what functional groups are in carvone

Carvone contains a ketone and two alkene functional groups. One of the alkenes is conjugated with the ketone (called a conjugated enone); the other alkene is not conjugated.

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Is carvone a volatile compound?

Apr 08, 2020 · What functional groups are in Carvone? Carvone contains a ketone and two alkene functional groups. One of the alkenes is conjugated with the ketone (called a conjugated enone); the other alkene is not conjugated.

What is the optically active form of L-carvone?

2005-03-26. Carvone is a p-menthane monoterpenoid that consists of cyclohex-2-enone having methyl and isopropenyl substituents at positions 2 and 5, respectively. It has a role as an allergen. It is a member of carvones and a botanical anti-fungal agent.

What is the IR spectrum of carvone?

MFCD00001578. (4R)- (-)-Carvone. Carvol. 5TO7X34D3D. p-Mentha-6,8-dien-2-one. (5R)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-one. (R)-5-Isopropenyl-2-methyl-2-cyclohexenone. (R)-5-isopropenyl-2-methylcyclohex-2-en-1-one. (5R)-2-methyl-5- (1-methylethenyl)-2-cyclohexen-1-one.

What is the product of reduction of carvone?

Group 1: carvone (104)–dihydrocarvones (105)–dihydrocarveol (106)–dihydrocarveol-8,9-epoxide (248)–dihydrobottrospicatols (107)–5-hydroxydihydrocarveols (232) Group 2: carvone (104)–carveols (100)–bottrospicatols (99)–5-hydroxy-cis-carveols (103) Group 3: carvone (104)–5-hydroxycarvone (108)–5-hydroxyneodihydrocarveols 240)

What is the structure of carvone?

What type of compound is carvone?

Is carvone a ketone?

How many functional groups does capsaicin have?

Is carvone a compound?

How many chiral centers does carvone have?

What other sources are there for carvone and limonene?

Is carvone optically active?

What does carvone smell like?

Is methyl a functional group?

Is ethyl a functional group?

Is ether a functional group?

How to treat a contaminated eye?

Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/

What is ICSS dashboard?

The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/ [USEPA; ICSS Dashboard Application; Available from, as of July 7, 2016: http://actor.epa.gov/dashboard/]

How long does it take for L-carvone to biodegrade?

AEROBIC: L-Carvone, present at 100 mg/L, reached 90% biodegradation in 4 weeks using an activated sludge inoculum in the Manometric Respirometry test and was determined to be readily biodegradable (1). / L-Carvone / [ (1) ECHA; Registered Substances. L-p-mentha-1

What is the BCF of 30?

An estimated BCF of 30 was calculated in fish for carvone (SRC), using an estimated log Kow of 3.07 (1) and a regression-derived equation (1) . According to a classification scheme (2), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate (SRC).

How long does carvone react with ozone?

Vapor-phase carvone may also react with ozone, the half-life for this reaction in air is estimated to be about 3 hours. Carvone contains chromophores that absorb at wavelengths >290 nm and, therefore, may be susceptible to direct photolysis by sunlight.

What is carvone oil?

Carvone is found in gingergrass oil and is the main constituent of spearmint oil (1,2). The optically active form D-carvone is found in caraway seed and dill seed oil and it has been isolated from mandarin peel oil (Citrus reticulata blanco, Rutaceae) (1). Optically active form L-carvone is found in spearmint and kuromoji oils (1). The most significant natural sources of carvone are spearmint, dill, and caraway. The term spearmint is applied to various Mentha species including M. cardiaca, M. gracilis, M. spicata, and M. viridis and these usually contain 55-75% of the (R)- (-)-enantiomer. The (S)- (+)-enantiomer is found in dill (Anethum graveolens) at levels of 30-65% and at 50-75% in caraway (Carum carvi) (3).

How does carvone release to the environment?

The optically active form L-carvone 's use as an active ingredient in pesticides will result in its direct release to the environment. Carvone is found naturally in caraway and dill seed oils, mandarin seed oil, spearmint oil, and gingergrass oil. If released to air, an estimated vapor pressure of 0.115 mm Hg at 25 °C indicates carvone will exist solely as a vapor in the atmosphere. Vapor-phase carvone will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 3 hours. Vapor-phase carvone may also react with ozone, the half-life for this reaction in air is estimated to be about 3 hours. Carvone contains chromophores that absorb at wavelengths >290 nm and, therefore, may be susceptible to direct photolysis by sunlight. If released to soil, carvone is expected to have high mobility based upon an estimated Koc of 140. Volatilization from moist soil surfaces may be an important fate process based upon an estimated Henry's Law constant of 7.73X10-5 atm-cu m/mole. Carvone has an estimated vapor pressure of 0.115 mm Hg and exists as a liquid under environmental conditions; therefore, carvone may volatilize from dry soil. Using the optically active form L-carvone in the Manometric Respirometry test, 90% biodegradation of L-carvone was reached in 4 weeks suggesting that biodegradation of carvone may be an important environmental fate process in soil and water. If released into water, carvone is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces may be an important fate process based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 11 hours and 9 days, respectively. An estimated BCF of 30 suggests the potential for bioconcentration in aquatic organisms is moderate. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions (pH 5 to 9). Occupational exposure to carvone may occur through inhalation and dermal contact with this compound at workplaces where carvone is produced or used. Use data indicate that the general population may be exposed to carvone via ingestion of food and dermal contact with consumer products containing carvone. (SRC)

