4 0.03-0.4 0-0.1 0.1 +b; 0.04y9; 0.2w4; 0.3w2; 0.7y4; 0.8 v1 trans-2-Octen-1-ol 18409-17-1 0.1 1-Octen-3-one 4312-99-6 +b Octenyl acetate (1-) 37366-04-4 0-0.1 1-Octen-3-yl acetate 2442-10-6 0.05c 7-Octen-1-yl acetate 1.1y4

K23588_Book.indb 658 4/15/16 9:39 AM Peppermint Oil 659

Table 5.68.2 Constituents identified in peppermint oils (continued)

Constituent CAS Percentage and range A B (3) C (16) D (49) E 3-Octyl acetate 4864-61-3 tr-0.1 0.07w2; 0.09p; 0.1w3,w4 Oleic acid 112-80-1 0-0.2 Pentadecanal 2765-11-9 0-0.1 Pentadecanoic acid 1002-84-2 0-0.1 1-Penten-3-ol 616-25-1 +b (E)-2-Penten-1-ol 1576-96-1 +b trans-2-(2-Pentenyl) 70424-14-5 +b furan 2-Pentylfuran 3777-69-3 +b Perillene 539-52-6 0.1e Perillyl alcohol 536-59-4 0-0.2 trw4 α-Phellandrene 99-83-2 0-0.4 +b; trh,k; 0.2z2 β-Phellandrene 555-10-2 0.03c; 0.2n; 0.4k; 0.8d,y6; 2.8e; 5.6w6 Phenylacetaldehyde 122-78-1 +b 2-Phenyl-(E)-2-butenal 4411-89-6 +b 2-Phenylethyl acetate 103-45-7 +b 2-Phenylethyl isova- 140-26-1 +b lerate 2-Phenylethyl 2-me- 24817-51-4 +b thylbutyrate α-Pinene 80-56-8 0.06-9.7 0.7-0.8 0.9 0.3-0.6 0.2-1.1v; 1.7v1; 2.2w8; 2.4t; 3.5l; 4.8e β-Pinene 127-91-3 0.2-6.5 1.1-1.3 1.3 0.5-0.8 0.8-3.7v; 1.9m; 2.0x6; 2.3w8; 2.5x8; 5.7e Pinocarveol 5947-36-4 0.2e trans-Pinocarveol 1674-08-4 +p; 0.2w3 Piperitenone 491-09-8 0-0.4 0-0.1 +b; 0.5l Piperitenone oxide 90582-88-0 0-tr 0.2j; 19.3y7; 55.6m cis-Piperitol 16721-38-3 tr-0.1 +b; 0.5x7 trans-Piperitol 16721-39-4 0-0.1 +b; <0.1w3 Piperitone 89-81-6 0.2-5.4 0.7-0.8 1.8 0.4-0.6 0.5-2.3v; 1.6o; 2.1e; 2.2z4; 2.3z3; 5.9z6 Piperitone oxide 148879-33-8 0-0.1 0.07y9; 0.5y5; 0.7m; 1.9y7 Propyl isovalerate 557-006 +b Pulegol 529-02-2 0.04-1.1 0.1z5; 0.2h Pulegone 89-82-7 0.2-5.4 0.2-2.2 1.2 0.2-7.5 1.2-15.4v; 3.9z2; 4.1d; 4.2n; 4.4w6; 5.0z4; 5.4w7; 6.4l; 9.7t; 13.0z6; 14.4x3; 15.4z3 Pyridine 110-86-1 +b Rosefuran oxide 92356-06-4 0.05w2 Sabinene 3387-41-5 0.1-2.1 0.4-0.7 0.3 0.2-0.9 0.6t; 0.7g; 1.8y7; 1.0m; 1.1y9; 1.2y5; 2.5r cis-Sabinene hydrate 15537-55-0 0.05-1.7 2.6-3.2 2.6 0-tr 0.3h; 0.4-4.8v; 0.5h; 0.8g; 1.4f; 1.5w3 trans-Sabinene hydrate 17699-16-0 0-0.2 0.3-0.7 0.2-1.8 0.4w3; 1.1k; 1.2w4; 1.4w7; 1.5w6; 4.4z6 Sabinol +b; 0.2d cis-Sabinol 3310-02-9 trw4 trans-Sabinol 471-16-9 0.03c Sabinyl acetate 53833-85-5 0-tr +b; 0.2e Santolinatriene 2153-66-4 0.5k Spathulenol 6750-60-3 0-0.1 0.8 0-0.1 0.1p,w3; 0.2e; 0.5f; 0.8l; 1.0o α-Terpinene 99-86-5 0.03-0.5 0.2 0.3 0.2i; 0.3k; 0.4n; 0.5w3; 0.7v1; 1.0d; 19.7y7 β-Terpinene 99-84-3 0.7k γ-Terpinene 99-85-4 0.02-0.7 0.3-0.4 1.7 0-0.2 0-1.1v; 0.3c; 0.4h; 0.5i; 0.6u; 0.9w3; 2.3v1 δ-Terpinene 586-62-9 0.3w1 τ-Terpinene 0.9o Terpinen-4-ol 562-74-3 0.1-2.7 tr-0.1 2.3 0.2-0.6 1.3y8; 1.5f; 1.6w3; 1.7y4; 2.7l; 3.0v1; 3.8x3 α-Terpineol 98-55-5 0.05-0.6 tr-0.1 0.5 0.3-0.5 0.6w2; 0.8e; 0.9x7; 1.3y4; 1.4d; 1.9w; 6.1l β-Terpineol 138-87-4 0.6d γ-Terpineol 586-81-2 2.6l; 2.7y7 δ-Terpineol 7299-42-5 0.1p Terpinolene (α-) 586-62-9 tr-0.2 0.1 tr 0-0.7 0.09c; 0.1r; 0.2d; 0.3e; 0.4j; 1.1o; 3.7y5 β-Terpinolene 1400450-37-4 0.02y9 Tetradecanoic acid 544-63-8 0-0.1 Tetradecanol 27196-00-5 0-tr

K23588_Book.indb 659 4/15/16 9:39 AM 660 Essential Oils: Contact Allergy and Chemical Composition

Table 5.68.2 Constituents identified in peppermint oils (continued)

Constituent CAS Percentage and range A B (3) C (16) D (49) E α-Thujene 2867-05-2 tr-0.2 0-0.1 tr-0.1 trk,w4; 0.04w1; 0.05w; 0.1z5; 0.2z6; 0.4u α- 546-80-5 0-0.1 trh Thujol 35732-37-7 0.4e Thujopsene 470-40-6 0.4l Thymol 89-83-8 0.1-0.3 +b; 0.1w4 Tricyclene 508-32-7 1.2y7 Valeraldehyde 110-62-3 +b Verbenene 4080-46-0 +b Verbenone 80-57-9 0.1e Viridifloral 0.2-0.6 0.05j Viridiflorene (ledene) 21747-46-6 0-0.1 0.7l Viridiflorol 552-02-3 0-0.5 1.9 0.2c,p; 0.3w1,w4; 0.4w6; 1.0z6; 2.0w7 Widdrol 6892-80-4 1.9x1 α-Ylangene 14912-44-8 0.3l

