Piperitone

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Piperitone [1]
Piperitone.png
Names
IUPAC name
6-Isopropyl-3-methyl-1-cyclohex-2-enone
Other names
3-Carvomenthenone; p-Menth-1-en-3-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.766 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9H,4-5H2,1-3H3 X mark.svgN
    Key: YSTPAHQEHQSRJD-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9H,4-5H2,1-3H3
    Key: YSTPAHQEHQSRJD-UHFFFAOYAC
  • CC1=CC(=O)C(CC1)C(C)C
Properties
C10H16O
Molar mass 152.23 g/mol
Density 0.9331 g/cm3
Melting point 232 to 233 °C (450 to 451 °F; 505 to 506 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Piperitone is a natural monoterpene ketone which is a component of some essential oils. Both stereoisomers, the D-form and the L-form, are known. The D-form has a peppermint-like aroma and has been isolated from the oils of plants from the genera Cymbopogon , Andropogon , and Mentha . [1] The L-form has been isolated from Sitka spruce. [1]

Contents

Occurrence

Eucalyptus dives Eucalyptus dives.jpg
Eucalyptus dives

Piperitone is found in many essential oils, including over thirty species of the genus eucalyptus . High levels are present in certain species of Eucalyptus and mentha . [2] In the genus Eucalyptus, the highest concentrations are found in Eucalyptus dives . [3] Both enantiomers occur naturally. In Eucalyptus species, (-)-piperitone is present; in mint species, (+)-piperitone is found; and some plants contain racemate piperitone. [2]

Properties

Piperitone is a colorless liquid with a distinct peppermint odor. [3]

Production

Piperitone can be synthesized from isopropyl acetoacetate and 3-buten-2-one. [4]

The primary source of D/L-piperitone is from Eucalyptus dives , produced mainly in South Africa. [5]

Reactions

Piperitone is used as the principal raw material for the production of synthetic menthol and thymol. [4] The reduction to menthol is achieved using hydrogen and a nickel catalyst. Oxidation to thymol is accomplished with iron(III) chloride and acetic acid. It also forms adducts with benzaldehyde and hydroxylamine (an oxime), which were historically useful for compound identification by the melting points of the derivatives. [3] Under light exposure, piperitone undergoes photodimerization, forming a polycyclic compound with a cyclobutane ring. [6]

Related Research Articles

<i>Mentha</i> Genus of flowering plants in the family Lamiaceae

Mentha, also known as mint, is a genus of flowering plants in the mint family, Lamiaceae. It is estimated that 13 to 24 species exist, but the exact distinction between species is unclear. Hybridization occurs naturally where some species' ranges overlap. Many hybrids and cultivars are known.

<span class="mw-page-title-main">Peppermint</span> Hybrid flowering plant in the family Lamiaceae

Peppermint is a hybrid species of mint, a cross between watermint and spearmint. Indigenous to Europe and the Middle East, the plant is now widely spread and cultivated in many regions of the world. It is occasionally found in the wild with its parent species.

<span class="mw-page-title-main">Spearmint</span> Species of mint

Spearmint, also known as garden mint, common mint, lamb mint and mackerel mint, is native to Europe and southern temperate Asia, extending from Ireland in the west to southern China in the east. It is naturalized in many other temperate parts of the world, including northern and southern Africa, North America, and South America. It is used as a flavouring in food and herbal teas. The aromatic oil, called oil of spearmint, is also used as a flavoring and sometimes as a scent.

<span class="mw-page-title-main">Essential oil</span> Hydrophobic liquid containing volatile aroma compounds from plants

An essential oil is a concentrated hydrophobic liquid containing volatile chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetheroleum, or simply as the oil of the plant from which they were extracted, such as oil of clove. An essential oil is essential in the sense that it contains the essence of the plant's fragrance—the characteristic fragrance of the plant from which it is derived. The term "essential" used here does not mean indispensable or usable by the human body, as with the terms essential amino acid or essential fatty acid, which are so called because they are nutritionally required by a living organism.

<span class="mw-page-title-main">Menthol</span> Organic compound used as flavouring and analgesic

Menthol is an organic compound, specifically a monoterpenoid, that occurs naturally in the oils of several plants in the mint family, such as corn mint and peppermint. It is a white or clear waxy crystalline substance that is solid at room temperature and melts slightly above. The main form of menthol occurring in nature is (−)-menthol, which is assigned the (1R,2S,5R) configuration.

<span class="mw-page-title-main">Thymol</span> Chemical compound found in plants including thyme

Thymol, C10H14O, is a natural monoterpenoid phenol derivative of p-Cymene, isomeric with carvacrol, found in oil of thyme, and extracted from Thymus vulgaris, ajwain, and various other plants as a white crystalline substance of a pleasant aromatic odor and strong antiseptic properties. Thymol also provides the distinctive, strong flavor of the culinary herb thyme, also produced from T. vulgaris. Thymol is only slightly soluble in water at neutral pH, but it is extremely soluble in alcohols and other organic solvents. It is also soluble in strongly alkaline aqueous solutions due to deprotonation of the phenol. Its dissociation constant (pKa) is 10.59±0.10. Thymol absorbs maximum UV radiation at 274 nm.

<span class="mw-page-title-main">Carvone</span> Chemical compound

Carvone is a member of a family of chemicals called terpenoids. Carvone is found naturally in many essential oils, but is most abundant in the oils from seeds of caraway, spearmint, and dill.

Carvacrol, or cymophenol, C6H3(CH3)(OH)C3H7, is a monoterpenoid phenol. It has a characteristic pungent, warm odor of oregano.

