Bicyclo[3.1.0]hexan-3-one, 4-methyl-1-(1-methylethyl)-, [1S-(1α,4β,5α)]-
- Formula: C10H16O
- Molecular weight: 152.2334
- IUPAC Standard InChI: InChI=1S/C10H16O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6-8H,4-5H2,1-3H3/t7-,8?,10-/m1/s1
- IUPAC Standard InChIKey: USMNOWBWPHYOEA-HUWCLSLFSA-N
- CAS Registry Number: 471-15-8
- 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:
- Other names: β-Thujone; Isothujone; 3-Thujanone, (1S,4S,5R)-(+)-; (+)-Isothujone; D-β-Thujone; D-Isothujone; Thujone, (+)-; (+)-Thujone; (+)-β-Thujone; 1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-one-, (1S,4S,5R)-; (E)-Thujone; Thujone trans; trans-Thujone; cis-Thujone (CAS); NSC 67392; (1S,4S,5R)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-one; 7785-59-3; 33766-29-9; cis-Thujone; trans-thujone (β-thujone); (d) 1-isopropyl-4-methylbicyclo[3.1.0]hexan-3-one (thujone)
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
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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 | DB-5 | HP-5MS | HP-5MS | ZB-5 | HP-5MS |
| Column length (m) | 30. | 30. | 30. | 30. | 30. |
| Carrier gas | He | He | He | He | 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) | 60. | 60. | 60. | 50. | 60. |
| Tend (C) | 240. | 280. | 280. | 250. | 280. |
| Heat rate (K/min) | 3. | 3. | 4. | 3. | 3. |
| Initial hold (min) | 5. | ||||
| Final hold (min) | |||||
| I | 1115. | 1110. | 1112. | 1115. | 1103. |
| Reference | Flamini, Cioni, et al., 2007 | Kundakovic, Fokialakis, et al., 2007 | Saroglou, Marin, et al., 2007 | Simoniatto, Bonani, et al., 2007 | Vagionas, Ngassapa, et al., 2007 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | SPB-1 | DB-5 | HP-5MS | RTX-1 | DB-5 |
| Column length (m) | 30. | 30. | 30. | 60. | 30. |
| Carrier gas | He | He | He | He | |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.2 | 0.25 | 0.22 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
| Tstart (C) | 50. | 50. | 60. | 60. | 40. |
| Tend (C) | 250. | 250. | 280. | 220. | 260. |
| Heat rate (K/min) | 5. | 5. | 4. | 2. | 2. |
| Initial hold (min) | 3. | 3. | 5. | 5. | |
| Final hold (min) | 15. | 15. | 20. | 20. | |
| I | 1123. | 1114. | 1116. | 1100. | 1101. |
| Reference | Blagojevic, Radulovic, et al., 2006 | Blagojevic, Radulovic, et al., 2006 | Saroglou, Dorizas, et al., 2006 | Cozzani, Muselli, et al., 2005 | Senatore, Napolitano, et al., 2005 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | SPB-1 | HP-5 | HP-5 | HP-5 | HP-5 |
| Column length (m) | 30. | 30. | 30. | 30. | 30. |
| Carrier gas | He | He | N2 | He | 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. | 60. | 60. | 60. | 60. |
| Tend (C) | 220. | 260. | 220. | 280. | 280. |
| Heat rate (K/min) | 3. | 3. | 5. | 4. | 3. |
| Initial hold (min) | 10. | 5. | |||
| Final hold (min) | 15. | ||||
| I | 1089. | 1116. | 1116. | 1114. | 1114. |
| Reference | Antunes, Sevinate-Pinto, et al., 2004 | Javidnia, Miri, et al., 2004 | Flamini, Luigi Cioni, et al., 2003 | Karioti, Skaltsa, et al., 2003 | Tsiri, Kretsi, et al., 2003 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | HP-5 | HP-5 | HP-5MS | HP-5 | HP-5 |
| Column length (m) | 30. | 30. | 30. | 30. | 30. |
