Carvone oxide
- Formula: C10H14O2
- Molecular weight: 166.2170
- IUPAC Standard InChI: InChI=1S/C10H14O2/c1-6(2)7-4-8(11)10(3)9(5-7)12-10/h7,9H,1,4-5H2,2-3H3
- IUPAC Standard InChIKey: YGMNGQDLUQECTO-UHFFFAOYSA-N
- CAS Registry Number: 33204-74-9
- 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:
- Other names: trans-Carvone oxide; Carvone-1,2-epoxide; carvon-1,2-oxide; trans-Carvone epoxide; 1-methyl-4-(1-methylvinyl)-7-oxabicyclo[4.1.0]heptan-2-one
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Gas Chromatography
Go To: Top, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-5 | 1277. | Lucero, Fredrickson, et al., 2006 | 30. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 60. C |
Kovats' RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | BP-1 | 1262. | Dwivedi, Khan, et al., 2004 | 25. m/0.25 mm/0.25 μm, N2; Program: 60C => 5C/min => 220C(5min) => 3C/min => 245C(5min) |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | HP-5 | 1279. | Stashenko, Jaramillo, et al., 2004 | 50. m/0.2 mm/0.2 μm, He, 35. C @ 15. min, 3. K/min, 250. C @ 40. min |
| Capillary | HP-1 | 1261. | Guilliard, Delgado, et al., 2001 | 60. m/0.25 mm/0.25 μm, He, 50. C @ 5. min, 2.5 K/min; Tend: 250. C |
| Capillary | HP-5 | 1277. | Guilliard, Delgado, et al., 2001 | 50. m/0.25 mm/0.25 μm, He, 50. C @ 5. min, 2.5 K/min; Tend: 250. C |
| Capillary | Methyl Silicone | 1262. | Sumathykutty, Rao, et al., 1999 | 50. m/0.25 mm/0.17 μm, N2, 2. K/min; Tstart: 80. C; Tend: 200. C |
Van Den Dool and Kratz RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-Wax | 1818. | 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 | 1817. | 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 | DB-Wax | 1837. | Kim, Thuy, et al., 2000 | 30. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 2. K/min, 200. C @ 20. min |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | OV-101 | 1251. | Benites, Moiteiro, et al., 2009 | 50. m/0.25 mm/0.25 μm, Helium, 2. K/min; Tstart: 70. C; Tend: 220. C |
| Capillary | RTX-5 MS | 1277. | Hudaib and Aburjai, 2007 | 30. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 45. C; Tend: 210. C |
| Capillary | HP-5MS | 1279. | Ebrahim Sajjadi and Mehregan, 2006 | 30. m/0.25 mm/0.25 μm, 4. K/min; Tstart: 60. C; Tend: 280. C |
| Capillary | HP-5 | 1280. | Mookdasanit, Tamura, et al., 2003 | Helium, 2. K/min, 210. C @ 60. min; Column length: 30. m; Column diameter: 0.32 mm; Tstart: 70. C |
| Capillary | HP-5 | 1279. | Stashenko, Jaramillo, et al., 2003 | 60. m/0.25 mm/0.25 μm, 40. C @ 15. min, 5. K/min; Tend: 250. C |
| Capillary | CP Sil 5 CB | 1266. | Monfared, Davarani, et al., 2002 | He, 5. K/min; Column length: 25. m; Column diameter: 0.25 mm; Tstart: 60. C; Tend: 220. C |
| Capillary | HP-5 | 1279. | Gallori, Flamini, et al., 2001 | 30. m/0.25 mm/0.25 μm, N2, 60. C @ 10. min, 5. K/min; Tend: 220. C |
| Capillary | OV-101 | 1260. | Menon, Chacko, et al., 1999 | N2, 1. K/min, 200. C @ 20. min; Column length: 50. m; Column diameter: 0.2 mm; Tstart: 80. C |
| Capillary | OV-101 | 1263. | Chacko, Jayalekshmy, et al., 1996 | 50. m/0.25 mm/0.17 μm, N2, 5. K/min; Tstart: 50. C; Tend: 220. C |
| Capillary | Methyl Silicone | 1261. | Gopalakrishnan, Menon, et al., 1993 | 50. m/0.25 mm/0.17 μm, N2, 2. K/min; Tstart: 80. C; Tend: 200. C |
| Capillary | Methyl Silicone | 1261. | Gopalakrishnan, Menon, et al., 1993 | 50. m/0.25 mm/0.17 μm, N2, 3. K/min; Tstart: 80. C; Tend: 200. C |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | HP-5 | 1280. | Riahi, Pourbasheer, et al., 2009 | Column length: 30. m; Column diameter: 0.32 mm; Program: not specified |
