(1R,3E,7E,11R)-1,5,5,8-Tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene
- Formula: C15H24O
- Molecular weight: 220.3505
- IUPAC Standard InChI: InChI=1S/C15H24O/c1-12-6-7-13-15(4,16-13)10-5-9-14(2,3)11-8-12/h5,8-9,13H,6-7,10-11H2,1-4H3/b9-5+,12-8-/t13-,15-/m0/s1
- IUPAC Standard InChIKey: QTGAEXCCAPTGLB-MQTWWMRFSA-N
- CAS Registry Number: 19888-34-7
- 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: 12-Oxabicyclo[9.1.0]dodeca-3,7-diene, 1,5,5,8-tetramethyl-, (1R,3E,7E,11R)-; 12-Oxabicyclo[9.1.0]dodeca-3,7-diene, 1,5,5,8-tetramethyl-, [1R-(1R*,3E,7E,11R*)]-; 1,5,5,8-Tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene-, (1R,3E,7E,11R); 12-Oxabicyclo[9.1.0]dodeca-3,7-diene, 1,5,5,8-tetramethyl-, (E,E)-(1R,11R)-(-)-; Humulene-1,2-epoxide; Humulene epoxide 2; Humulene epoxide II; Humulene oxide II; α-Humulene epoxide II; (-)-Humulene epoxide II; Humulene 6,7-epoxide; Humulene II epoxide; 1,5,5,8-Tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene
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- Other data available:
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Kovats' 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 | DB-5 | DB-1 | BP-1 | BP-1 |
| Column length (m) | 30. | 25. | 25. | 25. | 30. |
| Carrier gas | He | He | He | N2 | N2 |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.2 | 0.2 | 0.32 | 0.32 |
| Phase thickness (μm) | 0.25 | 0.15 | 0.25 | 0.25 | |
| Tstart (C) | 60. | 60. | 60. | 60. | 60. |
| Tend (C) | 220. | 220. | 220. | 220. | |
| Heat rate (K/min) | 3. | 3. | 3. | 5. | 5. |
| Initial hold (min) | 3. | 3. | |||
| Final hold (min) | 13. | 3. | |||
| I | 1609. | 1606. | 1599. | 1608. | 1607. |
| Reference | Lucero, Fredrickson, et al., 2006 | Mevy, Bessiere, et al., 2006 | Mevy, Bessiere, et al., 2006, 2 | Raina, Verma, et al., 2006 | Srivastava, Srivastava, et al., 2006 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | DB-5 | DB-5 | DB-5 | HP-5MS | DB-5MS |
| Column length (m) | 30. | 30. | 30. | 30. | 30. |
| Carrier gas | He | He | He | He | |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.26 | 0.26 | 0.25 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
| Tstart (C) | 40. | 60. | 60. | 50. | 60. |
| Tend (C) | 210. | 246. | 246. | 250. | 240. |
| Heat rate (K/min) | 2. | 3. | 3. | 3. | 3. |
| Initial hold (min) | 2. | 10. | |||
| Final hold (min) | 33. | 5. | |||
| I | 1600. | 1608. | 1606. | 1606. | 1610. |
| Reference | Sylvestre, Pichette, et al., 2006 | Adams, Morris, et al., 2005 | Adams and Nguyen, 2005 | Asuming, Beauchamp, et al., 2005 | Maia, Andrade, et al., 2005 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | HP-5 | DB-5MS | CP Sil 8 CB | DB-5 | BP-1 |
| Column length (m) | 30. | 30. | 30. | 30. | 25. |
| Carrier gas | He | He | H2 | He | N2 |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.55 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
| Tstart (C) | 60. | 60. | 50. | 60. | 60. |
| Tend (C) | 260. | 240. | 220. | 220. | |
| Heat rate (K/min) | 3. | 3. | 3. | 3. | 5. |
| Initial hold (min) | 2. | ||||
| Final hold (min) | 15. | ||||
| I | 1608. | 1606. | 1594. | 1608. | 1599. |