<span class="mw-page-title-main">Pulegone</span> Chemical compound

Pulegone is a naturally occurring organic compound obtained from the essential oils of a variety of plants such as Nepeta cataria (catnip), Mentha piperita, and pennyroyal. It is classified as a monoterpenoid, which means that it is an oxidized derivative of a terpene, a large class of naturally occuring C10 hydrocarbons.

<span class="mw-page-title-main">Eucalyptol</span> Chemical compound

Eucalyptol is a monoterpenoid colorless liquid, and a bicyclic ether. It has a fresh camphor-like odor and a spicy, cooling taste. It is insoluble in water, but miscible with organic solvents. Eucalyptol makes up about 70–90% of eucalyptus oil. Eucalyptol forms crystalline adducts with hydrohalic acids, o-cresol, resorcinol, and phosphoric acid. Formation of these adducts is useful for purification.

Menthone is a monoterpene with a minty flavor that occurs naturally in a number of essential oils. l-Menthone, shown at right, is the most abundant in nature of the four possible stereoisomers. It is structurally related to menthol, which has a secondary alcohol in place of the carbonyl. Menthone is used in flavoring, perfume and cosmetics for its characteristic aromatic and minty odor.

<i>Mentha arvensis</i> Species of flowering plant

Mentha arvensis, the corn mint, field mint, or wild mint, is a species of flowering plant in the mint family Lamiaceae. It has a circumboreal distribution, being native to the temperate regions of Europe and western and central Asia, east to the Himalaya and eastern Siberia, and North America. Mentha canadensis, the related species, is also included in Mentha arvensis by some authors as two varieties, M. arvensis var. glabrata Fernald and M. arvensis var. piperascens Malinv. ex L. H. Bailey.

<span class="mw-page-title-main">Eucalyptus oil</span> Distilled oil from the leaf of Eucalyptus

Eucalyptus oil is the generic name for distilled oil from the leaves of Eucalyptus, a genus of the plant family Myrtaceae, mostly native to Australia but cultivated worldwide. Eucalyptus oil has a history of wide application, as a pharmaceutical, antiseptic, repellent, flavouring and fragrance, as well as having industrial uses. The leaves of selected Eucalyptus species are steam distilled to extract eucalyptus oil.

Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear (acyclic) or contain rings (monocyclic and bicyclic). Modified terpenes, such as those containing oxygen functionality or missing a methyl group, are called monoterpenoids. Monoterpenes and monoterpenoids are diverse. They have relevance to the pharmaceutical, cosmetic, agricultural, and food industries.

<i>Eucalyptus dives</i> Species of eucalyptus

Eucalyptus dives, commonly known as the broad-leaved peppermint or blue peppermint, is a species of tree that is endemic to south-eastern Australia. It has rough, finely fibrous bark on the trunk and larger branches, smooth bark above, lance-shaped or curved adult leaves, flower buds in groups of eleven or more, white flowers and cup-shaped, hemispherical or conical fruit.

<i>Eucalyptus piperita</i> Species of eucalyptus

Eucalyptus piperita, commonly known as Sydney peppermint and urn-fruited peppermint, is a small to medium forest tree native to New South Wales, Australia.

<i>Mentha canadensis</i> Species of flowering plant

Mentha canadensis is a species of mint native to North America and the eastern part of Asia. In North America, it is commonly known as Canada mint, American wild mint, and in Asia as Chinese mint, Sakhalin mint, Japanese mint, and East Asian wild mint. The flowers are bluish or have a slight violet tint. The plant is upright, growing to about 4–18 in (10–46 cm) tall. Leaves grow opposite from each other, and flower bunches appear in the upper leaf axils. The mint grows in wet areas but not directly in water, so it will be found near sloughs, and lake and river edges. Plants bloom from July to August in their native habitats.

<span class="mw-page-title-main">Aromatherapy</span> Alternative medicine practice

Aromatherapy is a practice based on the use of aromatic materials, including essential oils and other aroma compounds, with claims for improving psychological well-being. It is used as a complementary therapy or as a form of alternative medicine, and typically is used via inhalation and not by ingestion.

Mentha grandiflora is a plant species in the genus Mentha, endemic to eastern Australia. The species was described in 1848 by botanist George Bentham. Its epithet, grandiflora, means "with large flowers".

<span class="mw-page-title-main">Pinocarvone</span> Chemical compound

Pinocarvone is a terpenoid. Structurally, it is a bicyclic ketone.

References

  1. 1 2 3 Merck Index , 11th Edition, '7443
  2. 1 2 Uzi Ravid, Eli Putievsky, Irena Katzir (March 1994), "Enantiomeric distribution of piperitone in essential oils of some mentha spp., calamintha incána (sm.) heldr. and artemisia judaica L", Flavour and Fragrance Journal, vol. 9, no. 2, pp. 85–87, doi:10.1002/ffj.2730090210 {{citation}}: CS1 maint: multiple names: authors list (link)
  3. 1 2 3 John Read, Henry George Smith (1921), "LXXXVII.—Piperitone. Part I. The occurrence, isolation, and characterisation of piperitone", J. Chem. Soc., Trans., vol. 119, no. 0, pp. 779–789, doi:10.1039/CT9211900779
  4. 1 2 Fritz Eiden (August 2007), "Carl Hagemann ...ein Mensch von großer Güte, ein richtiger Chemiker...", Chemie in unserer Zeit, vol. 41, no. 4, pp. 316–323, doi:10.1002/ciuz.200700411
  5. Boland, D.J., Brophy, J.J., and A.P.N. House, Eucalyptus Leaf Oils, 1991, ISBN   0-909605-69-6
  6. H. Ziffer, N.E. Sharpless, R.O. Kan (January 1966), "Photodimers of piperitone", Tetrahedron, vol. 22, no. 9, pp. 3011–3020, doi:10.1016/S0040-4020(01)82280-8 {{citation}}: CS1 maint: multiple names: authors list (link)