Carvone
General
Systematic name	2-methyl-5-(prop-1-en-2-yl) cyclohex-2-enone
Other names	Δ6:8(9)-p-menthadien-2-one 1-methyl-4-isopropenyl- Δ6-cyclohexen-2-one carvol (obsolete)
Molecular formula	C10H14O
SMILES	C=C(C)C(C1)CC=C(C)C1=O
Molar mass	150.22 g/mol
Appearance	Clear, colourless liquid
CAS number	[6485-40-1] ((R)-Carvone) [2244-16-8] ((S)-Carvone)
Properties
Density and phase	0.958 g/cm3,
Solubility in water	Insoluble (cold) Slightly soluble (hot)
Solubility in Ethanol	soluble
Solubility in Diethyl ether	soluble
Solubility in Chloroform	soluble
Melting point	89 °C
Boiling point	231 °C
Acidity (pKa)	?
Chiral rotation [α]D	-61° (R)-Carvone 61° (S)-Carvone,
Hazards
MSDS	External MSDS
Main hazards	inflammable
NFPA 704	2 1 0
R-phrases	22
S-phrases	36
RTECS number	OS8650000 (R) OS8670000 (S)
Supplementary data page
Structure and properties	n, εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Related compounds
Related ketones	menthone dihydrocarvone carvomenthone
Related compounds	limonene, menthol, p-cymene, carveol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Carvone is a member of a family of chemicals called terpenoids.^[1] Carvone is found naturally in many essential oils, but is most abundant in the oils from seeds of caraway (Carum carvi) and dill.^[2] Image File history File links No higher resolution available. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... This article or section does not cite any references or sources. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... In physics, density is mass m per unit volume V. 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R-phrases , , , S-phrases , Flash point Non-flammable U.S. Permissible exposure limit (PEL) 50 ppm (240 mg/m3) (OSHA) Supplementary data page Structure and properties n, εr, etc. ... The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ... Italic text This article is about the boiling point of liquids. ... The acid dissociation constant (Ka), also known as the acidity constant or the acid-ionization constant, is a specific equilibrium constant for the reaction of an acid with its conjugate base in aqueous solution [1]. // When an acid dissolves in water, it partly dissociates forming hydronium ions and its conjugate... The specific rotation of a chemical compound [α] is defined as the observed angle of optical rotation α when plane-polarized light is passed through a sample with a path length of 1 decimeter and a sample concentration of 1 gram per 1 millilitre. ... An example MSDS in a US format provides guidance for handling a hazardous substance and information on its composition and properties. ... The examples and perspective in this article or section may not represent a worldwide view. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... Image File history File links NFPA_704. ... R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... The refractive index (or index of refraction) of a medium is a measure for how much the speed of light (or other waves such as sound waves) is reduced inside the medium. ... The relative dielectric constant of a material under given conditions is a measure of the extent to which it concentrates electrostatic lines of flux. ... Ultraviolet-Visible Spectroscopy or Ultraviolet-Visible Spectrophotometry (UV/ VIS) involves the spectroscopy of photons (spectrophotometry). ... Infrared spectroscopy (IR Spectroscopy) is the subset of spectroscopy that deals with the IR region of the EM spectrum. ... It has been suggested that NMR Data Processing be merged into this article or section. ... Mass spectrometry (also known as mass spectroscopy (deprecated)[1] or informally, mass-spec and MS) is an analytical technique used to measure the mass-to-charge ratio of ions. ... Ketone group A ketone(key tone) is either the functional group characterized by a carbonyl group (O=C) linked to two other carbon atoms or a chemical compound that contains this functional group. ... l-Menthone Menthone is a naturally occurring organic compound with a molecular formula C10H18O. l-Menthone (or (5R, 2S)-trans-5-methyl-2-(l-methylethyl)cyclohexanone), shown at right, is the most abundant in nature of the four possible stereoisomers. ... Limonene is a hydrocarbon, classed as a terpene. ... Menthol is a covalent organic compound made synthetically or obtained from peppermint or other mint oils. ... Cymene, or p-cymene, is a naturally occurring aromatic organic compound. ... Carveol is a natural terpenoid alcohol that is a constituent of spearmint oil. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... Many terpenes are derived from conifer resins, here a pine. ... An essential oil is a concentrated, hydrophobic liquid containing volatile aromatic compounds from plants. ... Categories: | | | | ... Binomial name Anethum graveolens L. Dried Dill-umbel Dill (Anethum graveolens) is a short-lived annual herb, native to southwest and central Asia. ...

