4aα,7α,7aα-Nepetalactone
- Formula: C10H14O2
- Molecular weight: 166.2170
- IUPAC Standard InChI: InChI=1S/C10H14O2/c1-6-3-4-8-7(2)5-12-10(11)9(6)8/h5-6,8-9H,3-4H2,1-2H3/t6-,8+,9+/m1/s1
- IUPAC Standard InChIKey: ZDKZHVNKFOXMND-YEPSODPASA-N
- 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: cis,cis-Nepetalactone; Nepetalactone, 4aa,7a,7aa
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Gas Chromatography
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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 | HP-5MS | 1344. | Gkinis, Tzakou, et al., 2003 | 30. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 60. C; Tend: 280. C |
| Capillary | DB-5 | 1371. | Tzakou, Harvala, et al., 2000 | 50. C @ 5. min, 3. K/min; Column length: 30. m; Column diameter: 0.32 mm; Tend: 250. C |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | HP-5 | 1365. | Bertoli, Menichini, et al., 2004 | 30. m/0.25 mm/0.25 μm, N2, 60. C @ 10. min, 5. K/min; Tend: 220. C |
| Capillary | HP-5 | 1365. | Ertugrul, Dural, et al., 2003 | 30. m/0.25 mm/0.25 μm, N2, 60. C @ 10. min, 5. K/min; Tend: 220. C |
| Capillary | HP-5 | 1375. | Skaltsa, Lazari, et al., 2000 | 30. m/0.25 mm/0.25 μm, He, 50. C @ 5. min, 4. K/min; Tend: 280. C |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-5MS | 1370. | Eom S.H., Yang H.S., et al., 2006 | 30. m/0.25 mm/0.25 μm, He; Program: 50C(3min) => 200C(2min) => 15C/min => 300C(5min) |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-1 | 1322. | Sefidkon, Jamzad, et al., 2006 | He, 4. K/min; Column length: 60. m; Column diameter: 0.25 mm; Tstart: 40. C; Tend: 250. C |
| Capillary | DB-1 | 1322. | Sefidkon and Shaabani, 2004 | 60. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 4. K/min; Tend: 280. C |
| Capillary | DB-1 | 1317. | Dabiri and Sefidkon, 2003 | He, 4. K/min; Column length: 60. m; Column diameter: 0.25 mm; Tstart: 50. C; Tend: 250. C |
| Capillary | DB-1 | 1323. | Dabiri and Sefidkon, 2003, 2 | He, 4. K/min; Column length: 60. m; Column diameter: 0.25 mm; Tstart: 50. C; Tend: 250. C |
| Capillary | CP Sil 5 CB | 1337. | Rustaiyan and Nadji, 1999 | 25. m/0.25 mm/0.39 μm, N2, 5. K/min; Tstart: 60. C; Tend: 220. C |
| Capillary | OV-1 | 1344. | Kökdil, Kurucu, et al., 1997 | 30. m/0.32 mm/0.25 μm, He, 40. C @ 4. min, 2. K/min; Tend: 270. C |
| Capillary | OV-1 | 1322. | de Pooter, Nicolai, et al., 1988 | 50. m/0.20 mm/0.20 μm, He, 2. K/min; Tstart: 30. C; Tend: 220. C |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Optima-5MS | 1353. | HEuskin, Godin, et al., 2009 | 30. m/0.32 mm/0.25 μm, Helium; Program: 40 0C (5 min) 5 0C/min -> 230 0C 30 0C/min -> 280 0C (5 min) |
| Capillary | OV-1 | 1331. | Suschke, Sporer, et al., 2007 | 30. m/0.25 mm/0.25 μm, Helium; Program: 40 0C (2 min) 6 0C/min -> 130 0C 10 0C/min -> 300 0C |
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.
