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

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
IUPAC Standard InChIKey: NNWHUJCUHAELCL-UHFFFAOYSA-N
CAS Registry Number: 93-16-3
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
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Stereoisomers:
- (E)-Methyl isoeugenol
- Benzene, 1,2-dimethoxy-4-propenyl-, (Z)-
Other names: Benzene, 1,2-dimethoxy-4-propenyl-; Isoeugenol methyl ether; Isoeugenyl methyl ether; Isohomogenol; Methylisoeugenol; O-Methylisoeugenol; 1-(3,4-Dimethoxyphenyl)-1-propene; 1-Veratryl-1-propene; 3,4-Dimethoxypropenylbenzene; 4-Propenyl-1,2-dimethoxybenzene; 4-Propenylveratrole; 1-Propene, 1-(3,4-dimethoxyphenyl)-; 1,3,4-Isoeugenol methyl ether; Benzene, 4-(1-propenyl)-1,2-dimethoxy; Isomethyleugenol; Benzene, 1,2-dimethoxy-4-(1-propen-1-yl)-; NSC 46111; Veratrole, 4-propenyl-; 1,2-Dimethoxy-4-(1-propenyl)-benzene; 4-prop-1-enylveratrole
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Phase change data

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Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Quantity	Value	Units	Method	Reference	Comment
T_boil	536.2	K	N/A	Aldrich Chemical Company Inc., 1990	BS

Enthalpy of vaporization

Δ_vapH (kJ/mol)	Temperature (K)	Method	Reference	Comment
61.9	373.	A	Stephenson and Malanowski, 1987	Based on data from 358. to 521. K. See also Stull, 1947.; AC

Gas Chromatography

Go To: Top, Phase change data, References, Notes

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

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

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Column type	Active phase	I	Reference	Comment
Capillary	DB-5	1495.	Zeller and Rychlik, 2006	30. m/0.32 mm/0.25 μm, He, 40. C @ 1. min, 6. K/min; T_end: 230. C
Capillary	DB-5	1508.	Zhang, Xu, et al., 2005	30. m/0.25 mm/0.25 μm, N2, 45. C @ 10. min, 2.5 K/min, 180. C @ 20. min
Capillary	BPX-5	1520.	Zabaras and Wyllie, 2001	50. m/0.22 mm/0.25 μm, H2, 60. C @ 5. min, 4. K/min, 180. C @ 5. min
Capillary	HP-5	1455.	Lazari, Skaltsa, et al., 2000	30. m/0.25 mm/0.25 μm, He, 50. C @ 5. min, 4. K/min; T_end: 280. C
Capillary	OV-1	1461.	Bicchi, Fresia, et al., 1997	25. m/0.25 mm/0.3 μm, H2, 50. C @ 1. min, 3. K/min, 200. C @ 20. min

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

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	HP-5	1480.	García, Alvarez, et al., 2002	50. m/0.2 mm/0.33 μm, He; Program: 50C(2min) => 5C/min => 150C => 10C/min => 250C(30min)
Capillary	HP-5	1480.	García, Alvarez, et al., 2002	50. m/0.2 mm/0.33 μm, He; Program: 50C(2min) => 5C/min => 150C => 10C/min => 250C(30min)

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

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DB-FFAP	2189.	Zeller and Rychlik, 2006	30. m/0.32 mm/0.25 μm, He, 40. C @ 1. min, 6. K/min; T_end: 230. C
Capillary	Carbowax 20M	2196.	Bicchi, Fresia, et al., 1997	25. m/0.25 mm/0.3 μm, 50. C @ 1. min, 3. K/min, 200. C @ 20. min

