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Menthone
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Menthone
Menthone is a chemical compound of the monoterpene class of naturally occurring organic compounds found in a number of essential oils, one that presents with minty flavor. It is a specific pair of stereoisomers of the four possible such isomers for the chemical structure, 2-isopropyl-5-methylcyclohexanone. Of those, the stereoisoomer l-menthone—formally, the (2S,5R)-trans isomer of that structure, as shown at right—is the most abundant in nature. Menthone is structurally related to menthol, which has a secondary alcohol (>C-OH) in place of the carbon-oxygen double bond (carbonyl group) projecting from the cyclohexane ring.
Menthone is obtained for commercial use after purifying essential oils pressed from Mentha species (peppermint and corn mint). It is used as a flavorant and in perfumes and cosmetics for its characteristic aromatic and minty aroma.[not verified in body]
Menthone is a constituent of the essential oils of pennyroyal, peppermint, corn mint, pelargonium geraniums, and other plant species. In most essential oils, it is a minor component. Menthone was first synthesized by oxidation of menthol in 1881,[needs update] before being found as a component in essential oils in 1891.[citation needed] Of the isomers possible for this chemical structure (see below), the one termed l-menthone—formally, the (2S,5R)-trans-2-isopropyl-5-methylcyclohexanone (see infobox and below)—is the most abundant in nature.
Menthone is a liquid under standard conditions, and has a density of 0.895 g/cm3.[citation needed] Under the same conditions,[verification needed] the melting point is −6 °C, and its boiling point is 207 °C.[citation needed]
Menthone interacts cognitively with other components in food, drink, and other consumables, to present with what is termed a minty flavor. Pure l-menthone has been described as having an intensely minty clean aroma;[according to whom?] in contrast, d-isomenthone has a "green" note,[This quote needs a citation] increasing levels of which are perceived to detract from the aroma quality of l-menthone.[verification needed]
The structure of 2-isopropyl-5-methylcyclohexanone (menthones and isomenthones, see following) were established historically by establishing identity of natural and synthetic products after chemical synthesis of this structure from other chemical compounds of established structure; these inferential understandings have, in modern organic chemistry, been augmented by supporting mass spectrometric and spectroscopic evidence (e.g., from NMR spectroscopy and circular dichroism) to make the conclusions secure.[citation needed]
The structure 2-isopropyl-5-methylcyclohexanone has two asymmetric carbon centers, one at each attachment point of the two alkyl group substituents, the isopropyl in the 2-position and the methyl in the 5-position of the cyclohexane framework.[better source needed] The spatial arrangement of atoms—the absolute configuration—at these two points are designated by the descriptors R (Latin, rectus, right) or S (L., sinister, left) based on the Cahn–Ingold–Prelog priority rules. Hence, four unique stereoisomers are possible for this structure: (2S,5S), (2R,5S), (2S,5R) and (2R,5R).[better source needed]
The (2S,5S) and (2R,5R) stereoisomers project the isopropyl and methyl groups from the same "side" of the cyclohexane ring, are the so-called cis isomers, and are termed isomenthone; the (2R,5S) and (2S,5R) stereoisomers project the two groups on the opposite side of the ring, are the so-called trans isomers, and are referred to as menthone.[better source needed] Because the (2S,5R) isomer has an observed negative optical rotation, it is called l-menthone or (−)-menthone. It is the enantiomeric partner of the (2R,5S) isomer: (+)- or d-menthone.[better source needed][verification needed]
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Menthone
Menthone is a chemical compound of the monoterpene class of naturally occurring organic compounds found in a number of essential oils, one that presents with minty flavor. It is a specific pair of stereoisomers of the four possible such isomers for the chemical structure, 2-isopropyl-5-methylcyclohexanone. Of those, the stereoisoomer l-menthone—formally, the (2S,5R)-trans isomer of that structure, as shown at right—is the most abundant in nature. Menthone is structurally related to menthol, which has a secondary alcohol (>C-OH) in place of the carbon-oxygen double bond (carbonyl group) projecting from the cyclohexane ring.
Menthone is obtained for commercial use after purifying essential oils pressed from Mentha species (peppermint and corn mint). It is used as a flavorant and in perfumes and cosmetics for its characteristic aromatic and minty aroma.[not verified in body]
Menthone is a constituent of the essential oils of pennyroyal, peppermint, corn mint, pelargonium geraniums, and other plant species. In most essential oils, it is a minor component. Menthone was first synthesized by oxidation of menthol in 1881,[needs update] before being found as a component in essential oils in 1891.[citation needed] Of the isomers possible for this chemical structure (see below), the one termed l-menthone—formally, the (2S,5R)-trans-2-isopropyl-5-methylcyclohexanone (see infobox and below)—is the most abundant in nature.
Menthone is a liquid under standard conditions, and has a density of 0.895 g/cm3.[citation needed] Under the same conditions,[verification needed] the melting point is −6 °C, and its boiling point is 207 °C.[citation needed]
Menthone interacts cognitively with other components in food, drink, and other consumables, to present with what is termed a minty flavor. Pure l-menthone has been described as having an intensely minty clean aroma;[according to whom?] in contrast, d-isomenthone has a "green" note,[This quote needs a citation] increasing levels of which are perceived to detract from the aroma quality of l-menthone.[verification needed]
The structure of 2-isopropyl-5-methylcyclohexanone (menthones and isomenthones, see following) were established historically by establishing identity of natural and synthetic products after chemical synthesis of this structure from other chemical compounds of established structure; these inferential understandings have, in modern organic chemistry, been augmented by supporting mass spectrometric and spectroscopic evidence (e.g., from NMR spectroscopy and circular dichroism) to make the conclusions secure.[citation needed]
The structure 2-isopropyl-5-methylcyclohexanone has two asymmetric carbon centers, one at each attachment point of the two alkyl group substituents, the isopropyl in the 2-position and the methyl in the 5-position of the cyclohexane framework.[better source needed] The spatial arrangement of atoms—the absolute configuration—at these two points are designated by the descriptors R (Latin, rectus, right) or S (L., sinister, left) based on the Cahn–Ingold–Prelog priority rules. Hence, four unique stereoisomers are possible for this structure: (2S,5S), (2R,5S), (2S,5R) and (2R,5R).[better source needed]
The (2S,5S) and (2R,5R) stereoisomers project the isopropyl and methyl groups from the same "side" of the cyclohexane ring, are the so-called cis isomers, and are termed isomenthone; the (2R,5S) and (2S,5R) stereoisomers project the two groups on the opposite side of the ring, are the so-called trans isomers, and are referred to as menthone.[better source needed] Because the (2S,5R) isomer has an observed negative optical rotation, it is called l-menthone or (−)-menthone. It is the enantiomeric partner of the (2R,5S) isomer: (+)- or d-menthone.[better source needed][verification needed]