| Carrier gas | He | He | He | He | 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 | 0.50 |
| Tstart (C) | 60. | 60. | 60. | 60. | 60. |
| Tend (C) | 280. | 280. | 300. | 380. | 280. |
| Heat rate (K/min) | 3. | 3. | 3. | 3. | 3. |
| Initial hold (min) | |||||
| Final hold (min) | |||||
| I | 1114. | 1115. | 1116. | 1111. | 1115. |
| Reference | Tsiri, Kretsi, et al., 2003 | Tzakou, Couladis, et al., 2003 | Couladis, Chinou, et al., 2002 | Couladis, Tsortanidou, et al., 2001 | Couladis, Tzakou, et al., 2001 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | HP-5MS | HP-5MS | BPX-5 | DB-1 | DB-1 |
| Column length (m) | 30. | 30. | 50. | 60. | 60. |
| Carrier gas | He | He | H2 | He | |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.25 | 0.22 | 0.32 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 1. | 0.25 |
| Tstart (C) | 60. | 60. | 60. | -50. | 50. |
| Tend (C) | 280. | 280. | 180. | 175. | 220. |
| Heat rate (K/min) | 3. | 4. | 4. | 6. | 4. |
| Initial hold (min) | 5. | 5. | 5. | 2. | |
| Final hold (min) | 5. | ||||
| I | 1114. | 1115. | 1135. | 1108.3 | 1092. |
| Reference | Giamakis, Kretsi, et al., 2001 | Skaltsa, Mavrommati, et al., 2001 | Zabaras and Wyllie, 2001 | Helmig, Klinger, et al., 1999 | Mirza and Sefidkon, 1999 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary |
|---|---|---|
| Active phase | OV-1 | DB-5 |
| Column length (m) | 25. | 30. |
| Carrier gas | ||
| Substrate | ||
| Column diameter (mm) | 0.25 | 0.25 |
| Phase thickness (μm) | 0.3 | 0.25 |
| Tstart (C) | 50. | 50. |
| Tend (C) | 200. | 250. |
| Heat rate (K/min) | 3. | 3. |
| Initial hold (min) | 1. | |
| Final hold (min) | 20. | |
| I | 1092. | 1116. |
| Reference | Bicchi, Rubiolo, et al., 1998 | Isidorov, Zenkevich, et al., 1998 |
| 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.
Flamini, Cioni, et al., 2007
Flamini, G.; Cioni, P.L.; Morelli, I.; Bader, A.,
Essential oils of the aerial parts of three Salvia species from Jordan: Salvia lanigera, S. spinosa and S. syriaca,
Food Chem., 2007, 100, 2, 732-735, https://doi.org/10.1016/j.foodchem.2005.10.032
. [all data]
Kundakovic, Fokialakis, et al., 2007
Kundakovic, T.; Fokialakis, N.; Kovacevic, N.; Chinou, I.,
Essential oil composition of Achillea lingulata and A. umbellata,
Flavour Fragr. J., 2007, 22, 3, 184-187, https://doi.org/10.1002/ffj.1778
. [all data]
Saroglou, Marin, et al., 2007
Saroglou, V.; Marin, P.D.; Rancic, A.; Veljic, M.; Skaltsa, H.,
Composition and antimicrobial activity of the essential oil of six Hypericum species from Serbia,
Biochem. Syst. Ecol., 2007, 35, 3, 146-152, https://doi.org/10.1016/j.bse.2006.09.009
. [all data]
Simoniatto, Bonani, et al., 2007
Simoniatto, E.; Bonani, V.F.L.; Morel, A.F.; Poppi, N.R.; Raposo, J.L., Jr.; Stuker, C.Z.; Peruzzo, G.M.; Peres, M.T.L.P.; Hess, S.C.,
Chemical composition and evaluation of antibacterial and antioxidant activities of the essential oil of Croton urucurana Baillon (Euphorbiaceae) stem bark,
J. Braz. Chem., 2007, 18, 5, 879-885, https://doi.org/10.1590/S0103-50532007000500002
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Vagionas, Ngassapa, et al., 2007
Vagionas, K.; Ngassapa, O.; Runyoro, D.; Graikou, K.; Gortzi, O.; Chinou, I.,
Chemical analysis of edible aromatic plants growing in Tanzania,
