Thujone
- Formula: C10H16O
- Molecular weight: 152.2334
- 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
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- Other data available:
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Normal alkane RI, non-polar column, custom temperature program
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-1 | RTX-1 | HP-5 MS | HP-5 MS | HP-5 MS |
Column length (m) | 30. | 60. | 30. | 30. | 30. |
Carrier gas | Hydrogen | Helium | Helium | Helium | Helium |
Substrate | |||||
Column diameter (mm) | 0.25 | 0.22 | 0.25 | 0.25 | 0.25 |
Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
Program | 45 0C 3 0C/min -> 175 0C 15 0C/min -> 300 0C (10 min) | not specified | 40 0C (10 min) 3 0C/min -> 200 0C 2 0C/min -> 220 0C | 60 0C (1 min) 10 0C/min -> 180 0C (1 min) 20 0C/min -> 280 0C (15 min) | 40 0C (5 min) 2 0C/min -> 270 0C -> 260 0C (20 min) |
I | 1074. | 1086. | 1105. | 1114. | 1105. |
Reference | Albano, Lima, et al., 2012 | Bendiabdellah, El Amine Dib, et al., 2012 | Sharopov, Sulaimonova, et al., 2012 | Liu, Chu, et al., 2010 | Mancini, Arnold, et al., 2009 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
---|---|---|---|---|---|
Active phase | HP-5 | SLB-5 MS | SLB-5 MS | BP-5 | DB-5 MS |
Column length (m) | 30. | 30. | 30. | 30. | 30. |
Carrier gas | Helium | Helium | He | Helium | |
Substrate | |||||
Column diameter (mm) | 0.32 | 0.25 | 0.25 | 0.32 | 0.25 |
Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | |
Program | not specified | 50 0C 3 0C/min -> 250 0C (1 min) 10 0C/min -> 300 0C (5 min) | not specified | 60C => 4C/min => 150C => 10C/min => 220C | 60 0C 3 0C/min -> 210 0C 5 0C/min -> 250 0C |
I | 1114. | 1107. | 1101. | 1105. | 1102. |
Reference | Riahi, Pourbasheer, et al., 2009 | Costa, De Fina, et al., 2008 | Costa, De Fina, et al., 2008 | Hashemi, Abolghasemi, et al., 2007 | Haznagy-Radnai, Szigle, et al., 2007 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
---|---|---|---|---|---|
Active phase | BPX-5 | HP-5MS | CP Sil 8 CB | HP-5MS | SE-52 |
Column length (m) | 30. | 30. | 50. | 30. | 30. |
Carrier gas | He | He | He | He | He |
Substrate | |||||
Column diameter (mm) | 0.25 | 0.25 | 0.32 | 0.25 | 0.32 |
Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.15 |
Program | 50C => 3C/min => 150C(10min) => 10C/min => 250C | 40C(5min) => 2C/min => 250C(15min) => 10C/min => 270C | 60C(2min) => 5C/min => 160C(1min) => 10C/min => 250C (5min) | 40C(5min) => 2C/min => 250C (15min) => 10C/min => 270C | 45C => 1C/min => 100C => 5C/min => 250C (10min) |
I | 1118. | 1105. | 1102. | 1105. | 1102. |
Reference | Salamci, Kordali, et al., 2007 | Formisano C., Senatore F., et al., 2006 | Judzentiene and Buzelyte, 2006 | Senatore, Apostolides Arnold, et al., 2006 | Tognolini, Barocelli, et al., 2006 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
---|---|---|---|---|---|
Active phase | CP Sil 8 CB | DB-5 | BPX-5 | CP Sil 8 CB | HP-5 |
Column length (m) | 50. | 30. | 30. | 50. | 30. |
Carrier gas | He | He | He | ||
Substrate | |||||
Column diameter (mm) | 0.32 | 0.25 | 0.25 | 0.32 | 0.25 |
Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
Program | 50C(5min) => 2C/min => 90C => 15C/min => 240C(4min) | 40C(1min) => 9C/min => 130C => 2C/min => 230C | 60C(0.2min) => 3K/min => 186C => 10C/min => 240C (5min) | 60C(2min) => 5C/min => 160C(1min) => 10C/min => 250C (5min) | 40C(5min) => 2C/min => 250C(15min) => 10C/min => 270C |
