Benzene, 1,2,3-trimethoxy-5-(2-propenyl)-
- Formula: C12H16O3
- Molecular weight: 208.2536
- IUPAC Standard InChI: InChI=1S/C12H16O3/c1-5-6-9-7-10(13-2)12(15-4)11(8-9)14-3/h5,7-8H,1,6H2,2-4H3
- IUPAC Standard InChIKey: BPLQKQKXWHCZSS-UHFFFAOYSA-N
- CAS Registry Number: 487-11-6
- 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. - Other names: Benzene, 5-allyl-1,2,3-trimethoxy-; Elemicin; 3,4,5-Trimethoxyallylbenzene; 5-Allyl-1,2,3-trimethoxybenzene; 1,2,3-Trimethoxy-5-(2-propenyl)-benzene; 1,2,3-Trimethoxy-5-allylbenzene; 4-Allyl-1,2,6-trimethoxybenzene; Benzene, 5-(2-propenyl)-1,2,3-trimethoxy; Elemicine; 1,2,3-trimethoxy-5-allylbenzene (elemicin)
- 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, 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-5 MS | CP-Sil 5 CB | DB-5 | DB-1 | HP-5MS |
| Column length (m) | 30. | 25. | 30. | 30. | 60. |
| Carrier gas | Helium | Helium | Helium | Helium | Helium |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.25 | 0.32 | 0.25 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.15 | 0.25 | 0.25 | 0.25 |
| Tstart (C) | 60. | 50. | 60. | 50. | 70. |
| Tend (C) | 230. | 220. | 280. | 220. | 250. |
| Heat rate (K/min) | 3. | 3. | 4. | 3. | |
| Initial hold (min) | 2. | ||||
| Final hold (min) | 2. | ||||
| I | 1566. | 1553. | 1547. | 1548. | 1560. |
| Reference | Pripdeevech and Saansoomchai, 2013 | Ameen, Usman, et al., 2011 | Georgiou, Koutsaviti, et al., 2010 | Xu, Tang, et al., 2010 | Males, Plazibat, et al., 2009 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | DB-5 | HP-5 | DB-5 | SLB-5 MS | HP-5 |
| Column length (m) | 30. | 30. | 25. | 30. | 25. |
| Carrier gas | Nitrogen | Nitrogen | Nitrogen | Helium | Helium |
| 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 | 0.25 |
| Tstart (C) | 40. | 50. | 50. | 50. | 60. |
| Tend (C) | 250. | 280. | 300. | 250. | 240. |
| Heat rate (K/min) | 3. | 5. | 6.5 | 3. | 4. |
| Initial hold (min) | 1. | 1. | 2. | 2. | 2. |
| Final hold (min) | 10. | 1. | 7. | 10. | |
| I | 1557. | 1562. | 1512. | 1546. | 1554. |
| Reference | Rahimi-Nasrabadi, Gholivand, et al., 2009 | Bousaada, Ammar, et al., 2008 | Chieng, Assim, et al., 2008 | Lo Presti, Sciarrone, et al., 2008 | Verdian-rizi, 2008 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | HP-5 | HP-5 MS | HP-5 | DB-5 | HP-5 |
| Column length (m) | 30. | 30. | 30. | 30. | 60. |
| Carrier gas | Helium | Helium | He | He | He |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
| Phase thickness (μm) | 0.32 | 0.25 | 0.32 | 0.25 | 0.25 |
| Tstart (C) | 60. | 50. | 60. | 40. | 60. |
| Tend (C) | 250. | 230. | 250. | 260. | 250. |
| Heat rate (K/min) | 5. | 3. | 5. | 4. | 3. |
| Initial hold (min) | 30. | 10. | 30. | 5. | |
| Final hold (min) | 10. | ||||
| I | 1552. | 1554. | 1552. | 1552. | 1559. |
| Reference | Yassa and Akhani, 2008 | Adams, Beauchamp, et al., 2007 | Yassa and Akhani, 2007 | Askari and Sefidkon, 2006 | Bertrand, Comte, et al., 2006 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | DB-1 | DB-5 | CP Sil 5 CB | DB-1 | DB-1 |
| Column length (m) | 30. | 30. | 30. | 60. | 25. |
| Carrier gas | He | Helium | N2 | He | He |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | |
| Tstart (C) | 50. | 60. | 60. | 40. | 50. |
| Tend (C) | 265. | 260. | 300. | 250. | 250. |
