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Topic: Carvone

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	Molecule of the Day » Blog Archive » Carvone (You can smell chirality!)
		It’s also worth noting: carvones don’t just “smell like” caraway and spearmint, they are the flavors of caraway and spearmint.
		Also neat is that the same biochemical pathway, the HMG-CoA reductase pathway, produces molecules as diverse as carvone, cholesterol, carotene, and chlorophyll.
		Grapefruit mercaptan is such a singular compound because it is a nice-smelling thiol.
	www.moleculeoftheday.com /2006/05/12/carvone-you-can-smell-chirality (441 words)

	468. Carvone, d- and carvone, 1- (WHO Food Additives Series 14)
		Carvone was metabolized by the rabbit to 1,5-dimethyl-1,5- hexadien-1,6-dicarboxylic acid and a carbinol in which one ethylene linkage was saturated and the keto group was reduced (Fischer & Bielig, 1940; Opdyke, 1973; Opdyke, 1978).
		Carvone was found to be present in the urine of healthy adult humans (Zlatkis & Liebich, 1971; Zlatkis et al., 1973).
		Survival was depressed in the case of (+) carvone to approximately 80%, and in the case of (-) carvone to approximately 60% (Stoner et al., 1973).
	www.inchem.org /documents/jecfa/jecmono/v14je04.htm (738 words)

	Opopaea fosuma (Site not responding. Last check: 2007-10-29)
		Carvone, a natural compound from caraway seeds, was incorporated into mulch to reduce its inherent volatility.
		Moreover at the highest concentration of carvone (0.75 ml/l mulch) 50 % mortality was recorded over a period of 5 days, indicating a clear molluscicidal effect.
		The incorporation of a higher carvone concentration into mulch is still to be tested to confirm whether carvone-treated mulch can be recommended as an effective alternative approach to chemical slug control.
	zoology.unibe.ch /ecol/publ/abstracts/02-11.htm (198 words)

	Spartanburg SC \| GoUpstate.com \| Spartanburg Herald-Journal (Site not responding. Last check: 2007-10-29)
		Carvone is found naturally in many essential oils, but is most abundant in the oils from seeds of caraway (Carum Carvi) and dill.
		Carvone is available inexpensively in both enantiomerically pure forms, making it an attractive starting material for the asymmetric total synthesis of natural products.
		In the body, in vivo studies indicate that both enantiomers of carvone are mainly metabolized into dihydrocarvonic acid, carvonic acid and uroterpenolone.
	www.goupstate.com /apps/pbcs.dll/section?category=NEWS&template=wiki&text=L-Carvone (799 words)

	EJPAU 2005. BORTNOWSKA G. INFLUENCE OF OIL SUBSTITUTION BY INULIN ON THE HEADSPACE CONCENTRATIONS OF CARVONE AND ...
		Changes in carvone and limonene (the two major volatile substances producing odour in caraway) release to the model mixture headspace were assessed by comparing chromatographic peak areas of the substances relative to carvonene and limonene chromatographic peak areas in the control sample (without oil and/or inulin) headspace, similarly to [4].
		In addition, the amounts of carvone and limonene released from those model mixtures were higher in the caraway seed-flavoured samples than in the natural caraway flavouring-enriched ones, the difference being particularly pronounced at equivalent of fat component concentration lower than 5%, i.e., inulin concentrations of 1% at the maximum.
		The amounts of carvone and limonene in the headspace of model mixtures containing 3% and 5% equivalent of fat component concentrations, in which 80% of oil were replaced by inulin, were almost twice as high when the mixtures were flavoured with caraway seeds, compared to adding natural caraway flavouring.
	www.ejpau.media.pl /volume8/issue4/art-80.html (3398 words)

	ARS \| Publication request: Growth, Morphogenesis and Essential Oil Production in Mentha Spicata L. Shoots in Vitro
		Carvone is only produced from the foliar regions of cultured plants and was absent in callus and roots.
		However, carvone concentrations in shoots grown on agar were higher than in shoots grown on liquid medium.
		Carvone concentrations decreased in spearmint shoots grown in the APCS as the distance from the shoot terminus increased.
	www.ars.usda.gov /research/publications/publications.htm?seq_no_115=181915 (564 words)