A 157 peppermint essential oil samples from USA, India, Russia, China, France, Italy, Bulgaria, Spain, Morocco and Canada, analyzed between 1998 and 2013; lowest and highest concentrations given (E. Schmidt, unpublished data) B three lab-hydrodistilled oils from leaves of Mentha x piperita cultivated in home gardens (n=2) and commercially (n=1) in Estonia; lowest and highest concentrations given (ref. 3) C eleven lab-hydrodistilled oils from the aerial parts of five Indian cultivars and three wild accessions; highest concentrations given; for most components, the lower concentration was zero (i.e., absent in one or more oils); the following chemicals were found in all oils (with their lowest concentrations in brackets): menthol (30.3%), menthone (4.5%), 1,8-cineole (4.1%), neomenthol (1.5%), isomen- thone (1.0%), menthyl acetate (1.0%), β-caryophyllene (<0.1%), (E)-β-farnesene (<0.1%), menthofuran (<0.1%), pulegone (<0.1%) and α-terpineol (<0.1%) (ref. 16) D five lab-hydrodistilled oils from 5 accessions of M. piperita cultivars from India; lowest and highest concentrations given (ref. 49) E data from other studies (indicated with superscript letters); highest concentrations found in any study reviewed here given; when two or more oils were investigated, only the highest concentrations are mentioned, unless indicated otherwise a incorrect identification; b four lab-hydrodistilled oils from fresh and dried leaves of two harvests from M. piperita cultivated in Oregon, USA; as the amounts were expressed in a manner different from the other data (‘ppt’, not explained), they are indicated here with +b ; only the less common ingredients are indicated in the table (ref. 59); c one lab-hydrodistilled leaf oil from plants harvested in a medicinal garden in Poland (ref. 24); d one commercial oil purchased from an Indian company (ref. 25); e one commercial oil from an Indian com- pany (ref. 26); this analysis contains several mistakes, as indicated in ref. 65; f one commercial oil purchased from a USA company (ref. 32); g one commercial oil from Provence, France (ref. 35); h one commercial oil from a German company (refs. 17,38); i one lab-hydro- distilled oil from M. piperita cultivated in India (ref. 39); j one lab-hydrodistilled oil from the stems and leaves of peppermint cultivated in Egypt (ref. 40); k one commercial oil from Korea (ref. 42); l two lab-hydrodistilled oils from the leaves of plants cultivated in Pakistan and harvested in winter and summer (ref. 43); m one lab-hydrodistilled peppermint oil from Italy with an extremely atypical composition: high piperitenone oxide (55.6%) content and no menthol or menthone (ref. 48); n two lab-hydrodistilled oils from two successive har- vests of the same crop cultivated in Italy (ref. 50); o four lab-hydrodistilled oils from 4 cultivars from a botanical garden in Russia; one had an extremely atypical composition with 62.7% linalyl acetate and only 0.5% menthol (ref. 53); p one lab-hydrodistilled oil from pep- permint cultivated in West Siberia, Russia (ref. 54); q 82 oil samples produced in Tasmania (n=29), King Island (n=14), USA (n=3) and vari- ous other countries; the data from the oils other than from Tasmania and King Island were retrieved from older literature; lowest and highest concentrations given (ref. 55); r one lab-hydrodistilled oil from the aerial parts of M. piperita collected in Serbia (ref. 60); s five lab-hydrodistilled oils from 5 accessions of various origins cultivated in Finland and harvested in various stages; only the main compo- nents were investigated (ref. 21); t seven industrially steam-distilled oils from plants cultivated in France and harvested at 7 times between June and October (ref. 8); u one commercial oil from an Italian company (ref. 20); v twenty lab-hydrodistilled oils from 20 germplasm accessions of M. piperita from a gene bank in India; lowest and highest concentrations given (ref. 14); v1 seventeen lab- hydrodistilled oils from three Mentha piperita cultivars grown in India with age (30-180 days after transplanting) as variables (ref. 63); v2 one lab-hydrodistilled peppermint oil from Argentina (ref. 64); v3 one steam-distilled oil sample from a ‘pleasant smelling’ cultivar of Mentha x piperita grown in Portugal with an extremely atypical composition and dominated by linalyl acetate (72%) and linalool (12.3%) (ref. 78); v4 one lab-hydrodistilled oil sample prepared from Mentha piperita grown at a University Research Center in Brazil with an extremely atypical composition and dominated by linalool (51%), carvone (23.4%) and 3-octanol, without any menthone, isomen- thone, menthyl acetate, neomenthol or menthol detected (ref. 79); v5 one oil sample from Morocco with an extremely atypical composi- tion dominated by linalool (60.7%) and linalyl acetate (20.7%) (ref. 72); w one lab-hydrodistilled oil from fresh and one from dried aerial parts of peppermint from a botanical garden in Belarus (ref. 13); w1 one lab-hydrodistilled oil from the above ground parts of M. piperita cultivated in Iran and harvested at 50% bloom (ref. 12); w2 one steam-distilled oil from peppermint cultivated in Mongolia (ref. 10); w3 two lab-hydrodistilled leaf oils from two Bulgarian peppermint cultivars (ref. 9); w4 one steam-distilled oil from the fresh parts of flowering plants from Cuba (ref. 7);

K23588_Book.indb 660 4/15/16 9:39 AM Peppermint Oil 661

Table 5.68.2 Constituents identified in peppermint oils (continued)

w5 one lab-hydrodistilled oil from the aerial parts of M. piperita growing in South Italy (ref. 6); w6 one lab-hydrodistilled leaf oil from flowering peppermints cultivated in Iran (ref. 5); w7 one lab-hydrodistilled oil from the leaves of M. piperita from Egypt (ref. 4); w8 one commercial peppermint oil purchased in Poland (ref. 56); w9 one lab-hydrodistilled oil from the aerial parts of peppermint from Portugal (ref. 47); x eighteen lab-hydrodistilled oils from peppermint biomass harvested in Slovakia in 3 years and from April to September; only the main components were investigated (ref. 46); x1 one commercial oil from a German company (ref. 45); x2 twelve lab-hydrodistilled oils from dried and fresh M. piperita from the USA with 6 harvest times; only menthol, menthofuran and 1,8-cineole were investigated (ref. 37); x3 four commercial oils from various countries (ref. 36); x4 one laboratory steam-distilled oil from Egypt (ref. 34); x5 one com- mercial oil from Lithuania (ref. 30); x6 one lab-hydrodistilled oil from the aerial parts of peppermint growing wild in Algeria (ref. 29); x7 one lab-hydrodistilled oil from dried leaves of Persian peppermint (ref. 15); x8 three steam-distilled oils from the above ground parts of 3 cultivars of peppermint in the flowering phase grown in Bulgaria; only the main components were investigated (ref. 2); x9 fourteen lab-hydrodistilled oils from peppermint plants cultivated in India under different levels of farmyard manure and spacing and harvested in two years; only the main components were investigated (ref. 1); y menthofurolactone demonstrated in peppermint oil and synthe- sized (ref. 51); y1 two lab-hydrodistilled oils from fresh and dried peppermint leaves cultivated in Italy; as the amounts of the compo- nents cannot be compared to the other data, they are indicated with +y1; only the less common components found are presented (ref. 58); y2 one lab-hydrodistilled oil from stems and leaves of peppermint harvested in a botanical garden in Burkina Fasso (ref. 52); y3 one lab-hydrodistilled oil from the aerial flowering parts of M. piperita growing wild in Iran (ref. 57); y4 one lab-hydrodistilled leaf oil from Poland (ref. 44); y5 one lab-hydrodistilled oil from M. piperita cultivated in the USA (ref. 41); y6 one commercial mint oil from Italy (ref. 31); y7 one lab-hydrodistilled oil from M. piperita growing wild in Iran with a very atypical composition (ref. 28); y8 one commercial oil from Brazil (ref. 27); y9 one lab-hydrodistilled leaf oil from peppermint growing wild in Morocco (ref. 62); z twelve steam-distilled oils from the above ground parts of M. piperita cultivated in Canada under different nitrogen fertilization regimes and harvested in two years (ref. 11); z2 data from before 2000,cited in ref. 65; z3 five lab-hydrodistilled peppermint oils from five cultivars grown in India (refs. 66,67); z4 nine oils from the top, the lower part and the whole plant of three Indian peppermint cultivars (ref. 68); z5 one 50-year-old Bulgarian and one fresh USA commercial oil sample (ref. 69); z6 eight lab-hydrodistilled oils from commercial peppermint samples from 7 European countries purchased in 2000, 2001 and 2002 (ref. 74); z7 data from various studies published before 1997, cited in ref. 77; only chemicals not already present in other studies discussed are included (ref. 77) tr: trace (in columns B,C,D,Ek and Ew4: <0.1; in column El and Ew5: <0.05) + present in the oil investigated, but quantity not stated or presented in a manner which cannot be compared to the other data