| Heat rate (K/min) | 2.5 | 3. | 5. | 4. | 3. |
| Initial hold (min) | 1. | 4. | 3. | ||
| Final hold (min) | 20. | ||||
| I | 1512. | 1555. | 1520. | 1512. | 1531. |
| Reference | Iranshahi, Amin, et al., 2006 | Javidnia, Miri, et al., 2006 | Kurowska and Galazka, 2006 | Sefidkon, Jamzad, et al., 2006 | Cégiéla-Carlioz, Bessière, et al., 2005 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | DB-5 | CP Sil 8 CB | HP-5 | SE-54 | DB-1 |
| Column length (m) | 30. | 30. | 30. | 30. | 60. |
| Carrier gas | He | He | Helium | 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 | ||
| Tstart (C) | 40. | 60. | 40. | 60. | 35. |
| Tend (C) | 240. | 290. | 300. | 260. | 230. |
| Heat rate (K/min) | 4. | 3. | 4. | 2. | 2. |
| Initial hold (min) | 5. | 5. | 4. | ||
| Final hold (min) | 5. | 25. | |||
| I | 1552. | 1554. | 1546. | 1545. | 1515. |
| Reference | Sefidkon and Jamzad, 2005 | Suárez, Vásquez, et al., 2005 | Utsunomia, Kawata, et al., 2005 | Kilic, Hafizoglu, et al., 2004 | Park, Lee, et al., 2004 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | DB-1 | DB-1 | DB-1 | OV-101 | DB-1 |
| Column length (m) | 60. | 60. | 60. | 50. | 50. |
| Carrier gas | He | He | He | He | N2 |
| Substrate | |||||
| Column diameter (mm) | 0.32 | 0.32 | 0.32 | 0.2 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.5 | 0.25 |
| Tstart (C) | 35. | 35. | 35. | 50. | 90. |
| Tend (C) | 230. | 230. | 230. | 250. | 240. |
| Heat rate (K/min) | 2. | 2. | 2. | 2. | 4. |
| Initial hold (min) | 4. | 4. | 4. | ||
| Final hold (min) | 25. | 25. | 25. | ||
| I | 1516. | 1516. | 1517. | 1526. | 1517. |
| Reference | Park, Lee, et al., 2004 | Park, Lee, et al., 2004 | Park, Lee, et al., 2004 | Orav, Kailas, et al., 2003 | Velasco-Negueruela, Pérez-Alonso, et al., 2003 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | HP-5 | DB-5 | RSL-200 | DB-5 | SPB-1 |
| Column length (m) | 30. | 30. | 30. | 30. | 50. |
| Carrier gas | He | He | H2 | He | |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.25 | 0.32 | 0.25 | 0.2 |
| Phase thickness (μm) | 0.32 | 0.25 | 0.25 | 0.25 | 0.33 |
| Tstart (C) | 60. | 60. | 40. | 60. | 60. |
| Tend (C) | 250. | 280. | 280. | 270. | 260. |
| Heat rate (K/min) | 5. | 3. | 6. | 3. | 4. |
| Initial hold (min) | 30. | 5. | |||
| Final hold (min) | 30. | 5. | |||
| I | 1560. | 1540. | 1514. | 1558. | 1512. |
| Reference | Yassa, Akhani, et al., 2003 | Caredda, Marongiu, et al., 2002 | Jirovetz, Buchbauer, et al., 2002 | Palmeira, Conserva, et al., 2001 | Choo, Wong, et al., 1999 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | DB-1 | DB-1 | DB-1 | DB-1 | DB-1 |
| Column length (m) | 30. | 30. | 30. | 30. | 30. |
| Carrier gas | He | He | He | He | He |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | |
| Tstart (C) | 70. | 50. | 50. | 50. | 50. |
| Tend (C) | 300. | 240. | 240. | 240. | 240. |
| Heat rate (K/min) | 3. | 3. | 3. | 5. | 5. |
| Initial hold (min) | 5. | 5. | 5. | 3. | 3. |
| Final hold (min) | |||||
| I | 1515. | 1519. | 1530. | 1530. | 1531. |
| Reference | Guy and Vernin, 1996 | Shiota, 1993 | Shiota, 1993 | Shiota, 1993 | Shiota, 1993 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
References
Go To: Top, Normal alkane 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.
