Carvone

This article covers the chemical compound. For the Roman Limes fort see Carvo .

Structural formula
Simplified structural formula without stereochemistry
General
Surname	Carvone
other names	p -Mentha-6,8-dien-2-one 1-methyl-4-isopropenyl-6-cyclohexen-2-one
Molecular formula	C 10 H 14 O
External identifiers / databases
CAS number 99-49-0 ( racemate ) EC number 202-759-5 ECHA InfoCard 100,002,508 PubChem 7439 Wikidata Q416800
properties
Molar mass	150.22 g mol −1
Physical state	liquid
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution H and P phrases H: 317 P: 280-302 + 352-333 + 313
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Carvone (stress on the final syllable: Carv o n ) is a monocyclic monoterpene - ketone and component of essential oils .

Representative

There are two enantiomeric carvones, the ( S ) - (+) - carvone [also called D - (+) - carvone or (+) - carvone for short] and the ( R ) - (-) - carvone [also called L - (-) - Carvone or (-) - Carvone for short].

Enantiomers of carvone
Surname	( S ) - (+) - carvone	( R ) - (-) - carvone
other names	D - (+) - carvone	L - (-) - carvone
Structural formula
CAS number	2244-16-8	6485-40-1
	99-49-0 (racemate)
EC number	218-827-2	229-352-5
ECHA info card	100.017.117	100,026,684
PubChem	16724	439570
Wikidata	Q27889969	Q27089417
PubChem	16724	439570
Brief description	colorless oil, characteristic smell of caraway seeds	colorless oil, characteristic smell of mint
boiling point	228-230 ° C	230-231 ° C
solubility	heavy in water (1300 mg / l at 18 ° C)	practically insoluble in water (20 ° C)
LD 50	3.71 ml kg −1 (rat, perorally )	1640 mg kg −1 (rat, perorally )

Occurrence

Both enantiomeric forms of carvon occur in nature . ( S ) - (+) - Carvone is contained in caraway oil (approx. 94%), dill oil and mandarin peel . The ( R ) enantiomer is found in Krauseminz and Kuromoji oils . The ginger grass oil containing both enantiomeric forms of carvone ( racemate ).

• 

  Real caraway

• 

  Horse mint ( Mentha longifolia )

Manufacturing

( S ) - (+) - Carvone is obtained by steam distillation of caraway seeds and extraction of the distillate.

properties

Like all chiral fragrances , carvone also has different odor types of its enantiomers . The ( S ) - (+) - carvone has a caraway odor, its mirror image ( R ) - (-) - carvone smells like spearmint. Carvone has a germ-inhibiting effect.

Analytics

The qualitative and quantitative determination of the Carvones is possible after adequate sample preparation by coupling capillary gas chromatography and HPLC with mass spectrometry .

safety instructions

( R ) - (-) - Carvone is allergenic.

Web links

• Entry on Carvone. In: Römpp Online . Georg Thieme Verlag, accessed on January 3, 2015.
• Safety data sheets for ( S ) - (+) - Carvone:
  • Data sheet (S) - (+) - Carvon (PDF) from Carl Roth , accessed on January 8, 2008.
  • Data sheet (S) - (+) - Carvon (PDF) from Merck , accessed January 8, 2008.
• Safety data sheets for ( R ) - (-) - Carvone:
  • Data sheet (R) - (-) - Carvon (PDF) from Carl Roth , accessed on January 8, 2008.
  • Data sheet (R) - (-) - Carvon (PDF) from Merck , accessed January 8, 2008.

Individual evidence

1. ↑ ^{a b c d} Entry on (S) -2-methyl-5- (1-methylethenyl) cyclohex-2-en-1-one in the GESTIS substance database of the IFA , accessed on May 9, 2017(JavaScript required) .
2. ↑ ^{a b c d} Entry on (R) -2-methyl-5- (1-methylethenyl) cyclohex-2-en-1-one in the GESTIS substance database of the IFA , accessed on May 9, 2017(JavaScript required) .
3. ↑ Entry on d-carvone in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on June 17, 2017. Manufacturers or distributors can expand the harmonized classification and labeling .
4. ↑ Entry on (S) - (+) - carvone in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on April 1, 2017.
5. ^ Entry on (R) - (-) - carvone in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on April 1, 2017.
6. ↑ G. F. Russel, J. I. Hills: Odor Differences between Enantiomeric Isomers. In: Science . 172, 1971, pp. 1043-1044; doi: 10.1126 / science.172.3987.1043 .
7. ↑ L. Friedmann, J. G. Miller: Odor Incongruity and Chirality. In: Science. 172, 1971, pp. 1044-1046; doi: 10.1126 / science.172.3987.1044 .
8. ↑ Potatoes (Solanum tuberosum) - food .
9. ↑ C. Barba, R. M. Martínez, M. M. Calvo, G. Santa-María, M. Herraiz: Chiral analysis by online coupling of reversed-phase liquid chromatography to gas chromatography and mass spectrometry. In: Chirality. 24 (5), May 2012, pp. 420-426, PMID 22517436 .
10. ^ A. T. Karlberg, K. Magnusson, U. Nilsson: Air oxidation of d-limonene (the citrus solvent) creates potent allergens. In: Contact Dermatitis . 26 (5), 1992, pp. 332-340, PMID 1395597 .