analytical data from one of us (E.S.) are shown in Table 1,8-cineole (13.9%), trans-menthyl acetate (13.3%) and 5.68.2 in alphabetical order. In peppermint oils from neomenthol (7.4%). Well-known ingredients of pepper- various origins, over 335 chemicals have been identi- mint oils that were present in high concentrations (>7%) fied. About 59 per cent of these were found in a single in one or two studies were linalyl acetate (three stud- reviewed publication only. The major compounds found ies: 20.7%, 62.7% and 72.0%, see under Chemotypes), in peppermint oils from different sources are shown in linalool (four studies: 7.3%, 12.3%, 51.0% and 60.7%, see Table 5.68.3. They include (highest concentrations in under Chemotypes), isomenthyl acetate (three studies: any study given) menthol (76.7%), menthone (74.6%), 7.3%, 10.3% and 30.5%), carvone (23.4%), α-terpinene menthofuran (46.8%), menthyl acetate (32.8%), limo- (19.7%), β-caryophyllene (19.2%), myrcene (15.5%), nene (18.5%), isomenthone (15.5%), pulegone (15.4%), 3-octanol (10.1%), germacrene D (9.7%) and α-pinene

Table 5.68.3 Major constituents of peppermint oils

Constituent CAS Percentage and range A B (3) C (16) D (49) E Menthol 89-78-1 23.0-47.9 26.4-47.7 47.8 29.8-37.3 54.2y4; 55.3y3; 56.9t; 59.2x5; 76.7x Menthone 89-80-5 10.6-38.5 13.6-31.9 48.6 24.4-33.0 32.5o; 32.8p; 33.874.6s; 55.0t; 74.6s Menthofuran 494-90-6 0.07-7.0 3.3-4.5 14.6 0-0.8 17.9v1; 19.5u; 21.3z2; 27.2z3; 46.8z4 Menthyl acetate 16409-45-3 0.5-7.7 0.6-0.9 9.5 1.6-4.3 16.8z3; 17.2x; 17.4r; 29.5o; 32.8v1 Limonene 138-86-3 0.3-18.5 2.8-9.8 2.9 0.1-0.7 6.2v1; 6.9r; 7.7l; 9.6s; 10.0m; 10.6e; 10.8x Isomenthone 491-07-6 2.2-10.6 2.4-7.0 3.9 4.4-8.5 7.4f; 7.6l; 9.0w3; 11.8y5; 14.8e; 15.5z6 Pulegone 89-82-7 0.2-5.4 0.2-2.2 1.2 0.2-7.5 5.4w7; 6.4l; 9.7t; 13.0z6; 14.4x3; 15.4z3 1,8-Cineole 470-82-6 0.3-9.9 0-4.8 8.9 0.5-6.5 7.0u; 7.5s; 8.8z3; 9.6y5; 11.6m; 13.9v1 trans-Menthyl acetate 13.3w5 Neomenthol 3623-51-6 0.2-7.4 2.0-2.7 4.9 1.9-4.4 5.2z4; 6.0w1; 6.3y4; 6.5x7; 6.9x9; 7.1t

LEGEND: SEE UNDER TABLE 5.68.2

K23588_Book.indb 661 4/15/16 9:39 AM 662 Essential Oils: Contact Allergy and Chemical Composition

(9.7%). Uncommon or rare constituents of peppermint 5.68.2 column A), co-reacting with peppermint oil in 13 oils found in high concentrations (>7%) in single studies patients. Other possible allergens, which have shown include piperitenone oxide (55.6%), (E)-carveol (14.5%), co-reactions with peppermint oil and may be present in aromadendrene (10.2%) and α-gurjunene (8.9%). concentrations >5% are α-pinene, limonene, caryophyl- lene, piperitone and pulegone. Commercial oils The ten chemicals that had the highest maximum con- centrations in 157 commercial peppermint essential oil Testing in groups of patients samples (concentration ranges provided) are the fol- The results of patch tests with peppermint oil in routine lowing: menthol (23.0-47.9%), menthone (10.6-38.5%), testing (consecutive patients suspected of contact der- limonene (0.3-18.5%), isomenthone (2.2-10.6%), 1,8-cin- matitis) and in groups of selected patients are shown in eole (0.3-9.9%), α-pinene (0.06-9.7%), menthyl acetate Table 5.68.4. In routine testing, rates of positive reac- (0.5-7.7%), neomenthol (0.2-7.4%), menthofuran (0.07- tions ranged from 0.3% to 1.8%, whereas between 0.1% 7.0%) and β-pinene (0.2-6.5%) (Erich Schmidt, unpub- and 19% of patients in selected groups had positive lished analytical data). patch tests. The high positivity rate of 19% was seen in a small group of 16 patients known to be allergic to propo- Myroxylon pereirae Chemotypes lis and (126). Virtually all peppermint oils are dominated by menthol and menthone and/or related chemicals, including iso- Case reports menthone. There have, however, been several reports Occupational allergic contact dermatitis where high concentrations of linalool (up to 60%) and/ An aromatherapist had chronic hand dermatitis and or linalyl acetate (up to 72%) were found with men- was patch test positive to 17 of 20 oils used at her work thol/menthone in low concentrations or being absent (tested 1% and 5% in petrolatum), including pepper- (53,72,78,79). Whether this represents a specific chemo- mint oil (88). Another aromatherapist had occupational type or a mistake (botanical misidentification) was made, contact dermatitis with allergies to multiple essential e.g., the plant investigated was not Mentha piperita but oils used at work, including peppermint oil. The patient Mentha citrata (bergamot mint, known to be rich in lin- also reacted to geraniol, α-pinene, caryophyllene, the alool and linalyl acetate [25]) is at the moment unknown, fragrance mix and various other fragrance materials; though their smell should be quite different. We tend to α-pinene and caryophyllene were demonstrated by believe this to be a botanical misidentification. GC-MS in the peppermint oil. Menthol, the main ingredi- Additional analyses of peppermint oil not discussed in ent in peppermint oil, was not tested (89). α-Pinene has Table 5.68.2 can be found in refs. 22 (summary of pub- been found in commercial peppermint oils in a maximum lished compositions of M. piperita grown in Iran), 70,71,73 concentration of 9.7% and caryophyllene in a maximum and 75; these can all be accessed on-line. Older literature is concentration of 5.2% (Table 5.68.2, column A). Another reviewed in refs. 76 and 77. aromatherapist had occupational contact dermatitis from contact allergy to various essential oils, including CONTACT ALLERGY/ALLERGIC ‘mint oil’ (87). Occupational allergic contact dermatitis CONTACT DERMATITIS from peppermint oil occurred in an unknown number of food handlers (127, article not read). General Contact allergy to/allergic contact dermatitis from peppermint oil has been reported in over 45 publica- Cosmetics tions. The oil (2% in petrolatum) has been included in Four patients developed allergic contact dermatitis of the screening series of the North American Contact the lips (allergic contact cheilitis) and the perioral skin Dermatitis Group (NACDG) since 2009. In groups of con- from peppermint oil in a lip balm (93). One positive patch secutive patients suspected of contact dermatitis, prev- test reaction to peppermint oil, which was present in a alence rates of up to 1.8% positive patch test reactions cosmetic that had given a positive patch test or had been have been observed. In most studies, no relevance data positive in a usage test, was seen in a 9-year period in were provided, but in the NACDG investigations, ‘defi- one clinic in Belgium (82). One patient developed aller- nite’ + ‘probable’ relevance was only 36-39%. There have gic cosmetic dermatitis which proved to be caused by been many case reports of allergic reactions to products peppermint oil in a skin care product (130). In a group of with peppermint oil. Often, toothpastes, other oral prod- 39 patients with cosmetic allergy, where the causative ucts and peppermint in foods are causative products, allergen was identified with certainty or high probability, which may induce oral discomfort, cheilitis, stomatitis, peppermint oil was the allergen in one case (124). One oral ulcers, burning mouth syndrome, lip swelling and case of allergic contact dermatitis caused by a depila- lichenoid reactions of the oral mucosa. Some causative tory product from its ingredient peppermint oil has been products were cosmetics; occupational contact derma- reported (125). titis does occur, but its share appears to be smaller than in some other essential oils. The main allergen is prob- Toothpastes and other oral products ably menthol (which is also the main ingredient with Swelling of the tongue, lips and gingival mucosa from concentrations of 23-48% in commercial oils, see Table contact allergy to peppermint oil in an antiseptic spray