Pripdeevech and Saansoomchai, 2013
Pripdeevech, P.; Saansoomchai, J.,
Antibacterial activity and chemical composition of essential oil and various extracts of Fagraea fragrans Roxb. flowers,
Chiang Mai J. Sci., 2013, 40, 2, 214-223. [all data]
Ameen, Usman, et al., 2011
Ameen, O.M.; Usman, L.A.; Oganija, F.S.; Hamid, A.A.; Muhammed, N.O.; Zubair, M.F.; Adebayo, S.A.,
Chemical composition of leaf essential oil of Annona senegalensis Pers. (Annonaceae) growing in North Central Nigeria,
Int. J. Biol. Chem. Sci., 2011, 5, 1, 375-379. [all data]
Georgiou, Koutsaviti, et al., 2010
Georgiou, C.; Koutsaviti, A.; Bazos, I.; Tzakou, O.,
Chemical composition of Echinophora tenuifolia subsp. sibthorpiana essential oil from Greece,
Rec. Nat. Prod., 2010, 4, 3, 167-170. [all data]
Xu, Tang, et al., 2010
Xu, X.; Tang, Z.; Liang, Y.,
Comparative analysis of plant essential oils by GC-MS coupled with integrated chemometric resolution methods,
Anal. Methods, 2010, 2, 4, 359-367, https://doi.org/10.1039/b9ay00213h
. [all data]
Males, Plazibat, et al., 2009
Males, Z.; Plazibat, M.; Bucar, F.,
Essential oil of Portanschlagiella ramosissima from Croatia, a rich source of myristicin,
Croat. Chem. Acta, 2009, 82, 4, 725-728. [all data]
Rahimi-Nasrabadi, Gholivand, et al., 2009
Rahimi-Nasrabadi, M.; Gholivand, M.B.; Batooli, H.; Vatanara, A.,
Chemical composition of the essential oil from leaves and flowering aerial parts of Psammogeton canscens (DC). Vake from Iran,
J. Medicinal Plants, 2009, 8, 31, 82-86. [all data]
Bousaada, Ammar, et al., 2008
Bousaada, O.; Ammar, S.; Saidana, D.; Chriaa, J.; Chraif, I.; Daami, M.; Helal, A.N.; Mighri, Z.,
Chemical composition and antimicrobial activity of volatile components from capitula and aerial parts of Rhaponticum acaule DC growing wild in Tunisia,
Microbiol. Res., 2008, 163, 1, 87-95, https://doi.org/10.1016/j.micres.2007.02.010
. [all data]
Chieng, Assim, et al., 2008
Chieng, T.C.; Assim, Z.B.; Fasihuddin, B.A.,
Toxicity and antitermite activities of the essential oils from Piper sarmentosum,
The Malaysian J. Anal. Sci., 2008, 12, 1, 234-239. [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]
Verdian-rizi, 2008
Verdian-rizi, M.,
Phenological variations of Laurus nobilis L. essential oil from Iran,
Electronic J. Environ. Agricultural Food Chem., 2008, 7, 11, 3321-3325. [all data]
Yassa and Akhani, 2008
Yassa, N.; Akhani, H.,
The essential oils composition in two species of the genus Eriocycla Lindl. (Apiaceae) from Iran, 2008, retrieved from http://biology.ut.ac.ir/members/akhani/PdfReprintNumber/27.pdf. [all data]
Adams, Beauchamp, et al., 2007
Adams, R.P.; Beauchamp, P.S.; Dev, V.; Dutz, S.M.,
New Natural Products Isolated from One-Seeded Juniperus of the Southwestern United States: Isolation and Occurence of 2-Ethenyl-3-methyl Phanol and Its Derivatives,
J. Essent. Oil Res., 2007, 19, 2, 146-152, https://doi.org/10.1080/10412905.2007.9699247
. [all data]
Yassa and Akhani, 2007
Yassa, N.; Akhani, H.,