	Biosynthesis of the Monoterpenes Limonene and Carvone in the Fruit of Caraway . I. Demonstration of Enzyme Activities ...
		Biosynthesis of the Monoterpenes Limonene and Carvone in the Fruit of Caraway.
		The biosynthesis of the monoterpenes limonene and carvone in the fruit of caraway (Carum carvi L.) proceeds from geranyl diphosphate
		For both caraway forms, accumulation of limonene and carvone in the fruits is a developmentally regulated process.
	www.plantphysiol.org /cgi/content/full/117/3/901 (6522 words)

	vgn-ext-hidden_PubMed (Site not responding. Last check: 2007-10-29)
		The antifungal activity of Artemisia herba alba was found to be associated with two major volatile compounds isolated from the fresh leaves of the plant.
		Carvone and piperitone were isolated and identified by GC/MS, GC/IR, and NMR spectroscopy.
		The antifungal activity (IC(50)) of the purified compounds was estimated to be 5 micro g/ml, 2 micro g/ml against Penicillium citrinum and 7 micro g/ml, 1.5 micro g/ml against Mucora rouxii carvone and piperitone, respectively.
	www.asco.org /portal/site/ASCO/menuitem.a3fb42726842a82627c4c291ee37a01d/?vgnextoid=d70b3608f9958010VgnVCM100000f2730ad1RCRD&index=n&pmid=16484084 (152 words)

	ARS \| Publication request: Influence of Physical Parameters on the Growth, Morphogenesis, and Volatile Monoterpene ...
		Carvone levels were unaffected by any of the tested physical support treatments.
		Carvone was only produced from cultured spearmint shoots and was absent in either roots or callus cultures.
		Carvone levels decreased proportionally in spearmint shoots as the distance from the shoot terminus increased for plantlets grown in either the culture tubes or the APCS.
	www.ars.usda.gov /research/publications/publications.htm?SEQ_NO_115=161408 (415 words)

	Infotrieve Online
		Effect of nerodilol and carvone on in vitro permeation of nicorandil across rat epidermal membrane.
		The objective of the study was to investigate the effect of nerodilol and carvone on the in vitro transdermal delivery of nicorandil so as to fabricate a membrane-moderated transdermal therapeutic system.
		It was concluded that the terpenes, nerodilol and carvone, produced a marked penetration enhancing effect on the transdermal delivery of nicorandil that could be used in the fabrication of membrane-moderated transdermal therapeutic systems.
	www4.infotrieve.com /newmedline/detail.asp?NameID=16638680&Session=&searchQuery=Chandrasekhar&count=557 (291 words)

	Carvone (Site not responding. Last check: 2007-10-29)
		Carvone is found in large quantities in many essential oils.
		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 sulfuretted hydrogen, decomposing this by alcoholic potash, and distilling the product in a current of steam.
		The carvones are used in the food and flavor industry.
	www.guideofpills.com /Carvone.html (420 words)

	[No title] (Site not responding. Last check: 2007-10-29)
		The enantiomeric compositions of limonene, carvone and carveols were determined in hydrodistillates and hexane extracts of seeds of dill (Anethum graveolens), and annual and biennial caraway (Carum carvi).
		The correlations between enantiomers of limonene and carvone and the implications for the pathways of limonene and carvone formation in dill and caraway are discussed.
		As the enantiomeric composition of carvone is similar for dill, and annual and biennial caraway, all three are equally suited as carvone suppliers for sprouting inhibition in potatoes.
	libnts.avrdc.org.tw /scripts/minisa.dll/144/VAVLIB/VAVLIB_WEB_REPORT/SISN+36812?COMMANDSEARCH (313 words)

	Caraway
		The carvone content of caraway seed is said to be higher when the crop is grown under moist conditions.
		It was thought possible that carvone could also be used to replace maleic hydroxide for sprouting suppression of onions.
		However, carvone is applied to potatoes in storage whereas maleic hydrazide is applied to onions in the field.
	www.ienica.net /crops/caraway.htm (1578 words)

	Reference.com/Encyclopedia/Carvone
		Carvone forms two mirror image forms or enantiomers: S-(+)-carvone smells like caraway.
		The biosynthesis of carvone is by oxidation of limonene.
		Carvone may be cleaved using ozone followed by steam, giving dilactone 9, while KMnO
	www.reference.com /browse/wiki/Carvone (836 words)

