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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- Other data available:
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Normal alkane 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 | DB-5 | HP-5 | HP-5 MS | DB-5 MS | HP-5MS |
| Column length (m) | 30. | 30. | 30. | 30. | 30. |
| Carrier gas | Helium | Nitrogen | Helium | Helium | He |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
| Tstart (C) | 70. | 50. | 70. | 50. | 60. |
| Tend (C) | 240. | 280. | 210. | 300. | 250. |
| Heat rate (K/min) | 5. | 5. | 5. | 5. | 2. |
| Initial hold (min) | 1. | 1. | 5. | 8. | |
| Final hold (min) | 1. | 5. | 5. | 15. | |
| I | 1820. | 1820. | 1820. | 1802. | 1799. |
| Reference | Lawal and Oyedelji, 2009 | Bousaada, Ammar, et al., 2008 | Bouwmeester, de Kraker, et al., 2008 | Noudogbessi, Yedomonhan, et al., 2008 | Ferhat, Meklati, et al., 2007 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | HP-5MS | DB-1 | DB-1 | CP Sil 8 CB | RSL-200 |
| Column length (m) | 30. | 60. | 60. | 30. | 30. |
| Carrier gas | He | He | H2 | ||
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.32 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | |
| Tstart (C) | 60. | 70. | 70. | 60. | 40. |
| Tend (C) | 250. | 230. | 230. | 290. | 280. |
| Heat rate (K/min) | 2. | 2. | 2. | 3. | 6. |
| Initial hold (min) | 8. | 2. | 2. | 5. | 5. |
| Final hold (min) | 15. | 20. | 20. | 5. | |
| I | 1794. | 1774. | 1775. | 1799. | 1802. |
| Reference | Ferhat, Tigrine-Kordjani, et al., 2007 | Lan Phi N.T., Nishiyama C., et al., 2006 | Sawamura, Onishi, et al., 2006 | Suárez, Vásquez, et al., 2005 | Jirovetz, Buchbauer, et al., 2003 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | DB-5 | DB-5 | OV-101 | DB-5 | HP-5 |
| Column length (m) | 30. | 30. | 15. | 30. | 25. |
| Carrier gas | He | He | He | ||
| Substrate | |||||
| Column diameter (mm) | 0.32 | 0.32 | 0.32 | 0.32 | 0.2 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.5 | 0.33 | |
| Tstart (C) | 40. | 40. | 35. | 35. | 70. |
| Tend (C) | 290. | 290. | 250. | 275. | 290. |
| Heat rate (K/min) | 7. | 7. | 6. | 6. | 3. |
| Initial hold (min) | 8. | ||||
| Final hold (min) | 20. | ||||
| I | 1834. | 1835. | 1751. | 1790. | 1823. |
| Reference | Lin, Rouseff, et al., 2002 | Lin, Rouseff, et al., 2002 | Friedrich, Acree, et al., 2001 | Rouseff, Jella, et al., 2001 | Poiana, Sicari, et al., 1998 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|
| Active phase | DB-5 | OV-101 | OV-101 | OV-101 |
| Column length (m) | 30. | 50. | 50. | 50. |
| Carrier gas | Helium | N2 | ||
| Substrate | ||||
| Column diameter (mm) | 0.25 | 0.25 | 0.25 | 0.25 |
| Phase thickness (μm) | 0.25 | |||
| Tstart (C) | 60. | 80. | 80. | 80. |
| Tend (C) | 240. | 200. | 200. | 200. |
| Heat rate (K/min) | 3. | 2. | 2. | 2. |
| Initial hold (min) | ||||
| Final hold (min) | ||||
| I | 1798. | 1775. | 1780. | 1775. |
| Reference | Tellez, Estell, et al., 1997 | Tamura, Yang, et al., 1993 | Tamura, Yang, et al., 1993 | Sugisawa, Yamamoto, et al., 1989 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
References
Go To: Top, Normal alkane 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.