The essential oils composition in two species of the genus Eriocycla Lindl. (Apiaceae) from Iran, 2007, retrieved from http://biology.ut.ac.ir/members/akhani/PdfReprintNumber/27.pdf. [all data]
Askari and Sefidkon, 2006
Askari, F.; Sefidkon, F.,
Essential oil composition of Pimpinella affinis Ledeb. from two localities in Iran,
Flavour Fragr. J., 2006, 21, 5, 754-756, https://doi.org/10.1002/ffj.1619
. [all data]
Bertrand, Comte, et al., 2006
Bertrand, C.; Comte, G.; Piola, F.,
Solid-phase microextraction of volatile compounds from flowers of two Brunfelsia species,
Biochem. Syst. Ecol., 2006, 34, 5, 371-375, https://doi.org/10.1016/j.bse.2005.12.005
. [all data]
Iranshahi, Amin, et al., 2006
Iranshahi, M.; Amin, G.; Sourmaghi, M.S.; Shafiee, A.; Hadjiakhoondi, A.,
Sulphur-containing compounds in the essential oil of the root of Ferula persica Willd. var. persica,
Flavour Fragr. J., 2006, 21, 2, 260-261, https://doi.org/10.1002/ffj.1574
. [all data]
Javidnia, Miri, et al., 2006
Javidnia, K.; Miri, R.; Kamalinejad, M.; Mehdipour, A.R.,
Composition of the essential oil of Diplotaenia cachrydifolia Boiss. from Iran,
J. Ess. Oil Res., 2006, 18, 1, 86-87, https://doi.org/10.1080/10412905.2006.9699393
. [all data]
Kurowska and Galazka, 2006
Kurowska, A.; Galazka, I.,
Essential oil composition of the parsley seed of cultivars marketed in Poland,
Flavour Fragr. J., 2006, 21, 1, 143-147, https://doi.org/10.1002/ffj.1548
. [all data]
Sefidkon, Jamzad, et al., 2006
Sefidkon, F.; Jamzad, Z.; Mirza, M.,
Chemical composition of the essential oil of five Iranian Nepeta species (N. crispa, N. mahanensis, N. ispahanica, N. eremophila and N. rivularis),
Flavour Fragr. J., 2006, 21, 5, 764-767, https://doi.org/10.1002/ffj.1668
. [all data]
Cégiéla-Carlioz, Bessière, et al., 2005
Cégiéla-Carlioz, P.; Bessière, J.-M.; David, B.; Mariotte, A.-M.; Gibbons, S.; Dijoux-Franca, M.-G.,
Modulation of multi-drug resistance (MDR) in Staphylococcus aureus by Osha (Ligusticum porteri L., Apiaceae) essential oil compounds,
Flavour Fragr. J., 2005, 20, 6, 671-675, https://doi.org/10.1002/ffj.1584
. [all data]
Sefidkon and Jamzad, 2005
Sefidkon, F.; Jamzad, Z.,
Chemical composition of the essential oil of three Iranian Satureja species (S. mutica, S. macrantha and S. intermedia),
Food Chem., 2005, 91, 1, 1-4, https://doi.org/10.1016/j.foodchem.2004.01.027
. [all data]
Suárez, Vásquez, et al., 2005
Suárez, A.I.; Vásquez, L.J.; Manzano, M.A.; Compagnone, R.S.,
Essential oil composition of Croton cuneatus and Croton malambo growing in Venezuela,
Flavour Fragr. J., 2005, 20, 6, 611-614, https://doi.org/10.1002/ffj.1498
. [all data]
Utsunomia, Kawata, et al., 2005
Utsunomia, H.; Kawata, J.; Chanoki, W.; Shirakawa, N.; Miyazawa, M.,
Components of Essential Oil from Woods of Prunus mume Sieb. at Zucc.,
J. Oleo Sci., 2005, 54, 11, 609-612, https://doi.org/10.5650/jos.54.609
. [all data]
Kilic, Hafizoglu, et al., 2004
Kilic, A.; Hafizoglu, H.; Kollmannsberger, H.; Nitz, S.,
Volatile constituents and key odorants in leaves, buds, flowers, and fruits of Laurus nobilis L.,