	Infotrieve Online
		Carvone has previously been found to highly inhibit its own production at concentrations above 50 mM during conversion of a diastereomeric mixture of (-)-carveol by whole cells of Rhodococcus erythropolis.
		Adaptation of the cells to the presence of increasing concentrations of carveol and carvone in n-dodecane prior to biotransformation proved successful in overcoming carvone inhibition.
		After an incubation period of 268 h, a final carvone concentration of 1.03 M could be attained, together with high productivity [0.19 mg carvone h(-1) (ml organic phase)(-1)] and high yield (0.96 g carvone g carveol(-1)).
	www4.infotrieve.com /newmedline/detail.asp?NameID=15841371&Session=&searchQuery=Poretti&count=60 (169 words)

	Spatially Organized Response Zones in Rat Olfactory Epithelium -- Scott et al. 77 (4): 1950 -- Journal of ...
		The comparison of carvone, limonene, and cineole was tested in eight animals with the electrodes arrayed along the anterior
		The response to carvone was larger on electrode
		The cineole curves were not parallel to either the limonene or carvone curves and tended to show a pronounced peak at the
	jn.physiology.org /cgi/content/full/77/4/1950 (6948 words)

	Directory of open access journals
		In this study, carvone-scend clones of selected mint (Mentha sp.) from Turkey were studied for their yield, essential oil through field experiments in Randomized Block Design under semi-arid conditions in 1999 and 2000 in Central Anatolia of Turkey.
		Carvone content ranged from 78.3 to 82.2% for Clone 12 (M.
		Based on the results, the clones with high herbage yields and high essential oil and carvone contents are selected and used in the further variety improvements studies.
	www.doaj.org /doaj?func=abstract&id=181707&recNo=3&toc=1 (197 words)

	intas 93-3537 (Site not responding. Last check: 2007-10-29)
		The conversion of carvone into steroid skeletons was investigated and several new approaches based on the reactivity of silyl enol ethers of carvone have been investigated.
		The utility of carvone as starting material in the synthesis of sesquiterpenes has led to a new approach for the synthesis of cadinanes.
		It proved to be possible to add silyl enol ethers to the enone function in carvone or in methyl cyclopentenone in such a way that simultaneously the protecting silyl group is transferred to the former enone carbonyl group of carvone or methyl cyclopentenone.
	www.intas.be /catalog/93-3537.htm (898 words)

	Evaluation of Oil Compositions of Iranian Mints (Mentha ssp.) Journal of Essential Oil Research: JEOR - Find Articles
		Carvone, dihydrocarvone and their related compounds carveol, carvyl acetate, dihydrocarveol, and dihydrocarvyl acetate have been found as main components in a number of spearmint oils (4,5).
		The oil of M. spicata from Cuba was shown to be rich in piperitenone oxide (52.3%) (8).
		Carvone and dihydrocarvone have been reported as main constituents of the oils of M. longifolia plants growing in Italy, England and Turkey (9).
	www.findarticles.com /p/articles/mi_qa4091/is_200503/ai_n13505305 (753 words)

	botanical.com - A Modern Herbal \| Dill - Herb Profile and Information
		In spite of the difference in odour between Dill and Caraway oils, the composition of the two is almost identical, both consisting nearly entirely of limonene and carvone.
		English-distilled oils usually have the highest specific gravity, from 0.910 to 0.916, and are consequently held in the highest esteem.
		The oils from both Japanese and Indian dill differ from European dill oil, in having a higher specific gravity (0.948 to 0.968), which is ascribed to the presence of dill apiol, and in containing much less carvone than the European oil.
	www.botanical.com /botanical/mgmh/d/dill--13.html (1518 words)

	Guardian \| The appliance of science
		One of them includes a molecule called carvone, which comes in two forms, carvone + and carvone -.
		If you were to look at a diagram of carvone +, you'd see it is the mirror image of carvone -.
		Carvone is the key molecule in caraway, the distinctive flavouring of German and Scandinavian dishes.
	www.guardian.co.uk /print/0,,5150290-103425,00.html (297 words)