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Table 5.68.4 Results of testing groups of patients with peppermint oil

Years and Country Test conc. & vehicle Number of patients Selection of patients (S); Relevance (R); Comments (C) Ref. tested | positive (%) Routine testing 2011-12 USA, Canada 2% pet. 4,230 18 (0.4%) R: definite + probable relevance: 39% 117 2009-10 USA, Canada 2% pet. 4,303 26 (0.6%) R: definite + probable relevance: 36% 99 2000-2007 USA 2% pet. 500 5 (1.0%) R: 100%; C: weak study: a. high rate of macular 83 erythema and weak reactions, b. relevance figures include ‘questionable’ and ‘past’ relevance 2002-2003 Korea 2% pet. 422 5 (1.2%) R: not stated 96 1999-2000 Denmark 2% pet. 318 2 (0.6%) R: not specified; C: this study was part of the 128 international study mentioned below (ref. 118) 1998-2000 six 2% pet. 1,606 9 (0.6%) R: not specified for individual oils/chemicals 118 European countries 1983-1984 Italy 2% pet. 1,200 3 (0.3%) R: not stated 129 <1977 Poland 2% pet. 400 7 (1.8%) R: not stated 104 <1976 Poland 2% pet. 200 1 (0.5%) R: not stated 90 <1970 UK ? 1,147 4 (0.3%) data cited in ref. 95, no details known 96

Testing in groups of selected patients 2011-2012 Italy 1% pet. 122 3 (2.5%) S: patients who reported adverse cutaneous 114 reactions to products (notably cosmetics) containing botanical ingredients in a questionnaire; they were tested with a ‘botanical series’; R: all three reactions were relevant 2000-2008 IVDK 2% pet. 6,546 39 (0.6%) S: patients with dermatitis suspected of causal 115 exposure to fragrances; R: not stated <2005 USA 2% pet. 160 7 (4.4%) S: patients using consumer products containing 110 peppermint oil; R: ‘at least possibly relevant’ 1997-2000 Austria 2% pet. 747 1 (0.1%) S: patients suspected of fragrance allergy; R: not 85 stated 1997-1998 Italy 2% pet. 54 2 (3.7%) S: patients with cheilitis suspected of toothpaste 119 allergy; R: both reactions were relevant 1996-1997 UK 2% pet. 10 1 (10%) S: patients suspected of cosmetic dermatitis and 84 reacting to the fragrance mix; R: not stated 1994-1995 UK 2% pet. 40 2 (5%) S: patients previously reacting to the fragrance mix; 120 R: not stated; C: there was also one positive reaction in a patient negative to the fragrance mix <1986 Poland 2% pet. 86 6 (7.0%) S: patients previously reacting to the fragrance mix; 103 R: not stated <1983 Poland 2% pet. 16 3 (19%) S: patients known to be allergic to propolis and 126 Myroxylon pereirae; R: not stated <1978 Denmark 5% pet. 38 2 (5.3%) S: see text under Case reports 97 <1976 Poland 2% pet. 51 1 (2.0%) S: patients allergic to Myroxylon pereirae resin 90 (balsam of Peru) and/or turpentine and/or wood tar and/or colophony

IVDK Information Network of Departments of Dermatology, Germany, Switzerland, Austria (www.ivdk.org); pet.: petrolatum

used in dentistry, a mouthwash and candies; the patient, and isoeugenol and one to anethole, but these are not who had been sensitized primarily by turpentine oil, also important components of peppermint oils. The reac- reacted to limonene and α-pinene (94). Limonene has tions to peppermint oil were considered to be relevant, been found in commercial peppermint oils in concen- but the causative products were not specified (95). One trations up to 18.5% and α-pinene in a maximum con- patient with oral burning and discomfort and a lichen- centration of 9.7% (Table 5.68.2, column A). Six cases oid reaction of the oral mucosa had positive patch test of allergic reactions to peppermint oil in patients with reactions to peppermint oil and menthol; the symptoms burning mouth syndrome (n=2), recurrent oral ulcers improved after avoiding mint-flavored mouthwashes (n=2) or lichenoid mucosal reactions (n=2); five also and food (102). One patient had allergic contact cheilitis reacted to menthol (main ingredient), two to eugenol from peppermint oil in toothpaste (111). Another patient