Stereoisomerism and odour

Carvone forms two mirror image forms or enantiomers: S-(+)-carvone smells like caraway. Its mirror image, R-(–)-carvone, smells like spearmint.^[3] The fact that the two enantiomers are perceived as smelling differently is proof that olfactory receptors must contain chiral groups, allowing them to respond more strongly to one enantiomer than to the other. Not all enantiomers have distinguishable odours. Squirrel monkeys have also been found to be able to discriminate between carvone enantiomers.^[4] In chemistry two stereoisomers are said to be enantiomers if one can be superimposed on the mirror image of the other, and vice versa. ... Categories: | | | | ... Binomial name Mentha spicata Crantz Spearmint (Mentha spicata, syn ) is a species of mint native to central and southern Europe, where it grows in wet soils. ... Olfactory receptors are a type of G protein-coupled receptor in olfactory receptor neurons. ... Optical isomerism is a form of isomerism (specifically stereoisomerism) where the two different isomers are the same in every way except being non-superposable mirror images of each other. ... Type species Simia sciurea Linnaeus, 1758 Species Saimiri oerstedii Saimiri sciureus Saimiri ustus Saimiri boliviensis Saimiri vanzolini The squirrel monkeys are the New World monkeys of the genus Saimiri. ...

The two forms are also referred to by older names, with dextro-, d- referring to S-carvone, and laevo-, l- referring to R-carvone. Dextrorotation is the property of rotating plane polarized light clockwise. ... Levorotation (also spelled laevorotation) is the counterclockwise rotation of plane polarized light. ...

Occurrence

S-(+)-Carvone is the principal constituent (50-70%) of the oil from caraway seeds (Carum carvi),^[5], which is produced on a scale of about 10 tonnes per year. ^[2] It also occurs to the extent of about 40-60% in dill seed oil (from Anethum graveolens), and also in mandarin orange peel oil. R-(–)-Carvone is present at levels greater than 51% in spearmint oil (Mentha spicata), which is produced on a scale of around 1500 tonnes annually. This isomer also occurs in kuromoji oil. Some oils, like gingergrass oil, contain a mixture of both enantiomers. Many other natural oils, for example peppermint oil, contain lower concentrations of carvones. Binomial name Anethum graveolens L. Dried Dill-umbel Dill (Anethum graveolens) is a short-lived annual herb, native to southwest and central Asia. ... Binomial name Citrus reticulata The Mandarin orange or mandarin is a small citrus tree (Citrus reticulata) with fruit resembling the orange. ... Binomial name Mentha spicata Crantz Spearmint (Mentha spicata, syn ) is a species of mint native to central and southern Europe, where it grows in wet soils. ... Binomial name Mentha × piperita L. Peppermint (Mentha × piperita) is a (usually) sterile hybrid mint, a cross between watermint (Mentha aquatica) and spearmint (Mentha spicata). ...

History

Caraway was used for medicinal purposes by the ancient Romans^[2], but carvone was probably not isolated as a pure compound until Varrentrapp obtained it in1841.^[1] It was originally called carvol by Schweizer. Goldschmidt and Zűrrer identified it as a ketone related to limonene, and the structure was finally elucidated by Wagner in 1894.^[6] Limonene is a hydrocarbon, classed as a terpene. ...

Preparation

The dextro-form is obtained practically pure by the fractional distillation of caraway oil; the laevo-form from the oils containing it, by first forming its addition compound with hydrogen sulfide, decomposing this by potassium hydroxide in ethanol, and distilling the product in a current of steam. It may be synthetically prepared from limonene nitrosochloride, alcoholic converting this compound into 1-carvoxime, which on boiling with dilute sulfuric acid yields l-carvone. Categories: | | | | ... Hydrogen sulfide (hydrogen sulphide in British English), H2S, is a colorless, toxic, flammable gas that is responsible for the foul odor of rotten eggs and flatulence. ... The chemical compound potassium hydroxide, (KOH) sometimes known as caustic potash, potassa, potash lye, and potassium hydrate, is a metallic base. ... Grain alcohol redirects here. ... Limonene is a hydrocarbon, classed as a terpene. ... Sulfuric (or sulphuric) acid, H2SO4, is a strong mineral acid. ...

The biosynthesis of carvone is by oxidation of limonene. Biosynthesis is a phenomenon where chemical compounds are produced from simpler reagents. ... Limonene is a hydrocarbon, classed as a terpene. ...