	Sensitivity-dependent Hierarchical Receptor Codes for Odors -- Hamana et al. 28 (2): 87 -- Chemical Senses
		Amino acid sequence similarities among the 25 carvone ORs (colored in red and marked with triple asterisks) responsive to enantiomeric carvones were compared with the other 97 murine ORs for the TM3—TM6 regions using the Clustal X program.
		Some of the carvone ORs were clustered in neighborhoods, indicating that they are more similar to one another than to other ORs.
		D3 (with double asterisks) was reported to be responsive to the carvones.
	chemse.oxfordjournals.org /cgi/content/full/28/2/87 (8273 words)

	Metabolism of carveol and dihydrocarveol in Rhodococcus erythropolis DCL14 -- van der Werf and Boot 146 (5): 1129 -- ...
		carvone reductase activity, indicating that the cofactor is
		Conversion of carvone under anaerobic conditions by cell extracts of (4R)-carveol-grown cells of R.
		Hirata, T., Hamada, H., Aoki, T. and Suga, T. Stereoselectivity of the reduction of carvone and dihydrocarvone by suspensions of cells of Nicotiana tabacum.
	mic.sgmjournals.org /cgi/content/full/146/5/1129 (4221 words)

	Perceptual Correlates of Neural Representations Evoked by Odorant Enantiomers -- Linster et al. 21 (24): 9837 -- ...
		Carvone differs from limonene by possessing a single ketone functional group, whereas terpinen-4-ol differs from limonene by possessing a hydroxyl group at the chiral carbon and by lacking a double bond in its isopropyl group.
		Individual pseudocolor-enhanced autoradiograph sections are shown for one bulb of each rat exposed to carvone enantiomers.
		the neural representations of carvone enantiomers in a dorsal
	www.jneurosci.org /cgi/content/full/21/24/9837 (4143 words)

	Grob-type fragmentation of a carvone derived beta-hydroxymesylate: application to the synthesis of chiral lavandulol ... (Site not responding. Last check: 2007-10-29)
		Grob-type fragmentation of a carvone derived beta-hydroxymesylate: application to the synthesis of chiral lavandulol derivatives
		Mehta, Goverdhan and Karmakar, Swastik and Chattopadhyay, Shital K (2004) Grob-type fragmentation of a carvone derived beta-hydroxymesylate: application to the synthesis of chiral lavandulol derivatives.
		Grob-type fragmentation of the carvone derived diol-monosulphonate 5 has been utilised for the enantioselective synthesis of various lavandulol derivatives
	eprints.iisc.ernet.in /archive/00000416 (109 words)

	About Sun West Ingredients - Producers of Essential Oils
		Along with flavor, fragrance, taste and smell, carvone is the standard by which dill oil is measured.
		As with any plant, slightly differing soil conditions, variations in the weather, time of harvest, and other factors affect the carvone produced from crop to crop.
		Sun West utilizes these natural variations to adjust carvone levels to meet your specifications, while maintaining the natural consistency of the oil and its all-natural composition.
	www.sunwestingredients.com /aboutsunwest.html (317 words)

	Chem2OA3 - Experiment 2 - Isolation of Natural Products (Site not responding. Last check: 2007-10-29)
		Another example of chiral recognition can be found in the toxicity of the two carvone isomers; the toxicity of (+)-carvone in rats is 400 times greater than that of (-)-carvone.
		Ideally, you should connect the gas collection tube just before the carvone elutes from the column and remove the tube as soon as all the carvone has been collected.
		In this method, a GC peak is approximated as a triangle, the area of which is proportional to the amount of material detected.
	www.chemistry.mcmaster.ca /courses/2oa3/labmanual_2002-03/2oa3_exp2.html (3338 words)

	Olfactory Discrimination Ability of Human Subjects for Ten Pairs of Enantiomers -- Laska and Teubner 24 (2): 161 -- ...
		Hormann, C.A. and Cowart, B.J. Olfactory discrimination of carvone enantiomers.
		Jones, F.N. and Velasquez, V. Effect of repeated discrimination on the identifiability of the enantiomers of carvone.
		Pike, L.M., Enns, M.P. and Hornung, D.E. Intensity effects on the odor of the enantiomers of carvone.
	chemse.oxfordjournals.org /cgi/content/full/24/2/161 (5379 words)

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