D-Carvone

Formula: C₁₀H₁₄O
Molecular weight: 150.2176
IUPAC Standard InChI: InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3/t9-/m1/s1
IUPAC Standard InChIKey: ULDHMXUKGWMISQ-SECBINFHSA-N
CAS Registry Number: 2244-16-8
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript.
Stereoisomers:
- (-)-Carvone
- Carvone
Other names: D-(+)-Carvone; 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (S)-; p-Mentha-6,8-dien-2-one, (S)-(+)-; (+)-Carvone; (S)-(+)-Carvone; (S)-Carvone; Carvone, (+)-; d-p-Mentha-6,8(9)-dien-2-one; d-1-Methyl-4-isopropenyl-6-cyclohexen-2-one; 5-Isopropenyl-2-methyl-2-cyclohexen-1-one, (S)-; (S)-(+)-p-Mentha-6,8-dien-2-one; 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)-, (5S)-; l-carvone; (+)-(4S)-carvone; (+)-Carvon; (S)-2-methyl-5-(1-methylvinyl)cyclohex-2-en-1-one
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Other data available:
- Phase change data
- Mass spectrum (electron ionization)
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IR Spectrum

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Data compiled by: Coblentz Society, Inc.

SOLUTION (10% CCl4 FOR 4000-1330, 10% CS2 FOR 1330-450 CM^-1) VS SOLVENT; CARY 90 (GRATING); 2 cm^-1 resolution

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Gas Chromatography

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Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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Column type	Active phase	Temperature (C)	I	Reference	Comment
Capillary	ZB-1	100.	1212.83	Hoskovec, Grygarová, et al., 2005	30. m/0.32 mm/0.25 μm, He
Capillary	ZB-1	110.	1216.93	Hoskovec, Grygarová, et al., 2005	30. m/0.32 mm/0.25 μm, He
Capillary	ZB-1	120.	1221.14	Hoskovec, Grygarová, et al., 2005	30. m/0.32 mm/0.25 μm, He
Capillary	ZB-1	130.	1225.42	Hoskovec, Grygarová, et al., 2005	30. m/0.32 mm/0.25 μm, He
Capillary	ZB-1	140.	1229.89	Hoskovec, Grygarová, et al., 2005	30. m/0.32 mm/0.25 μm, He
Capillary	ZB-1	150.	1234.47	Hoskovec, Grygarová, et al., 2005	30. m/0.32 mm/0.25 μm, He
Capillary	ZB-1	160.	1239.	Hoskovec, Grygarová, et al., 2005	30. m/0.32 mm/0.25 μm, He
Capillary	ZB-1	50.	1194.54	Hoskovec, Grygarová, et al., 2005	30. m/0.32 mm/0.25 μm, He
Capillary	ZB-1	60.	1197.94	Hoskovec, Grygarová, et al., 2005	30. m/0.32 mm/0.25 μm, He
Capillary	ZB-1	70.	1201.12	Hoskovec, Grygarová, et al., 2005	30. m/0.32 mm/0.25 μm, He
Capillary	ZB-1	80.	1205.05	Hoskovec, Grygarová, et al., 2005	30. m/0.32 mm/0.25 μm, He
Capillary	ZB-1	90.	1208.89	Hoskovec, Grygarová, et al., 2005	30. m/0.32 mm/0.25 μm, He

Kovats' RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	OV-101	1223.	Padrayuttawat, Tamura, et al., 1996	50. m/0.25 mm/0.2 μm, N2, 2. K/min, 200. C @ 60. min; T_start: 80. C