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developed stomatitis and lip dermatitis from contact LITERATURE allergy to peppermint oil and menthol present in tooth- 1 Meena GRL, Nag M, Pathania VL, Kaul VK, Singh B, pastes (121). Six cases of contact stomatitis and contact Singh RD, Ahuja PS. Effect of organic manure and plant dermatitis from contact allergy to oil of peppermint, oil spacing on biomass and quality of Mentha piperita L. of spearmint, carvone and anethole in toothpastes have in Himalaya in India. J Essent Oil Res 2013;25:354-357 been described; unknown how many cases were caused 2 Jirovetz L, Wlcek K, Buchbauer G, Gochev V, Girova by peppermint oil (123) (article not read). T, Dobreva A, et al. Chemical composition and antifungal activity of essential oils from various Other products Bulgarian Mentha x piperita L. cultivars against clin- A patient developed allergic contact dermatitis from ical isolates of Candida albicans. J Essent Oil Bear peppermint oil and its main component menthol in a Plants 2007;10:412-420 transdermal therapeutic system (92). Three patients 3 Orav A, Kapp K, Raal A. Chemosystematic mark- with allergic contact dermatitis from peppermint oil ers for the essential oils in leaves of Mentha spe- were seen in Japan (article not read); the allergens were cies cultivated or growing naturally in Estonia. Proc menthol (the main component of peppermint oil), piperi- Eston Acad Sci 2013;62(3):175-186. doi: 10.3176/ tone and pulegone (106). Both piperitone and pulegone proc.2013.3.03. Available online at www.eap.ee/ have been found in a maximum concentration of 5.4% proceedings in commercial peppermint oils (Table 5.68.2, column A). 4 Elansary HO, Ashmawy NA. Essential oils of mint One patient had orofacial granulomatosis, mainly of the between benefits and hazards. J Essent Oil Bear lower lip; he was allergic to peppermint oil and menthol. Plants 2013;16:429-438 An exclusion diet resulted in reduction of the swelling; 5 Moghaddam M, Pourbaige M, Tabar HK, Farhadi upon re-exposure to menthol, further episodes of lip N, Mohammad S, Hosseini A. Composition and swelling occurred (108). One positive patch test reaction antifungal activity of peppermint (Mentha piper- to peppermint oil was observed in a group of 53 women ita) essential oil from Iran. J Essent Oil Bear Plants with chronic anogenital dermatitis and was considered 2013;16:506-512 to be relevant (116). 6 Senatore F, De Fusco R, Grassia A, Moro CO, Rigano D, Napolitano F. Chemical composition and anti- Positive patch tests (relevance unknown, bacterial activity of essential oils from five culi- uncertain or not stated) nary herbs of the Lamiaceae family growing in Two positive patch test reactions to peppermint oil Campania, Southern Italy. J Essent Oil Bear Plants were seen in a group of 32 patients with sore mouth, 2003;6:166-173 stomatitis and/or dermatitis around the mouth or den- 7 Pino JA, Borges P, Martinez MA, Vargas M, Flores tist personnel. One also reacted to spearmint oil and its H, Martín del Campo ST, Fuentes V. Essential oil of ingredient carvone. The causative products were sup- Mentha piperita L. grown in Jalisco. J Essent Oil Res posed to be toothpastes (97). A positive patch test to 2002;14:189-190 peppermint oil was observed in an aromatherapist with 8 Chalchat J-C, Garry R-P, Michet A. Variation of the occupational contact dermatitis from multiple essential chemical composition of essential oil of Mentha oils; it was uncertain whether this oil had been used by piperita L. during the growing time. J Essent Oil Res the patient (86). A positive patch test reaction to pep- 1997;9:463-465 permint oil was seen in a patient who had airborne aller- 9 Stojanova A, Paraskevova P, Anastassov Ch. A com- gic contact dermatitis from tea tree oil and lavender parative investigation on the essential oil composi- oil (91). One positive patch test to peppermint oil was tion of two Bulgarian cultivars of Mentha piperita L. observed in a women who drank large amounts of pep- J Essent Oil Res 2000;12:438-440 permint tea, which appeared to induce vulvar dermatitis 10 Karasawa D, Shatar S, Erdenechimeg A, Okamoto Y, (100). Four positive patch test reactions to peppermint Tateba H, Shimizu S. A study on Mongolian mints. A oil occurred in 7 patients with allergic contact dermatitis new chemotype from Mentha asiatica Borriss and con- from compound tincture of benzoin (104). Two patients stituents of M. arvensis L. and M. piperita L. J Essent Oil with cheilitis, who both reacted to peppermint oil and to Res 1995;7:255-260 menthol have been presented; the causative products 11 Court WA, Roy RC, Pocs R, More AF, White PH. were not specified, but presumably toothpastes were Optimum nitrogen fertilizer rate for peppermint implicated (107). One patient had prolonged lip swelling, (Mentha piperita L.) in Ontario, Canada. J Essent Oil apparently from contact allergy to peppermint oil and Res 1993;5:663-666 menthol (112). One positive patch test reaction to pep- 12 Saharkhiz MJ, Goudarzi T. Foliar application of sali- permint oil in a patient allergic to , an allergen cylic acid changes essential oil content and chemi- in tea tree oil (negative to tea tree oil itself) (113). cal compositions of peppermint (Mentha piperita A useful review of peppermint oil allergy is provided in L.). J Essent Oil Bear Plants 2014;17:435-440 ref. 98. Menthol, the main ingredient of peppermint oil, is 13 Shutava HG, Kavalenka NH, Supichenka HN, Leontiev said to have a low sensitizing potential (101). Older litera- VN, Shutava TG. Essential oils of Lamiaceae with ture on contact allergy to peppermint oil can be found in high content of α-, β-pinene and limonene enantio- ref. 109 (article not read). mers. J Essent Oil Bear Plants 2014;17:18-25

