Benzene, 1,2-dimethoxy-4-propenyl-, (Z)-

Formula: C₁₁H₁₄O₂
Molecular weight: 178.2277
IUPAC Standard InChI: InChI=1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4-8H,1-3H3/b5-4-
IUPAC Standard InChIKey: NNWHUJCUHAELCL-PLNGDYQASA-N
CAS Registry Number: 6380-24-1
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:
- (E)-Methyl isoeugenol
- Benzene, 1,2-dimethoxy-4-(1-propenyl)-
Other names: cis-Methyl isoeugenol; cis-4-Propenyl veratrole; Benzene, 1,2-dimethoxy-4-(1-propenyl)-, (Z)-; (Z)-1,2-Dimethoxy-4-(prop-1-en-1-yl)benzene; (Z)-Methyl isoeugenol; cis-Methyl eugenol; (Z)-1,2-Dimethoxy-4-propenylbenzene; (Z)-Methyl eugenol
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Gas Chromatography

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

Column type	Active phase	Temperature (C)	I	Reference	Comment
Capillary	SE-30	100.	1422.0	Tudor, 1997	40. m/0.35 mm/0.35 μm

Kovats' RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	DB-5	1451.	Adams, González Elizondo, et al., 2006	30. m/0.26 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 246. C
Capillary	BP-1	1433.	Raina, Srivastava, et al., 2003	25. m/0.32 mm/0.25 μm, N2, 5. K/min, 220. C @ 15. min; T_start: 60. C

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	HP-1	1422.	Nath, Sarma, et al., 2002	24. m/0.32 mm/0.17 μm, He, 60. C @ 2. min, 4. K/min, 250. C @ 20. min
Capillary	CP Sil 5 CB	1420.	Pino, Marbot, et al., 2001	50. m/0.32 mm/0.4 μm, He, 60. C @ 10. min, 3. K/min, 280. C @ 60. min

Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	HP-5MS	1460.8	Andriamaharavo, 2014	30. m/0.25 mm/0.25 μm, He; Program: 60C (1 min) => 5 C/min => 210C => 10 C/min => 280C (15 min)
Capillary	SE-52	1494.	Sacchetti, Guerrini, et al., 2006	30. m/0.32 mm/0.15 μm, He; Program: 45C => 1C/min => 100C => 5C/min => 250C(10min)
Capillary	SE-52	1454.	Sacchetti, Guerrini, et al., 2006	30. m/0.32 mm/0.15 μm, He; Program: 45C => 1C/min => 100C => 5C/min => 250C(10min)

Van Den Dool and Kratz RI, polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	AT-Wax	2059.	Pino, Marbot, et al., 2001	60. m/0.32 mm/0.25 μm, He, 65. C @ 10. min, 2. K/min, 250. C @ 60. min
Capillary	CP-Wax 52CB	2008.	Chevance and Farmer, 1999	60. C @ 5. min, 4. K/min, 220. C @ 30. min; Column length: 50. m; Column diameter: 0.32 mm
Capillary	CP-Wax 52CB	2008.	Chevance and Farmer, 1999, 2	60. C @ 5. min, 4. K/min, 220. C @ 30. min; Column length: 50. m; Column diameter: 0.32 mm

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	ZB-5	1456.	Mohottalage, Tabacchi, et al., 2007	30. m/0.25 mm/0.25 μm, 60. C @ 5. min, 4. K/min, 220. C @ 20. min
Capillary	HP-5	1500.	Bertrand, Comte, et al., 2006	60. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 250. C
Capillary	DB-1	1450.	Velasco-Negueruela, Pérez-Alonso, et al., 2005	50. m/0.25 mm/0.25 μm, N2, 4. K/min; T_start: 90. C; T_end: 240. C
Capillary	DB-5	1452.	Miyazawa, Fuhita, et al., 2004	Helium, 2. K/min, 240. C @ 999. min; Column length: 30. m; Column diameter: 0.25 mm; T_start: 60. C
Capillary	DB-5	1452.	Miyazawa, Fujita, et al., 2004	Helium, 2. K/min, 240. C @ 999. min; Column length: 50. m; Column diameter: 0.25 mm; T_start: 60. C
Capillary	HP-5	1461.	Yassa, Akhani, et al., 2003	30. m/0.25 mm/0.32 μm, He, 60. C @ 30. min, 5. K/min; T_end: 250. C

Normal alkane RI, non-polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	HP-5MS	1460.	Cole, Haber, et al., 2007	30. m/0.25 mm/0.25 μm, He; Program: 40C(10min) => 3C/min => 200C => 2C/min => 220C
Capillary	CP Sil 8 CB	1454.	Radusiene, Judzentiene, et al., 2007	50. m/0.32 mm/0.25 μm, Helium; Program: 60 0C (2 min) 5 0C/min -> 160 0C (1 min) 10 0C/min -> 280 0C (3 min)
Capillary	SE-30	1409.	Vinogradov, 2004	Program: not specified

Normal alkane RI, polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	Carbowax 20M	2070.	Vinogradov, 2004	Program: not specified

