trans-Isoeugenol

Formula: C₁₀H₁₂O₂
Molecular weight: 164.2011
IUPAC Standard InChI: InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3-7,11H,1-2H3/b4-3+
IUPAC Standard InChIKey: BJIOGJUNALELMI-ONEGZZNKSA-N
CAS Registry Number: 5932-68-3
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:
- Phenol, 2-methoxy-4-(1-propenyl)-, (Z)-
- Phenol, 2-methoxy-4-(1-propenyl)-
Other names: Phenol, 2-methoxy-4-(1-propenyl)-, (E)-; Phenol, 2-methoxy-4-propenyl-, (E)-; (E)-Isoeugenol; trans-p-Propenylquaiacol; trans-2-Methoxy-4-propenylphenol; iso-Eugenol 2; Isoeugenol E; 4-(1-Propenyl)-2-methoxyphenol; E-4-Propenyl-2-methoxyphenol; trans-2-Methoxy-4-(1-propenyl)phenol; (E)-2-Methoxy-4-(prop-1-enyl)phenol; NSC 209522; 4-(1-Propenyl)-2-methoxyphenol (trans-isoeugenol)
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Other data available:
- Mass spectrum (electron ionization)
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Phase change data

Go To: Top, Gas Chromatography, References, Notes

Data compiled by: William E. Acree, Jr., James S. Chickos

Enthalpy of vaporization

Δ_vapH (kJ/mol)	Temperature (K)	Method	Reference	Comment
69.1	378.	A	Stephenson and Malanowski, 1987	Based on data from 363. to 420. K.

Gas Chromatography

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

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

Kovats' RI, non-polar column, isothermal

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Column type	Active phase	Temperature (C)	I	Reference	Comment
Capillary	SE-30	100.	1436.4	Tudor, 1997	40. m/0.35 mm/0.35 μm

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

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Column type	Active phase	I	Reference	Comment
Capillary	BP-1	1429.	Duquesnoy, Dinh, et al., 2006	50. m/0.22 mm/0.25 μm, He, 2. K/min, 220. C @ 20. min; T_start: 60. C
Capillary	DB-5	1449.	Adams, Habte, et al., 2004	30. m/0.26 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 246. C
Capillary	SPB-5	1447.	Pino, Marbot, et al., 2004	30. m/0.25 mm/0.25 μm, He, 60. C @ 2. min, 4. K/min, 250. C @ 20. min
Capillary	BPX-5	1465.	Zabaras and Wyllie, 2001	50. m/0.22 mm/0.25 μm, H2, 60. C @ 5. min, 4. K/min, 180. C @ 5. 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	DB-5	1447.	Andrade, Sampaio, et al., 2007	30. m/0.25 mm/0.25 μm, He; Program: 40C(2min) => 4C/min => 220C => 20C/min => 280C
Capillary	DB-5MS	1473.	Varlet, Serot, et al., 2007	30. m/0.32 mm/0.5 μm, He; Program: 70C => 5C/min => 85C(1min) => 3C/min => 165C => 10C/min => 280C(3min)
Capillary	DB-5MS	1473.	Varlet V., Knockaert C., et al., 2006	30. m/0.32 mm/0.5 μm, He; Program: 70C(1min) => 3C/min => 80C(1min) => 5C/min => 150C => 10C/min => 280C (4min)
Capillary	LM-5	1458.4	Ré-Poppi and Santiago-Silva, 2002	30. m/0.25 mm/0.25 μm, He; Program: 60C(2min) => 15C/min => 180C => 5C/min => 280C(5min)

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

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Column type	Active phase	I	Reference	Comment
Capillary	BP-20	2352.	Duquesnoy, Dinh, et al., 2006	50. m/0.22 mm/0.25 μm, He, 2. K/min, 220. C @ 20. min; T_start: 60. C
Capillary	AT-Wax	2309.	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	HP-Wax	2394.	Christensen, Jakobsen, et al., 1997	50. m/0.2 mm/0.4 μm, He, 30. C @ 1. min, 5. K/min, 220. C @ 30. min

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

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Column type	Active phase	I	Reference	Comment
Capillary	Stabilwax	2347.	Natali N., Chinnici F., et al., 2006	30. m/0.25 mm/0.25 μm, He; Program: 40C => 3C/min => 100C => 5C/min => 240C(10min)