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	DB-5	1492.	Andrade, Cardoso, et al., 2011	30. m/0.25 mm/0.25 μm, Helium, 3. K/min; T_start: 60. C; T_end: 240. C
Capillary	DB-5	1492.	Ho, Wang, et al., 2009	30. m/0.25 mm/0.25 μm, Helium, 50. C @ 2. min, 5. K/min; T_end: 250. C
Capillary	DB-5	1492.	Rahimi-Nasrabadi, Gholivand, et al., 2009	30. m/0.25 mm/0.25 μm, Nitrogen, 40. C @ 1. min, 3. K/min, 250. C @ 10. min
Capillary	CP Sil 8 CB	1504.	Suárez, Vásquez, et al., 2005	He, 60. C @ 5. min, 3. K/min; Column length: 30. m; Column diameter: 0.25 mm; T_end: 290. C
Capillary	DB-5	1491.	Caredda, Marongiu, et al., 2002	30. m/0.25 mm/0.25 μm, He, 3. K/min, 280. C @ 30. min; T_start: 60. C
Capillary	OV-101	1468.	Menon, Chacko, et al., 1999	N2, 1. K/min, 200. C @ 20. min; Column length: 50. m; Column diameter: 0.2 mm; T_start: 80. C
Capillary	OV-101	1468.	Sugisawa, Yamamoto, et al., 1989	N2, 2. K/min; Column length: 50. m; Column diameter: 0.25 mm; T_start: 80. C; T_end: 200. C

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

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DB-5	1492.	Andrade, Cardoso, et al., 2011	30. m/0.25 mm/0.25 μm, Helium; Program: not specified
Capillary	DB-1	1466.	Delort and Jaquier, 2009	60. m/0.25 mm/0.25 μm, Helium; Program: 50 0C (5 min) 3 0C/min -> 120 0C 5 0C/min -> 250 0C (3 min) 15 0C/min -> 300 0C (20 min)
Capillary	HP-5MS	1462.	Deng, Li, et al., 2004	30. m/0.25 mm/0.25 μm, He; Program: 60C => 10C/min => 160C => 12C/min => 300C (5min)

Normal alkane RI, polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	Carbowax	2126.	Singh, Kumar, et al., 2007	60. m/0.25 mm/0.25 μm, He, 5. K/min; T_start: 40. C; T_end: 180. C
Capillary	Innowax	2185.	Joichi, Yomogida, et al., 2005	60. m/0.25 mm/0.25 μm, He, 5. K/min, 240. C @ 30. min; T_start: 60. C
Capillary	TC-Wax	2176.	Miyazawa, Yamafuji, et al., 2003	3. K/min; Column length: 60. m; Column diameter: 0.25 mm; T_start: 80. C; T_end: 240. C
Capillary	Supelcowax-10	2194.	Choo, Wong, et al., 1999	30. m/0.25 mm/0.25 μm, 4. K/min; T_start: 60. C; T_end: 220. C

References

Go To: Top, Phase change data, Gas Chromatography, Notes

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [all data]

Zeller and Rychlik, 2006
Zeller, A.; Rychlik, M., Character impact odorants of fennel fruits and fennel tea, J. Agric. Food Chem., 2006, 54, 10, 3686-3692, https://doi.org/10.1021/jf052944j . [all data]

Zhang, Xu, et al., 2005
Zhang, F.; Xu, Q.; Fu, S.; Ma, X.; Xiao, H.; Liang, X., Chemical constituents of the essential oil of Asarum forbesii Maxim (Aristolochiaceae), Flavour Fragr. J., 2005, 20, 3, 318-320, https://doi.org/10.1002/ffj.1423 . [all data]

Zabaras and Wyllie, 2001
Zabaras, D.; Wyllie, S.G., Quantitative analysis of terpenoids in the gas phase using headspace solid-phase microextraction (HS-SPME), Flavour Fragr. J., 2001, 16, 6, 411-416, https://doi.org/10.1002/ffj.1025 . [all data]

Lazari, Skaltsa, et al., 2000
Lazari, D.M.; Skaltsa, H.D.; Constantinidis, T., Volatile constituents of Cerastium candidissimum, a Greek endemic species, Flavour Fragr. J., 2000, 15, 3, 174-176, https://doi.org/10.1002/1099-1026(200005/06)15:3<174::AID-FFJ886>3.0.CO;2-Y . [all data]

