Thujone
- 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-MRTMQBJTSA-N
- CAS Registry Number: 546-80-5
- Chemical structure:
This structure is also available as a 2d Mol file - Species with the same structure:
- Stereoisomers:
- Other names: Bicyclo[3.1.0]hexan-3-one, 4-methyl-1-(1-methylethyl)-, [1S-(1α,4α,5α)]-; α-Thujone; Thujone, cis; 3-Thujanone, (1S,4R,5R)-(-)-; Thujon; 3-Thujanone, (-)-; l-Thujone; 4-Methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-one-, (1S,4R,5R)-; 3-Thujone; cis-Thujone; (Z)-Thujone; (-)-Thujone; Bicyclo(3.1.0)hexan-3-one, 4-methyl-1-(1-methylethyl)-, (1S,4R,5R)-; NSC 93742; (1S,4R,5R)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-one; 1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-one
- 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 | HP-5MS | BP-1 | DB-5 | HP-5MS | HP-5MS |
| Column length (m) | 30. | 50. | 30. | 30. | 30. |
| Carrier gas | He | He | He | He | He |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.22 | 0.32 | 0.25 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.5 | 0.25 | 0.25 |
| Tstart (C) | 60. | 60. | 40. | 60. | 60. |
| Tend (C) | 280. | 220. | 265. | 280. | 280. |
| Heat rate (K/min) | 3. | 2. | 7. | 4. | 3. |
| Initial hold (min) | 5. | ||||
| Final hold (min) | 20. | 5. | |||
| I | 1105. | 1096. | 1100. | 1105. | 1102. |
| Reference | Kundakovic, Fokialakis, et al., 2007 | Lesueur, de Rocca Serra, et al., 2007 | Mahattanatawee K., Perez-Cacho P.R., et al., 2007 | Saroglou, Arfan, 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 | CP Sil 5 CB | CP Sil 5 CB | RTX-1 |
| Column length (m) | 30. | 30. | 25. | 25. | 60. |
| Carrier gas | He | He | H2 | He | |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.2 | 0.25 | 0.25 | 0.22 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.4 | 0.25 | |
| Tstart (C) | 50. | 50. | 80. | 80. | 60. |
| Tend (C) | 250. | 250. | 270. | 270. | 220. |
| Heat rate (K/min) | 5. | 5. | 10. | 10. | 2. |
| Initial hold (min) | 3. | 3. | |||
| Final hold (min) | 15. | 15. | 20. | ||
| I | 1113. | 1102. | 1089. | 1089. | 1087. |
| Reference | Blagojevic, Radulovic, et al., 2006 | Blagojevic, Radulovic, et al., 2006 | Ziegenbein, Hanssen, et al., 2006 | Ziegenbein, Hanssen, et al., 2006, 2 | Cozzani, Muselli, et al., 2005 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | HP-5MS | DB-5 | BP-1 | HP-5 | DB-5 |
| Column length (m) | 30. | 30. | 50. | 30. | 30. |
| Carrier gas | He | He | He | He | |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.25 | 0.22 | 0.25 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | |
| Tstart (C) | 60. | 40. | 60. | 60. | 60. |
| Tend (C) | 250. | 260. | 220. | 260. | 260. |
| Heat rate (K/min) | 4. | 2. | 2. | 3. | 3. |
| Initial hold (min) | 2. | 5. | |||
| Final hold (min) | 20. | 20. | 20. | ||
| I | 1102. | 1110. | 1069. | 1107. | 1115. |
| Reference | Pino, Mesa, et al., 2005 | Senatore, Napolitano, et al., 2005 | Gonny, Bradesi, et al., 2004 | Javidnia, Miri, et al., 2004 | Javidnia, Miri, et al., 2004, 2 |
| 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-5 | HP-5 | HP-5 |
| Column length (m) | 50. | 30. | 30. | 30. | 30. |
| Carrier gas | He | He | He | He | He |
| Substrate | |||||
| Column diameter (mm) | 0.2 | 0.25 | 0.25 | 0.25 | 0.25 |
| Phase thickness (μm) | 0.2 | 0.25 | 0.25 | 0.25 | 0.25 |
| Tstart (C) | 35. | 60. | 60. | 60. | 60. |
| Tend (C) | 250. | 280. | 280. | 280. | 380. |
| Heat rate (K/min) | 3. | 4. | 3. | 3. | 3. |
| Initial hold (min) | 15. | 5. | 5. | ||
| Final hold (min) | 40. | ||||
| I | 1106. | 1102. | 1106. | 1112. | 1099. |
| Reference | Stashenko, Jaramillo, et al., 2004 | Karioti, Skaltsa, et al., 2003 | Tzakou, Couladis, et al., 2003 | Aligiannis, Kalpoutzakis, et al., 2001 | Couladis, Tsortanidou, et al., 2001 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | HP-5 | BPX-5 | DB-1 | DB-1 | HP-1 |
| Column length (m) | 30. | 50. | 60. | 30. | 60. |
| Carrier gas | He | H2 | He | ||
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.22 | 0.32 | 0.25 | 0.25 |
| Phase thickness (μm) | 0.50 | 0.25 | 1. | 0.25 | 0.25 |
| Tstart (C) | 60. | 60. | -50. | 50. | 50. |
| Tend (C) | 280. | 180. | 175. | 220. | 250. |
| Heat rate (K/min) | 3. | 4. | 6. | 3. | 2.5 |
| Initial hold (min) | 5. | 2. | 3. | 5. | |
| Final hold (min) | 5. | ||||
| I | 1106. | 1124. | 1097.4 | 1091. | 1099. |
| Reference | Couladis, Tzakou, et al., 2001 | Zabaras and Wyllie, 2001 | Helmig, Klinger, et al., 1999 | Muselli, Hoi, et al., 1999 | Stashenko, Cervantes, et al., 1999 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary |
|---|---|
| Active phase | OV-1 |
| Column length (m) | 25. |
| Carrier gas | |
| Substrate | |
| Column diameter (mm) | 0.25 |
| Phase thickness (μm) | 0.3 |
| Tstart (C) | 50. |
| Tend (C) | 200. |
| Heat rate (K/min) | 3. |
| Initial hold (min) | 1. |
| Final hold (min) | 20. |
| I | 1083. |
| Reference | Bicchi, Rubiolo, et al., 1998 |
| Comment | 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.