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14 Shasany AK, Gupta S, Gupta MK, Singh AK, Naqvi 29 Djenane D, Aïder M, Yangüela J, Idir L, Gómez D, AA, Khanuja SPS. Chemotypic comparison of Roncalés P. Antioxidant and antibacterial effects of AFLP analyzed Indian peppermint germplasm to Lavandula and Mentha essential oils in minced beef selected peppermint oils of other countries. J inoculated with E. coli O157:H7 and S. aureus dur- Essent Oil Res 2007;19:138-145 ing storage at abuse refrigeration temperature. Meat 15 Fatemi F, Dini S, Rezaei MB, Dadkhah A, Dabbagh Science 2012;92:667-674 R, Naij S. The effect of γ-irradiation on the chemi- 30 Lazutka JR, Mierauskiene J, Slapsyte G, Dedonyte cal composition and antioxidant activities of pep- V. Genotoxocity of dill (Anethum graveolens L.), permint essential oil and extract. J Essent Oil Res peppermint (Mentha x piperita L.) and pine (Pinus 2014;26:97-104 sylvestris L.) essential oils on human lymphocytes 16 Padalia RC, Verma RS, Chanotiya CS. Variability in and Drosophila melanogaster. Food Chem Toxicol volatile terpenoid compositions of peppermint cul- 2001;39:485-492 tivars and some wild accession from northern India. 31 Tyagi AK, Gottardi D, Malik A, Guerzoni ME. Anti- J Essent Oil Res 2011;23:29-33 yeast activity of Mentha oil and vapours through 17 Jirovetz L, Buchbauer G, Bail S, Denkova Z, Slavchev in vitro and in vivo (real fruit juices) assays. Food A, Stoyanova A, Schmidt E, Geissler M. Antimicrobial Chem 2013;137:108-114 activities of essential oils of mint and peppermint as 32 Nikolić M, Jovanović KK, Marković T, Marković D, well as some of their main compounds. J Essent Oil Gligorijević N, Radulović S, Soković, M. Chemical Res 2009;21:363-366. Data also presented in ref. 38 composition, antimicrobial, and cytotoxic proper- 18 Lawrence BM. The genus Mentha. Boca Raton, FL, ties of five Lamiaceae essential oils. Ind Crops Prod USA: CRC Press, 2006 2014;61:225-232 19 Lawrence BM. Peppermint oil. Carol Stream, IL, 33 Kamatou GPP, Vermaak I, Viljoen AM, Lawrence BM. USA: Allured Publishing Corp, 2007 Menthol: A simple with remarkable 20 Giamperi L, Fraternale D, Ricci D. The in vitro action biological properties. Phytochem 2013;96:15-25 of essential oils on different organisms. J Essent Oil 34 Oraby MM, El-Borollosy AM. Essential oils from Res 2002;14:312-318 some Egyptian aromatic plants as an antimicrobial 21 Aflatuni A, Heikkinen K, Tomperi P, Jalonen J, Laine agent and for prevention of potato virus Y transmis- K. Variation in the extract composition of mints of sion by aphids. Ann Agricult Sci 2013;58:97-103 different origin cultivated in Finland. J Essent Oil 35 Rolli E, Marieschi M, Maietti S, Sacchetti M, Bruni Res 2000;12:462-466 R. Comparative phytotoxicity of 25 essential oils on 22 Hassanzadeh MK, Emami SA, Asili J, Najaran ZT. pre- and post-emergence development of Solanum Review of the essential oil composition of Iranian lycopersicum L.: A multivariate approach. Ind Crops Lamiaceae. J Essent Oil Res 2011;23:35-74 Prod 2014;60:280-290 23 European Medicines Agency. Assessment report 36 Işcan G, Kirimer N, Kürkcüoğlu M, Başer KHC, on Mentha x piperita L., aetheroleum. London, Demirci F. Antimicrobial screening of Mentha UK, Doc Ref EMEA/HMPC/349465/2006: 2008. piperita essential oils. J Agric Food Chem Available at: http://www.ema.europa.eu 2002;50:3943-3946 24 Skalicka-Wozniak K, Walasek M. Preparative sepa- 37 Zheljazkov VD, Cantrell CL, Astatkie T, Hristov A. ration of menthol and pulegone from pepper- Yield, content, and composition of peppermint and mint oil (Mentha piperita L.) by high-performance spearmint as a function of harvesting time and dry- counter-current chromatography. Phytochem Lett ing. J Agr Food Chem 2010;58:11400-11407 2014;10:94-98 38 Schmidt E, Bail S, Buchbauer G, Stoilova I, Atanasova 25 Kumar P, Mishra S, Malik A, Satya S. Efficacy of T, Stoyanova A, Krastanov A, Jirovetz L. Chemical Mentha × piperita and Mentha citrata essential composition, olfactory evaluation and antioxidant oils against housefly, Musca domestica L. Ind Crops effects of essential oil from Mentha × piperita. Nat Prod 2012;39:106-112 Prod Commun 2009;8:1107-1112. Data also pre- 26 Tyagi AK, Malik A. Antimicrobial potential and sented in ref. 17 chemical composition of Mentha piperita oil in liq- 39 Verma RS, Pandey V, Padalia RC, Saikia D, Krishna B. uid and vapour phase against food spoiling micro- Chemical composition and antimicrobial potential organisms. Food Control 2011;22:1707-1714 of aqueous distillate volatiles of Indian peppermint 27 Katiki LM, Chagas ACS, Bizzo HR, Ferreira JFS, (Mentha piperita) and spearmint (Mentha spicata). Amarante AFT. Anthelmintic activity of Cymbopogon J Herbs Spic Med Plants 2011;17:258-267 martinii, Cymbopogon schoenanthus and Mentha 40 Aziz EE, Craker LE. Essential oil constituents of piperita essential oils evaluated in four different in peppermint, pennyroyal, and apple mint grown vitro tests. Vet Parasitol 2011;183:103-108 in a desert agrosystem. J Herbs Spic Med Plants 28 Yadegarinia D, Gachkar L, Rezaei MB, Taghizadeh M, 2010;15:361-367 Astaneh SA, Rasooli I. Biochemical activities of Iranian 41 Aziz EE, Al-Amier H, Craker LE. Influence of salt stress Mentha piperita L. and Myrtus communis L. essential on growth and essential oil production in peppermint, oils. Phytochem 2006;67:1249-1255. Data also pre- pennyroyal, and apple mint. J Herbs Spic Med Plants sented in ref. 80 2008;14:177-87

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42 Yang S-A, Jeon S-K, Lee E-J, Shim C-H, Lee I-S. 55 Clark RJ, Menary RC. Variations in composition Comparative study of the chemical composition of peppermint oil in relation to production areas. and antioxidant activity of six essential oils and their Economic Botany 1981;35:59-69 components. Nat Prod Res 2010;24:140-151 56 Golebiowski M, Ostrowski B, Paszkiewicz M, 43 Hussain AI, Anwar F, Nigam PS, Ashraf M, Gilani AH. Czerwicka M, Kumirska J, Halinski L, et al. Chemical Seasonal variation in content, chemical composi- composition of commercially available essential oils tion and antimicrobial and cytotoxic activities of from blackcurrant, ginger, and peppermint. Chem essential oils from four Mentha species. J Sci Food Nat Comp 2008;44:794-796 Agric 2010;90:1827-1836 57 Saharkhiz MJ, Motamedi M, Zomorodian K, Pakshir 44 Freire MM, Jham GN, Dhingra OK, Jardim CM, Coura K, Miri R, Hemyari K. Chemical composition, antifun- Barcelos R, Moreira Valente VM. Composition, antifun- gal and antibiofilm activities of the essential oil of gal activity and main fungitoxic components of the essen- Mentha piperita L. ISRN Pharmaceutics 2012, Article tial oil of Mentha piperita L. J Food Saf 2012;32:29-36 ID 718645, 6 pages. doi:10.5402/2012/718645 45 Akhtary Y, Pages E, Stevens A, Bradbury R, da Camara 58 Orio L, Cravotto G, Binello A, Pignata G, Nicola S, CAG, Ismany MB. Effect of chemical complexity of Chemat F. Hydrodistillation and in situ micro- essential oils on feeding deterrence in larvae of the wave generated hydrodistillation of fresh and cabbage looper. Physiol Entomol 2012;37:81-91 dried mint leaves: a comparison study. J Sci Food 46 Grulova D, De Martino L, Mancini E, Salamon I, De Agric 2012;92: 3085-3090 Feo V. Seasonal variability of the main components 59 Chen MZ, Trinnaman L, Bardsley K, St Hilaire CJ, in essential oil of Mentha × piperita L. J Sci Food Da Costa NC. Volatile compounds and sensory Agric 2015;95:621-627 analysis of both harvests of double-cut Yakima 47 Machado M, Santoro G, Sousa MC, Salgueiro L, peppermint (Mentha piperita L.). J Food Sci Cavaleiro C. Activity of essential oils on the growth 2011;76:C1032-C1038 of Leishmania infantum promastigotes. Flavour 60 Soković M, Glamočlija J, Marin PD, Brkić D, van Fragr J 2010;25:156-160 Griensven LJLD. Antibacterial effects of the essential 48 Fiocco D, Fiorentino D, Frabboni L, Benvenuti S, oils of commonly consumed medicinal herbs using an Orlandini G, Pellati F, Gallone A. Lavender and in vitro model. Molecules 2010;15:7532-7546. Data peppermint essential oils as effective mushroom also presented in ref. 61 tyrosinase inhibitors: a basic study. Flavour Fragr J 61 Sokovic MD, Vukojevic J, Marin PD, Brkic DD, Vajs V, 2011;26:441-446 van Griensven LJLD. Chemical composition of essen- 49 Dwivedi S, Khan M, Srivastava SK, Syamasunnder tial oils of Thymus and Mentha species and their anti- KV, Srivastava A. Essential oil composition of dif- fungal activities. Molecules 2009;14:238-249. Data ferent accessions of Mentha piperita L. grown also presented in ref. 60 on the northern plains of India. Flavour Fragr J 62 Derwich E, Chabir R, Taouil R, Senhaji O. In-vitro anti- 2004;19:437-440 oxidant activity and GC/MS studies on the leaves of 50 Piccaglia R, Marotti M. Characterization of several Mentha piperita (Lamiaceae) from Morocco. Int J aromatic plants grown in Northern Italy. Flavour Pharm Sci Drug Res 2011;3:130-136 Fragr J 1993;8:115-122 63 Verma RS, Rahman L, Verma RK, Chauhan A, 51 Frérot E, Bagnoud A, Vuilleumier C. Menthofurolactone: Yadav AK, Singh A. Essential oil composition of a new p-menthane lactone in Mentha piperita L.: menthol mint (Mentha arvensis) and peppermint analysis, synthesis and olfactory properties. Flavour (Mentha piperita) cultivars at different stages Fragr J 2002;17:218-226 of plant growth from Kumaun region of west- 52 Bassolé IH, Lamien-Meda A, Bayala B, Tirogo S, Franz ern Himalaya. Open Access J Med Arom Plants C, Novak J, et al. Composition and antimicrobial 2010;1:13-18 activities of Lippia multiflora Moldenke, Mentha × 64 Palacios SM, Bertoni A, Rossi Y, Santander R, Urzúa piperita L. and Ocimum basilicum L. essential oils A. Efficacy of essential oils from edible plants as and their major monoterpene alcohols alone and insecticides against the house fly, Musca domestica in combination. Molecules 2010;15:7825-7839 L. Molecules 2009;14:1938-1947 53 Kurilov DV, Kirichenko EB, Bidyukova GF, Olekhnovich 65 Lawrence BM. Progress in essential oils. Perfum LS, Ku LD. Composition of the essential oil of intro- Flavor 2013;38(April):47-54 duced mint forms of Mentha piperita and Mentha 66 Khanuja SPS, Shasany AK, Kalsa A, Patra NK, Darokar arvensis species. Doklady Biological Sciences MP, Padmapriya T, et al. A sweet smelling pepper- 2009;429:538-540 mint plant, ‘CIM-Madhuras.’ J Med Arom Plant Sci 54 Myadelets MA, Domrachev DV, Cheremushkina VA. 2004;26:790-794. Data cited in ref. 65 A study of the chemical composition of essential 67 Khanuja SPS, Patra NK, Shasany AK, Kumar B, Gupta oils of some species from the Lamiaceae L. family S, Gupta MK, et al. High menthofuran chemotype cultivated in the western Siberian region. Russian J ‘CIM-Indus’ of Mentha x piperita. J Med Arom Plant Bioorgan Chem 2013;39:733-738 Sci 2005;27:721-726. Data cited in ref. 65