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	ZB-5	1238.	Ruiz Perez-Cacho, Mahattanatawee, et al., 2007	30. m/0.32 mm/0.5 μm, He, 7. K/min, 265. C @ 5. min; T_start: 40. C
Capillary	ZB-5	1242.	Mahattanatawee, Rouseff, et al., 2005	30. m/0.32 mm/0.5 μm, He, 7. K/min, 265. C @ 5. min; T_start: 40. C
Capillary	DB-5	1254.	Högnadóttir and Rouseff, 2003	30. m/0.32 mm/0.5 μm, 7. K/min, 265. C @ 5. min; T_start: 40. C
Capillary	DB-5	1256.	Högnadóttir and Rouseff, 2003	30. m/0.32 mm/0.5 μm, 7. K/min, 265. C @ 5. min; T_start: 40. C
Capillary	CP Sil 8 CB	1240.	Chevance and Farmer, 1999	60. C @ 5. min, 4. K/min, 220. C @ 30. min; Column length: 50. m; Column diameter: 0.32 mm

Van Den Dool and Kratz RI, non-polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	BPX-5	1257.	Dharmawan, Kasapis, et al., 2007	30. m/0.25 mm/0.25 μm, He; Program: 35C => 4C/min => 200C => 30C/min => 300C (3min)
Capillary	DB-5	1246.	Wang, Finn, et al., 2005	30. m/0.32 mm/1. μm, He; Program: 40C(2min) => 5C/min => 100C => 4C/min => 230C (10min)
Capillary	DB-5	1234.	Klesk and Qian, 2003	30. m/0.25 mm/0.25 μm, He; Program: 40C(2min) => 5C/min => 100C => 4C/min => 230C(10min)
Capillary	DB-5	1249.	Klesk and Qian, 2003, 2	30. m/0.32 mm/1. μm, He; Program: 40C(2min) => 2C/min => 100C => 10C/min => 230C (5min)

Van Den Dool and Kratz RI, polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1752.	Ruiz Perez-Cacho, Mahattanatawee, et al., 2007	30. m/0.32 mm/0.5 μm, He, 7. K/min, 240. C @ 5. min; T_start: 40. C
Capillary	DB-Wax	1740.	Choi, 2005	60. m/0.25 mm/0.25 μm, N2, 70. C @ 2. min, 2. K/min, 230. C @ 20. min
Capillary	DB-Wax	1747.	Mahattanatawee, Rouseff, et al., 2005	30. m/0.32 mm/0.5 μm, He, 7. K/min, 240. C @ 5. min; T_start: 40. C
Capillary	DB-Wax	1751.	Högnadóttir and Rouseff, 2003	30. m/0.32 mm/0.5 μm, 7. K/min, 240. C @ 5. min; T_start: 40. C
Capillary	DB-Wax	1744.	Choi and Sawamura, 2000	60. m/0.25 mm/0.25 μm, N2, 70. C @ 2. min, 2. K/min, 230. C @ 20. min
Capillary	CP-Wax 52CB	1714.	Chevance and Farmer, 1999	60. C @ 5. min, 4. K/min, 220. C @ 30. min; Column length: 50. m; Column diameter: 0.32 mm
Capillary	CP-Wax 52CB	1718.	Chevance and Farmer, 1999, 2	60. C @ 5. min, 4. K/min, 220. C @ 30. min; Column length: 50. m; Column diameter: 0.32 mm
Capillary	DB-FFAP	1717.	Guillard, le Quere, et al., 1997	H2, 3. K/min; Column length: 30. m; Column diameter: 0.32 mm; T_start: 40. C; T_end: 220. C
Capillary	DB-FFAP	1719.	Guillard, le Quere, et al., 1997	H2, 3. K/min; Column length: 30. m; Column diameter: 0.32 mm; T_start: 40. C; T_end: 220. C

Van Den Dool and Kratz RI, polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	Stabilwax	1745.	Wang, Finn, et al., 2005	30. m/0.32 mm/1. μm, He; Program: 40C(2min) => 5C/min => 100C => 4C/min => 230C (10min)
Capillary	Stabilwax	1749.	Klesk and Qian, 2003	30. m/0.32 mm/1. μm, He; Program: 40C(2min) => 5C/min => 100C => 4C/min => 230C(10min)
Capillary	DB-Wax	1751.	Klesk and Qian, 2003, 2	30. m/0.25 mm/0.5 μm, He; Program: 40C(2min) => 2C/min => 100C => 10C/min => 230C (5min)

