Carvone
Structural formula | ||||||||||||||||
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Simplified structural formula without stereochemistry | ||||||||||||||||
General | ||||||||||||||||
Surname | Carvone | |||||||||||||||
other names |
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Molecular formula | C 10 H 14 O | |||||||||||||||
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properties | ||||||||||||||||
Molar mass | 150.22 g mol −1 | |||||||||||||||
Physical state |
liquid |
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safety instructions | ||||||||||||||||
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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 ).
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
- ↑ 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) .
- ↑ 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) .
- ↑ 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 .
- ↑ Entry on (S) - (+) - carvone in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on April 1, 2017.
- ^ Entry on (R) - (-) - carvone in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on April 1, 2017.
- ↑ 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 .
- ↑ L. Friedmann, J. G. Miller: Odor Incongruity and Chirality. In: Science. 172, 1971, pp. 1044-1046; doi: 10.1126 / science.172.3987.1044 .
- ↑ Potatoes (Solanum tuberosum) - food .
- ↑ 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 .
- ^ 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 .