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68 Singh AK, Yadav A, Singh Chanotiya C, Gupta AK, Bahl 81 Rhind JP. Essential oils. A handbook for aromather- JR, Khanuja SPS. Quality evaluation of Mentha piperita apy practice, 2nd Edition. London: Singing Dragon, leaf oils and their relation to position on stem, pre- 2012 storage temperature shock treatment and storage. J 82 Nardelli A, Drieghe J, Claes L, Boey L, Goossens A. Med Arom Plant Sci 2008;30:298-303. Data cited in Fragrance allergens in ‘specific’ cosmetic products. ref. 65 Contact Dermatitis 2011;64:212-219 69 Schmidt E, Wanner J, Bail S, Jirovetz L, Buchbauer 83 Wetter DA, Yiannias JA, Prakash AV, Davis MD, G, Gocher V, et al. Comparative analysis of histori- Farmer SA, el-Azhary RA, et al. Results of patch test- cal peppermint oil from Bulgaria and a commer- ing to personal care product allergens in a standard cial oil of North American origin. Perfum Flavor series and a supplemental cosmetic series: an anal- 2009;34(11):46-50 ysis of 945 patients from the Mayo Clinic Contact 70 Golparvar AR, Hadipanah A. Chemical compositions Dermatitis Group, 2000-2007. J Am Acad Dermatol of the essential oil from peppermint (Mentha piper- 2010;63:789-798 ita L.) cultivated in Isfahan conditions. J Herb Drugs 84 Thomson KF, Wilkinson SM. Allergic contact der- 2013;4:75-80 matitis to plant extracts in patients with cosmetic 71 Moghtader M. In vitro antifungal effects of the essen- dermatitis. Br J Dermatol 2000;142:84-88 tial oil of Mentha piperita L. and its comparison with 85 Wöhrl S, Hemmer W, Focke M, Götz M, Jarisch R. synthetic menthol on Aspergillus niger. Afr J Plant Sci The significance of fragrance mix, balsam of Peru, 2013;7:521-527 colophonium and propolis as screening tools in 72 Debbab A, Mosaddak B, Aly AH, Hakiki A, Mosaddak the detection of fragrance allergy. Br J Dermatol M. Chemical characterization and toxicological 2001;145:268-273 evaluation of the essential oil of Mentha piperita 86 Bleasel N, Tate B, Rademaker M. Allergic contact L. growing in Morocco. Scientific Study & Research dermatitis following exposure to essential oils. 2007;8:281-288. Data cited in ref. 44 Australas J Dermatol 2002;43:211-213 73 Tsai M-L, Wu C-T, Lin T-F, Lin W-C, Huang Y-C, Yang 87 Boonchai W, Lamtharachai P, Sunthonpalin P. C-H. Chemical composition and biological prop- Occupational allergic contact dermatitis from essen- erties of essential oils of two mint species. Trop J tial oils in aromatherapists. Contact Dermatitis Pharm Res 2013;12:577-582 2007;56:181-182 74 Orav A, Raal A, Arak E. Comparative chemical com- 88 Selvaag E, Holm J, Thune P. Allergic contact der- position of the essential oil of Mentha × piperita L. matitis in an aromatherapist with multiple sen- from various geographical sources. Proc Estonian sitizations to essential oils. Contact Dermatitis Acad Sci Chem 2004;53:174-181 1995;33:354-355 75 Mkolo NM, Olowoyo JO, Sako KB, Mdakane STR, 89 Dharmagunawardena B, Takwale A, Sanders KJ, Mitonga MMA, Magano SR. Repellency and toxicity Cannan S, Roger A, Ilchyshyn A. Gas chromatog- of essential oils of Mentha piperita and Mentha spi- raphy: an investigative tool in multiple allergies to cata on larvae and adult of Amblyomma hebraeum essential oils. Contact Dermatitis 2002;47:288-292 (Acari: Ixodidae). Sci J Microbiol 2011, available at: 90 Rudzki E, Grzywa Z, Bruo WS. Sensitivity to 35 www.sjpub.org/sjmb/N.M.%20Mkoloa%20et%20al. essential oils. Contact Dermatitis 1976;2:196-200 pdf 91 De Groot AC. Airborne allergic contact der- 76 Lawrence BM. Progress in essential oils. Perfum matitis from tea tree oil. Contact Dermatitis Flavor 1993;18(4):59-72 1996;35:304-305 77 Lawrence BM. Progress in essential oils. Perfum 92 Foti C, Conserva A, Antelmi A, Lospalluti L, Angelini Flavor 1997;22(July/Aug):57-74 G. Contact dermatitis from peppermint and men- 78 Martins MM, Costa SB, Neves C, Cavaleiro C, thol in a local action transcutaneous patch. Contact Salgueiro l, Costa MLB. Olive oil flavoured by the Dermatitis 2003;49:312-313 essential oils of Mentha piperita and Thymus mas- 93 Tran A, Pratt M, DeKoven J. Acute allergic contact tichina L. Food Qual Prefer 2004;15:447-452 dermatitis of the lips from peppermint oil in a lip 79 Duarte MCT, Figueira GM, Sartoratto A, Rehder balm. Dermatitis 2010;21:111-115 VLG, Delarmelina C. Anti-Candida activity of 94 Dooms-Goossens A, Degreef H, Holvoet C, Maertens Brazilian medicinal plants. J Ethnopharmacol M. Turpentine-induced hypersensitivity to pepper- 2005;97:305-311 mint oil. Contact Dermatitis 1977;3:304-308 80 Rasooli I, Gachkar L, Yadegarinia D, Rezaei MB, 95 Morton CA, Garioch J, Todd P, Lamey PJ, Forsyth Alipoorastaneh SD. Antibacterial and antioxida- A. Contact sensitivity to menthol and peppermint tive characterization of essential oils from Mentha in patients with intra-oral symptoms. Contact piperita and Mentha spicata grown in Iran. Acta Dermatitis 1995;32:281-284 Aliment 2008;37: 41-52. Data cited in ref. 44. Data 96 Calnan CD. Oil of cloves, laurel, lavender, pepper- also presented in ref. 28 mint. Contact Dermatitis Newsletter 1970;7:148