I | 1102. | 1111. | 1102. | 1102. | 1105. |
Reference | Butkienë, Nivinskienë, et al., 2005 | Hamm, Bleton, et al., 2005 | Judzentiene and Mockute, 2005 | Judpentienë and Mockutë, 2004 | Senatore, Apostolides Arnold, et al., 2004 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
---|---|---|---|---|---|
Active phase | SE-30 | SE-30 | CP Sil 8 CB | DB-1 | DB-5 |
Column length (m) | 50. | 30. | 30. | ||
Carrier gas | He | He | He | ||
Substrate | |||||
Column diameter (mm) | 0.32 | 0.25 | 0.25 | ||
Phase thickness (μm) | 0.25 | 0.25 | 0.25 | ||
Program | not specified | not specified | 60C(1min) => 5C/min => 160C => 10C/min => 250C(5min) | 45C => 3C/min => 175C => 15C/min => 240C (10min) | 60C => 3C/min => 240C => 30C/min => 300C |
I | 1107. | 1088. | 1102. | 1073. | 1117. |
Reference | Vinogradov, 2004 | Vinogradov, 2004 | Mockute, Nivinskiene, et al., 2003 | Baratta, Dorman, et al., 1998 | Yusuf, Begum, et al., 1998 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
---|---|---|---|---|---|
Active phase | CP Sil 5 CB | Polydimethyl siloxanes | DB-5 | Methyl Silicone | OV-101 |
Column length (m) | 30. | 30. | |||
Carrier gas | N2 | ||||
Substrate | |||||
Column diameter (mm) | 0.25 | 0.25 | |||
Phase thickness (μm) | |||||
Program | not specified | not specified | not specified | not specified | not specified |
I | 1091. | 1094. | 1113. | 1086. | 1084. |
Reference | Weyerstahl, Marschall, et al., 1997 | Zenkevich, 1997 | Jean, Garneau, et al., 1993 | Grundschober, 1991 | De Pooter, Vermeesch, et al., 1989 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
Column type | Packed |
---|---|
Active phase | OV-101 |
Column length (m) | 2.5 |
Carrier gas | N2 |
Substrate | Chromosorb G 60-80mesh DMCS |
Column diameter (mm) | |
Phase thickness (μm) | |
Program | not specified |
I | 1100. |
Reference | Swigar and Silverstein, 1981 |
Comment | MSDC-RI |
References
Go To: Top, Normal alkane RI, non-polar column, custom temperature program, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Albano, Lima, et al., 2012
Albano, S.M.; Lima, A.S.; Miguel, M.G.; Pedro, L.G.; Barroso, J.G.; Figueiredo, A.C.,
Antioxidant, anti-5-lipoxygenase and antiacetylcholinesterase activities of essential oils and decoction water of some aromatic plants,
Rec. Nat. Prod., 2012, 6, 1, 35-48. [all data]
Bendiabdellah, El Amine Dib, et al., 2012
Bendiabdellah, A.; El Amine Dib, M.; Djabou, N.; Allali, H.; Tabti, B.; Costa, J.; Myseli, A.,
Biological activities and volatile cinstituents of Daucus muricatus L. from Algeria,
Chem. Centr. J., 2012, 6, 48, 1-22. [all data]
Sharopov, Sulaimonova, et al., 2012
Sharopov, F.S.; Sulaimonova, V.A.; Setzer, W.N.,
Composition of the essential oil of Ertemisia absinthium from Tajikistan,
Rec. Nat. Prod., 2012, 6, 2, 127-134. [all data]
Liu, Chu, et al., 2010
Liu, Z.L.; Chu, S.S.; Liu, Q.R.,
Chemical composition and insecticidial activity against Sitophilus zeamais of the essential oils of Artemisia capillaris and Artemisia mongolica,
Molecules, 2010, 15, 4, 2600-2608, https://doi.org/10.3390/molecules15042600
. [all data]
Mancini, Arnold, et al., 2009
Mancini, E.; Arnold, N.A.; De Martino, L.; De Feo, V.; Formisano, C.; Rigano, D.; Senatore, F.,
Chemical composition and phytotoxic effects of essential oils of Salvia hierosolymitana Boiss. and Salvia multicaulis Vahl. var. simplicifolia Boiss. growing wild in Lebanon,