J. Agric. Food Chem., 2004, 52, 6, 1601-1606, https://doi.org/10.1021/jf0306237
. [all data]
Park, Lee, et al., 2004
Park, B.-S.; Lee, K.-G.; Takeoka, G.R.,
Comparison of three sample preparation methods on the recovery of volatiles from taheebo (Tabebuia impetiginosa Martius ex DC),
Flavour Fragr. J., 2004, 19, 4, 287-292, https://doi.org/10.1002/ffj.1345
. [all data]
Orav, Kailas, et al., 2003
Orav, A.; Kailas, T.; Jegorova, A.,
Composition of the essential oil of dill, celery, and parsley from Estonia,
Proc. Est. Acad. Sci. Chem., 2003, 52, 4, 147-154. [all data]
Velasco-Negueruela, Pérez-Alonso, et al., 2003
Velasco-Negueruela, A.; Pérez-Alonso, M.J.; Pérez de Paz, P.L.; Palá-Paúl, J.; Sanz, J.,
Analysis by gas chromatography-mass spectrometry of the essential oils from the aerial parts of Rutheopsis herbanica (Bolle) Hans. Kunk., gathered in Fuerteventura (Canary Islands),
J. Chromatogr. A, 2003, 984, 1, 159-162, https://doi.org/10.1016/S0021-9673(02)01742-9
. [all data]
Yassa, Akhani, et al., 2003
Yassa, N.; Akhani, H.; Aqaahmadi, M.; Salimian, M.,
Essential oils from two endemic species of Apiaceae from Iran,
Z. Naturforsch. C:, 2003, 58, 459-463. [all data]
Caredda, Marongiu, et al., 2002
Caredda, A.; Marongiu, B.; Porcedda, S.; Soro, C.,
Supercritical carbon dioxide extraction and characterization of Laurus nobilis essential oil,
J. Agric. Food Chem., 2002, 50, 6, 1492-1496, https://doi.org/10.1021/jf0108563
. [all data]
Jirovetz, Buchbauer, et al., 2002
Jirovetz, L.; Buchbauer, G.; Ngassoum, M.B.; Geissler, M.,
Aroma compound analysis of Piper nigrum and Piper guineense essential oils from Cameroon using solid-phase microextraction-gas chromatography, solid-phase microextraction-gas chromatography-mass spectrometry and olfactometry,
J. Chromatogr. A, 2002, 976, 1-2, 265-275, https://doi.org/10.1016/S0021-9673(02)00376-X
. [all data]
Palmeira, Conserva, et al., 2001
Palmeira, S.F., Jr.; Conserva, L.M.; Andrade, E.H.A.; Guilhon, G.M.S.P.,
Analysis by GC-MS of the hexane extract of the aerial parts of Aristolochia acutifolia Duchtr.,
Flavour Fragr. J., 2001, 16, 2, 85-88, https://doi.org/10.1002/1099-1026(200103/04)16:2<85::AID-FFJ948>3.0.CO;2-2
. [all data]
Choo, Wong, et al., 1999
Choo, L.-C.; Wong, S.-M.; Liew, K.-Y.,
Essential oil of nutmeg pericarp,
J. Sci. Food Agric., 1999, 79, 13, 1954-1957, https://doi.org/10.1002/(SICI)1097-0010(199910)79:13<1954::AID-JSFA460>3.0.CO;2-I
. [all data]
Guy and Vernin, 1996
Guy, I.; Vernin, G.,
Minor compounds from Cistus ladaniferus L. essential oil from esterel. 2. Acids and phenols,
J. Essent. Oil Res., 1996, 8, 4, 455-462, https://doi.org/10.1080/10412905.1996.9700666
. [all data]
Shiota, 1993
Shiota, H.,
New esteric components in the volatiles of banana fruit (Musa sapientum L.),
J. Agric. Food Chem., 1993, 41, 11, 2056-2062, https://doi.org/10.1021/jf00035a046
. [all data]
Notes
Go To: Top, Normal alkane 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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