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]
Lesueur, de Rocca Serra, et al., 2007
Lesueur, D.; de Rocca Serra, D.; Bighelli, A.; Hoi, T.M.; Ban, N.K.; Thai, T.H.; Casanova, J.,
Chemical composition and antibacterial activity of the essential oil of Michelia foveolata Merryll ex Dandy from Vietnam,
Flavour Fragr. J., 2007, 22, 4, 317-321, https://doi.org/10.1002/ffj.1799
. [all data]
Mahattanatawee K., Perez-Cacho P.R., et al., 2007
Mahattanatawee K.; Perez-Cacho P.R.; Davenport T.; Rouseff R.,
Comparison of three lychee cultivar odor profiles using gas chromatography-olfactometry and gas chromatography-sulfur detection,
J. Agric. Food Chem., 2007, 55, 5, 1939-1944, https://doi.org/10.1021/jf062925p
. [all data]
Saroglou, Arfan, et al., 2007
Saroglou, V.; Arfan, M.; Shabir, A.; Hadjipavlou-Litina, D.; Skaltsa, H.,
Composition and antioxidant activity of the essential oil of Teucrium royleanum Wall. ex Benth growing in Pakistan,
Flavour Fragr. J., 2007, 22, 2, 154-157, https://doi.org/10.1002/ffj.1774
. [all data]
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]
Ziegenbein, Hanssen, et al., 2006
Ziegenbein, F.C.; Hanssen, H.-P.; König, W.A.,
Secondary metabolites from Ganoderma lucidum and Spongiporus leucomallellus,
Phytochemistry, 2006, 67, 2, 202-211, https://doi.org/10.1016/j.phytochem.2005.10.025
. [all data]
Ziegenbein, Hanssen, et al., 2006, 2
Ziegenbein, F.C.; Hanssen, H.-P.; König, W.A.,
Chemical constituents of the essential oils of three wood-rotting fungi,
Flavour Fragr. J., 2006, 21, 5, 813-816, https://doi.org/10.1002/ffj.1732
. [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]
Pino, Mesa, et al., 2005
Pino, J.A.; Mesa, J.; Muñoz, Y.; Martí, M.P.; Marbot, R.,
Volatile components from mango (Mangifera indica L.) cultivars,
J. Agric. Food Chem., 2005, 53, 6, 2213-2223, https://doi.org/10.1021/jf0402633
. [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]
Gonny, Bradesi, et al., 2004
Gonny, M.; Bradesi, P.; Casanova, J.,
Identification of the components of the essential oil from wild Corsican Daucus carota L. using 13C-NMR spectroscopy,
Flavour Fragr. J., 2004, 19, 5, 424-433, https://doi.org/10.1002/ffj.1330
. [all data]
Javidnia, Miri, et al., 2004
Javidnia, K.; Miri, R.; Kamalinejad, M.; Sarkarzadeh, H.; Jamalian, A.,
Chemical composition of the essential oils of Anthemis altissima L. grown in Iran,
Flavour Fragr. J., 2004, 19, 3, 213-216, https://doi.org/10.1002/ffj.1277
. [all data]
Javidnia, Miri, et al., 2004, 2
Javidnia, K.; Miri, R.; Sadeghpour, H.,
Composition of the volatile oil of Achillea wilhelmsii C. Koch from Iran,
DARU, 2004, 12, 2, 63-66, retrieved from http://www1.tums.ac.ir/daru/. [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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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]
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
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Aligiannis, Kalpoutzakis, et al., 2001
Aligiannis, N.; Kalpoutzakis, E.; Chinou, I.B.; Mitaku, S.; Gikas, E.; Tsarbopoulos, A.,
Composition and antimicrobial activity of the essential oils of five taxa of Sideritis from Greece,
J. Agric. Food Chem., 2001, 49, 2, 811-815, https://doi.org/10.1021/jf001018w
. [all data]
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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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.,
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Muselli, Hoi, et al., 1999
Muselli, A.; Hoi, T.M.; Cu, L.D.; Moi, L.D.; Bessière, J.-M.; Bighelli, A.; Casanova, J.,
Composition of the essential oil of Acanthopanax trifoliatus (L.) Merr. (Araliacaea) from Vietnam,
Flavour Fragr. J., 1999, 14, 1, 41-44, https://doi.org/10.1002/(SICI)1099-1026(199901/02)14:1<41::AID-FFJ781>3.0.CO;2-B
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Stashenko, Cervantes, et al., 1999
Stashenko, E.E.; Cervantes, M.; Combariza, Y.; Fuentes, H.; Martínez, J.R.,
HRGC/FID and HRGC/MSD analysis of the secondary metabolites obtained by different extraction methods from Lepechinia schiedeana, an in vitro evaluation of its antioxidant activity,
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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
. [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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