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	DB-5	1245.	Choi, 2006	30. m/0.25 mm/0.25 μm, N2, 70. C @ 2. min, 2. K/min, 230. C @ 20. min
Capillary	DB-5	1242.	Agnihotri, Thappa, et al., 2004	30. m/0.25 mm/0.25 μm, He, 90. C @ 2. min, 7. K/min, 220. C @ 5. min
Capillary	DB-1	1222.	Choi, 2004	60. m/0.25 mm/0.25 μm, N2, 70. C @ 2. min, 2. K/min, 230. C @ 20. min
Capillary	ZB-5	1263.	Jürgens and Dötterl, 2004	60. m/0.25 mm/0.25 μm, He, 40. C @ 4.6 min, 6. K/min, 260. C @ 1. min
Capillary	RSL-200	1231.	Jirovetz, Buchbauer, et al., 2003	30. m/0.25 mm/0.25 μm, H2, 40. C @ 2. min, 6. K/min, 280. C @ 10. min
Capillary	DB-1	1270.	Hedin, McKibben, et al., 2000	30. m/0.32 mm/0.25 μm, 45. C @ 2. min, 15. K/min, 300. C @ 5. min
Capillary	OV-101	1228.	Egolf and Jurs, 1993	2. K/min; Column length: 50. m; Column diameter: 0.22 mm; T_start: 80. C; T_end: 200. C
Capillary	SPB-5	1249.	King and Knight, 1992	8. K/min; Column length: 30. m; Phase thickness: 1.0 μm; T_start: 50. C; T_end: 250. C

Normal alkane RI, non-polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	HP-1	1210.	Carpino, Mallia, et al., 2004	12. m/0.32 mm/0.52 μm; Program: 35C(3min) => 6C/min => 190C => 30C/min => 225C

Normal alkane RI, polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1748.	Choi, 2006	60. m/0.25 mm/0.25 μm, N2, 70. C @ 2. min, 2. K/min, 230. C @ 20. min
Capillary	DB-Wax	1728.	Lee, Umano, et al., 2005	30. m/0.25 mm/0.25 μm, He, 3. K/min, 180. C @ 40. min; T_start: 50. C
Capillary	DB-Wax	1741.	Choi, 2004	60. m/0.25 mm/0.25 μm, N2, 70. C @ 2. min, 2. K/min, 230. C @ 20. min
Capillary	DB-Wax	1721.	Umano, Hagi, et al., 2002	60. m/0.25 mm/0.25 μm, He, 40. C @ 2. min, 2. K/min; T_end: 200. C
Capillary	DB-Wax	1729.	Umano, Hagi, et al., 2000	60. m/0.25 mm/0.25 μm, He, 40. C @ 2. min, 2. K/min; T_end: 200. C
Capillary	Carbowax 20M	1715.	Egolf and Jurs, 1993	2. K/min; Column length: 80. m; Column diameter: 0.2 mm; T_start: 70. C; T_end: 170. C

References

Go To: Top, IR Spectrum, Gas Chromatography, Notes

Hoskovec, Grygarová, et al., 2005
Hoskovec, Michal; Grygarová, Dana; Cvacka, Josef; Streinz, Ludvík; Zima, Jirí; Verevkin, Sergey P.; Koutek, Bohumír, Determining the vapour pressures of plant volatiles from gas chromatographic retention data, Journal of Chromatography A, 2005, 1083, 1-2, 161-172, https://doi.org/10.1016/j.chroma.2005.06.006 . [all data]

Padrayuttawat, Tamura, et al., 1996
Padrayuttawat, A.; Tamura, H.; Yamao, M., A split injection system for the analysis of purge and trap headspace of the volatile components in Citrus sudachi, J. Hi. Res. Chromatogr., 1996, 19, 6, 365-369, https://doi.org/10.1002/jhrc.1240190613 . [all data]

Ruiz Perez-Cacho, Mahattanatawee, et al., 2007
Ruiz Perez-Cacho, P.; Mahattanatawee, K.; Smoot, J.M.; Rouseff, R., Identification of Sulfur Volatiles in Canned Orange Juices Lacking Orange Flavor, J. Agric. Food Chem., 2007, 55, 14, 5761-5767, https://doi.org/10.1021/jf0703856 . [all data]