| Capillary | SE-52 | 1276. | Tognolini, Barocelli, et al., 2006 | 30. m/0.32 mm/0.15 μm, He; Program: 45C => 1C/min => 100C => 5C/min => 250C (10min) |
| Capillary | SE-30 | 1261. | Vinogradov, 2004 | Program: not specified |
| Capillary | 5 % Phenyl methyl siloxane | 1261. | Sagrero-Nieves and Bartley, 1995 | Program: not specified |
Normal alkane RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-Wax | 1809. | 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 | 1817. | Njoroge, Koaze, et al., 2005 | 60. m/0.25 mm/0.25 μm, N2, 70. C @ 2. min, 2. K/min, 230. C @ 20. min |
| Capillary | DB-Wax | 1808. | Choi, 2004 | 60. m/0.25 mm/0.25 μm, N2, 70. C @ 2. min, 2. K/min, 230. C @ 20. min |
| Capillary | HP-Innowax | 1800. | Stashenko, Jaramillo, et al., 2003 | 50. m/0.2 mm/0.2 μm, 50. C @ 5. min, 4. K/min; Tend: 220. C |
| Capillary | Carbowax | 1805. | Menon, Chacko, et al., 1999 | N2, 1. K/min, 200. C @ 20. min; Column length: 50. m; Column diameter: 0.2 mm; Tstart: 80. C |
Normal alkane RI, polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Carbowax 20M | 1805. | Hudaib and Aburjai, 2007 | 30. m/0.25 mm/0.25 μm, He; Program: not specified |
| Capillary | Innowax FSC | 1856. | Kosar, Özek, et al., 2005 | 60. m/0.25 mm/0.25 μm, He; Program: 60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C |
| Capillary | HP-Innowax FSC | 1856. | Viljoen, Subramoney, et al., 2005 | 60. m/0.25 mm/0.25 μm, He; Program: 60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C |
| Capillary | Carbowax 20M | 1805. | Vinogradov, 2004 | Program: not specified |
| Capillary | HP-Innowax | 1856. | Baser, Demirci, et al., 2001 | 60. m/0.25 mm/0.25 μm, He; Program: 60 0C (10 min) 10 K/min -> 220 0C (10 min) 1K/min -> 240 0C |
| Capillary | HP-Innowax | 1856. | Tabanca, Kirimer, et al., 2001 | 60. m/0.25 mm/0.25 μm, He; Program: 60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C |
References
Go To: Top, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Lucero, Fredrickson, et al., 2006
Lucero, M.E.; Fredrickson, E.L.; Estell, R.E.; Morrison, A.A.; Richman, D.B.,
Volatile Composition of Gutierrezia sarothrae (Broom Snakeweed) as Determined by Steam Distillation and Solid Phase Microextraction,
J. Essent. Oil Res., 2006, 18, 2, 121-125, https://doi.org/10.1080/10412905.2006.9699039
. [all data]
Dwivedi, Khan, et al., 2004
Dwivedi, S.; Khan, M.; Srivastava, S.K.; Syamasunnder, K.V.; Srivastava, A.,
Essential oil composition of different accessions of Mentha × piperita L. grown on the northern plains of India,
Flavour Fragr. J., 2004, 19, 5, 437-440, https://doi.org/10.1002/ffj.1333
. [all data]
Stashenko, Jaramillo, et al., 2004
Stashenko, E.E.; Jaramillo, B.E.; Martínez, J.R.,
Comparison of different extraction methods for the analysis of volatile secondary metabolites of Lippia alba (Mill.) N.E. Brown, grown in Colombia, and evaluation of its in vitro antioxidant activity,
J. Chromatogr. A, 2004, 1025, 1, 93-103, https://doi.org/10.1016/j.chroma.2003.10.058
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Guilliard, Delgado, et al., 2001
Guilliard, M.; Delgado, W.; Martínez, J.R.; Stashenko, E.,
Determination of the enantiomeric purity of carvone, main component of Colombian Lippia alba (Mill) oil by means of bidimensional gas chromatography (23rd International Symposium on Capillary Chromatography), 2001, retrieved from http://www.richrom.com/assets/CD23PDF/i01.pdf. [all data]
