Nootkatone
- Formula: C15H22O
- Molecular weight: 218.3346
- IUPAC Standard InChI: InChI=1S/C15H22O/c1-10(2)12-5-6-13-8-14(16)7-11(3)15(13,4)9-12/h8,11-12H,1,5-7,9H2,2-4H3/t11-,12-,15+/m0/s1
- IUPAC Standard InChIKey: WTOYNNBCKUYIKC-SLEUVZQESA-N
- CAS Registry Number: 4674-50-4
- 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. - Other names: 2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, [4R-(4α,4aα,6β)]-; (4R,4aS,6R)-4,4a-Dimethyl-6-(prop-1-en-2-yl)-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one; 4βH,5α-Eremophila-1(10),11-dien-2-one; 4βH,5α-Eremorphila-1(10)11-dien-2-one; 4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-2(3H)-naphthalenone, [4R-(4α,4aα,6β)]-; 6-Isopropenyl-4,4a-dimethyl-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalenone-, [4R-(4α,4aα,6β)]-; (+)-5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one; 2(3H)-Naphthalenone, 4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)-; (+)-Nootkatone; Nootkanone; Nootkatane; [4R-(4α,4aα,6β)]-4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylvinyl)naphthalen-2(3H)-one
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Van Den Dool and Kratz RI, non-polar column, temperature ramp
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
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | BP-1 | Mega 5MS | ZB-5 | DB-5 | RTX-5 |
| Column length (m) | 50. | 30. | 30. | 60. | 30. |
| Carrier gas | He | He | Helium | Helium | He |
| Substrate | |||||
| Column diameter (mm) | 0.22 | 0.25 | 0.32 | 0.25 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.50 | 0.25 | 0.25 |
| Tstart (C) | 60. | 40. | 40. | 40. | 45. |
| Tend (C) | 220. | 240. | 265. | 250. | 300. |
| Heat rate (K/min) | 2. | 3. | 7. | 7. | 3. |
| Initial hold (min) | 2. | 6. | |||
| Final hold (min) | 20. | 5. | 10. | ||
| I | 1781. | 1780. | 1834. | 1823. | 1798. |
| Reference | Gonny, Cavaleiro, et al., 2006 | Verzera, Trozzi, et al., 2005 | Bell, 2004 | Bell, 2004 | Dugo, Mondello, et al., 2004 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | CP Sil 5 CB | SPB-1 | DB-5 | DB-5 | HP-5 |
| Column length (m) | 30. | 30. | 30. | 30. | 30. |
| Carrier gas | N2 | He | He | ||
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.25 | 0.32 | 0.32 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.5 | 0.5 | 0.25 |
| Tstart (C) | 50. | 35. | 40. | 40. | 60. |
| Tend (C) | 200. | 225. | 265. | 265. | 280. |
| Heat rate (K/min) | 5. | 4. | 7. | 7. | 4. |
| Initial hold (min) | 5. | 5. | |||
| Final hold (min) | 20. | 5. | 5. | ||
| I | 1819. | 1763. | 1834. | 1833. | 1800. |
| Reference | Martinez, Rosa, et al., 2004 | Chisholm, Jell, et al., 2003 | Högnadóttir and Rouseff, 2003 | Högnadóttir and Rouseff, 2003 | Skaltsa, Demetzos, et al., 2003 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | Mega 5MS | DB-1 | Mega 5MS | Mega 5MS | DB-5 |
| Column length (m) | 30. | 30. | 30. | 30. | 30. |
| Carrier gas | He | He | He | H2 | |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.32 | 0.25 | 0.25 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
| Tstart (C) | 40. | 40. | 40. | 40. | 60. |
| Tend (C) | 240. | 240. | 240. | 240. | 240. |
| Heat rate (K/min) | 3. | 7. | 3. | 3. | 3. |
| Initial hold (min) | 2. | 2. | 2. | ||
| Final hold (min) | 5. | ||||
| I | 1780. | 1775. | 1780. | 1780. | 1803. |
| Reference | Verzera, Trozzi, et al., 2003 | Lin and Rouseff, 2001 | Verzera, la Rosa, et al., 2000 | Verzera, Trozzi, et al., 2000 | Nogueira, Marsaioli, et al., 1998 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary |
|---|---|---|
| Active phase | OV-101 | OV-101 |
| Column length (m) | 50. | 50. |
| Carrier gas | N2 | N2 |
| Substrate | ||
| Column diameter (mm) | 0.25 | 0.25 |
| Phase thickness (μm) | ||
| Tstart (C) | 80. | 80. |
| Tend (C) | 200. | 200. |
| Heat rate (K/min) | 2. | 2. |
| Initial hold (min) | ||
| Final hold (min) | ||
| I | 1775. | 1780. |
| Reference | Yang, Sugisawa, et al., 1992 | Yang, Sugisawa, et al., 1992 |
| Comment | MSDC-RI | MSDC-RI |
References
