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)
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- Other data available:
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Normal alkane RI, 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 | RTX-Wax | Supelcowax-10 | FFAP | NB-20M | HP-Innowax |
| Column length (m) | 60. | 30. | 20. | 30. | 30. |
| Carrier gas | Helium | He | He | He | He |
| Substrate | |||||
| Column diameter (mm) | 0.22 | 0.2 | 0.25 | 0.2 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.2 | 0.25 | 0.25 | 0.17 |
| Tstart (C) | 60. | 70. | 90. | 50. | 60. |
| Tend (C) | 230. | 220. | 250. | 250. | 210. |
| Heat rate (K/min) | 2. | 3. | 6. | 2. | 4. |
| Initial hold (min) | 3. | ||||
| Final hold (min) | 30. | 15. | 15. | ||
| I | 1422. | 1442. | 1450. | 1438. | 1452. |
| Reference | Museli, Pau, et al., 2009 | Pinto, Salgueiro, et al., 2007 | Kitchlu, Bakshi, et al., 2006 | Orav, Raal, et al., 2006 | Ferretti, Maggi, et al., 2005 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | DB-Wax | DB-Wax | SW-10 | Supelcowax-10 | HP-20M |
| Column length (m) | 60. | 60. | 50. | 30. | 50. |
| Carrier gas | N2 | N2 | He | He | He |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.25 | 0.20 | 0.25 | 0.2 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.2 |
| Tstart (C) | 70. | 70. | 50. | 60. | 70. |
| Tend (C) | 230. | 230. | 230. | 240. | 180. |
| Heat rate (K/min) | 2. | 2. | 2. | 4. | 4. |
| Initial hold (min) | 2. | 2. | 4. | ||
| Final hold (min) | 20. | 20. | 10. | ||
| I | 1448. | 1447. | 1409. | 1444. | 1425. |
| Reference | Choi, 2004 | Choi, 2004, 2 | Raal, Paaver, et al., 2004 | Cabanillas, Lopez, et al., 2003 | Juteau, Jerkovic, et al., 2003 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | Innowax | Supelcowax | Supelcowax | PEG-20M | DB-Wax |
| Column length (m) | 60. | 30. | 30. | 50. | 60. |
| Carrier gas | He | He | He | He | He |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.25 | 0.25 | 0.2 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | ||
| Tstart (C) | 60. | 40. | 40. | 70. | 40. |
| Tend (C) | 220. | 240. | 240. | 220. | 200. |
| Heat rate (K/min) | 4. | 2. | 2. | 2. | 2. |
| Initial hold (min) | 10. | 2. | |||
| Final hold (min) | 10. | ||||
| I | 1451. | 1399. | 1400. | 1435. | 1436. |
| Reference | Suleimenov, Atazharova, et al., 2003 | Chiasson, Bélanger, et al., 2001 | Chiasson, Bélanger, et al., 2001 | Orav and Kann, 2001 | Umano, Hagi, et al., 2000 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|
| Active phase | CW 20M | Supelcowax-10 | Supelcowax-10 | DB-Wax |
| Column length (m) | 25. | 30. | ||
| Carrier gas | Hydrogen | H2 | ||
| Substrate | ||||
| Column diameter (mm) | 0.32 | 0.25 | ||
| Phase thickness (μm) | 0.25 | 0.25 | ||
| Tstart (C) | 50. | 40. | 40. | 50. |
| Tend (C) | 220. | 210. | 210. | 250. |
| Heat rate (K/min) | 3. | 2. | 2. | 5. |
| Initial hold (min) | 1. | 2. | 2. | |
| Final hold (min) | 10. | 120. | 120. | |
| I | 1421. | 1440. | 1441. | 1435. |
| Reference | Bicchi, Binello, et al., 1999 | Collin, Deslauriers, et al., 1993 | Collin, Deslauriers, et al., 1993 | Perry, Baxter, et al., 1986 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
References
Go To: Top, Normal alkane RI, 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.