Gkinis, Tzakou, et al., 2003
Gkinis, G.; Tzakou, O.; Iliopoulou, D.; Roussis, V.,
Chemical Composition and Biological Activity of Nepeta parnassica Oils and Isolated Nepetalactones,
Z. Naturforsch. C:, 2003, 58, 681-686. [all data]
Tzakou, Harvala, et al., 2000
Tzakou, O.; Harvala, C.; Galati, E.M.; Sanogo, R.,
Essential oil composition of Nepeta argolica Borey et Chaub. subsp. argolica,
Flavour Fragr. J., 2000, 15, 2, 115-118, https://doi.org/10.1002/(SICI)1099-1026(200003/04)15:2<115::AID-FFJ877>3.0.CO;2-9
. [all data]
Bertoli, Menichini, et al., 2004
Bertoli, A.; Menichini, F.; Noccioli, C.; Morelli, I.; Pistelli, L.,
Volatile constituents of different organs of Psoralea bituminosa L.,
Flavour Fragr. J., 2004, 19, 2, 166-171, https://doi.org/10.1002/ffj.1315
. [all data]
Ertugrul, Dural, et al., 2003
Ertugrul, K.; Dural, H.; Tugay, O.; Flamini, G.; Cioni, P.L.; Morelli, I.,
Essential oils from flowers of Centaurea kotschyi var. kotschyi and C. kotschyi var. decumbens from Turkey,
Flavour Fragr. J., 2003, 18, 2, 95-97, https://doi.org/10.1002/ffj.1168
. [all data]
Skaltsa, Lazari, et al., 2000
Skaltsa, H.D.; Lazari, D.M.; Loukis, A.E.; Constantinidis, T.,
Essential oil analysis of Nepeta argolica Bory Chaub. subsp. argolica (Lamiaceae) growing wild in Greece,
Flavour Fragr. J., 2000, 15, 2, 96-99, https://doi.org/10.1002/(SICI)1099-1026(200003/04)15:2<96::AID-FFJ873>3.0.CO;2-F
. [all data]
Eom S.H., Yang H.S., et al., 2006
Eom S.H.; Yang H.S.; Weston L.A.,
An evaluation of the allelopathic potential of selected perennial groundcovers: Foliar volatiles of catmint (Nepeta x faassenii) inhibit seedling growth,
J. Chem. Ecol., 2006, 32, 8, 1835-1848, https://doi.org/10.1007/s10886-006-9112-1
. [all data]
Sefidkon, Jamzad, et al., 2006
Sefidkon, F.; Jamzad, Z.; Mirza, M.,
Chemical composition of the essential oil of five Iranian Nepeta species (N. crispa, N. mahanensis, N. ispahanica, N. eremophila and N. rivularis),
Flavour Fragr. J., 2006, 21, 5, 764-767, https://doi.org/10.1002/ffj.1668
. [all data]
Sefidkon and Shaabani, 2004
Sefidkon, F.; Shaabani, A.,
Essential oil composition of Nepeta meyeri Benth. from Iran,
Flavour Fragr. J., 2004, 19, 3, 236-238, https://doi.org/10.1002/ffj.1294
. [all data]
Dabiri and Sefidkon, 2003
Dabiri, M.; Sefidkon, F.,
Chemical composition of the essential oil of Nepeta racemosa Lam. from Iran,
Flavour Fragr. J., 2003, 18, 2, 157-158, https://doi.org/10.1002/ffj.1151
. [all data]
Dabiri and Sefidkon, 2003, 2
Dabiri, M.; Sefidkon, F.,
Chemical compositional of Nepeta crassifolia Boiss. Buhse oil from Iran,
Flavour Fragr. J., 2003, 18, 3, 225-227, https://doi.org/10.1002/ffj.1199
. [all data]
Rustaiyan and Nadji, 1999
Rustaiyan, A.; Nadji, K.,
Composition of the essential oils of Nepeta ispahanica Boiss. and Nepeta binaludensis Jamzad from Iran,
Flavour Fragr. J., 1999, 14, 1, 35-37, https://doi.org/10.1002/(SICI)1099-1026(199901/02)14:1<35::AID-FFJ776>3.0.CO;2-N
. [all data]
Kökdil, Kurucu, et al., 1997
Kökdil, G.; Kurucu, S.; Topcu, G.,
Chemical constituents of the essential oils of Nepeta italica L. and Nepeta sulfuriflora P. H. Davis,
Flavour Fragr. J., 1997, 12, 1, 33-35, https://doi.org/10.1002/(SICI)1099-1026(199701)12:1<33::AID-FFJ609>3.0.CO;2-V
. [all data]
de Pooter, Nicolai, et al., 1988
de Pooter, H.L.; Nicolai, B.; De Laet, J.; De Buyck, L.F.; Schamp, N.M.; Goetghebeur, P.,
The Essential Oils of Five Nepeta Species. A Preliminary Evaluation of their Use in Chemotaxonomy by Cluster Analysis,
Flavour Fragr. J., 1988, 3, 4, 155-159, https://doi.org/10.1002/ffj.2730030404
. [all data]
HEuskin, Godin, et al., 2009
HEuskin, S.; Godin, B.; Leroy, P.; Quentin C.; Wathelet, J.-P.; Verheggen, F.; Haubruge, E.; Lognay, G.,
Fast gas chromatography characterization of purified semiochemicals from essential oils of Matricaria chamomilla L. (Asteraceae) and Nepeta cataria L. (Lamiaceae),
J. Chromatorg. A., 2009, 1216, 14, 2768-2775, https://doi.org/10.1016/j.chroma.2008.09.109
. [all data]
Suschke, Sporer, et al., 2007
Suschke, U.; Sporer, F.; Schneele, J.; Geiss, H.K.; Reichling, J.,
Antibacterial and Cytotoxic activity of Nepeta cataria L., Nepeta cataria var. citriodora (Beck.) Balb. and Melissa officinalis L. essential oils,
Natural Product Communications, 2007, 2, 12, 1277-1286. [all data]
Notes
Go To: Top, Gas Chromatography, References
- Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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