Chemical properties

Reduction

There are three double bonds in carvone capable of reduction; the product of reduction depends on the reagents and conditions used. Catalytic hydrogenation of carvone (1) can give either carvomenthol (2) or carvomenthone (3). Zinc and acetic acid reduce carvone to give dihydrocarvone (4). MPV reduction using propan-2-ol and aluminium isopropoxide effects reduction of the carbonyl group only to provide carveol (5); a combination of sodium borohydride and CeCl₃ (Luche reduction) is also effective. Hydrazine and potassium hydroxide give limonene (6) via a Wolff-Kishner reduction. General Name, Symbol, Number zinc, Zn, 30 Chemical series transition metals Group, Period, Block 12, 4, d Appearance bluish pale gray Standard atomic weight 65. ... Acetic acid, also known as ethanoic acid, is an organic chemical compound with the formula CH3COOH best recognized for giving vinegar its sour taste and pungent smell. ... Isopropyl alcohol or isopropanol is a common name for 2-propanol, an alcohol commonly used for application to the skin, and popularly referred to as rubbing alcohol. ... Aluminium isopropoxide is an inorganic compound and the adduct of aluminum and isopropyl alcohol. ... Carbonyl group In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom : C=O. The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex (a metal carbonyl, e. ... Carveol is a natural terpenoid alcohol that is a constituent of spearmint oil. ... Sodium borohydride, also known as sodium tetrahydroborate, has the chemical formula NaBH4. ... Cerium(III) chloride (CeCl3), also known as cerous chloride or cerium trichloride, is a compound of cerium and chlorine. ... Hydrazine should not be confused with Hydergine (Ergoloid mesylates) an ergot alkaloid Hydrazine is the chemical compound with formula N2H4, widely used in chemical synthesis. ... The chemical compound potassium hydroxide, (KOH) sometimes known as caustic potash, potassa, potash lye, and potassium hydrate, is a metallic base. ... Limonene is a hydrocarbon, classed as a terpene. ... The Wolff-Kishner reduction is a chemical reaction that fully reduces a ketone (or aldehyde) to an alkane. ...

Image File history File links No higher resolution available. ...

Oxidation

Oxidation of carvone can also lead to a variety of products. In the presence of an alkali such as Ba(OH)₂, carvone is oxidised by air or oxygen to give the diketone 7. With hydrogen peroxide the epoxide 8 is formed. Carvone may be cleaved using ozone followed by steam, giving dilactone 9, while KMnO₄ gives 10. Illustration of a redox reaction Redox (shorthand for oxidation/reduction reaction) describes all chemical reactions in which atoms have their oxidation number (oxidation state) changed. ... Barium hydroxide is a basic chemical compound, with the chemical formula Ba(OH)2. ... Look up air in Wiktionary, the free dictionary. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... Hydrogen peroxide (H2O2) is a very pale blue liquid which appears colourless in a dilute solution, slightly more viscous than water. ... An epoxide is a cyclic ether with only three ring atoms. ... It has been suggested that Ozone generator be merged into this article or section. ... A lactone is a cyclic ester in organic chemistry. ... Potassium permanganate is the chemical compound KMnO4. ...

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Conjugate additions

As an α,beta;-unsaturated ketone, carvone undergoes conjugate additions of nucleophiles. For example, carvone reacts with lithium dimethylcuprate to place a methyl group trans to the isopropenyl group with good stereoselectivity. The resulting enolate can then be allylated using allyl bromide to give ketone 11.^[7] An enone is an unsaturated chemical compound or functional group consisting of a conjugated system of an alkene and a ketone. ... Nucleophilic conjugate addition Nucleophilic conjugate addition is a type of organic reaction. ... A Gilman reagent is a lithium and copper (diorganocopper) reagent compound, , where R is an organic radical. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... In chemistry, a stereoselectivity is the property of a chemical reaction that yields an unequal mixture of stereoisomers from a single reactant. ... Enol (or, more officially, but less commonly: alkenol) is an alkene with hydroxyl group on one of the carbon atoms of the double bond. ... R-phrases , S-phrases , A, , , , , Flash point -2 - -1 °C Autoignition temperature 280 °C Explosive limits 4. ...

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Uses

Both carvones are used in the food and flavor industry. R-(-)-Carvone is also used for air freshening products and, like many essential oils, oils containing carvones are used in aromatherapy and alternative medicine. An essential oil, is a concentrated, hydrophobic liquid containing volatile aromatic compounds extracted from plants. ... It has been suggested that Aromatherapy Candles be merged into this article or section. ... Alternative medicine is defined as any of various systems of healing or treating disease (as chiropractic, homeopathy, or faith healing) not included in the traditional medical curricula taught in the United States and Britain.[1] Complementary medicine is defined as any of the practices (as acupuncture) of alternative medicine accepted...