Molecules, 2009, 14, 11, 4725-4736, https://doi.org/10.3390/molecules14114725
. [all data]
Riahi, Pourbasheer, et al., 2009
Riahi, S.; Pourbasheer, E.; Ganjali, M.R.; Norouzi, P.,
Investigation of different linear and non-linear chemometric methods for modeling of retention index of essential oil components: Concerns to support vector mashine,
J. Hazard. Mat., 2009, 166, 2-3, 853-859, https://doi.org/10.1016/j.jhazmat.2008.11.097
. [all data]
Costa, De Fina, et al., 2008
Costa, R.; De Fina, M.R.; Valentino, M.R.; Rustaiyan, A.; Dugo, P.; Dugo, G.; Mondello, L.,
An investigation on the volatile composition of some Artemisia species from Iran,
Flavour Fragr. J., 2008, 24, 2, 75-82, https://doi.org/10.1002/ffj.1919
. [all data]
Hashemi, Abolghasemi, et al., 2007
Hashemi, P.; Abolghasemi, M.M.; Fakhari, A.R.; Ebrahimi, S.N.; Ahmadi, S.,
Hydrodistillation-Solvent Microextraction and GC-MS Identification of Volatile Components of Artemisia aucheri,
Chromatographia, 2007, 66, 3-4, 283-286, https://doi.org/10.1365/s10337-007-0289-4
. [all data]
Haznagy-Radnai, Szigle, et al., 2007
Haznagy-Radnai, E.; Szigle, Sz.; Mathe, I.,
Analysis of the essential oil of Downy wounderwort (Stachys Germanica L.),
Acta Fac. Pharm. Univer. Comenianae, 2007, 54, 78-83. [all data]
Salamci, Kordali, et al., 2007
Salamci, E.; Kordali, S.; Kotan, R.; Cakir, A.; Kaya, Y.,
Chemical compositions, antimicrobial and herbicidal effects of essential oils isolated from Turkish Tanacetum aucheranum and Tanacetum chiliophyllum var. chiliophyllum,
Biochem. Syst. Ecol., 2007, 35, 9, 569-581, https://doi.org/10.1016/j.bse.2007.03.012
. [all data]
Formisano C., Senatore F., et al., 2006
Formisano C.; Senatore F.; Bruno M.; Bellone G.,
Chemical composition and antimicrobial activity of the essential oil of Phlomis ferruginea Ten. (Lamiaceae) growing wild in Southern Italy,
Flavour Fragr. J., 2006, 21, 5, 848-851, https://doi.org/10.1002/ffj.1740
. [all data]
Judzentiene and Buzelyte, 2006
Judzentiene, A.; Buzelyte, J.,
Chemical composition of essential oils of Artemisia vulgaris L. (mugwort) from North Lithuania,
Chemija, 2006, 17, 1, 12-15. [all data]
Senatore, Apostolides Arnold, et al., 2006
Senatore, F.; Apostolides Arnold, N.; Piozzi, F.; Formisano, C.,
Chemical composition of the essential oil of Salvia microstegia Boiss. et Balansa growing wild in Lebanon,
J. Chromatogr. A, 2006, 1108, 2, 276-278, https://doi.org/10.1016/j.chroma.2006.01.066
. [all data]
Tognolini, Barocelli, et al., 2006
Tognolini, M.; Barocelli, E.; Ballabeni, V.; Bruni, R.; Bianchi, A.; Chiavarini, M.; Impicciatore, M.,
Comparative screening of plant essential oils: Phenylpropanoid moiety as basic core for antiplatelet activity,
Life Sciences, 2006, 78, 13, 1419-1432, https://doi.org/10.1016/j.lfs.2005.07.020
. [all data]
Butkienë, Nivinskienë, et al., 2005
Butkienë, R.; Nivinskienë, O.; Mockutë, D.,
α-Pinene chemotype of leaf (needle) essential oils of Juniperus communis L. growing wild in Vilnius district,
Chemija, 2005, 16, 1, 53-60. [all data]
Hamm, Bleton, et al., 2005
Hamm, S.; Bleton, J.; Connan, J.; Tchapla, A.,
A chemical investigation by headspace SPME and GC-MS of volatile and semi-volatile terpenes in various olibanum samples,
Phytochemistry, 2005, 66, 12, 1499-1514, https://doi.org/10.1016/j.phytochem.2005.04.025
. [all data]
Judzentiene and Mockute, 2005