Sumathykutty, Rao, et al., 1999
Sumathykutty, M.A.; Rao, J.M.; Padmakumari, K.P.; Narayanan, C.S.,
Essential oil constituents of some Piper species,
Flavour Fragr. J., 1999, 14, 5, 279-282, https://doi.org/10.1002/(SICI)1099-1026(199909/10)14:5<279::AID-FFJ821>3.0.CO;2-0
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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
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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]
Kim, Thuy, et al., 2000
Kim, T.H.; Thuy, N.T.; Shin, J.H.; Baek, H.H.; Lee, H.J.,
Aroma-active compounds of miniature beefsteakplant (Mosla dianthera Maxim.),
J. Agric. Food Chem., 2000, 48, 7, 2877-2881, https://doi.org/10.1021/jf000219x
. [all data]
Benites, Moiteiro, et al., 2009
Benites, J.; Moiteiro, C.; Miguel, G.; Rojo, L.; Lopez, J.; Venancio, F.; Ramalho, L.; Feio, S.; Dandlen, S.; Casanova, H.; Torres, I.,
Composition and biological activity of the essential oil of Peruvial Lantana camara,
J. Chilean Chem. Soc., 2009, 54, 4, 379-384, https://doi.org/10.4067/S0717-97072009000400012
. [all data]
Hudaib and Aburjai, 2007
Hudaib, M.; Aburjai, T.,
Volatile components of Thymus vulgaris L. from wild-growing and cultivated plants in Jordan,
Flavour Fragr. J., 2007, 22, 4, 322-327, https://doi.org/10.1002/ffj.1800
. [all data]
Ebrahim Sajjadi and Mehregan, 2006
Ebrahim Sajjadi, S.; Mehregan, I.,
Volatile constituents of flowers and leaves of Anthemis hyalina,
Chem. Nat. Compd. (Engl. Transl.), 2006, 42, 5, 531-533, https://doi.org/10.1007/s10600-006-0207-2
. [all data]
Mookdasanit, Tamura, et al., 2003
Mookdasanit, J.; Tamura, H.; Yoshizawa T.; Tokunaga T.; Nakanishi, K.,
Trace Volatile Compounds in Essential Oil of Citrus Sudachi by Means of Modified Solvent Extraction Method,
Food Sci Technol. Res., 2003, 9, 1, 54-61, https://doi.org/10.3136/fstr.9.54
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Stashenko, Jaramillo, et al., 2003
Stashenko, E.E.; Jaramillo, B.E.; Martínez, J.R.,
Comparación de la composición química y de la actividad antioxidante in vitro de los metabolitos secundarios volátiles de plantas de la familia verbenaceae,
Rev. Acad. Colomb. Cienc. Exactas Fis. Nat., 2003, 27, 105, 579-597. [all data]
Monfared, Davarani, et al., 2002
Monfared, A.; Davarani, S.S.H.; Rustaiyan, A.; Masoudi, S.,
Composition of the essential oil of Tanacetum balsamita L. ssp. balsamitoides (Schultz Bip.) Grierson from Iran,
J. Essent. Oil Res., 2002, 14, 1, 1-2, https://doi.org/10.1080/10412905.2002.9699741
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Gallori, Flamini, et al., 2001
Gallori, S.; Flamini, G.; Bilia, A.R.; Morelli, I.; Landini, A.; Vincieri, F.F.,
Chemical composition of some traditional herbal drug preparations: essential oil and aromatic water of costmary (Balsamita suaveolens Pers.),
J. Agric. Food Chem., 2001, 49, 12, 5907-5910, https://doi.org/10.1021/jf0107656
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Menon, Chacko, et al., 1999
Menon, A.N.; Chacko, S.; Narayanan, C.S.,
Free and glycosidically bound volatiles of cardamom (Eletteria cardamomum Maton var. miniscula Burkill),
Flavour Fragr. J., 1999, 14, 1, 65-68, https://doi.org/10.1002/(SICI)1099-1026(199901/02)14:1<65::AID-FFJ789>3.0.CO;2-A
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Chacko, Jayalekshmy, et al., 1996