Food applications

As the compound most responsible for the flavour of caraway, dill and spearmint, carvone has been used for millennia in food. Wrigley's Spearmint Gum is gum soaked in R-(–)-carvone and powdered with sugar. Magnification of grains of sugar, showing their monoclinic hemihedral crystalline structure. ...

Agriculture

S-(+)-Carvone is also used to prevent premature sprouting of potatoes during storage, being marketed in the Netherlands for this purpose under the name Talent.

Organic synthesis

Carvone is available inexpensively in both enantiomerically pure forms, making it an attractive starting material for the asymmetric total synthesis of natural products. For example, (S)-(+)-carvone was used to begin a 1998 synthesis of the terpenoid quassin^[8]: The two optical isomers of bromochlorofluoromethane Asymmetric synthesis, also called chiral synthesis, enantioselective synthesis or stereoselective synthesis, is organic synthesis which introduces one or more new and desired elements of chirality. ... A total synthesis is the complete chemical synthesis of complex organic molecules from simple, commercially available (petrochemical) precursors. ... It has been suggested that this article or section be merged into natural product. ... Quassin is a white bitter, crystaline substance extracted from the quassia tree. ...

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Metabolism

In the body, in vivo studies indicate that both enantiomers of carvone are mainly metabolized into dihydrocarvonic acid, carvonic acid and uroterpenolone.^[9] (4R,6S)-(–)-carveol is also formed as a minor product via reduction by NADPH. (4S)-(+)-carvone is likewise converted to (4S,6S)-(+)-carveol.^[10] This mainly occurs in the liver and involves cytochrome P450 oxidase. Carvonic acid or α-methylene-4-methyl-5-oxo-3-cyclohexene-1-acetic acid is a terpenoid, formed by metabolism of carvone in humans. ... Carvonic acid or α-methylene-4-methyl-5-oxo-3-cyclohexene-1-acetic acid is a terpenoid, formed by metabolism of carvone in humans. ... Carveol is a natural terpenoid alcohol that is a constituent of spearmint oil. ... Nicotinamide adenine dinucleotide (NAD+) Nicotinamide adenine dinucleotide (NAD) and nicotinamide adenine dinucleotide phosphate (NADP) are two important coenzymes found in cells. ... Cytochrome P450 Oxidase (CYP2E1) Cytochrome P450 oxidase (commonly abbreviated CYP) is a generic term for a large number of related, but distinct, oxidative enzymes (EC 1. ...

References

1. ^  Simonsen, J. L. (1953) The Terpenes (2nd edition) Vol. 1 Cambridge:Cambridge University Press, pp 394-408.
2. ^  De Carvalho, C. C. C. R; Da Fonseca, M. M. R. "Carvone: Why and how should one bother to produce this terpene" Food Chemistry 2006, 95, 413-422.
3. ^  TJ Leitereg, DG Guadagni, J Harris, TR Mon, ... (1971). "Chemical and sensory data supporting the difference between the odors of the enantiomeric carvones". Journal of Agricultural and Food Chemistry 19 (4): 785. 
4. ^  Laska, M.; Liesen, A.; Teubner, P. American Journal of Physiology- Regulatory Integrative and Comparative Physiology, 1999, 277, R1098-R1103.
5. ^  Hornok, L. Cultivation and Processing of Medicinal Plants, John Wiley & Sons, Chichester, UK, 1992.
6. ^  Wagner, G. Chemische Berichte 1894, 27, 2270.
7. ^  Srikrishna, A.; Jagadeeswar Reddy, T. Tetrahedron, 1998, 54, 11517-11524.
8. ^  (a) Shing, T. K. M.; Jiang, Q; Mak, T. C. W. J. Org. Chem. 1998, 63, 2056-2057. (b) Shing, T. K. M.; Tang, Y. J. Chem. Soc. Perkin Trans. 1 1994, 1625.
9. ^  Engel, W. J. Agric. Food Chem., 2001, 49 (8), 4069-4075.
10. ^  Jager, W.; Mayer, M.; Platzer, P.; Reznicek, G.; Dietrich, H.; Buchbauer, G.; Journal of Pharmacy and Pharmacology 2000, 52, 191-197.

Italic text The Journal of Organic Chemistry (abbreviated as or JOC) is a scientific journal for original contributions of fundamental research in organic and bioorganic chemistry. ...

External links

MSDS