Museli, Pau, et al., 2009
Museli, A.; Pau, M.; Desjobert, J.-M.; Foddai, M.; Usai, M.; Costa, J.,
Volatile constituents of Achllea ligustica All. by HS-SPME/GC/GC-MS. Comparison with essential oils obtained by hydrodistillation from Corsica and Sardinia,
Chromatographia, 2009, 69, 5/6, 575-585, https://doi.org/10.1365/s10337-008-0939-1
. [all data]
Pinto, Salgueiro, et al., 2007
Pinto, E.; Salgueiro, L.R.; Cavaleiro, C.; Palmeira, A.; Goncalves, M.J.,
In vitro susceptibility of some species of yeasts and filamentous fungi to essential oils of Salvia of?cinalis,
Ind. Crops Prod., 2007, 26, 2, 135-141, https://doi.org/10.1016/j.indcrop.2007.02.004
. [all data]
Kitchlu, Bakshi, et al., 2006
Kitchlu, S.; Bakshi, S.K.; Kaul, M.K.; Bhan, M.K.; Thapa, R.K.; Agarwal, S.G.,
Tanacetum gracile Hook. f T. A new source of lavandulol from Ladakh Himalaya (India),
Flavour Fragr. J., 2006, 21, 4, 690-692, https://doi.org/10.1002/ffj.1674
. [all data]
Orav, Raal, et al., 2006
Orav, A.; Raal, A.; Arak, E.; Müürisepp, M.; Kailas, T.,
Composition of the essential oil of Artemisia absinthium L. of different geographical origin,
Proc. Est. Acad. Sci. Chem., 2006, 55, 3, 155-165. [all data]
Ferretti, Maggi, et al., 2005
Ferretti, G.; Maggi, F.; Tirillini, B.,
Essential oil composition of Hypericum richeri Vill. from Italy,
Flavour Fragr. J., 2005, 20, 3, 295-298, https://doi.org/10.1002/ffj.1412
. [all data]
Choi, 2004
Choi, H.-S.,
Volatile constituents of satsuma mandarins growing in Korea,
Flavour Fragr. J., 2004, 19, 5, 406-412, https://doi.org/10.1002/ffj.1283
. [all data]
Choi, 2004, 2
Choi, H.-S.,
Aroma evaluation of an aquatic herb, changpo (Acorus calamus Var. angustatus Bess), by AEDA and SPME,
J. Agric. Food Chem., 2004, 52, 26, 8099-8104, https://doi.org/10.1021/jf040239p
. [all data]
Raal, Paaver, et al., 2004
Raal, A.; Paaver, U.; Arak, E.; Orav, A.,
Content and composition of the essential oil of Thymus serpyllum L. growing wild in Estonia,
Medicina (Kaunas), 2004, 40, 8, 795-800. [all data]
Cabanillas, Lopez, et al., 2003
Cabanillas, C.M.; Lopez, M.L.; Daniele, G.; Zygadlo, J.A.,
Essential oil composition of Aloysia polystachya (Griseb.) Moldenke under rust disease,
Flavour Fragr. J., 2003, 18, 5, 446-448, https://doi.org/10.1002/ffj.1249
. [all data]
Juteau, Jerkovic, et al., 2003
Juteau, F.; Jerkovic, I.; Masotti, V.; Milos, M.; Mastelic, J.; Bessière, J.-M.; Viano, J.,
Composition and antimicrobial activity of the essential oil of Artemisia absinthium from Croatia and France,
Planta Medica, 2003, 69, 2, 158-161, https://doi.org/10.1055/s-2003-37714
. [all data]
Suleimenov, Atazharova, et al., 2003
Suleimenov, E.M.; Atazharova, G.A.; Demirchi, B.; Baser, K.H.C.; Adekenov, S.M.,
Essential oil composition of Artemisia Lercheana and A. Sieversiana of Kazakhstan flora
in Recent problems of development of new medicines of natural origin, Proceedings of symposium, St.Petersburg - Pushkin, 2003, 382-385. [all data]
Chiasson, Bélanger, et al., 2001
Chiasson, H.; Bélanger, A.; Bostanian, N.; Vincent, C.; Poliquin, A.,
Acaricidal properties of Artemisia absinthium and Tanacetum vulgare (Asteraceae) essential oils obtained by three methods of extraction,
J. Econ. Entomol., 2001, 94, 1, 167-171, https://doi.org/10.1603/0022-0493-94.1.167
. [all data]
Orav and Kann, 2001
Orav, A.; Kann, J.,
Determination of peppermint and orange aroma compounds in food and beverages,
Proc. Est. Acad. Sci. Chem., 2001, 50, 4, 217-225. [all data]
Umano, Hagi, et al., 2000
Umano, K.; Hagi, Y.; Nakahara, K.; Shoji, A.; Shibamoto, T.,
Volatile chemicals identified in extracts from leaves of Japanese mugwort (Artemisia princeps Pamp.),
J. Agric. Food Chem., 2000, 48, 8, 3463-3469, https://doi.org/10.1021/jf0001738
. [all data]
Bicchi, Binello, et al., 1999
Bicchi, C.; Binello, A.; D'Amato, A.; Rubiolo, P.,
Reliability of Van den Dool retention indices in the analysis of essential oils,
J. Chromatogr. Sci., 1999, 37, 8, 288-294, https://doi.org/10.1093/chromsci/37.8.288
. [all data]
Collin, Deslauriers, et al., 1993
Collin, G.J.; Deslauriers, H.; Pageau, N.; Gagnon, M.,
Essential oil of Tansy (Tanacetum vulgare L.) of Canadian origin,
J. Essent. Oil Res., 1993, 5, 6, 629-638, https://doi.org/10.1080/10412905.1993.9698296
. [all data]
Perry, Baxter, et al., 1986
Perry, N.B.; Baxter, A.J.; Brennan, N.J.; van Klink, J.W.,
Dalmatian Sage. PArt 1. Differing oil yields and compositions from flowering and non-flowering accessions,
Flavour Fragr. J., 1986, 11, 4, 231-238, https://doi.org/10.1002/(SICI)1099-1026(199607)11:4<231::AID-FFJ572>3.0.CO;2-0
. [all data]
Notes
Go To: Top, Normal alkane RI, 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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