Mahattanatawee, Rouseff, et al., 2005
Mahattanatawee, K.; Rouseff, R.; Filomena Valim, M.; Naim, M., Identification and aroma impact of norisoprenoids in orange juice, J. Agric. Food Chem., 2005, 53, 2, 393-397, https://doi.org/10.1021/jf049012k . [all data]

Högnadóttir and Rouseff, 2003
Högnadóttir, Á.; Rouseff, R.L., Identification of aroma active compounds in organce essence oil using gas chromatography-olfactometry and gas chromatography-mass spectrometry, J. Chromatogr. A, 2003, 998, 1-2, 201-211, https://doi.org/10.1016/S0021-9673(03)00524-7 . [all data]

Chevance and Farmer, 1999
Chevance, F.F.V.; Farmer, L.J., Identification of major volatile odor compounds in frankfurters, J. Agric. Food Chem., 1999, 47, 12, 5151-5160, https://doi.org/10.1021/jf990515d . [all data]

Dharmawan, Kasapis, et al., 2007
Dharmawan, J.; Kasapis, S.; Curran, P.; Johnson, J.R., Characterization of volatile compounds in selected citrus fruits from Asia. Part I: freshly-squeezed juice, Flavour Fragr. J., 2007, 22, 3, 228-232, https://doi.org/10.1002/ffj.1790 . [all data]

Wang, Finn, et al., 2005
Wang, Y.; Finn, C.; Qian, M.C., Impact of Growing Environment on Chickasaw Blackberry ( Rubus L.) Aroma Evaluated by Gas Chromatography Olfactometry Dilution Analysis, J. Agric. Food Chem., 2005, 53, 9, 3563-3571, https://doi.org/10.1021/jf048102m . [all data]

Klesk and Qian, 2003
Klesk, K.; Qian, M., Aroma extract dilution analysis of Cv. Marion (Rubus spp. hyb) and Cv. Evergreen (R. Iaciniatus L.) blackberries, J. Agric. Food Chem., 2003, 51, 11, 3436-3441, https://doi.org/10.1021/jf0262209 . [all data]

Klesk and Qian, 2003, 2
Klesk, K.; Qian, M., Preliminary aroma comparison of Marion (Rubus spp. hyb) and Evergreen (R. laciniatus L.) blackberries by dynamic headspace/OSME technique, J. Food Sci., 2003, 68, 2, 697-700, https://doi.org/10.1111/j.1365-2621.2003.tb05734.x . [all data]

Choi, 2005
Choi, H.-S., Characteristic odor components of kumquat (Fortunella japonica Swingle) peel oil, J. Agric. Food Chem., 2005, 53, 5, 1642-1647, https://doi.org/10.1021/jf040324x . [all data]

Choi and Sawamura, 2000
Choi, H.-S.; Sawamura, M., Composition of the essential oil of Citrus tamurana Hort. ex Tanaka (Hyuganatsu), J. Agric. Food Chem., 2000, 48, 10, 4868-4873, https://doi.org/10.1021/jf000651e . [all data]

Chevance and Farmer, 1999, 2
Chevance, F.F.V.; Farmer, L.J., Release of volatile odor compounds from full-fat and reduced-fat frankfurters, J. Agric. Food Chem., 1999, 47, 12, 5161-5168, https://doi.org/10.1021/jf9905166 . [all data]

Guillard, le Quere, et al., 1997
Guillard, A.-S.; le Quere, J.-L.; Vendeuvre, J.-L., Emerging research approaches benefit to the study of cooked cured ham flavour, Food Chem., 1997, 59, 4, 567-572, https://doi.org/10.1016/S0308-8146(97)00001-0 . [all data]

Choi, 2006
Choi, H.-S., Headspace analyses of fresh leaves and stems of Angelica gigas Nakai, a Korean medicinal herb, Flavour Fragr. J., 2006, 21, 4, 604-608, https://doi.org/10.1002/ffj.1602 . [all data]

