Carvones D-carvone

The main constituents of spearmint oil are /-carvone (Fig. 13.12.7) and /-limonene (Fig. 13.12.8). Oil of spearmint contains from 45 to 60% l-carvone, 6 to 20% of alcohols, and 4 to 20% of esters and terpenes, mainly /-limonene and cineole (see Fig. 13.12.4)J2J The optically isomeric form of carvone, d-carvone, is found in oil of caraway and oil of dill. Carvone appears to co-occur with limonene when present in a plant. 

SYNS (+)-CARVONE d(+)-CARVONE (S)-CARVONE (S)-(+)-CARVONE FEMA No. 2249 d-p-MENTHA-6,8,(9)-DIEN-2-ONE d-l-METHYL-4-ISOPROPENYL-6-CYCLOHEXEN-2-ONE (S)-2-METHYL-5-(1-METHYLETHENYL)-2-CYCL0HEXEN-1-ONE... 

Synonyms (+)-Carvone d(+)-Carvone (S)-Carvone d-p-Mentha-6,8,(9)-dien-2-one d-1-Methyl-4-isopropenyl-6-cyclohexen-2-one (S)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-one... 

Butyl lactate Butyl laurate Butyl levulinate N-Butyl-2-methylbutyrate Butylparaben Butyl phenylacetate n-Butyl propionate Butyl salicylate Butyl stearate Butyl sulfide Butyl 10-undecenoate Butyl valerate n-Butyraldehyde n-Butyric acid Cadinene Camphene Caproic acid Caprylic alcohol Carvacrol Carvacryl ethyl ether Carveol 4-Carvomenthenol Carvone d-Carvone cis-Carvone oxide... 

Other synthetics with cost advantages and large volume productions are L-carvone [6485-40-17, the primary component in natural spearmint essence D-carvone [2244-16-8], the primary component in natural diU and caraway anethol [4180-23-8], in place of anise and fennel spices and smaller amounts of thymol [89-83-8] replacing thyme and disulfide synthetics for onion and gadic. AH of these synthetics must be labeled as artificial which may limit their use among consumers. 

Construction of the A ring fragment starts with epoxidation of chiral d-carvone (114) to afford epoxide 115. 

The mammalian olfactory system possesses enormous discriminatory power. It is claimed that humans can perceive many thousands of different odorous molecules, termed odorants. Even slight alterations in the structure of an odorant can lead to profound changes in perceived odor quality. One commonly cited example is carvone, whose L- and D-stereoisomers are perceived as spearmint and caraway, respectively. However, more subtle molecular alterations can also generate striking changes in perception. 

A total synthesis of functionalized 8,14-seco steroids with five- and six-membered D rings has been developed (467). The synthesis is based on the transformation of (S)-carvone into a steroidal AB ring moiety with a side chain at C(9), which allows the creation of a nitrile oxide at this position. The nitrile oxides are coupled with cyclic enones or enol derivatives of 1,3-diketones, and reductive cleavage of the obtained cycloadducts give the desired products. The formation of a twelve-membered ring compound has been reported in the cycloaddition of one of the nitrile oxides with cyclopentenone and as the result of an intramolecular ene reaction, followed by retro-aldol reaction. 

Anethum graveoleus L. Shi Luo (Dill) (fruit, young shoot) Essential oils, d-carvone, dillapiole, limonene, bergapten, umbelliprenin, camphene, dihydrocarvone, dillapiole, dipentene, isomyristicin 48-50 Carminative, stimulant. 

Carum carvi L. Ye Hao (Caraway) (fruit, aerial part) Essential oil, d-carvone, coumarin, chromone, polyacetylene, hemiarin, scopoletin, umbelliferone, d-limonene, phytosterols.48-50-250-450 Carminative, treat stomach pain. 

Carum carvi L. China Essential oil, d-carvone, d-limonene, phytosterols.48 50 Carminative, treat stomach pain. 

Noncarcinogens atropine, benzyl alcohol, benzyl isothiocyanate, benzyl N=34 thiocyanate, biphenyl, d-carvone, codeine, deserpidine,... 

C. Samples were withdrawn every two days from the samples stored at 45 C and every three days from the samples stored at 37 C. Pulled samples were stored in screw cap vials at 0 C until analsis by gas chromatography (GC). The products were monitored for the formation of limonene-1,2-epoxide and L-carvone, both oxidation products of d-limonene (3). 

Cold pressed orange oil contains over 95 by weight monoterpene hydrocarbons. The principal constituent, d-limonene, ranges from 83-97 percent (9), Limonene degradation has been well docu-meted in the literature (LO, 1 1). Anandaraman identified limonene-1,2-epoxide and carvone as two of the earliest degradation products of d-limonene (12, 13). 

The GC was calibrated using a mixture of known quantities of d-limonene, d-limonene oxide (cis and trans), 2-octanone, and carvone. GC analyses were performed by injecting 1 pi samples with 1 40 split (column flow split flow), into a Hewlett-Packard 5840A GC equipped with a flame ionization detector. A fused silica capillary column 50m x 0.25 mm i.d., coated with OV-101 as a liquid phase was used. Column temperature was programmed from 50-250 C at 10 C/min, and helium was used as the carrier gas. 

TERPENELESS OIL. An essential oil from which the teqoene components have been removed by extraction and fractionation, either alone or in combination. The optical activity of the oil is thus reduced. The terpene-less grades are much more highly concentrated than the original oil (15—30 times). Removal of terpenes is necessary to inhibit spoilage, particularly of oils derived from citrus sources. O11 atmospheric oxidation the specific terpenes form compounds that impair the value of the oil for example, d-limonene oxidazes to carvone and y-terpinene to p-cymene. Terpeneless grades of citrus oils are commercially available. 

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