Bicyclo[3.1.0]hexan-3-one, 4-methyl-1-(1-methylethyl)-, [1S-(1α,4β,5α)]-
- Formula: C10H16O
- Molecular weight: 152.2334
- 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:
- Options:
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 | HP-5 MS | Polydimethyl siloxane with 5 % Ph groups | Polydimethyl siloxane with 5 % Ph groups | HP-5 |
Column length (m) | 30. | 30. | 30. | 30. | 25. |
Carrier gas | Hydrogen | Helium | Helium | Helium | Hydrogen |
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 | 0.52 |
Program | 45 0C 3 0C/min -> 175 0C 15 0C/min -> 300 0C (10 min) | 40 0C (10 min) 3 0C/min -> 200 0C 2 0C/min -> 220 0C | 50 0C 4 0C/min -> 200 0C (5 min) 20 0C/min -> 280 0C | 50 0C 4 0C/min -> 200 0C (5 min) 20 0C/min -> 280 0C | not specified |
I | 1081. | 1115. | 1106. | 1117. | 1102. |
Reference | Albano, Lima, et al., 2012 | Sharopov, Sulaimonova, et al., 2012 | da Silva, de Souza, et al., 2012 | da Silva, de Souza, et al., 2012 | Velickovic, Ristic, et al., 2012 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
---|---|---|---|---|---|
Active phase | HP-5 | ZB-5 | ZB-5 | HP-5 MS | SLB-5 MS |
Column length (m) | 25. | 30. | 30. | 30. | 30. |
Carrier gas | Hydrogen | Nitrogen | Nitrogen | Helium | Helium |
Substrate | |||||
Column diameter (mm) | 0.32 | 0.25 | 0.25 | 0.25 | 0.25 |
Phase thickness (μm) | 0.52 | 0.25 | 0.25 | 0.25 | 0.25 |
Program | not specified | not specified | not specified | 40 0C (5 min) 2 0C/min -> 270 0C -> 260 0C (20 min) | 50 0C 3 0C/min -> 250 0C (1 min) 10 0C/min -> 300 0C (5 min) |
I | 1114. | 1081. | 1081. | 1115. | 1118. |
Reference | Velickovic, Ristic, et al., 2012 | Vazques, Aimar, et al., 2011 | Vazquez, Demmel, et al., 2011 | Mancini, Arnold, et al., 2009 | Costa, De Fina, et al., 2008 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
---|---|---|---|---|---|
Active phase | SLB-5 MS | SLB-5 MS | BP-5 | BPX-5 | HP-5MS |
Column length (m) | 30. | 30. | 30. | 30. | 30. |
Carrier gas | Helium | Helium | He | He | He |
Substrate | |||||
Column diameter (mm) | 0.25 | 0.25 | 0.32 | 0.25 | 0.25 |
Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
Program | not specified | not specified | 60C => 4C/min => 150C => 10C/min => 220C | 50C => 3C/min => 150C(10min) => 10C/min => 250C | 40C(5min) => 2C/min => 250C(15min) => 10C/min => 270C |
I | 1112. | 1117. | 1116. | 1124. | 1115. |
Reference | Costa, De Fina, et al., 2008 | Lo Presti, Sciarrone, et al., 2008 | Hashemi, Abolghasemi, et al., 2007 | Salamci, Kordali, et al., 2007 | Formisano C., Senatore F., et al., 2006 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
---|---|---|---|---|---|
Active phase | HP-5 | CP Sil 8 CB | HP-5MS | SE-52 | BPX-5 |
Column length (m) | 30. | 50. | 30. | 30. | 30. |
Carrier gas | He | He | He | He | |
Substrate | |||||
Column diameter (mm) | 0.25 | 0.32 | 0.25 | 0.32 | 0.25 |
Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.15 | 0.25 |
Program | 60C(4min) => 1C/min => 64C => 2.5C/min => 155C => 5C/min => 250C | 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) | 60C(0.2min) => 3K/min => 186C => 10C/min => 240C (5min) |
I | 1158. | 1114. | 1115. | 1114. | 1114. |