What are the three double bonds in carvone?

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 CeCl 3 ( Luche reduction) is also effective. Hydrazine and potassium hydroxide give limonene ( 6) via a Wolff-Kishner reduction .

What is carvone used for?

As the compound most responsible for the flavor of caraway, dill and spearmint, carvone has been used for millennia in food. Wrigley's Spearmint Gum and spearmint flavored Life Savers are major users of natural spearmint oil from Mentha spicata. Caraway seed is extracted with alcohol to make the European drink Kümmel.

When was carvone first discovered?

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

Is carvone a minor product?

(–)-Carveol is also formed as a minor product via reduction by NADPH. (+)-Carvone is likewise converted to (+)-carveol. This mainly occurs in the liver and involves cytochrome P450 oxidase and (+)-trans-carveol dehydrogenase .

Does carvone react with lithium?

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.

Is carvone a pure substance?

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:

What is carvone essential oil?

Carvone belongs to the subgroup of the monoterpenoids, which can be found in many essential oils [1–3]. (+)-Carvone ( 1) is caraway reminiscent, while its enantiomer (−)-carvone (2) is spearmint-like, and both of them are main components of the corresponding essential oils. A variety of extraction techniques and purification ...

How to extract carvone from herbs?

A variety of extraction techniques and purification of carvone from herbs and spices have been used from traditional soaking and decoction, steam distillation, and Soxhlet extraction to modern ultrasonication and solid-phase extraction methods [4–13]. Ultrasound-assisted extraction gained attention because degradation of herbal constituents was reduced with high-frequency sonication [5]. Supercritical fluid extraction is one of the newer extraction techniques which have become widely used in recent years [4,8,12]. Solid-phase extraction is a method of sample purification that separates and concentrates the carvone from a solution of a crude extract through adsorption onto a disposable solid-phase cartridge [6,7]. There are different types of purification processes: distillation (steam, water, fractional, molecular), solvent extraction (including subcritical and supercritical solvents), membrane technologies (ultrafiltration and reverse osmosis), and preparative chromatography and columns (adsorption and exclusion) [9]. The content of S - (+)-carvone and R - (−)-carvone in some of these oils may range from 50% to 60% which makes their isolation as pure compounds easy [10,11]. Consequently, they are readily available and relatively cheap [3]. The high optical purity and structural characteristics of S - and R -carvone make them ideal chiral starting materials for enantioselective syntheses of various natural and biologically active compounds. It is worth noting that S -carvone itself possesses high-antioxidant activity compared to α-tocopherol [9].

What is carvone used for?

These are mostly used as a folk remedy for diarrhea, acidity, and other gastric disorders. Carvone has a variety of pharmacological effects such as being an antioxidant, antinociceptive, insecticidal, anticancer, and having blood lipid lowering activity. It can be used as prophylaxis of different cardiovascular diseases since it can be included in our daily diet. Carvone is a calcium channel blocker (Yu et al., 2005 ).

What is the alternative to carvone?

In considering carvone replacements, piperidine 13, represented an attractive alternative for further exploration. The initial piperidine analogs were prepared as an approximately 10:1 mixture of diastereomers favoring cis, which were eventually separated and the optimal 3 R ,4 R -configuration established as the series progressed. 15 This template had the potential to address several of the liabilities of the cycloalkyl-derived compounds. First, introduction of a heteroatom in the ring decreased the c log P by at least one unit as compared to similar cyclohexyl compounds. Second, the piperidine nitrogen provided a synthetic handle to rapidly explore SAR in the C-5′ region of the carvone lead. Finally, the introduction of nitrogen in the ring simplified the structures by eliminating a stereocenter present in the carvone series. In pursuing the piperidine series, a concerted effort was made to balance polarity with potency, while attempting to limit the introduction of unnecessary molecular weight. While parameters such as ligand efficiency and lipophilic efficiency (LipE) were not widely known or used at the time of this program, the team's strategy to move to the piperidine series was consistent with the design elements behind LipE. As such, a retrospective analysis of LipE reveals the progress that was made in improving this parameter during this stage of the program; these data are included in Table 25.1.