| Reference | Lopes, Strobl, et al., 2004 | Palmeira, Moura, et al., 2004 | Schwob, Bessiere, et al., 2004 | Lucero, Estell, et al., 2003 | Srivastava, Ahmad, et al., 2003 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | DB-1 | BP-1 | HP-5MS | BP-1 | HP-1 |
| Column length (m) | 25. | 25. | 30. | 30. | 50. |
| Carrier gas | He | N2 | He | N2 | He |
| Substrate | |||||
| Column diameter (mm) | 0.2 | 0.55 | 0.25 | 0.32 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | |
| Tstart (C) | 60. | 60. | 50. | 60. | 100. |
| Tend (C) | 220. | 220. | 250. | 220. | 250. |
| Heat rate (K/min) | 3. | 5. | 3. | 5. | 5. |
| Initial hold (min) | 7. | ||||
| Final hold (min) | 15. | 13. | |||
| I | 1608. | 1612. | 1607. | 1596. | 1599. |
| Reference | Mevy, Bessiere, et al., 2002 | Raina, Srivastava, et al., 2002 | Salido, Altarejos, et al., 2002 | Shawl, Srivastava, et al., 2002 | Raina, Srivastava, 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 | SE-54 | DB-5 | DB-5 | HP-5MS |
| Column length (m) | 30. | 30. | 30. | 30. | 30. |
| Carrier gas | He | He | He | He | He |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.26 | 0.26 | 0.26 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
| Tstart (C) | 60. | 60. | 60. | 60. | 60. |
| Tend (C) | 280. | 246. | 240. | 246. | 280. |
| Heat rate (K/min) | 3. | 3. | 3. | 3. | 3. |
| Initial hold (min) | |||||
| Final hold (min) | |||||
| I | 1604. | 1606. | 1606. | 1606. | 1606. |
| Reference | Tzakou and Couladis, 2001 | Adams, 2000 | Adams, 2000, 2 | Adams, 2000, 3 | Roussis, Tsoukatou, et al., 2000 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary |
|---|---|
| Active phase | DB-5 |
| Column length (m) | 30. |
| Carrier gas | He |
| Substrate | |
| Column diameter (mm) | 0.26 |
| Phase thickness (μm) | 0.25 |
| Tstart (C) | 60. |
| Tend (C) | 246. |
| Heat rate (K/min) | 3. |
| Initial hold (min) | |
| Final hold (min) | |
| I | 1606. |
| Reference | Adams, 1999 |
| Comment | MSDC-RI |
References
Go To: Top, Kovats' 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.
Lucero, Fredrickson, et al., 2006
Lucero, M.E.; Fredrickson, E.L.; Estell, R.E.; Morrison, A.A.; Richman, D.B.,
Volatile Composition of Gutierrezia sarothrae (Broom Snakeweed) as Determined by Steam Distillation and Solid Phase Microextraction,
J. Essent. Oil Res., 2006, 18, 2, 121-125, https://doi.org/10.1080/10412905.2006.9699039
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Mevy, Bessiere, et al., 2006
Mevy, J.-P.; Bessiere, J.-M.; Greff, S.; Zombre, G.; Viano, J.,
Composition of the volatile oil from the leaves of Ximenia americana L.,
Biochem. Syst. Ecol., 2006, 34, 7, 549-553, https://doi.org/10.1016/j.bse.2006.01.007
. [all data]
Mevy, Bessiere, et al., 2006, 2
Mevy, J.P.; Bessiere, J.M.; Rabier, J.; Dherbomez, M.; Ruzzier, M.; Millogo, J.; Viano, J.,
Composition and antimicrobial activities of the essential oil of Triumfetta rhomboidea Jacq.,
Flavour Fragr. J., 2006, 21, 1, 80-83, https://doi.org/10.1002/ffj.1511
. [all data]
Raina, Verma, et al., 2006
Raina, V.K.; Verma, S.C.; Dhawan, S.; Khan, M.; Ramesh, S.; Singh, S.C.; Yadav, A.; Srivastava, S.K.,
Essential oil composition of Murraya exotica from the plains of northern India,
Flavour Fragr. J., 2006, 21, 1, 140-142, https://doi.org/10.1002/ffj.1547
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Srivastava, Srivastava, et al., 2006
