Carvone

Carvone
Names
	Preferred IUPAC name 2-Methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one
	Other names 2-Methyl-5-(prop-1-en-2-yl)cyclohex-2-enone; 2-Methyl-5-(1-methylethenyl)-2-cyclohexenone; Δ6:8(9)-p-Menthadien-2-one; 1-Methyl-4-isopropenyl-Δ6-cyclohexen-2-one; Carvol (obsolete)
Identifiers
CAS Number	99-49-0 (R/S) ; 6485-40-1 (R) ; 2244-16-8 (S) ;
3D model (JSmol)	(R): Interactive image ; (S): Interactive image ;
ChEBI	CHEBI:38265 ;
ChEMBL	ChEMBL15676 ;
ChemSpider	21106424 (R/S) ; 15855 (S) ; 388655 (R) ;
ECHA InfoCard	100.002.508
KEGG	C01767 ;
PubChem CID	7439 ;
RTECS number	OS8650000 (R); OS8670000 (S);
UNII	75GK9XIA8I (R/S) ; 5TO7X34D3D (R) ; 4RWC1CMS3X (S) ;
CompTox Dashboard (EPA)	DTXSID8047426 ;
	InChI InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3 Key: ULDHMXUKGWMISQ-UHFFFAOYSA-N ; InChI=1/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3 Key: ULDHMXUKGWMISQ-UHFFFAOYAB;
	SMILES (R):O=C1C[C@@H](C\C=C1\C)C(C)=C; (S):O=C1C[C@H](C\C=C1\C)C(C)=C;
Properties
Chemical formula	C10H14O
Molar mass	150.22 g/mol
Appearance	Clear, colorless liquid
Density	0.96 g/cm3
Melting point	25.2 °C (77.4 °F; 298.3 K)
Boiling point	231 °C (448 °F; 504 K) (91 °C @ 5 mmHg)
Solubility in water	Insoluble (cold); Slightly soluble (hot)/soluble in trace amounts
Solubility in ethanol	Soluble
Solubility in diethyl ether	Soluble
Solubility in chloroform	Soluble
Chiral rotation ([α]D)	−61° (R)-Carvone; 61° (S)-Carvone
Magnetic susceptibility (χ)	−92.2×10−6 cm3/mol
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Flammable
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H304, H315, H317, H411
Precautionary statements	P261, P264, P270, P272, P273, P280, P301+P310, P301+P312, P302+P352, P321, P330, P331, P332+P313, P333+P313, P362, P363, P391, P405, P501
NFPA 704 (fire diamond)	1 2 0
Safety data sheet (SDS)	External MSDS
Related compounds
Related ketone	menthone ; dihydrocarvone ; carvomenthone
Related compounds	limonene, menthol,; p-cymene, carveol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Last updated November 17, 2024

Carvone is a member of a family of chemicals called terpenoids.^[2] Carvone is found naturally in many essential oils, but is most abundant in the oils from seeds of caraway (Carum carvi), spearmint (Mentha spicata), and dill.^[3]

Uses

Food applications

Both carvones are used in the food and flavor industry. As the compound most responsible for the flavor of caraway, dill, and spearmint, carvone has been used for millennia in food.^[3] Food applications are mainly met by carvone made from limonene. R-(−)-Carvone is also used for air freshening products and, like many essential oils, oils containing carvones are used in aromatherapy and alternative medicine.

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.^[3]

Insect control

R-(−)-Carvone has been approved by the U.S. Environmental Protection Agency for use as a mosquito repellent.^[4]

Stereoisomerism and odor

Carvone forms two mirror image forms or enantiomers: R-(−)-carvone, has a sweetish minty smell, like spearmint leaves. Its mirror image, S-(+)-carvone, has a spicy aroma with notes of rye, like caraway seeds.^[5]^[6] The fact that the two enantiomers are perceived as smelling different is evidence that olfactory receptors must respond more strongly to one enantiomer than to the other. Not all enantiomers have distinguishable odors. Squirrel monkeys have also been found to be able to discriminate between carvone enantiomers.^[7]

The two forms are also referred to, in older texts, by their optical rotations of laevo (l) referring to R-(−)-carvone, and dextro (d) referring to S-(+)-carvone. Modern naming refers to levorotatory isomers with the sign (-) and dextrorotatory isomers with the sign (+) in the systematic name.