What is Fig 4.47?

Fig. 4.47. Determination of the carvone content in volatile oil.

How to determine carvone content in volatile oil?

The carvone content in a volatile oil is determined by a method similar to the aldehyde content determination method. Here, the volatile oil is treated with a hydroxylamine solution and then the red-colored solution is titrated with 90% ethanolic KOH solution, with heating on a water bath. Small increments of potassium hydroxide solution are added to neutralize the solution. After 40 min, the final yellow color indicates completion of the reaction. The carvone content is determined from the endpoint. If necessary, the process may be repeated by the addition of 0.5 mL of 0.5 M KOH and then 1 mL 0.5 M KOH (90%) in ethanol is equivalent to 0.1514 g carvone ( Mukherjee, 2002 ). The details of the method are presented in Fig. 4.47.

Which isoprenylation inhibitors are more potent than Mo4?

Carvone (Mo15) and perillic acid ( Mo31 ), which are possible metabolites of Mo4, have more potent inhibitory activity than Mo4 towards the isoprenylation enzymes in rat brain cytosol [42]. The relative effectiveness of 26 menthane-type monoterpenoids for inhibiting protein isoprenylation and cell proliferation has been determined [50]. Many monoterpenoids were found to be more potent than Mo4 as inhibitors of small G protein isoprenylation and cell proliferation. The relative potency of limonene-derived monoterpenoids was found to be: monohydroxyl = ester = aldehyde > thiol > acid = diol = epoxide > triol = unsubstituted. The structure-activity relationship observed among the monoterpenoid isoprenylation inhibitors support a role for small G proteins in cell proliferation [50]. The structure-activity relationships among Mo4 and three hydroxylated derivatives in the prevention of DMBA-induced mammary tumor were studied [53]. Rats were fed control diets or diets with 1% Mo4, carveol ( Mo21 ), sobrerol ( Mo26) or uroterpenol ( Mo27) from 2 weeks before to one week after carcinogen administration. Mo21, Mo26 and Mo27 significantly prolonged tumor latency and decreased tumor yield. Mo26 was the most potent of the monoterpenoids tested, decreasing tumor yield to half that of the control, a level previously achieved with 5% Mo4 diets. Mo26 is thus 5-fold more potent than Mo4 both in enhancing carcinogen excretion and in preventing tumor formation. These data demonstrate that hydroxylation of monoterpenoid affects chemopreventive potential, with 2 hydroxyl groups > 1 > 0. Induction of the detoxifying enzyme GST in several mouse target tissues of anethofuran ( Mo35 ), Mo15, and Mo4 has been reported [54]. The α, β-unsaturated ketone system in Mo15 appeared to be critical for the high enzyme-inducing activity.

What are some examples of chirality?

There are numerous examples of chirality and pharmacological activity. The most interesting examples are flavor-related: carvone and limonene. As shown in Figure 4.20, the (R) stereoisomer of carvone smells like caraway seeds, and the (S) stereoisomer of cavone smells like spearmint.

What is spearmint oil used for?

The spearmint oil, characterized by the high participation of carvone, dihydrocarvone, and their related alcohols and esters, is mainly used in the flavoring of chewing gums, toothpastes, and other oral products. View chapter Purchase book. Read full chapter.

What are essential oils used for?

Some essential oils, and the isolated components from essential oils (such as nerolidol, limonene, cineole, pinene, and carvone), are used to enhance drug delivery (Krishnaiah et al 2006; Krishnaiah et al 2008; Ahad et al 2011; Valgimigli et al 2012; Shen et al 2013 ). Essential oil components appear to enhance drug absorption by interacting with the polar domain of the skin lipids ( Chen et al 2013 ). Some components, such as carvone, can also reverse the permeation enhancement effect so that vital skin barrier function is restored and not permanently changed after the application of dermal enhancers ( Kang et al 2007; Aggarwal et al 2012 ). Some components enhance the permeation of other components; for example, limonene enhances the absorption of citronellol and eugenol ( Schmitt et al 2009) via the skin. Therefore, it is recommended that essential oils are not used on the skin close to conventional drug patch therapy.

What enzyme reduces ketones to ketones?

Enoate reductases are NADH- or NADPH-dependent enzymes that reduce α,β-unsaturated ketones to saturated ketones. When an alkyl group is located in the alpha position, the enzyme shows great stereoselectivity, leading to the 2- R-stereomer as in the case of the reduction of carvones, where (1R ,4 R )-dihydrocarvone and (1 R ,4 S )- iso -dihydrocarvone are obtained from 4 R -carvone and 4 S -carvone, respectively.

What drugs are single enantiomers?

Currently there are also many drugs marketed as single enantiomers, including atorvastatin, simbastatin, pravastatin, and enalapril ( Figure 4.23 ).