References

Go To: Top, Gas Chromatography, Notes

Tudor, 1997
Tudor, E., Temperature dependence of the retention index for perfumery compounds on a SE-30 glass capillary column. I. Linear equations, J. Chromatogr. A, 1997, 779, 1-2, 287-297, https://doi.org/10.1016/S0021-9673(97)00453-6 . [all data]

Adams, González Elizondo, et al., 2006
Adams, R.P.; González Elizondo, M.S.; González Elizondo, M.; Slinkman, E., DNA fingerprinting and terpenoid analysis of Juniperus blancoi var. huehuentensis (Cupressaceae), a new subalpine variety from Durango, Mexico, Biochem. Syst. Ecol., 2006, 34, 3, 205-211, https://doi.org/10.1016/j.bse.2005.11.004 . [all data]

Raina, Srivastava, et al., 2003
Raina, V.K.; Srivastava, S.K.; Syamasunder, K.V., Essential oil composition of Acorus calamus L. from the lower region of the Himalayas, Flavour Fragr. J., 2003, 18, 1, 18-20, https://doi.org/10.1002/ffj.1136 . [all data]

Nath, Sarma, et al., 2002
Nath, S.C.; Sarma, K.K.; Vajezikova, I.; Leclercq, P.A., Comparison of volatile inflorescence oils and taxonomy of certain Cymbopogon taxa described as Cymbopogon flexuosus (Nees ex Steud.) Wats., Biochem. Syst. Ecol., 2002, 30, 2, 151-162, https://doi.org/10.1016/S0305-1978(01)00066-7 . [all data]

Pino, Marbot, et al., 2001
Pino, J.A.; Marbot, R.; Vázquez, C., Characterization of volatiles in strawberry guava (Psidium cattleianum Sabine) fruit, J. Agric. Food Chem., 2001, 49, 12, 5883-5887, https://doi.org/10.1021/jf010414r . [all data]

Andriamaharavo, 2014
Andriamaharavo, N.R., Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2014. [all data]

Sacchetti, Guerrini, et al., 2006
Sacchetti, G.; Guerrini, A.; Noriega, P.; Bianchi, A.; Bruni, R., Essential oil of wild Ocotea quixos (Lam.) Kosterm. (Lauraceae) leaves from Amazonian Ecuador, Flavour Fragr. J., 2006, 21, 4, 674-676, https://doi.org/10.1002/ffj.1648 . [all data]

Chevance and Farmer, 1999
Chevance, F.F.V.; Farmer, L.J., Identification of major volatile odor compounds in frankfurters, J. Agric. Food Chem., 1999, 47, 12, 5151-5160, https://doi.org/10.1021/jf990515d . [all data]

Chevance and Farmer, 1999, 2
Chevance, F.F.V.; Farmer, L.J., Release of volatile odor compounds from full-fat and reduced-fat frankfurters, J. Agric. Food Chem., 1999, 47, 12, 5161-5168, https://doi.org/10.1021/jf9905166 . [all data]

Mohottalage, Tabacchi, et al., 2007
Mohottalage, S.; Tabacchi, R.; Guerin, P.M., Components from Sri Lankan Piper betle L. leaf oil and their analogues showing toxicity against the housefly, Musca domestica, Flavour Fragr. J., 2007, 22, 2, 130-138, https://doi.org/10.1002/ffj.1770 . [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]

Velasco-Negueruela, Pérez-Alonso, et al., 2005
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 Pimpinella anagodendron Bolle and Pimpinella rupicola Svent., two endemic species to the Canary Islands, Spain, J. Chromatogr. A, 2005, 1095, 1-2, 180-184, https://doi.org/10.1016/j.chroma.2005.09.074 . [all data]

Miyazawa, Fuhita, et al., 2004
Miyazawa, M.; Fuhita, T.; Yamafuji, C.; Matsui, M.; Kasahara, N.; Takagi, Y.; Ishikawa, Y., Chemical composition of volatile oil from the roots of Periploca sepium, J. Oleo Sci., 2004, 53, 10, 511-513, https://doi.org/10.5650/jos.53.511 . [all data]

Miyazawa, Fujita, et al., 2004
Miyazawa, M.; Fujita, T.; Yamafuji, C.; Matsui, M.; Kasahara, N.; Takagi, Y.; Ishikawa, Y., Chemical composition of volatile oil from the roots of Periploca sepium, J. Oleo Sci., 2004, 53, 11, 511-513, https://doi.org/10.5650/jos.53.511 . [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]

Cole, Haber, et al., 2007
Cole, R.A.; Haber, W.A.; Setzer, W.N., Chemical composition of essential oils of seven species of Eugenia from Monteverde, Costa Rica, Biochem. Syst. Ecol., 2007, 35, 12, 877-886, https://doi.org/10.1016/j.bse.2007.06.013 . [all data]

Radusiene, Judzentiene, et al., 2007
Radusiene, J.; Judzentiene, A.; Peciulyte, D.; Janulis, V., Essential Oil Composition and Antimicrobial Assay of Acorus calamus Leaves from Different Wild Populations, Plant Genetic Resources: Characterization and Utilization, 2007, 5, 1, 37-44, https://doi.org/10.1017/S1479262107390928 . [all data]

Vinogradov, 2004
Vinogradov, B.A., Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]

Notes

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Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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