Occurrence

S-(+)-Carvone is the principal constituent (60–70%) of the oil from caraway seeds (Carum carvi),^[8] which is produced on a scale of about 10 tonnes per year.^[3] 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 also the most abundant compound in the essential oil from several species of mint, particularly spearmint oil ( Mentha spicata ), which is composed of 50–80% R-(−)-carvone.^[9] Spearmint is a major source of naturally produced R-(−)-carvone. However, the majority of R-(−)-carvone used in commercial applications is synthesized from R-(+)-limonene.^[10] The R-(−)-carvone 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 trace quantities of carvones.

History

Caraway was used for medicinal purposes by the ancient Romans,^[3] but carvone was probably not isolated as a pure compound until Franz Varrentrapp (1815–1877) obtained it in 1849.^[2]^[11] It was originally called carvol by Schweizer. Goldschmidt and Zürrer identified it as a ketone related to limonene,^[12] and the structure was finally elucidated by Georg Wagner (1849–1903) in 1894.^[13]

Preparation

Carvone can be obtained from natural sources but insufficient is available to meet demand. Instead most carvone is produced from limonene.

The dextro-form, S-(+)-carvone is obtained practically pure by the fractional distillation of caraway oil. The levo-form obtained from the oils containing it usually requires additional treatment to produce high purity R-(−)-carvone. This can be achieved by the formation of an addition compound with hydrogen sulfide, from which carvone may be regenerated by treatment with potassium hydroxide followed by steam distillation.

Carvone may be synthetically prepared from limonene by first treating limonene nitrosyl chloride. Heating this nitroso compound gives carvoxime. Treating carvoxime with oxalic acid yields carvone.^[14] This procedure affords R-(−)-carvone from R-(+)-limonene.

The major use of d-limonene is as a precursor to S-(+)-carvone. The large scale availability of orange rinds, a byproduct in the production of orange juice, has made limonene cheaply available, and synthetic carvone correspondingly inexpensively prepared.^[15]

The biosynthesis of carvone is by oxidation of limonene.

Chemical properties

Reduction

There are three double bonds in carvone capable of reduction; the product of reduction depends on the reagents and conditions used.^[2] 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.

Oxidation

Oxidation of carvone can also lead to a variety of products.^[2] 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.

Conjugate additions

As an α,β;-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.^[16]

Other

Beinng available inexpensively in enantiomerically pure forms, carvone is 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:^[17]

Metabolism

In the body, in vivo studies indicate that both enantiomers of carvone are mainly metabolized into dihydrocarvonic acid, carvonic acid and uroterpenolone.^[18] (–)-Carveol is also formed as a minor product via reduction by NADPH. (+)-Carvone is likewise converted to (+)-carveol.^[19] This mainly occurs in the liver and involves cytochrome P450 oxidase and (+)-trans-carveol dehydrogenase.

Related Research Articles

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">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.

Caraway, also known as meridian fennel and Persian cumin, is a biennial plant in the family Apiaceae, native to western Asia, Europe, and North Africa.

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.

In chemistry, a molecule or ion is called chiral if it cannot be superposed on its mirror image by any combination of rotations, translations, and some conformational changes. This geometric property is called chirality. The terms are derived from Ancient Greek χείρ (cheir) 'hand'; which is the canonical example of an object with this property.

Linalool refers to two enantiomers of a naturally occurring terpene alcohol found in many flowers and spice plants. Together with geraniol, nerol, citronellol, linalool is one of the rose alcohols. Linalool has multiple commercial applications, the majority of which are based on its pleasant scent.

<span class="mw-page-title-main">Limonene</span> Liquid terpene hydrocarbon fragrance and flavor, extract of citrus peel

Limonene is a colorless liquid aliphatic hydrocarbon classified as a cyclic monoterpene, and is the major component in the essential oil of citrus fruit peels. The (+)-isomer, occurring more commonly in nature as the fragrance of oranges, is a flavoring agent in food manufacturing. It is also used in chemical synthesis as a precursor to carvone and as a renewables-based solvent in cleaning products. The less common (-)-isomer has a piny, turpentine-like odor, and is found in the edible parts of such plants as caraway, dill, and bergamot orange plants.

Spearmint is a flavour that is either naturally or artificially created to taste like the oil of the herbaceous Mentha spicata (spearmint) plant.