Go To: Top, Van Den Dool and Kratz RI, non-polar column, temperature ramp, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Gonny, Cavaleiro, et al., 2006
Gonny, M.; Cavaleiro, C.; Salgueiro, L.; Casanova, J.,
Analysis of Juniperus communis subsp. alpina needle, berry, wood and root oils by combination of GC, GC/MS and 13C-NMR,
Flavour Fragr. J., 2006, 21, 1, 99-106, https://doi.org/10.1002/ffj.1527
. [all data]
Verzera, Trozzi, et al., 2005
Verzera, A.; Trozzi, A.; Zappala, M.; Condurso, C.; Cotroneo, A.,
Essential Oil Composition of Citrus meyerii Y. Tan. and Citrus medica L. cv. Diamante and Their Lemon Hybrids,
J. Agric. Food Chem., 2005, 53, 12, 4890-4894, https://doi.org/10.1021/jf047879c
. [all data]
Bell, 2004
Bell, W.A.-M.,
Examination of Aroma Volatiles Formed from Thermal Processing of Florida Reconstituted Grapefruit Juice. A Thesis presented to the graduate school of the university of Florida in partial fulfillment of the requirements for the degree of master of science, 2004. [all data]
Dugo, Mondello, et al., 2004
Dugo, P.; Mondello, L.; Zappia, G.; Bonaccorsi, I.; Cotroneo, A.; Russo, M.T.,
The composition of the volatile fraction and the enantiomeric distribution of five volatile components of faustrime oil (Monocitrus australatica x Fortunella sp. x Citrus aurantifolia),
J. Essent. Oil Res., 2004, 16, 4, 328-333, https://doi.org/10.1080/10412905.2004.9698734
. [all data]
Martinez, Rosa, et al., 2004
Martinez, J.; Rosa, P.T.V.; Menut, C.; Leydet, A.; Brat, P.; Pallet, D.; Meireles, M.A.A.,
Valorization of Brazilian vetiver (Vetiveria zizanioides (L.) Nash ex Small) oil,
J. Agric. Food Chem., 2004, 52, 21, 6578-6584, https://doi.org/10.1021/jf049182x
. [all data]
Chisholm, Jell, et al., 2003
Chisholm, M.G.; Jell, J.A.; Cass, D.M., Jr.,
Characterization of the major odorants found in the peel oil of Citrus reticulata Blanco cv. Clementine using gas chromatography-olfactometry,
Flavour Fragr. J., 2003, 18, 4, 275-281, https://doi.org/10.1002/ffj.1188
. [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]
Skaltsa, Demetzos, et al., 2003
Skaltsa, H.D.; Demetzos, C.; Lazari, D.; Sokovic, M.,
Essential oil analysis and antimicrobial activity of eight Stachys species from Greece,
Phytochemistry, 2003, 64, 3, 743-752, https://doi.org/10.1016/S0031-9422(03)00386-8
. [all data]
Verzera, Trozzi, et al., 2003
Verzera, A.; Trozzi, A.; Gazea, F.; Cicciarelloi, G.; Cotroneo, A.,
Effects of rootstock on the composition of bergamot (Citrus bergamia Risso et Poiteau) essential oil,
J. Agric. Food Chem., 2003, 51, 1, 206-210, https://doi.org/10.1021/jf0206872
. [all data]
Lin and Rouseff, 2001
Lin, J.; Rouseff, R.L.,
Characterization of aroma-impact compounds in cold-pressed grapefruit oil using time-intensity GC-olfactometry and GC-MS,
Flavour Fragr. J., 2001, 16, 6, 457-463, https://doi.org/10.1002/ffj.1041
. [all data]
Verzera, la Rosa, et al., 2000
Verzera, A.; la Rosa, G.; Zappalà, M.; Cotroneo, A.,
Essential oil composition of different cultivars of bergamot grown in Sicily,
Ital. J. Food Sci., 2000, 12, 4, 493-501. [all data]
Verzera, Trozzi, et al., 2000
Verzera, A.; Trozzi, A.; Cotroneo, A.; Lorenzo, D.; Dellacassa, E.,
Uruguayan essential oil. 12. Composition of Nova and Satsuma mandarin oils,
J. Agric. Food Chem., 2000, 48, 7, 2903-2909, https://doi.org/10.1021/jf990734z
. [all data]
Nogueira, Marsaioli, et al., 1998
Nogueira, P.C.L.; Marsaioli, A.J.; Amaral, M.C.E.; Bittrich, V.,
The fragrant floral oils of Tovomita species,
Phytochemistry, 1998, 49, 4, 1009-1012, https://doi.org/10.1016/S0031-9422(97)01046-7
. [all data]
Yang, Sugisawa, et al., 1992
Yang, R.; Sugisawa, H.; Nakatani, H.; Tamura, H.; Takagi, N.,
Comparison of odor quality in peel oils of acid citrus,
Nippon Shokuhin Kogyo Gakkaishi, 1992, 39, 1, 16-24, https://doi.org/10.3136/nskkk1962.39.16
. [all data]
Notes
Go To: Top, Van Den Dool and Kratz RI, non-polar column, temperature ramp, References
- Symbols used in this document:
Tend Final temperature Tstart Initial temperature - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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