Srivastava, A.K.; Srivastava, S.K.; Syamsundar, K.V.,
Volatile composition of Curcuma angustifolia Roxb. rhizome from central and southern India,
Flavour Fragr. J., 2006, 21, 3, 423-426, https://doi.org/10.1002/ffj.1680
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Sylvestre, Pichette, et al., 2006
Sylvestre, M.; Pichette, A.; Longtin, A.; Nagau, F.; Legault, J.,
Essential oil analysis and anticancer activity of leaf essential oil of Croton flavens L. from Guadeloupe,
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Adams, Morris, et al., 2005
Adams, R.P.; Morris, J.A.; Pandey, R.N.; Schwarzbach, A.E.,
Cryptic speciation between Juniperus deltoides and Juniperus oxycedrus (Cupressaceae) in the Mediterranean,
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Adams and Nguyen, 2005
Adams, R.P.; Nguyen, S.,
Infra-specific variation in Juniperus deppeana and F. Sperryi in the Davis Mountains of Texas: variation in leaf essential oils and random amplified polymorphic DNAS (RAPDS),
Phytologia, 2005, 87, 2, 96-108. [all data]
Asuming, Beauchamp, et al., 2005
Asuming, W.A.; Beauchamp, P.S.; Descalzo, J.T.; Dev, B.C.; Dev, V.; Frost, S.; Ma, C.W.,
Essential oil composition of four Lomatium Raf. species and their chemotaxonomy,
Biochem. Syst. Ecol., 2005, 33, 1, 17-26, https://doi.org/10.1016/j.bse.2004.06.005
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Maia, Andrade, et al., 2005
Maia, J.G.S.; Andrade, E.H.A.; da Silva, A.C.M.; Oliveira, J.; Carreira, L.M.M.; Araújo, J.S.,
Leaf volatile oils from four Brazilian Xylopia species,
Flavour Fragr. J., 2005, 20, 5, 474-477, https://doi.org/10.1002/ffj.1499
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Lopes, Strobl, et al., 2004
Lopes, D.; Strobl, H.; Kolodziejczyk, P.,
14-Methylpentadecano-15-lactone (Muscolide): a new macrocyclic lactone from the oil of Angelica archangelica L.,
Chemistry and Biodiversity, 2004, 1, 12, 1880-1887, https://doi.org/10.1002/cbdv.200490144
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Palmeira, Moura, et al., 2004
Palmeira, S.F., Jr.; Moura, F.S.; Alves, V.L.; de Oliveira, F.M.; Bento, E.S.; Conserva, L.M.; Andrade, E.H.A.,
Neutral components from hexane extracts of Croton sellowii,
Flavour Fragr. J., 2004, 19, 1, 69-71, https://doi.org/10.1002/ffj.1298
. [all data]
Schwob, Bessiere, et al., 2004
Schwob, I.; Bessiere, J.-M.; Masotti, V.; Viano, J.,
Changes in essential oil composition in Saint John's wort (Hypericum perforatum L.) aerial parts during its phenological cycle,
Biochem. Syst. Ecol., 2004, 32, 8, 735-745, https://doi.org/10.1016/j.bse.2003.12.005
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Lucero, Estell, et al., 2003
Lucero, M.E.; Estell, R.E.; Frederickson, E.L.,
The essential oil composition of Psorothamnus scoparius (A. Gray) Rydb.,
J. Essent. Oil Res., 2003, 15, 2, 108-111, https://doi.org/10.1080/10412905.2003.9712083
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Srivastava, Ahmad, et al., 2003
Srivastava, S.K.; Ahmad, A.; Syamsunder, K.V.; Aggarwal, K.K.; Shanuja, S.P.S.,
Essential oil composition of Callistemon viminalis leaves from India,
Flavour Fragr. J., 2003, 18, 5, 361-363, https://doi.org/10.1002/ffj.1143
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Mevy, Bessiere, et al., 2002