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

Borneol is a bicyclic organic compound and a terpene derivative. The hydroxyl group in this compound is placed in an endo position. The exo diastereomer is called isoborneol. Being chiral, borneol exists as enantiomers, both of which are found in nature.

Orange oil is an essential oil produced by cells within the rind of an orange fruit. In contrast to most essential oils, it is extracted as a by-product of orange juice production by centrifugation, producing a cold-pressed oil. It is composed of mostly d-limonene, and is often used in place of pure d-limonene. D-limonene can be extracted from the oil by distillation.

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

Humulene, also known as α-humulene or α-caryophyllene, is a naturally occurring monocyclic sesquiterpene (C₁₅H₂₄), containing an 11-membered ring and consisting of 3 isoprene units containing three nonconjugated C=C double bonds, two of them being triply substituted and one being doubly substituted. It was first found in the essential oils of Humulus lupulus (hops), from which it derives its name. Humulene is an isomer of β-caryophyllene, and the two are often found together as a mixture in many aromatic plants.

Carveol is a natural unsaturated, monocyclic monoterpenoid alcohol that is a constituent of spearmint essential oil in the form of cis-(−)-carveol. It is a colorless fluid soluble in oils, but insoluble in water and has an odor and flavor that resemble those of spearmint and caraway. Consequently, it is used as a fragrance in cosmetics and as a flavor additive in the food industry.

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.

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

Fenchone is an organic compound classified as a monoterpenoid and a ketone. It is a colorless oily liquid. It has a structure and an odor similar to those of camphor. Fenchone is a constituent of absinthe and the essential oil of fennel. Fenchone is used as a flavor in foods and in perfumery.

In enzymology, a carveol dehydrogenase (EC 1.1.1.243) is an enzyme that catalyzes the chemical reaction

In enzymology, a (R)-limonene 6-monooxygenase (EC 1.14.13.80) is an enzyme that catalyzes the chemical reaction

In enzymology, a (S)-limonene 6-monooxygenase (EC 1.14.13.48) is an enzyme that catalyzes the chemical reaction

The enzyme (4S)-limonene synthase catalyzes the chemical reaction

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

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. The L-form has been isolated from Sitka spruce.