Bicchi, Fresia, et al., 1997
Bicchi, C.; Fresia, M.; Rubiolo, P.; Monti, D.; Franz, C.; Goehler, I., Constituents of Tagetes lucida Cav. ssp. lucida essential oil, Flavour Fragr. J., 1997, 12, 1, 47-52, https://doi.org/10.1002/(SICI)1099-1026(199701)12:1<47::AID-FFJ610>3.0.CO;2-7 . [all data]

García, Alvarez, et al., 2002
García, D.; Alvarez, A.; Tornos, P.; Fernandez, A.; Sáenz, T., Gas chromatographic-mass spectrometry study of the essential oils of Pimenta racemosa var. terebinthina and P. racemosa var. grisea, Z. Naturforsch., 2002, 57c, 449-451. [all data]

Andrade, Cardoso, et al., 2011
Andrade, M.A.; Cardoso, M.G.; Batista, L.R.; Freire, J.M.; Nelson, D.L., Antimicrobial activity and chemical composition of essential oil of Pelargonium odoratissimum, Braz. J. Pharmacognosy, 2011, 21, 1, 47-52. [all data]

Ho, Wang, et al., 2009
Ho, C.-L.; Wang, E.I.-C.; Su, Y.-C., Essential oil compositions and bioactivities of the various parts of Cinnamomum camphora Sieb. var. linallolifera Fujuta, Journal title only in Chinese, 2009, 31, 2, 77-96. [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]

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]

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]

Menon, Chacko, et al., 1999
Menon, A.N.; Chacko, S.; Narayanan, C.S., Free and glycosidically bound volatiles of cardamom (Eletteria cardamomum Maton var. miniscula Burkill), Flavour Fragr. J., 1999, 14, 1, 65-68, https://doi.org/10.1002/(SICI)1099-1026(199901/02)14:1<65::AID-FFJ789>3.0.CO;2-A . [all data]

Sugisawa, Yamamoto, et al., 1989
Sugisawa, H.; Yamamoto, M.; Tamura, H.; Takagi, N., The comparison of volatile components in peel oil from four species of navel orange, Nippon Shokuhin Kogio Gakkaishi, 1989, 36, 6, 455-462, https://doi.org/10.3136/nskkk1962.36.6_455 . [all data]

Delort and Jaquier, 2009
Delort, E.; Jaquier, A., Novel terpenyl esters from Australian finger lime (Citrus australasica) peel extract, Flav. Fragr. J., 2009, 24, 3, 123-132, https://doi.org/10.1002/ffj.1922 . [all data]

Deng, Li, et al., 2004
Deng, C.; Li, N.; Zhang, X., Rapid determination of essential oil in Acorus tatarinowii Schott. by pressurized hot water extraction followed by solid-phase microextraction and gas chromatography-mass spectrometry, J. Chromatogr. A, 2004, 1059, 1-2, 149-155, https://doi.org/10.1016/j.chroma.2004.10.005 . [all data]

Singh, Kumar, et al., 2007
Singh, B.; Kumar, R.; Bhandari, S.; Pathania, S.; Lal, B., Volatile constituents of natural Boswellia serrata oleo-gum-resin and commercial samples, Flavour Fragr. J., 2007, 22, 2, 145-147, https://doi.org/10.1002/ffj.1772 . [all data]

Joichi, Yomogida, et al., 2005
Joichi, A.; Yomogida, K.; Awano, K.; Ueda, Y., Volatile components of tea-scented modern roses and ancient Chinese roses, Flavour Fragr. J., 2005, 20, 2, 152-157, https://doi.org/10.1002/ffj.1388 . [all data]

Miyazawa, Yamafuji, et al., 2003
Miyazawa, M.; Yamafuji, C.; Kurose, K.; Ishikawa, Y., Volatile components of the rhizomes of Cirsium japonicum DC, Flavour Fragr. J., 2003, 18, 1, 15-17, https://doi.org/10.1002/ffj.1135 . [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]

Notes

Go To: Top, Phase change data, Gas Chromatography, References

Symbols used in this document:

T_boil Boiling point

Δ_vapH Enthalpy of vaporization
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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