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	Optima-5	1453.	Al-Qudah, Muhaidat, et al., 2012	30. m/0.25 mm/0.25 μm, Helium, 60. C @ 1. min, 3. K/min; T_end: 246. C
Capillary	ZB-5	1458.	Harrison and Priest, 2009	30. m/0.25 mm/0.25 μm, Helium, 40. C @ 1. min, 6. K/min, 280. C @ 9. min
Capillary	HP-5 MS	1453.	Zhao, Zeng, et al., 2009	30. m/0.25 mm/0.25 μm, Helium, 4. K/min; T_start: 50. C; T_end: 280. C
Capillary	HP-5MS	1449.	Setzer, Noletto, et al., 2006	30. m/0.25 mm/0.25 μm, He, 60. C @ 5. min, 3. K/min; T_end: 280. C
Capillary	ZB-5	1463.	Dötterl, Wolfe, et al., 2005	60. m/0.25 mm/0.25 μm, He, 40. C @ 7. min, 6. K/min, 250. C @ 1. min
Capillary	SPB-5	1474.	Kilic, Kollmannsberger, et al., 2005	He, 5. K/min; Column length: 30. m; Column diameter: 0.53 mm; T_start: 100. C; T_end: 250. C
Capillary	SE-54	1444.	Kilic, Hafizoglu, et al., 2004	30. m/0.25 mm/0.25 μm, He, 60. C @ 5. min, 2. K/min; T_end: 260. C
Capillary	SE-54	1474.	Kilic, Hafizoglu, et al., 2004	30. m/0.053 mm/1.5 μm, He, 5. K/min; T_start: 100. C; T_end: 250. C
Capillary	DB-1	1411.	Kjällstrand, Ramnäs, et al., 1998	30. m/0.25 mm/0.25 μm, He, 5. K/min; T_start: 50. C; T_end: 200. C

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

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Column type	Active phase	I	Reference	Comment
Capillary	VF-5	1455.	Shivashankar, Roy, et al., 2012	30. m/0.25 mm/0.25 μm, Helium; Program: 50 0C (2 min) 3 0C/min -> 200 0C (3 min) 10 0C/min -> 220 0C (8 min)
Capillary	VF-5	1459.	Shivashankar, Roy, et al., 2012	30. m/0.25 mm/0.25 μm, Helium; Program: not specified
Capillary	ZB-5	1451.	de Simon, Estruelas, et al., 2009	30. m/0.25 mm/0.25 μm, Helium; Program: 45 0C 3 0C/min -> 230 0C (10 min) 10 0C/min -> 270 0C (21 min)
Capillary	RTX-5	1457.	Zachariah, Leela, et al., 2008	30. m/0.25 mm/0.25 μm, Helium; Program: 60 0C (5 min) 5 0C/min -> 110 0C 3 0C/min -> 220 0C (5 min)
Capillary	HP-5 MS	1451.	Setzer, Stokes, et al., 2007	Helium; Column length: 30. m; Column diameter: 0.25 mm; Program: 40 0C (10 min) 3 oC/min -> 200 0C 2 0C/min -> 220 0C
Capillary	DB-1	1420.	Sung, Stone, et al., 2007	Helium; Column length: 30. m; Column diameter: 0.25 mm; Program: 120 0C (2 min( 5 0C/min -> 200 0C 10 0C/min -> 290 0C (5 min)
Capillary	Polydimethyl siloxane with 5 % Ph groups	1447.	Pino, Marbot, et al., 2005	Program: not specified
Capillary	SE-30	1409.	Vinogradov, 2004	Program: not specified
Capillary	SE-54	1430.	Kilic, 2002	Program: not specified

Normal alkane RI, polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	ZB-Wax	2383.	Wierda R.L., Fletcher G., et al., 2006	60. m/0.32 mm/0.5 μm, He, 40. C @ 2. min, 3. K/min, 250. C @ 10. min
Capillary	DB-Wax	2372.	Culleré, Escudero, et al., 2004	30. m/0.32 mm/0.5 μm, H2, 40. C @ 5. min, 4. K/min; T_end: 200. C
Capillary	DB-Wax	2355.	Parada and Duque, 1998	30. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 4. K/min, 240. C @ 10. min
Capillary	DB-Wax	2368.	Parada and Duque, 1998	30. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 4. K/min, 240. C @ 10. min
Capillary	TC-Wax	2373.	Shuichi, Masazumi, et al., 1996	80. C @ 5. min, 3. K/min; Column length: 60. m; Column diameter: 0.25 mm; T_end: 240. C

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	Supelcowax-10	2314.	de Simon, Estruelas, et al., 2009	30. m/0.25 mm/0.25 μm, Helium; Program: 45 0C 3 0C/min -> 230 0C (10 min) 10 0C/min -> 270 0C (21 min)
Capillary	Carbowax 20M	2339.	Vinogradov, 2004	Program: not specified

References

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

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]

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]

Duquesnoy, Dinh, et al., 2006
Duquesnoy, E.; Dinh, N.H.; Castola, V.; Casanova, J., Composition of a Pyrolytic oil from Cupressus funebris Endl. of Vietnamese origin, Flavour Fragr. J., 2006, 21, 3, 453-457, https://doi.org/10.1002/ffj.1676 . [all data]