References

↑ Vollhardt, K. Peter C.; Schore, Neil E. (2007). Organic Chemistry (5th ed.). New York: W. H. Freeman. p. 173.
1 2 3 4 Simonsen, J. L. (1953). The Terpenes. Vol. 1 (2nd ed.). Cambridge: Cambridge University Press. pp. 394–408.
1 2 3 4 5 De Carvalho, C. C. C. R.; Da Fonseca, M. M. R. (2006). "Carvone: Why and how should one bother to produce this terpene". Food Chemistry. 95 (3): 413–422. doi:10.1016/j.foodchem.2005.01.003.
↑ "Document Display (PURL) | NSCEP | US EPA". nepis.epa.gov. Retrieved 2020-11-10.
↑ Theodore J. Leitereg; Dante G. Guadagni; Jean Harris; Thomas R. Mon; Roy Teranishi (1971). "Chemical and sensory data supporting the difference between the odors of the enantiomeric carvones". J. Agric. Food Chem. 19 (4): 785–787. doi:10.1021/jf60176a035.
↑ Morcia, Caterina; Tumino, Giorgio; Ghizzoni, Roberta; Terzi, Valeria (2016). "Carvone (Mentha spicata L.) Oils - Essential Oils in Food Preservation, Flavor and Safety - Chapter 35". Essential Oils in Food Preservation, Flavor and Safety: 309–316. doi:10.1016/B978-0-12-416641-7.00035-3.
↑ Laska, M.; Liesen, A.; Teubner, P. (1999). "Enantioselectivity of odor perception in squirrel monkeys and humans". American Journal of Physiology. Regulatory, Integrative and Comparative Physiology. 277 (4): R1098–R1103. doi:10.1152/ajpregu.1999.277.4.r1098. PMID 10516250.
↑ Hornok, L. Cultivation and Processing of Medicinal Plants, John Wiley & Sons, Chichester, UK, 1992.
↑ Archived 2012-04-10 at the Wayback Machine , Chemical composition of essential oil from several species of mint (Mentha spp.)
↑ Fahlbusch, Karl-Georg; Hammerschmidt, Franz-Josef; Panten, Johannes; Pickenhagen, Wilhelm; Schatkowski, Dietmar; Bauer, Kurt; Garbe, Dorothea; Surburg, Horst (2003). "Flavors and Fragrances". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a11_141. ISBN 978-3-527-30673-2.
↑ Handwörterbuch der reinen und angewandten Chemie [Concise dictionary of pure and applied chemistry] (Braunschweig, (Germany): Friedrich Vieweg und Sohn, 1849), vol. 4, pages 686-688. [Notes: (1) Varrentrapp purified carvone by mixing oil of caraway with alcohol that had been saturated with hydrogen sulfide and ammonia; the reaction produced a crystalline precipitate, from which carvone could be recovered by adding potassium hydroxide in alcohol to the precipitate, and then adding water; (2) Varrentrapp's empirical formula for carvone is incorrect because chemists at that time used the wrong atomic masses for the elements; e.g., carbon (6 instead of 12).]
↑ Heinrich Goldschmidt and Robert Zürrer (1885) "Ueber das Carvoxim," Berichte der Deutschen Chemischen Gesellschaft, 18 : 1729–1733.
↑ Georg Wagner (1894) "Zur Oxydation cyklischer Verbindungen" (On the oxidation of cyclic compounds), Berichte der Deutschen chemischen Gesellschaft zu Berlin, vol. 27, pages 2270-2276. [Notes: (1) Georg Wagner (1849–1903) is the Germanized form of "Egor Egorovich Vagner", who was born in Russia and worked in Warsaw (See brief biography here.); (2) Wagner did not prove the structure of carvone in this paper; he merely proposed it as plausible; its correctness was proved later.]
↑ Rothenberger, Otis S.; Krasnoff, Stuart B.; Rollins, Ronald B. (1980). "Conversion of (+)-Limonene to (−)-Carvone: An organic laboratory sequence of local interest". Journal of Chemical Education. 57 (10): 741. Bibcode:1980JChEd..57..741R. doi:10.1021/ed057p741.
↑ Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe, Horst Surburg "Flavors and Fragrances" in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi : 10.1002/14356007.a11_141.
↑ Srikrishna, A.; Jagadeeswar Reddy, T. (1998). "Enantiospecific synthesis of (+)-(1S, 2R, 6S)-1, 2-dimethylbicyclo [4.3. 0] nonan-8-one and (−)-7-epibakkenolide-A". Tetrahedron. 54 (38): 11517–11524. doi:10.1016/S0040-4020(98)00672-3.
↑ (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. 11994, 1625.
↑ Engel, W. (2001). "In vivo studies on the metabolism of the monoterpenes S-(+)- and R-(−)-carvone in humans using the metabolism of ingestion-correlated amounts (MICA) approach". J. Agric. Food Chem. 49 (8): 4069–4075. doi:10.1021/jf010157q. PMID 11513712.
↑ Jager, W.; Mayer, M.; Platzer, P.; Reznicek, G.; Dietrich, H.; Buchbauer, G. (2000). "Stereoselective metabolism of the monoterpene carvone by rat and human liver microsomes". Journal of Pharmacy and Pharmacology. 52 (2): 191–197. doi: 10.1211/0022357001773841 . PMID 10714949. S2CID 41116690.

External links

Carvone at The Periodic Table of Videos (University of Nottingham)

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[1] Vollhardt, K. Peter C.; Schore, Neil E. (2007). Organic Chemistry (5th ed.). New York: W. H. Freeman. p. 173.

[simonsen-2] 1 2 3 4 Simonsen, J. L. (1953). The Terpenes. Vol. 1 (2nd ed.). Cambridge: Cambridge University Press. pp. 394–408.

[carvalho-3] 1 2 3 4 5 De Carvalho, C. C. C. R.; Da Fonseca, M. M. R. (2006). "Carvone: Why and how should one bother to produce this terpene". Food Chemistry. 95 (3): 413–422. doi:10.1016/j.foodchem.2005.01.003.

[4] "Document Display (PURL) | NSCEP | US EPA". nepis.epa.gov. Retrieved 2020-11-10.

[5] Theodore J. Leitereg; Dante G. Guadagni; Jean Harris; Thomas R. Mon; Roy Teranishi (1971). "Chemical and sensory data supporting the difference between the odors of the enantiomeric carvones". J. Agric. Food Chem. 19 (4): 785–787. doi:10.1021/jf60176a035.