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97 Andersen KE. Contact allergy to toothpaste flavors. 115 Uter W, Schmidt E, Geier J, Lessmann H, Schnuch Contact Dermatitis 1978;4:195-198 A, Frosch P. Contact allergy to essential oils: current 98 Herro E, Jacob SE. Mentha piperita (peppermint). patch test results (2000–2008) from the Information Dermatitis 2010;21:327-329 Network of Departments of Dermatology (IVDK). 99 Warshaw EM, Belsito DV, Taylor JS, Sasseville D, Contact Dermatitis 2010;63:277-283 DeKoven JG, Zirwas MJ, et al. North American Contact 116 Vermaat H, Smienk F, Rustemeyer Th, Bruynzeel Dermatitis Group patch test results: 2009 to 2010. DP, Kirtschig G. Anogenital allergic contact derma- Dermatitis 2013;24:50-59 titis, the role of spices and flavour allergy. Contact 100 Vermaat H, van Meurs T, Rustemeyer T, Bruynzeel Dermatitis 2008;59:233-237 DP, Kirtschig G. Vulval allergic contact dermati- 117 Warshaw EM, Maibach HI, Taylor JS, Sasseville tis due to peppermint oil in herbal tea. Contact D, DeKoven JG, Zirwas MJ, et al. North American Dermatitis 2008;58:364-365 Contact Dermatitis Group patch test results: 2011- 101 Ale SI, Hostynek JJ, Maibach HI. Menthol: a review 2012. Dermatitis 2015;26:49-59 of its sensitisation potential. Exog Dermatol 118 Frosch PJ, Johansen JD, Menné T, Pirker C, Rastogi 2002:1:74-80 SC, Andersen KE, et al. Further important sensitizers 102 Fleming CJ, Forsyth A. D5 patch test reactions in patients sensitive to fragrances. II. Reactivity to to menthol and peppermint. Contact Dermatitis essential oils. Contact Dermatitis 2002;47:279-287 1998;38:337 119 Francalanci S, Sertoli A, Giorgini S, Pigatto P, Santucci 103 Rudzki E, Grzywa Z. Allergy to perfume mixture. B, Valsecchi R. Multicentre study of allergic con- Contact Dermatitis 1986;15:115-116 tact cheilitis from toothpastes. Contact Dermatitis 104 Fettig J, Taylor J, Sood A. Post-surgical allergic con- 2000;43:216-222 tact dermatitis to compound tincture of benzoin 120 Katsarma G, Gawkrodger DJ. Suspected fragrance and association with reactions to fragrances and allergy requires extended patch testing to indi- essential oils. Dermatitis 2014;25:211-212 vidual fragrance allergens. Contact Dermatitis 105 Rudzki E, Grzywa Z. Balsam of Peru as screening 1999;41:193-197 agent for essential oils sensitivity. Dermatologica 121 Downs AMR, Lear JT, Sansom JE. Contact sensitivity 1977;155:115-121 in patients with oral symptoms. Contact Dermatitis 106 Saito F, Oka K. Allergic contact dermatitis due to 1998; 39:258-259 peppermint oil. Skin Res 1990;32:161-167 122 Magnusson B, Wilkinson DS. Cinnamic aldehyde 107 Wilkinson SM, Beck MH. Allergic contact dermatitis in toothpaste. 1. Clinical aspects and patch tests. from menthol in peppermint. Contact Dermatitis Contact Dermatitis 1975;1:70-76 1994;30:42-43 123 Hjorth N, Jervoe P. Allergisk Kontaktstomatitis og 108 Lewis FM, Shah M, Gawkrodger DJ. Contact sensi- Kontaktdermatitis fremkaldt of smagsstoffer i tand- tivity to food additives can cause oral and perioral pasta. Tandlaegebladet 1967;71:937-942. Data symptoms. Contact Dermatitis 1995;33:429-430 cited in ref. 122 109 Smith IL. Acute allergic reaction following the 124 de Groot AC. Contact allergy to cosmetics: causative use of toothpaste—a case report. Br Dent J ingredients. Contact Dermatitis 1987;17:26-34 1968;125:304-305 125 Travassos AR, Claes L, Boey L, Drieghe J, Goossens 110 Guin JD. Use of consumer product ingredients for A. Non-fragrance allergens in specific cosmetic patch testing. Dermatitis 2005;16:71-77 products. Contact Dermatitis 2011;65:276-285 111 Freeman S, Stephens R. Cheilitis: Analysis of 75 126 Rudzki E, Grzywa Z. Dermatitis from propolis. cases referred to a contact dermatitis clinic. Am J Contact Dermatitis 1983;9:40-45 Cont Derm 1999;10:198-200 127 Peltonen L, Wickstrom G, Vaahtoranta M. 112 Shah M, Lewis M, Gawkrodger DJ. Contact allergy in Occupational dermatoses in the food industry. patients with oral symptoms: a study of 47 patients. Dermatosen 1985;33:166-169 Am J Cont Derm 1996;7:146-151 128 Paulsen E, Andersen KE. Colophonium and 113 Christoffers WA, Blömeke B, Coenraads P-J, Compositae mix as markers of fragrance allergy: Schuttelaar M-LA. The optimal patch test concen- Cross-reactivity between fragrance terpenes, colo- tration for ascaridole as a sensitizing component of phonium and Compositae plant extracts. Contact tea tree oil. Contact Dermatitis 2014;71:129-137 Dermatitis 2005;53:285-291 114 Corazza M, Borghi A, Gallo R, Schena D, Pigatto 129 Santucci B, Cristaudo A, Cannistraci C, Picardo P, Lauriola MM, et al. Topical botanically derived M. Contact dermatitis to fragrances. Contact products: use, skin reactions, and usefulness of Dermatitis 1987;16:93-95 patch tests. A multicentre Italian study. Contact 130 de Groot AC. Contact allergy to cosmetics: causative Dermatitis 2014;70:90-97 ingredients. Contact Dermatitis 1987;17:26-34

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