Agnihotri, Thappa, et al., 2004
Agnihotri, V.K.; Thappa, R.K.; Meena, B.; Kapahi, B.K.; Saxena, R.K.; Qazi, G.N.; Agarwal, S.G., Essential oil composition of aerial parts of Angelica glauca growing wild in North-West Himalaya (India), Phytochemistry, 2004, 65, 16, 2411-2413, https://doi.org/10.1016/j.phytochem.2004.07.004 . [all data]

Choi, 2004
Choi, H.-S., Volatile constituents of satsuma mandarins growing in Korea, Flavour Fragr. J., 2004, 19, 5, 406-412, https://doi.org/10.1002/ffj.1283 . [all data]

Jürgens and Dötterl, 2004
Jürgens, A.; Dötterl, S., Chemical composition of anther volatiles in Ranunculaceae: genera-specific profiles in Aemone, Aquilegia, Caltha, Pulsatilla, Ranunculus, and Trollius species, American Journal of Botany, 2004, 91, 12, 1969-1980, https://doi.org/10.3732/ajb.91.12.1969 . [all data]

Jirovetz, Buchbauer, et al., 2003
Jirovetz, L.; Buchbauer, G.; Stoyanova, A.S.; Georgiev, E.V.; Damianova, S.T., Composition, quality control, and antimicrobial activity of the essential oil of long-time stored dill (Anethum graveolens L.) seeds from Bulgaria, J. Agric. Food Chem., 2003, 51, 13, 3854-3857, https://doi.org/10.1021/jf030004y . [all data]

Hedin, McKibben, et al., 2000
Hedin, P.A.; McKibben, G.H.; Dollar, D.A., Role of ground trash volatiles in the selection of hibernation sites by boll weevils, J. Agric. Food Chem., 2000, 48, 8, 3673-3676, https://doi.org/10.1021/jf991001h . [all data]

Egolf and Jurs, 1993
Egolf, L.M.; Jurs, P.C., Quantitative structure-retention and structure-odor intensity relationships for a diverse group of odor-active compounds, Anal. Chem., 1993, 65, 21, 3119-3126, https://doi.org/10.1021/ac00069a027 . [all data]

King and Knight, 1992
King, J.R.; Knight, R.J., Volatile components of the leaves of various avocado cultivars, J. Agric. Food Chem., 1992, 40, 7, 1182-1185, https://doi.org/10.1021/jf00019a020 . [all data]

Carpino, Mallia, et al., 2004
Carpino, S.; Mallia, S.; Licitra, G.; van Soest, P.J.; Acree, T.E., Aroma compounds of some Hyblean pasture species, Flavour Fragr. J., 2004, 19, 4, 293-297, https://doi.org/10.1002/ffj.1346 . [all data]

Lee, Umano, et al., 2005
Lee, S.-J.; Umano, K.; Shibamoto, T.; Lee, K.-G., Identification of volatile components in basil (Ocimum basilicum L.) and thyme leaves (Thymus vulgaris L.) and their antioxidant properties, Food Chem., 2005, 91, 1, 131-137, https://doi.org/10.1016/j.foodchem.2004.05.056 . [all data]

Umano, Hagi, et al., 2002
Umano, K.; Hagi, Y.; Shibamoto, T., Volatile chemicals identified in extracts from newly hybrid citrus, dekopon (Shiranuhi mandarin Suppl. J.), J. Agric. Food Chem., 2002, 50, 19, 5355-5359, https://doi.org/10.1021/jf0203951 . [all data]

Umano, Hagi, et al., 2000
Umano, K.; Hagi, Y.; Nakahara, K.; Shoji, A.; Shibamoto, T., Volatile chemicals identified in extracts from leaves of Japanese mugwort (Artemisia princeps Pamp.), J. Agric. Food Chem., 2000, 48, 8, 3463-3469, https://doi.org/10.1021/jf0001738 . [all data]

Notes

Go To: Top, IR Spectrum, Gas Chromatography, References

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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