Chacko, S.; Jayalekshmy, A.; Gopalakrishnan, M.; Narayanan, C.S.,
Roasting studies on black pepper (Piper nigrum L.),
Flavour Fragr. J., 1996, 11, 5, 305-310, https://doi.org/10.1002/(SICI)1099-1026(199609)11:5<305::AID-FFJ588>3.0.CO;2-1
. [all data]
Gopalakrishnan, Menon, et al., 1993
Gopalakrishnan, M.; Menon, N.; Padmakumari, K.P.; Jayalekshmy, A.; Narayanan, C.S.,
GC Analysis and Odor Profiles of Four New Indian Genotypes of Piper nigrum L.,
J. Essent. Oil Res., 1993, 5, 3, 247-253, https://doi.org/10.1080/10412905.1993.9698217
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Riahi, Pourbasheer, et al., 2009
Riahi, S.; Pourbasheer, E.; Ganjali, M.R.; Norouzi, P.,
Investigation of different linear and non-linear chemometric methods for modeling of retention index of essential oil components: Concerns to support vector mashine,
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Tognolini, Barocelli, et al., 2006
Tognolini, M.; Barocelli, E.; Ballabeni, V.; Bruni, R.; Bianchi, A.; Chiavarini, M.; Impicciatore, M.,
Comparative screening of plant essential oils: Phenylpropanoid moiety as basic core for antiplatelet activity,
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Vinogradov, 2004
Vinogradov, B.A.,
Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]
Sagrero-Nieves and Bartley, 1995
Sagrero-Nieves, L.; Bartley, J.P.,
Volatile Constituents from the Leaves of Chenopodium ambrosioides L.,
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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
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Njoroge, Koaze, et al., 2005
Njoroge, S.M.; Koaze, H.; Karanja, P.N.; Sawamura, M.,
Essential oil constituents of three varieties of Kenyan sweet oranges (Citrus sinensis),
Flavour Fragr. J., 2005, 20, 1, 80-85, https://doi.org/10.1002/ffj.1377
. [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]
Kosar, Özek, et al., 2005
Kosar, M.; Özek, T.; Göger, F.; Kürkcüoglu, M.; Hüsnü Can Baser, K.,
Comparison of Microwave-Assisted Hydrodistillation and Hydrodistillation Methods for the Analysis of Volatile Secondary Metabolites,
Pharm. Biol., 2005, 43, 6, 491-495, https://doi.org/10.1080/13880200500220136
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Viljoen, Subramoney, et al., 2005
Viljoen, A.M.; Subramoney, S.; van Vuuren, S.F.; Baser, K.H.C.; Demirci, B.,
The composition, geographical variation and antimicrobial activity of Lippia javanica (Verbenaceae) leaf essential oils,
J. Ethnopharmacol., 2005, 96, 1-2, 271-277, https://doi.org/10.1016/j.jep.2004.09.017
. [all data]
Baser, Demirci, et al., 2001
Baser, K.H.C.; Demirci, B.; Tabanca, N.; Özek, T.; Gören, N.,
Composition of the essential oils of Tanacetum armenum (DC.) Schultz Bip., T. balsamita L., T. chiliophyllum (Fisch. Mey.) Schultz Bip. var. chiliophyllum and T. haradjani (Rech. fil.) Grierson and the enantiomeric distribution of camphor and carvone,
Flavour Fragr. J., 2001, 16, 3, 195-200, https://doi.org/10.1002/ffj.977
. [all data]
Tabanca, Kirimer, et al., 2001
Tabanca, N.; Kirimer, N.; Demirci, B.; Demirci, F.; Can Baser, K.H.,
Composition and antimicrobial activity of the essential oils of Micromeria cristata subsp. phrygia and the enantiomeric distribution of borneol,
J. Agric. Food Chem., 2001, 49, 9, 4300-4303, https://doi.org/10.1021/jf0105034
. [all data]
Notes
Go To: Top, Gas Chromatography, References
- Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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