[6] Morcia, Caterina; Tumino, Giorgio; Ghizzoni, Roberta; Terzi, Valeria (2016). "Carvone (Mentha spicata L.) Oils - Essential Oils in Food Preservation, Flavor and Safety - Chapter 35". Essential Oils in Food Preservation, Flavor and Safety: 309–316. doi:10.1016/B978-0-12-416641-7.00035-3.

[7] Laska, M.; Liesen, A.; Teubner, P. (1999). "Enantioselectivity of odor perception in squirrel monkeys and humans". American Journal of Physiology. Regulatory, Integrative and Comparative Physiology. 277 (4): R1098–R1103. doi:10.1152/ajpregu.1999.277.4.r1098. PMID 10516250.

[8] Hornok, L. Cultivation and Processing of Medicinal Plants, John Wiley & Sons, Chichester, UK, 1992.

[Chemical_composition_of_spearmint_oil-9] Archived 2012-04-10 at the Wayback Machine , Chemical composition of essential oil from several species of mint (Mentha spp.)

[Ullmann-10] Fahlbusch, Karl-Georg; Hammerschmidt, Franz-Josef; Panten, Johannes; Pickenhagen, Wilhelm; Schatkowski, Dietmar; Bauer, Kurt; Garbe, Dorothea; Surburg, Horst (2003). "Flavors and Fragrances". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a11_141. ISBN 978-3-527-30673-2.

[11] Handwörterbuch der reinen und angewandten Chemie [Concise dictionary of pure and applied chemistry] (Braunschweig, (Germany): Friedrich Vieweg und Sohn, 1849), vol. 4, pages 686-688. [Notes: (1) Varrentrapp purified carvone by mixing oil of caraway with alcohol that had been saturated with hydrogen sulfide and ammonia; the reaction produced a crystalline precipitate, from which carvone could be recovered by adding potassium hydroxide in alcohol to the precipitate, and then adding water; (2) Varrentrapp's empirical formula for carvone is incorrect because chemists at that time used the wrong atomic masses for the elements; e.g., carbon (6 instead of 12).]

[12] Heinrich Goldschmidt and Robert Zürrer (1885) "Ueber das Carvoxim," Berichte der Deutschen Chemischen Gesellschaft, 18 : 1729–1733.

[13] Georg Wagner (1894) "Zur Oxydation cyklischer Verbindungen" (On the oxidation of cyclic compounds), Berichte der Deutschen chemischen Gesellschaft zu Berlin, vol. 27, pages 2270-2276. [Notes: (1) Georg Wagner (1849–1903) is the Germanized form of "Egor Egorovich Vagner", who was born in Russia and worked in Warsaw (See brief biography here.); (2) Wagner did not prove the structure of carvone in this paper; he merely proposed it as plausible; its correctness was proved later.]

[14] Rothenberger, Otis S.; Krasnoff, Stuart B.; Rollins, Ronald B. (1980). "Conversion of (+)-Limonene to (−)-Carvone: An organic laboratory sequence of local interest". Journal of Chemical Education. 57 (10): 741. Bibcode:1980JChEd..57..741R. doi:10.1021/ed057p741.

[Ullmann2-15] Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe, Horst Surburg "Flavors and Fragrances" in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi : 10.1002/14356007.a11_141.

[Srikrishna1998-16] Srikrishna, A.; Jagadeeswar Reddy, T. (1998). "Enantiospecific synthesis of (+)-(1S, 2R, 6S)-1, 2-dimethylbicyclo [4.3. 0] nonan-8-one and (−)-7-epibakkenolide-A". Tetrahedron. 54 (38): 11517–11524. doi:10.1016/S0040-4020(98)00672-3.

[17] (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. 11994, 1625.

[18] Engel, W. (2001). "In vivo studies on the metabolism of the monoterpenes S-(+)- and R-(−)-carvone in humans using the metabolism of ingestion-correlated amounts (MICA) approach". J. Agric. Food Chem. 49 (8): 4069–4075. doi:10.1021/jf010157q. PMID 11513712.

[19] Jager, W.; Mayer, M.; Platzer, P.; Reznicek, G.; Dietrich, H.; Buchbauer, G. (2000). "Stereoselective metabolism of the monoterpene carvone by rat and human liver microsomes". Journal of Pharmacy and Pharmacology. 52 (2): 191–197. doi: 10.1211/0022357001773841 . PMID 10714949. S2CID 41116690.

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