Food Chem., 2007, 105, 4, 1711-1717, https://doi.org/10.1016/j.foodchem.2007.05.029
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Blagojevic, Radulovic, et al., 2006
Blagojevic, P.; Radulovic, N.; Palic, R.; Stojanovic, G.,
Chemical composition of the essential oils of Serbian wild-growing Srtemisia absinthium and Artemisia vulgaris,
J. Agric. Food Chem., 2006, 54, 13, 4780-4789, https://doi.org/10.1021/jf060123o
. [all data]
Saroglou, Dorizas, et al., 2006
Saroglou, V.; Dorizas, N.; Kypriotakis, Z.; Skaltsa, H.D.,
Analysis of the essential oil composition of eight Anthemis species from Greece,
J. Chromatogr. A, 2006, 1104, 1-2, 313-322, https://doi.org/10.1016/j.chroma.2005.11.087
. [all data]
Cozzani, Muselli, et al., 2005
Cozzani, S.; Muselli, A.; Desjobert, J.-M.; Bernardini, A.-F.; Tomi, F.; Casanova, J.,
Chemical composition of essential oil of Teucrium polium subsp. capitatum (L.) from Corsica,
Flavour Fragr. J., 2005, 20, 4, 436-441, https://doi.org/10.1002/ffj.1463
. [all data]
Senatore, Napolitano, et al., 2005
Senatore, F.; Napolitano, F.; Arnold, N.A.; Bruno, M.; Herz, W.,
Composition and antimicrobial activity of the essential oil of Achillea falcata L. (Asteraceae),
Flavour Fragr. J., 2005, 20, 3, 291-294, https://doi.org/10.1002/ffj.1411
. [all data]
Antunes, Sevinate-Pinto, et al., 2004
Antunes, T.; Sevinate-Pinto, I.; Barroso, J.G.; Cavaleiro, C.; Salgueiro, L.R.,
Micromorphology of trichomes and composition of essential oil of Teucrium capitatum,
Flavour Fragr. J., 2004, 19, 4, 336-340, https://doi.org/10.1002/ffj.1310
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Javidnia, Miri, et al., 2004
Javidnia, K.; Miri, R.; Jafari, A.; Rezai, H.,
Analysis of the volatile constituents of Nepeta macrosiphon Boiss. grown in Iran,
Flavour Fragr. J., 2004, 19, 2, 156-158, https://doi.org/10.1002/ffj.1287
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Flamini, Luigi Cioni, et al., 2003
Flamini, G.; Luigi Cioni, P.; Morelli, I.,
Short communication. Use of solid-phase micro-extraction as a sampling technique in the determination of volatiles emitted by flowers, isolated flower parts and pollen,
J. Chromatogr. A, 2003, 998, 1-2, 229-233, https://doi.org/10.1016/S0021-9673(03)00641-1
. [all data]
Karioti, Skaltsa, et al., 2003
Karioti, A.; Skaltsa, H.; Demetzos, C.; Perdetzoglou, D.; Economakis, C.D.; Salem, A.B.,
Effect of nitrogen concentration of the nutrient solution on the volatile constituents of leaves of Salvia fruticosa Mill. in solution culture,
J. Agric. Food Chem., 2003, 51, 22, 6505-6508, https://doi.org/10.1021/jf030308k
. [all data]
Tsiri, Kretsi, et al., 2003
Tsiri, D.; Kretsi, O.; Chinou, I.B.; Spyropoulos, C.G.,
Composition of fruit volatiles and annual changes in the volatiles of leaves of Eucalyptus camaldulensis Dehn. growing in Greece,
Flavour Fragr. J., 2003, 18, 3, 244-247, https://doi.org/10.1002/ffj.1220
. [all data]
Tzakou, Couladis, et al., 2003
Tzakou, O.; Couladis, M.; Slavkovska, V.; Mimica-Dukic, N.; Jancic, R.,
The essential oil composition of Salvia brachyodon Vandas,
Flavour Fragr. J., 2003, 18, 1, 2-4, https://doi.org/10.1002/ffj.1132
. [all data]
Couladis, Chinou, et al., 2002
Couladis, M.; Chinou, I.B.; Tzakou, O.; Loukis, A.,