Adams, Habte, et al., 2004
Adams, R.P.; Habte, M.; Park, S.; Dafforn, M.R., Preliminary comparison of vetiver root essential oils from cleansed (bacteria- and fungus-free) versus non-cleansed (normal) vetiver plants, Biochem. Syst. Ecol., 2004, 32, 12, 1137-1144, https://doi.org/10.1016/j.bse.2004.03.013 . [all data]

Pino, Marbot, et al., 2004
Pino, J.A.; Marbot, R.; Rosado, A.; Vázquez, C., Volatile constituents of Malay rose apple [Syzygium malaccense (L.) Merr. Perry], Flavour Fragr. J., 2004, 19, 1, 32-35, https://doi.org/10.1002/ffj.1269 . [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]

Andrade, Sampaio, et al., 2007
Andrade, M.S.; Sampaio, T.S.; Nogueira, P.C.L.; Ribeiro, A.S.; Bittrich, V.; Amaral, M.C.E., Volatile compounds of the leaves, flowers and fruits of Kielmeyera rugosa Choisy (Clusiaceae), Flavour Fragr. J., 2007, 22, 1, 49-52, https://doi.org/10.1002/ffj.1751 . [all data]

Varlet, Serot, et al., 2007
Varlet, V.; Serot, T.; Cardinal, M.; Knockaert, C.; Prost, C., Olfactometric Determination of the Most Potent Odor-Active Compounds in Salmon Muscle (Salmo salar) Smoked by Using Four Smoke Generation Techniques, J. Agric. Food Chem., 2007, 55, 11, 4518-4525, https://doi.org/10.1021/jf063468f . [all data]

Varlet V., Knockaert C., et al., 2006
Varlet V.; Knockaert C.; Prost C.; Serot T., Comparison of odor-active volatile compounds of fresh and smoked salmon, J. Agric. Food Chem., 2006, 54, 9, 3391-3401, https://doi.org/10.1021/jf053001p . [all data]

Ré-Poppi and Santiago-Silva, 2002
Ré-Poppi, N.; Santiago-Silva, M.R., Identification of polycyclic aromatic hydrocarbons and methoxylated phenols in wood smoke emitted during production of charcoal, Chromatographia, 2002, 55, 7/8, 475-481, https://doi.org/10.1007/BF02492280 . [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]

Christensen, Jakobsen, et al., 1997
Christensen, L.P.; Jakobsen, H.B.; Kristiansen, K.; Møller, J., Volatiles emitted from flowers of γ-radiated and nonradiated Jasminum polyanthum Franch. in Situ, J. Agric. Food Chem., 1997, 45, 6, 2199-2203, https://doi.org/10.1021/jf960961q . [all data]

Natali N., Chinnici F., et al., 2006
Natali N.; Chinnici F.; Riponi C., Characterization of volatiles in extracts from oak chips obtained by accelerated solvent extraction (ASE), J. Agric. Food Chem., 2006, 54, 21, 8190-8198, https://doi.org/10.1021/jf0614387 . [all data]

Al-Qudah, Muhaidat, et al., 2012
Al-Qudah, M.A.; Muhaidat, R.; Trawenh, I.N.; Jaber, H.I.; Abu Zarga, M.H.; Abu Orabi, S.T., Volatile constituents of leaves and bulbs of Gynandriris Sisyrinchicum and their antimicrobial activities, Jordan J. Chem., 2012, 7, 3, 287-295. [all data]

Harrison and Priest, 2009
Harrison, B.M.; Priest, F.G., Composition of peaks used in the preparation of malt for Scotch Whisky production - influence of geographical source and extraction depth, J. Agric. Food Chem., 2009, 57, 6, 2385-2391, https://doi.org/10.1021/jf803556y . [all data]

Zhao, Zeng, et al., 2009
Zhao, C.; Zeng, Y.; Wan, M.; Li, R.; Liang, Y.; Li, C.; Zeng, Z.; Chau, F.-T., Comparative analysis of essential oils from eight herbal medicines with pungent flavor and cool nature by GC-MS and chemometric resolution methods, J. Sep. Sci., 2009, 32, 4, 660-670, https://doi.org/10.1002/jssc.200800484 . [all data]

Setzer, Noletto, et al., 2006
Setzer, W.N.; Noletto, J.A.; Lawton, R.O., Chemical composition of the floral essential oil of Randia matudae from Monteverde, Costa Rica, Flavour Fragr. J., 2006, 21, 2, 244-246, https://doi.org/10.1002/ffj.1567 . [all data]

Dötterl, Wolfe, et al., 2005
Dötterl, S.; Wolfe, L.M.; Jürgens, A., Qualitative and quantitative analyses of flower scent in Silene latifolia, Phytochemistry, 2005, 66, 2, 203-213, https://doi.org/10.1016/j.phytochem.2004.12.002 . [all data]