What is Figure 4.21?

Figure 4.21. Pharmacological activity of certain drugs based on their configuration, R and S

What is the pharmacological activity of drugs?

The pharmacological activity of drugs depends on how the drugs interact with proteins, enzymes, receptors, nucleic acid, or biomembranes. Figure 4.19 illustrates the interaction between a stereoisomeric drug and biological receptors. The left structure fits well compared with the right one, so the left one is biologically active and the right one is biologically inactive because of the mismatch with biological receptors.

What was TLC performed to verify?

by functional group identification. TLC was also performed to verify isolation of carvone by

What is the temperature of steam distillation?

temperature tables (Table 1 and 2) indicated that the temperature of the vapor of mixture was significantly lower (~87 oC for Caraway seeds and ~101 oC for spearmint leaves) and stayed constant over the collection of 75 mL. This would indicate that the vapor pressure of the system was high enough to cause the vaporization of both the water and carvone from both samples. Thereby, showing the theory of steam distillation discussed in the beginning of the paper.

What is the difference between S and R?

The difference between the (S)- (+)- Carvone and (R)- (-)-Carvone enantiomers can be noted by asymmetric reactions in stereochemical environments, such as the human nose. As a result of this, (R)- (-)-Carvone from spearmint leaves has a characteristic “minty” smell, while (S)- (+)-Carvone has an “earthy” smell. This phenomenon reflects the idea that the human nose has chiral environment and can detect stereochemical differences in compounds. Another difference between the two types of carvones is the direction of the optical activity not the magnitude. Therefore, (S) enantiomer is (+) and R enantiomer is (-). Note that there is no relationship between the direction and the S and R of an enantiomer. Since carvone is chiral it is optically active which means that polarized light waves can either twist counterclockwise or clockwise.

How to isolate carvone from caraway seeds?

In order to isolate the carvone from the caraway seeds and spearmint leaves, steam distillation technique were used. Although, simple and fractional distillation are usually used to separate a mixture of liquids, they are not suitable for isolating liquids with high boiling points and are unstable at high temperature. In this situations, the steam distillation is applicable to substances that are immiscible with water, nonreactive with water, stable at 100 oC, and have a vapor pressure greater than or equal to 5 Torr at 100 oC. Thus, Steam distillation is used to separate volatile organic compounds that are immiscible with water. Carvone, which is nonpolar, is immiscible with water because water gets its polarity from the hydrogen bonds. Water is not linear compound, the lone pairs on the oxygen makes water a bent shape which increases its dipole movement and makes water a polar compound. As a result of immiscibility, the partial pressure of the each compound is independent of the mole fraction of each substance. This can be ascertained from Raoult’s Law, which states that partial pressure (Px) is equal to the mole fraction multiplied by the equilibrium vapor pressure. This means that the total pressure will be higher than the vapor pressure of the volatile component in the mixture, while the boiling point of the immiscible compound is reduced to a level below the boiling point of the lowest boiling point component. Thus, this allows for the immiscible component, carvone, to be collected in the steam distillation process.

What are the two types of carvones?

Carvone is a chemical found in essential oils. It is also found in both caraway seeds and spearmint leave s. This two types of carvones are extremely similar. However, they are not identical – they are enantiomers. Enantiomers are compounds that are mirror images of one another. Caraway seeds have the (S)- (+)-Carvone configuration, while spearmint leaves have the (R)- (-)-Carvone configuration. Each enantiomer of carvone is physically identical to the other and contains many of the same properties (as shown in figure 1), such as molecular formula, color, boiling point, melting point and density. The IR spectra and thin layer chromatography analysis are identical for each enantiomer as well.

Why did Baeyer test for color change?

Yet another test, Baeyer test, was done to support our data which involved dipping the final TLC plate into KMnO 4 in order to see if the color changes from purple to yellowish. This test for the unsaturation number and in the presence of carbon-carbon double bonds, it oxidizes the bonds and turns them into diols hence producing the different color. This test also helped us to clearly see and locate the positions of three spots because they were not visible on the normal TLC plate.

What is the boiling point of a liquid?

In addition, the boiling point of a liquid can be defined as the temperature at which the vapor pressure of a liquid will be equal to the atmospheric pressure, which at normal conditions is about 760 Torr. From the pressure-temperature graph (Figure 2), we can determine that the boiling point of the components of our mixture as separate substances. At 760 Torr, the temperature of the water is about 100oC, the temperature of Limonene is about 180oC, and the temperature of Carvone is about 240oC. Steam distillation utilizes this theory to separate components that have high boiling points, at a reasonable lower temperature.

Overview

Chemical properties

Uses

Stereoisomerism and odor

Occurrence

History

Preparation

Metabolism