Reference | Jordan, Martinez, et al., 2006 | Judzentiene and Buzelyte, 2006 | Senatore, Apostolides Arnold, et al., 2006 | Tognolini, Barocelli, et al., 2006 | Judzentiene and Mockute, 2005 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
---|---|---|---|---|---|
Active phase | OV-1 | CP Sil 8 CB | HP-5 | HP-5 | |
Column length (m) | 15. | 50. | 30. | 30. | |
Carrier gas | He | He | He | ||
Substrate | |||||
Column diameter (mm) | 0.317 | 0.32 | 0.25 | 0.25 | |
Phase thickness (μm) | 0.25 | 0.25 | 0.25 | ||
Program | not specified | 50C(4min) => 4C/min => 90C => 10C/min => 300C(10min) | 60C(2min) => 5C/min => 160C(1min) => 10C/min => 250C (5min) | 40C(5min) => 2C/min => 250C(15min) => 10C/min => 270C | 60C(4min) => 1C/min => 64C => 2.5C/min => 155C => 5C/min => 250C |
I | 1090. | 1086. | 1114. | 1115. | 1158. |
Reference | El-Shazily, Hafez, et al., 2004 | El-Shazly and Hussein, 2004 | Judpentienë and Mockutë, 2004 | Senatore, Apostolides Arnold, et al., 2004 | Sotomayor, Martínez, 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 | HP-5 | CP Sil 8 CB | HP-5 | DB-1 |
Column length (m) | 30. | 50. | 30. | 30. | |
Carrier gas | He | He | He | He | |
Substrate | |||||
Column diameter (mm) | 0.25 | 0.32 | 0.25 | 0.25 | |
Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | |
Program | not specified | 60C (4min) => 1C/min => 64C => 2.5C/min => 155C => 5C/min => 250C | 60C(1min) => 5C/min => 160C => 10C/min => 250C(5min) | 50 0C 3 K/min -> 200 0C 8 K/min -> 280 0C | 45C => 3C/min => 175C => 15C/min => 240C (10min) |
I | 1102. | 1158. | 1114. | 1106. | 1081. |
Reference | Vinogradov, 2004 | Jordán, Martínez, et al., 2003 | Mockute, Nivinskiene, et al., 2003 | Usubillaga, Aparicio, et al., 2001 | Baratta, Dorman, et al., 1998 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
Column type | Capillary | Capillary | Capillary | Capillary |
---|---|---|---|---|
Active phase | CP Sil 5 CB | Polydimethyl siloxanes | Methyl Silicone | OV-101 |
Column length (m) | 30. | |||
Carrier gas | N2 | |||
Substrate | ||||
Column diameter (mm) | 0.25 | |||
Phase thickness (μm) | ||||
Program | not specified | not specified | not specified | not specified |
I | 1100. | 1102. | 1098. | 1096. |
Reference | Weyerstahl, Marschall, et al., 1997 | Zenkevich, 1997 | Grundschober, 1991 | De Pooter, Vermeesch, et al., 1989 |
Comment | MSDC-RI | MSDC-RI | MSDC-RI | 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]
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]
da Silva, de Souza, et al., 2012
da Silva, A.C.; de Souza, P.E.; Machado, J. daC.; da Silva, B.M.; Pinto, J.E.B.P.,
Effectiveness of essential oils in the treatment of Colletotrichum truncatum-infected soybean seeds,
Tropical Plant Patology, 2012, 37, 5, 305-313, https://doi.org/10.1590/S1982-56762012000500001
. [all data]
Velickovic, Ristic, et al., 2012
Velickovic, D.T.; Ristic, M.S.; Karabegovic, I.T.; Stojicevic, S.S.; Lazic, M.L.,
The influence of the distillation method on the chemical composition of the essential oil of sage (Salvia officinalis L.),
Advanced Technologies, 2012, 1, 1, 47-51. [all data]
Vazques, Aimar, et al., 2011
Vazques, A.M.; Aimar, M.L.; Demmel, G.I.; Criado, S.G.; Ruiz, G.M.; Cantero, J.J.; Rossi, L.I.; Velasco, M.I.,
Determination of volatile organic compounds of Tagetes argentina Cabrera (asteraceae) using HS-SPME analysis,
