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Names | |
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Preferred IUPAC name (5R)-5-Methyl-2-(propan-2-ylidene)cyclohexan-1-one | |
Other names p-Menth-4(8)-en-3-one; δ-4(8)-p-Menthen-3-one; (R)-2-Isopropylidene-5-methylcyclohexanone; (R)-p-Menth-4(8)-en-3-one; (R)-(+)-Pulegone | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.001.767 ![]() |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C10H16O | |
Molar mass | 152.237 g·mol−1 |
Appearance | Colorless oil |
Density | 0.9346 g/cm3 |
Boiling point | 224 °C (435 °F; 497 K) |
Insoluble | |
Solubility in Ethanol Ether Chloroform | Miscible |
Hazards | |
Safety data sheet | MSDS [2] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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Infobox references | |
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. [3] [4] It is classified as a monoterpene.
Pulegone is a clear colorless oily liquid and has a pleasant odor similar to pennyroyal, peppermint and camphor. It is used in flavoring agents, in perfumery, and in aromatherapy.
It was reported that the chemical is toxic to rats if a large quantity is consumed. [5] [6]
Pulegone is also an insecticide − the most powerful of three insecticides naturally occurring in many mint species. [7]
As of October 2018, the FDA withdrew authorization for the use of pulegone as a synthetic flavoring substance for use in food, but that naturally-occurring pulegone can continue to be used. [8]
Mentha is a genus of plants in the family Lamiaceae. The exact distinction between species is unclear; it is estimated that 13 to 24 species exist. Hybridization occurs naturally where some species' ranges overlap. Many hybrids and cultivars are known.
Peppermint is a hybrid 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.
Spearmint, also known as garden mint, common mint, lamb mint and mackerel mint, is a species of mint, Mentha spicata, 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 flavouring and sometimes as a scent.
Mentha pulegium, commonly (European) pennyroyal, or pennyrile, also called mosquito plant and pudding grass, is a species of flowering plant in the mint family, Lamiaceae, native to Europe, North Africa, and the Middle East. Crushed pennyroyal leaves emit a very strong fragrance similar to spearmint. Pennyroyal is a traditional folk remedy, emmenagogue, abortifacient, and culinary herb, but is toxic to the liver and has caused some deaths. European pennyroyal is related to an American species, Hedeoma pulegioides. Though they differ in genera, they share similar chemical properties.
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 given living organism.
Menthol is an organic compound, more specifically a monoterpenoid, made synthetically or obtained from the oils of corn mint, peppermint, or other mints. It is a waxy, crystalline substance, clear or white in color, which is solid at room temperature and melts slightly above.
Safrole is an organic compound with the formula CH2O2C6H3CH2CH=CH2. It is a colorless oily liquid, although impure samples can appear yellow. A member of the phenylpropanoid family of natural products, it is found in sassafras plants, among others. Small amounts are found in a wide variety of plants, where it functions as a natural antifeedant. Ocotea pretiosa, which grows in Brazil, and Sassafras albidum, which grows in eastern North America, are the main natural sources of safrole. It has a characteristic "sweet-shop" aroma.
Myristicin is a naturally occurring compound found in common herbs and spices, the most well known being nutmeg. It is an insecticide, and has been shown to enhance the effectiveness of other insecticides in combination. Myristicin is also a precursor for substituted amphetamine derivative compounds structurally related to MDMA; it is believed to be metabolized into MMDA in the body to produce hallucinogenic effects, and can be converted to MMDMA in controlled chemical synthesis. It interacts with many enzymes and signaling pathways in the body, is cytotoxic to living cells, and may also have chemoprotective properties.
Cinnamaldehyde is an organic compound with the formula C6H5CH=CHCHO. Occurring naturally as predominantly the trans (E) isomer, it gives cinnamon its flavor and odor. It is a phenylpropanoid that is naturally synthesized by the shikimate pathway. This pale yellow, viscous liquid occurs in the bark of cinnamon trees and other species of the genus Cinnamomum. The essential oil of cinnamon bark is about 90% cinnamaldehyde.
Linalool refers to two enantiomers of a naturally occurring terpene alcohol found in many flowers and spice plants. Linalool has multiple commercial applications, the majority of which are based on its pleasant scent. A colorless oil, linalool is classified as an acyclic monoterpenoid. In plants, it is a metabolite, a volatile oil component, an antimicrobial agent, and an aroma compound. Linalool has uses in manufacturing of soaps, fragrances, food additives as flavors, household products, and insecticides.
Anethole is an organic compound that is widely used as a flavoring substance. It is a derivative of phenylpropene, a type of aromatic compound that occurs widely in nature, in essential oils. It is in the class of phenylpropanoid organic compounds. It contributes a large component of the odor and flavor of anise and fennel, anise myrtle (Myrtaceae), liquorice (Fabaceae), magnolia blossoms, and star anise (Schisandraceae). Closely related to anethole is its isomer estragole, abundant in tarragon (Asteraceae) and basil (Lamiaceae), that has a flavor reminiscent of anise. It is a colorless, fragrant, mildly volatile liquid. Anethole is only slightly soluble in water but exhibits high solubility in ethanol. This trait causes certain anise-flavored liqueurs to become opaque when diluted with water, the ouzo effect.
An insect repellent is a substance applied to skin, clothing, or other surfaces to discourage insects from landing or climbing on that surface. Insect repellents help prevent and control the outbreak of insect-borne diseases such as malaria, Lyme disease, dengue fever, bubonic plague, river blindness, and West Nile fever. Pest animals commonly serving as vectors for disease include insects such as flea, fly, and mosquito; and the arachnid tick.
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.
Eucalyptol is a monoterpenoid. A colorless liquid, it is a bicyclic ether. Eucalyptol has a fresh mint-like smell and a spicy, cooling taste. It is insoluble in water, but miscible with organic solvents. Eucalyptol makes up 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.
Peppermint extract is an herbal extract of peppermint made from the essential oils of peppermint leaves. Peppermint is a hybrid of water mint and spearmint and was indigenous to Europe and the Middle East before it became common in other regions, such as North America and Asia.
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.
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.
Menthofuran is an organic compound found in a variety of essential oils including that of pennyroyal. It is highly toxic and believed to be the primary toxin in pennyroyal responsible for its potentially fatal effects. After ingestion of menthofuran, it is metabolically activated to chemically reactive intermediates that are hepatotoxic.
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".