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Peppermint Oil 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 menthol 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 Limonene 138-86-3 1.0 3.0 its origin. The yield of essential oil from the flowering Pulegone 89-82-7 0.5 3.0 aerial tops and leaves of Mentha x piperita L. gener- trans-Sabinene 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 K23588_Book.indb 653 4/15/16 9:39 AM 654 Essential Oils: Contact Allergy and Chemical Composition 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
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