Boletin Latinoamericano y del Caribe Plantas Medicinales y Aromaticas, 2011, 10, 5, 463-469. [all data]
Vazquez, Demmel, et al., 2011
Vazquez, A.M.; Demmel, G.I.; Criado, S.G.; Aimar, M.L.; Cantero, J.; Rossi, L.I.; Velasco, M.I.,
Phytochemistry of TAgetes minuta L. (Asteraceae) from Cordoba, Argentina: comparative study between essential oil and HS-SPME analyses,
Boletin Latinoamericano y del Caribe Plantas Medicinales y Aromaticas, 2011, 10, 4, 351-362. [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]
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]
Lo Presti, Sciarrone, et al., 2008
Lo Presti, M.; Sciarrone, D.; Crupi, M.C.; Costa, R.; Ragusa, S.; Dugo, G.; Mondello, L.,
Evaliation of the volatile and chiral composition in Pistacia lentiscus L. essential oil,
Flavour Fragr. J., 2008, 23, 4, 249-257, https://doi.org/10.1002/ffj.1878
. [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]
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]
Jordan, Martinez, et al., 2006
Jordan, M.J.; Martinez, R.M.; Goodner, K.L.; Baldwin, E.A.; Sotomayor, J.A.,
Seasonal variation of Thymus hyemalis Lange and Spanish Thymus vulgaris L. essential oils composition,
Ind. Crops Prod., 2006, 24, 3, 253-263, https://doi.org/10.1016/j.indcrop.2006.06.011
. [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]
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]
El-Shazily, Hafez, et al., 2004
El-Shazily, A.M.; Hafez, S.S.; Wink, M.,
Comparative study of the essential oils and extracts of Achillea fragrantissima (Forssk.) Sch. Bip. and Achillea santolina L. (Asteraceae) from Egypt,
Pharmazie, 2004, 59, 226-230. [all data]
El-Shazly and Hussein, 2004
El-Shazly, A.M.; Hussein, K.T.,
Chemical analysis and biological activities of the essential oil of Teucrium leucocladum Boiss. (Lamiaceae),
Biochem. Syst. Ecol., 2004, 32, 7, 665-674, https://doi.org/10.1016/j.bse.2003.12.009
. [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]
Sotomayor, Martínez, et al., 2004
Sotomayor, J.A.; Martínez, R.M.; García, A.J.; Jordán, M.J.,
Thymus zygis Subsp. Gracilis: watering level effect on phytomass production and essential oil quality,
J. Agric. Food Chem., 2004, 52, 17, 5418-5424, https://doi.org/10.1021/jf0496245
. [all data]
Vinogradov, 2004
Vinogradov, B.A.,
Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]
Jordán, Martínez, et al., 2003
Jordán, M.J.; Martínez, R.M.; Cases, M.A.; Sotomayor. J.A.,
Watering level effect on Thymus hyemalis lange essential oil yield and composition,
J. Agric. Food Chem., 2003, 51, 18, 5420-5427, https://doi.org/10.1021/jf034335m
. [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]
Usubillaga, Aparicio, et al., 2001
Usubillaga, A.; Aparicio, R.; Romero, M.; Rojas, L.B.; Khouri, N.,
Volatile constituents from the leaves of four Libanothamus species from the Venezuelan Andes,
Flavour Fragr. J., 2001, 16, 3, 209-211, https://doi.org/10.1002/ffj.981
. [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]
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]
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]
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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