Kilic, Kollmannsberger, et al., 2005
Kilic, A.; Kollmannsberger, H.; Nitz, S., Glycosidically bound volatiles and flavor precursors in Laurus nobilis L., J. Agric. Food Chem., 2005, 53, 6, 2231-2235, https://doi.org/10.1021/jf040373+ . [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]

Kjällstrand, Ramnäs, et al., 1998
Kjällstrand, J.; Ramnäs, O.; Petersson, G., Gas chromatographic and mass spectrometric analysis of 36 lignin-related methoxyphenols from uncontrolled combustion of wood, J. Chromatogr. A, 1998, 824, 2, 205-210, https://doi.org/10.1016/S0021-9673(98)00698-0 . [all data]

Shivashankar, Roy, et al., 2012
Shivashankar, S.; Roy, T.K.; Moorthy, P.N.R., Headspace solid phase micro extraction and GC/MS analysis of the volatile components in seed and cake of Azadirachta indica A. juss, Chem. Bull. of Politechnika Univ. Timisoara, Romania, 2012, 57(71), 1, 1-6. [all data]

de Simon, Estruelas, et al., 2009
de Simon, B.F.; Estruelas, E.; Munoz, A.M.; Cadahia, E.; Sanz, M., Volatile compounds in acacia, chestnut, cherry, ash, and oak woods, with a view to their use in cooperage, J. Agric. Food Chem., 2009, 57, 8, 3217-3227, https://doi.org/10.1021/jf803463h . [all data]

Zachariah, Leela, et al., 2008
Zachariah, T.J.; Leela, N.K.; Maya, K.M.; Rema, J.; Mathew, P.A.; Vipin, T.M.; Krishnamoorthy, B., Chemical composition of leaf oils of Myristica beddomeii (King), Myristica fragrans (Houtt.) and Myristica malabarica (Lamk.), J. Spices Arom. Crops, 2008, 17, 1, 10-15. [all data]

Setzer, Stokes, et al., 2007
Setzer, W.N.; Stokes, S.L.; Penton, A.F.; Takaku, S.; Haber, W.A.; Hansell, E.; Caffrey, C.R.; McKerrow, J.H., Cruzain inhibitory activity of leaf essential oils of neotropical Lauraceae and essential oil components, Natural Product Communications, 2007, 2, 12, 1203-1210. [all data]

Sung, Stone, et al., 2007
Sung, W.-C.; Stone, M.; Sun, F.-M., Analysis of volatile constituents of different temperature rice hulls liquid smoke, Chi-Nan Annual Bull., 2007, 33, 1-12. [all data]

Pino, Marbot, et al., 2005
Pino, J.A.; Marbot, R.; Rosado, A.; Vázquez, C., Volatile constituents of Malay rose apple [Syzygium malaccense (L.) Merr. Perry], Flavour Fragr. J., 2005, 20, 98-100. [all data]

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

Kilic, 2002
Kilic, A., Volatile compounds of buds, flowers and fruits of bay (Laurus nobilis L.) and their odour contribution, Proc. ICNP-2002 - Trabzon/Turkiye, 2002, 338-341. [all data]

Wierda R.L., Fletcher G., et al., 2006
Wierda R.L.; Fletcher G.; Xu L.; Dufour J.P., Analysis of volatile compounds as spoilage indicators in fresh king salmon (Oncorhynchus tshawytscha) during storage using SPME-GC-MS, J. Agric. Food Chem., 2006, 54, 22, 8480-8490, https://doi.org/10.1021/jf061377c . [all data]

Culleré, Escudero, et al., 2004
Culleré, L.; Escudero, A.; Cacho, J.; Ferreira, V., Gas chromatography-olfactometry and chemical quantitative study of the aroma of six premium auality Spanish aged red wines, J. Agric. Food Chem., 2004, 52, 6, 1653-1660, https://doi.org/10.1021/jf0350820 . [all data]

Parada and Duque, 1998
Parada, F.; Duque, C., Studies on the aroma of piñuela fruit pulp (Bromelia plumieri): Free and bound volatile composition and characterization of some glucoconjugates as aroma precursors, J. Hi. Res. Chromatogr., 1998, 21, 10, 577-581, https://doi.org/10.1002/(SICI)1521-4168(19981001)21:10<577::AID-JHRC577>3.0.CO;2-V . [all data]

Shuichi, Masazumi, et al., 1996
Shuichi, H.; Masazumi, N.; Hiromu, K.; Kiyoshi, F., Comparison of volatile compounds berween the crude drugs, Onji-tsutsu and Onji-niki, Nippon nogei kagaku kaishi, 1996, 70, 2, 151-160. [all data]

Notes

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

Symbols used in this document:

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