Mevy, J.P.; Bessiere, J.-M.; Dherbomez, M.; Viano, J.,
Composition and some biological activities of the essential oils from an African pasture grass: Elionurus elegans Kunth.,
J. Agric. Food Chem., 2002, 50, 15, 4240-4243, https://doi.org/10.1021/jf0115140
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Raina, Srivastava, et al., 2002
Raina, V.K.; Srivastava, S.K.; Jain, N.; Ahmad, A.; Syamasundar, K.V.; Aggarwal, K.K.,
Essential oil composition of Curcuma longa L. cv. Roma from the plains of northern India,
Flavour Fragr. J., 2002, 17, 2, 99-102, https://doi.org/10.1002/ffj.1053
. [all data]
Salido, Altarejos, et al., 2002
Salido, S.; Altarejos, J.; Nogueras, M.; Sánchez, A.; Pannecouque, C.; Witvrouw, M.; De Clercq, E.,
Chemical studies of essential oils of Juniperus oxycedrus ssp. badia,
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Shawl, Srivastava, et al., 2002
Shawl, A.S.; Srivastava, S.K.; Syamasundar, K.V.; Tripathi, S.; Raina, V.K.,
Essential oil composition of Achillea millefolium L. growing wild in Kashmir, India,
Flavour Fragr. J., 2002, 17, 3, 165-168, https://doi.org/10.1002/ffj.1074
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Raina, Srivastava, et al., 2001
Raina, V.K.; Srivastava, S.K.; Aggarwal, K.K.; Syamasundar, K.V.; Kumar, S.,
Essential oil composition of Syzygium aromaticum leaf from Little Andaman, India,
Flavour Fragr. J., 2001, 16, 5, 334-336, https://doi.org/10.1002/ffj.1005
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Tzakou and Couladis, 2001
Tzakou, O.; Couladis, M.,
The essential oil of Micromeria graeca (L.) Bentham et Reichenb. growing in Greece,
Flavour Fragr. J., 2001, 16, 2, 107-109, https://doi.org/10.1002/ffj.955
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Adams, 2000
Adams, R.P.,
Systematics of smooth leaf margin Juniperus of the western hemisphere based on leaf essential oils and RAPD DNA fingerprinting,
Biochem. Syst. Ecol., 2000, 28, 2, 149-162, https://doi.org/10.1016/S0305-1978(99)00047-2
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Adams, 2000, 2
Adams, R.P.,
Systematics of Juniperus section Juniperus based on leaf essential oils and random amplified polymorphic DNAs (RAPDs),
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Adams, 2000, 3
Adams, R.P.,
The serrate leaf margined Juniperus (Section Sabina) of the western hemisphere: systematics and evolution based on leaf essential oils and Random Amplified Polymorphic DNAs (RAPDs),
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Roussis, Tsoukatou, et al., 2000
Roussis, V.; Tsoukatou, M.; Petrakis, P.V.; Chinou, I.; Skoula, M.; Harborne, J.B.,
Volatile constituents of four Helichrysum species growing in Greece,
Biochem. Syst. Ecol., 2000, 28, 2, 163-175, https://doi.org/10.1016/S0305-1978(99)00046-0
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Adams, 1999
Adams, R.P.,
Systematics of multi-seeded eastern hemisphere Juniperus based on leaf essential oils and RAPD DNA fingerprinting,
Biochem. Syst. Ecol., 1999, 27, 7, 709-725, https://doi.org/10.1016/S0305-1978(99)00016-2
. [all data]
Notes
Go To: Top, Kovats' 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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