Composition and antimicrobial activity of the essential oil of Ballota pseudodictamnus L. Bentham,
Phytother. Res., 2002, 16, 8, 723-726, https://doi.org/10.1002/ptr.1043
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Couladis, Tsortanidou, et al., 2001
Couladis, M.; Tsortanidou, V.; Francisco-Ortega, J.; Santos-Guerra, A.; Harvala, C.,
Composition of the essential oils of Argyranthemum species growing in the Canary Islands,
Flavour Fragr. J., 2001, 16, 2, 103-106, https://doi.org/10.1002/ffj.954
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Couladis, Tzakou, et al., 2001
Couladis, M.; Tzakou, O.; Stojanovic, D.; Mimica-Dukic, N.; Jancic, R.,
The essential oil composition of Salvia argentea L.,
Flavour Fragr. J., 2001, 16, 3, 227-229, https://doi.org/10.1002/ffj.989
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Giamakis, Kretsi, et al., 2001
Giamakis, A.; Kretsi, O.; Chinou, I.; Spyropoulos, C.G.,
Eucalyptus camaldulensis: volatiles from immature flowers and high production of 1,8-cineole and β-pinene by in vitro cultures,
Phytochemistry, 2001, 58, 2, 351-355, https://doi.org/10.1016/S0031-9422(01)00193-5
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Skaltsa, Mavrommati, et al., 2001
Skaltsa, H.D.; Mavrommati, A.; Constantinidis, T.,
A chemotaxonomic investigation of volatile constituents in Stachys subsect. Swainsonianeae (Labiatae),
Phytochemistry, 2001, 57, 2, 235-244, https://doi.org/10.1016/S0031-9422(01)00003-6
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Zabaras and Wyllie, 2001
Zabaras, D.; Wyllie, S.G.,
Quantitative analysis of terpenoids in the gas phase using headspace solid-phase microextraction (HS-SPME),
Flavour Fragr. J., 2001, 16, 6, 411-416, https://doi.org/10.1002/ffj.1025
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Helmig, Klinger, et al., 1999
Helmig, D.; Klinger, L.F.; Guenther, A.; Vierling, L.; Geron, C.; Zimmerman, P.,
Biogenic volatile organic compound emissions (BVOCs). I. Identifications from three continental sites in the U.S.,
Chemosphere, 1999, 38, 9, 2163-2187, https://doi.org/10.1016/S0045-6535(98)00425-1
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Mirza and Sefidkon, 1999
Mirza, M.; Sefidkon, F.,
Essential oil composition of two Salvia species from Iran, Salvia nemorosa L. and Salvia reuterana Boiss.,
Flavour Fragr. J., 1999, 14, 4, 230-232, https://doi.org/10.1002/(SICI)1099-1026(199907/08)14:4<230::AID-FFJ816>3.0.CO;2-L
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Bicchi, Rubiolo, et al., 1998
Bicchi, C.; Rubiolo, P.; Marschall, H.; Weyerstahl, P.; Laurent, R.,
Constituents of Artemisia roxburghiana Besser essential oil,
Flavour Fragr. J., 1998, 13, 1, 40-46, https://doi.org/10.1002/(SICI)1099-1026(199801/02)13:1<40::AID-FFJ688>3.0.CO;2-Z
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Isidorov, Zenkevich, et al., 1998
Isidorov, V.A.; Zenkevich, I.G.; Dubis, E.N.; Slowikowski, A.; Wojciuk, E.,
Group identification of essential oils components using partition coefficients in a hexane-acetonitrile system,
J. Chromatogr. A, 1998, 814, 1-2, 253-260, https://doi.org/10.1016/S0021-9673(98)00398-7
. [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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