Lawal and Oyedelji, 2009
Lawal, O.A.; Oyedelji, A.O.,
Chemical composition of the essential oils of Cyperus rotundus L. from South Africa,
Molecules, 2009, 14, 8, 2909-2917, https://doi.org/10.3390/molecules14082909
. [all data]
Bousaada, Ammar, et al., 2008
Bousaada, O.; Ammar, S.; Saidana, D.; Chriaa, J.; Chraif, I.; Daami, M.; Helal, A.N.; Mighri, Z.,
Chemical composition and antimicrobial activity of volatile components from capitula and aerial parts of Rhaponticum acaule DC growing wild in Tunisia,
Microbiol. Res., 2008, 163, 1, 87-95, https://doi.org/10.1016/j.micres.2007.02.010
. [all data]
Bouwmeester, de Kraker, et al., 2008
Bouwmeester, H.J.; de Kraker, J.-W.; Schurink, M.; Bino, R.J.; de Groot, A.,
Plant Enzymes for Bioconversion, 2008, 57. [all data]
Noudogbessi, Yedomonhan, et al., 2008
Noudogbessi, J.-P.; Yedomonhan, P.; Sohounhloue, D.C.K.; Chalchat, J.-C.; Figueredo, G.,
Chemical composition of essential oil of syzygium guineense (Willd.) DC. var. guineense (Myrtaceae) from Benin,
Rec. Nat. Prod., 2008, 33-38. [all data]
Ferhat, Meklati, et al., 2007
Ferhat, M.A.; Meklati, B.Y.; Chemat, F.,
Comparison of different isolation methods of essential oil from Citrus fruits: cold pressing, hydrodistillation and microwave dry distillation,
Flavour Fragr. J., 2007, 22, 6, 494-504, https://doi.org/10.1002/ffj.1829
. [all data]
Ferhat, Tigrine-Kordjani, et al., 2007
Ferhat, M.A.; Tigrine-Kordjani, N.; Chemat, S.; Meklati, B.Y.; Chemat, F.,
Rapid Extraction of Volatile Compounds Using a New Simultaneous Microwave Distillation: Solvent Extraction Device,
Chromatographia, 2007, 65, 3-4, 217-222, https://doi.org/10.1365/s10337-006-0130-5
. [all data]
Lan Phi N.T., Nishiyama C., et al., 2006
Lan Phi N.T.; Nishiyama C.; Choi H.-S.; Sawamura M.,
Evaluation of aroma characteristic compounds of Citrus natsudaidai Hayata (Natsudaidai) cold-pressed peel oil,
Biosci. Biotechnol. Biochem., 2006, 70, 8, 1832-1838, https://doi.org/10.1271/bbb.50705
. [all data]
Sawamura, Onishi, et al., 2006
Sawamura, M.; Onishi, Y.; Ikemoto, J.; Tu, N.T.M.; Phi, N.T.L.,
Characteristic odour components of bergamot (Citrus bergamia Risso) essential oil,
Flavour Fragr. J., 2006, 21, 4, 609-615, https://doi.org/10.1002/ffj.1604
. [all data]
Suárez, Vásquez, et al., 2005
Suárez, A.I.; Vásquez, L.J.; Manzano, M.A.; Compagnone, R.S.,
Essential oil composition of Croton cuneatus and Croton malambo growing in Venezuela,
Flavour Fragr. J., 2005, 20, 6, 611-614, https://doi.org/10.1002/ffj.1498
. [all data]
Jirovetz, Buchbauer, et al., 2003
Jirovetz, L.; Buchbauer, G.; Shafi, M.P.; Leela, N.K.,
Analysis of the essential oils of the leaves, stems, rhizomes and roots of the medicinal plant Alpinia galanga from southern India,
Acta Pharm. Hung., 2003, 53, 73-81. [all data]
Lin, Rouseff, et al., 2002
Lin, J.; Rouseff, R.L.; Barros, S.; Naim, M.,
Aroma composition changes in early season grapefruit juice produced from thermal concentration,
J. Agric. Food Chem., 2002, 50, 4, 813-819, https://doi.org/10.1021/jf011154g
. [all data]
Friedrich, Acree, et al., 2001
Friedrich, J.E.; Acree, T.E.; Lavin, E.H.,
Selecting standards for gas chromatography - olfactometry,
Am. Chem. Soc. Symp. Ser., 2001, 782, 148-155. [all data]
Rouseff, Jella, et al., 2001
Rouseff, R.; Jella, P.; Bazemore, R.; Yang, J.-J.,
Aroma active internal standards for gas chromatography-olfactometry of grapefruit juices,
Am. Chem. Soc. Symp. Ser., 2001, 782, 73-87. [all data]
Poiana, Sicari, et al., 1998
Poiana, M.; Sicari, V.; Mincione, B.,
Supercritical carbon dioxide (SC-CO2) extraction of grapefruit flavedo,
Flavour Fragr. J., 1998, 13, 2, 125-130, https://doi.org/10.1002/(SICI)1099-1026(199803/04)13:2<125::AID-FFJ708>3.0.CO;2-#
. [all data]
Tellez, Estell, et al., 1997
Tellez, M.R.; Estell, R.E.; Frederickson, E.L.; Havstad, K.M.,
Essntial oil of Flourensia cernua DC,
J. Essent. Oil Res., 1997, 9, 6, 619-624, https://doi.org/10.1080/10412905.1997.9700799
. [all data]
Tamura, Yang, et al., 1993
Tamura, H.; Yang, R.-H.; Sugisawa, H.,
Aroma profiles of peel oils of acid citrus,
ACS Sym. Ser., 1993, 525, 121-136. [all data]
Sugisawa, Yamamoto, et al., 1989
Sugisawa, H.; Yamamoto, M.; Tamura, H.; Takagi, N.,
The comparison of volatile components in peel oil from four species of navel orange,
Nippon Shokuhin Kogio Gakkaishi, 1989, 36, 6, 455-462, https://doi.org/10.3136/nskkk1962.36.6_455
. [all data]
Notes
Go To: Top, Normal alkane 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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