Judzentiene, A.; Mockute, D.,
The inflorescence and leaf essential oils of Tanacetum vulgare L. var. vulgare growing wild in Lithuania,
Biochem. Syst. Ecol., 2005, 33, 5, 487-498, https://doi.org/10.1016/j.bse.2004.11.003
. [all data]
Judpentienë and Mockutë, 2004
Judpentienë, A.; Mockutë, D.,
Chemical composition of essential oils of Artemisia absinthium L. (wormwood) growing wild in Vilnius,
Chemija, 2004, 15, 4, 64-68. [all data]
Senatore, Apostolides Arnold, et al., 2004
Senatore, F.; Apostolides Arnold, N.; Piozzi, F.,
Chemical composition of the essential oil of Salvia multicaulis Vahl. var. simplicifolia Boiss. growing wild in Lebanon,
J. Chromatogr. A, 2004, 1052, 1-2, 237-240, https://doi.org/10.1016/j.chroma.2004.08.095
. [all data]
Vinogradov, 2004
Vinogradov, B.A.,
Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]
Mockute, Nivinskiene, et al., 2003
Mockute, D.; Nivinskiene, O.; Bernotiene, G.; Butkiene, R.,
The cis-thujone chemotype of Salvia officinalis L. essential oils,
Chemija, 2003, 14, 4, 216-220. [all data]
Baratta, Dorman, et al., 1998
Baratta, M.T.; Dorman, H.J.; Deans, S.G.; Figueiredo, A.C.; Barroso, J.G.; Ruberto, G.,
Antimicrobial and antioxidant properties of some commercial essential oils,
Flavour Fragr. J., 1998, 13, 4, 235-244, https://doi.org/10.1002/(SICI)1099-1026(1998070)13:4<235::AID-FFJ733>3.0.CO;2-T
. [all data]
Yusuf, Begum, et al., 1998
Yusuf, M.; Begum, J.; Mondello, L.; Stagno d'Alcontres, I.S.,
Studies on the essential oil bearing plants of Bangladesh. Part VI. Composition of the oil of Ocimum gratissimum L.,
Flavour Fragr. J., 1998, 13, 3, 163-166, https://doi.org/10.1002/(SICI)1099-1026(199805/06)13:3<163::AID-FFJ714>3.0.CO;2-1
. [all data]
Weyerstahl, Marschall, et al., 1997
Weyerstahl, P.; Marschall, H.; Seelmann, I.; Rustaiyan, A.,
Constituents of the essential oil of Achillea eriophora DC,
Flavour Fragr. J., 1997, 12, 2, 71-78, https://doi.org/10.1002/(SICI)1099-1026(199703)12:2<71::AID-FFJ620>3.0.CO;2-E
. [all data]
Zenkevich, 1997
Zenkevich, I.G.,
Analytical Parameters of Components of Essential Oils for their Chromatographic and Chromato-Spectral Identificaiton. Oxsigenated derivatives of Mono- and Sesquiterpene Hydrocarbons,
Rastit, Resursy (Rus.), 1997, 33, 1, 16-28. [all data]
Jean, Garneau, et al., 1993
Jean, F.-I.; Garneau, F.-X.; Collin, G.J.; Bouhajib, M.; Zamir, L.O.,
The essential oil and glycosidically bound volatile compounds of Taxus canadensis marsh,
J. Essent. Oil Res., 1993, 5, 1, 7-11, https://doi.org/10.1080/10412905.1993.9698163
. [all data]
Grundschober, 1991
Grundschober, F.,
The identification of individual components in flavourings and flavoured foods,
Z. Lebensm. Unters. Forsch., 1991, 192, 6, 530-534, https://doi.org/10.1007/BF01202508
. [all data]
De Pooter, Vermeesch, et al., 1989
De Pooter, H.L.; Vermeesch, J.; Schamp, N.M.,
The Essential Oils of Tanacetum vulgare L. and Tanacetum parthenium (L.) Schultz-Bip,
J. Essent. Oil Res., 1989, 1, 1, 9-13, https://doi.org/10.1080/10412905.1989.9699438
. [all data]
Swigar and Silverstein, 1981
Swigar, A.A.; Silverstein, R.M.,
Monoterpenes, Aldrich Chemical Company, Milwaukee, WI, USA, 1981, 130. [all data]
Notes
Go To: Top, Normal alkane RI, non-polar column, custom temperature program, References
- Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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