Phenol, 2,6-dimethoxy-4-(2-propenyl)-

Formula: C₁₁H₁₄O₃
Molecular weight: 194.2271
IUPAC Standard InChI: InChI=1S/C11H14O3/c1-4-5-8-6-9(13-2)11(12)10(7-8)14-3/h4,6-7,12H,1,5H2,2-3H3
IUPAC Standard InChIKey: FWMPKHMKIJDEMJ-UHFFFAOYSA-N
CAS Registry Number: 6627-88-9
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: Phenol, 4-allyl-2,6-dimethoxy-; Methoxyeugenol; 2,6-Dimethoxy-4-allylphenol; 4-Allyl-2,6-dimethoxyphenol; 4-Hydroxy-3,5-dimethoxyallylbenzene; 2,6-Dimethoxy-4-(2-propenyl)phenol; 4-(2-Propenyl)-2,6-dimethoxyphenol (4-allylsyringol); 4-Allyl-2,6-dimetoxyphenol; 4-Allylsyringol; Phenol, 4-(2-propenyl)-2,6-dimethoxy
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Other data available:
- Mass spectrum (electron ionization)
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Phase change data

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Data compiled by: Robert L. Brown and Stephen E. Stein

Reduced pressure boiling point

T_boil (K)	Pressure (atm)	Reference
441.7	0.014	Aldrich Chemical Company Inc., 1990

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	1602.	Nogueira, Marsaioli, et al., 1998	30. m/0.25 mm/0.25 μm, H2, 3. K/min; T_start: 60. C; T_end: 240. C
Capillary	DB-1	1574.	Wu, Kuo, et al., 1991	50. m/0.32 mm/1.05 μm, He, 2. K/min, 260. C @ 40. min; T_start: 40. C

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-5MS	1606.5	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	DB-5MS	1615.	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	1615.	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	1609.	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

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax Etr	2543.	Aubert C. and Pitrat M., 2006	30. m/0.25 mm/0.25 μm, He, 40. C @ 3. min, 5. K/min, 250. C @ 15. min

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	HP-5 MS	1612.	Pripdeevech and Saansoomchai, 2013	30. m/0.25 mm/0.25 μm, Helium, 3. K/min; T_start: 60. C; T_end: 230. C
Capillary	DP-5	1581.	Vijayakumar, Duraipandiyan, et al., 2012	30. m/0.25 mm/0.25 μm, Helium, 80. C @ 1. min, 4. K/min, 300. C @ 40. min
Capillary	DP-5	1581.	Vijayakumar, Duraipandiyan, et al., 2012	30. m/0.25 mm/0.25 μm, Helium, 80. C @ 1. min, 4. K/min, 300. C @ 40. min
Capillary	DP-5	1581.	Vijayakumar, Duraipandiyan, et al., 2012	30. m/0.25 mm/0.25 μm, Helium, 80. C @ 1. min, 4. K/min, 300. C @ 40. min
Capillary	SPB-1	1546.	Choo, Wong, et al., 1999	50. m/0.2 mm/0.33 μm, 4. K/min; T_start: 60. C; T_end: 260. C
Capillary	DB-1	1558.	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
Capillary	DB-1	1569.	Shiota, 1993	30. m/0.25 mm/0.25 μm, He, 50. C @ 5. min, 3. K/min; T_end: 240. C
Capillary	DB-1	1579.	Shiota, 1993	30. m/0.25 mm/0.25 μm, He, 50. C @ 5. min, 3. K/min; T_end: 240. C
Capillary	DB-1	1575.	Shiota, 1993	30. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 5. K/min; T_end: 240. C
Capillary	DB-1	1579.	Shiota, 1993	30. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 5. K/min; T_end: 240. C

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

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	ZB-1 MS	1581.	Al-Reza, Rahman, et al., 2009	30. m/0.25 mm/0.25 μm, Helium; Program: 50 0C 3 0C/min -> 150 0C (10 min) 10 0C/min -> 250 0C
Capillary	HP-5	1604.	Zhao, Li, et al., 2008	30. m/0.25 mm/0.25 μm; Program: 40 0C (2 min) 5 0C/min -> 80 0C 7 oC/min -> 160 0C 9 0C/min -> 200 0C 20 0C/min -> 280 0C (10 min)
Capillary	HP-5	1609.	Zhao, Li, et al., 2008	30. m/0.25 mm/0.25 μm; Program: not specified
Capillary	HP-5MS	1609.	Ansorena, Gimeno, et al., 2001	30. m/0.25 mm/0.25 μm, He; Program: 40C (10min) => 3C/min => 120C => 10C/min => 250C (5min)
Capillary	HP-1	1560.	Teai, Claude-Lafontaine, et al., 2001	50. m/0.32 mm/0.52 μm, N2; Program: 40C => 2C/min => 130C => 4C/min => 250C

Normal alkane RI, polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax Etr	2563.	Ibarz, Ferreira, et al., 2006	60. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 2. K/min, 230. C @ 100. min
Capillary	DB-Wax	2570.	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	Supelcowax-10	2544.	Choo, Wong, et al., 1999	30. m/0.25 mm/0.25 μm, 4. K/min; T_start: 60. C; T_end: 220. C

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	2563.	Loscos, Hernandez-Orte, et al., 2009	60. m/0.25 mm/0.50 μm, Helium; Program: 40 0C (3 min) 10 0C/min -> 90 0C 2 0C/min -> 230 0C (37 min)
Capillary	DB-Wax Etr	2563.	Loskos, Hernandez-Orte, et al., 2007	60. m/0.25 mm/0.5 μm, He; Program: 40C(3min) => 10C/min => 90C => 2C/min => 230C (37min)

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]

Nogueira, Marsaioli, et al., 1998
Nogueira, P.C.L.; Marsaioli, A.J.; Amaral, M.C.E.; Bittrich, V., The fragrant floral oils of Tovomita species, Phytochemistry, 1998, 49, 4, 1009-1012, https://doi.org/10.1016/S0031-9422(97)01046-7 . [all data]

Wu, Kuo, et al., 1991
Wu, P.; Kuo, M.-C.; Hartman, T.G.; Rosen, R.T.; Ho, C.-T., Free and glycosidically bound aroma compounds in pineapple (Ananas comosus L. Merr.), J. Agric. Food Chem., 1991, 39, 1, 170-172, https://doi.org/10.1021/jf00001a033 . [all data]

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

Aubert C. and Pitrat M., 2006
Aubert C.; Pitrat M., Volatile compounds in the skin and pulp of Queen Anne's pocket melon, J. Agric. Food Chem., 2006, 54, 21, 8177-8182, https://doi.org/10.1021/jf061415s . [all data]

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]

Vijayakumar, Duraipandiyan, et al., 2012
Vijayakumar, A.; Duraipandiyan, V.; Jeyarai, B.; Agastian, P.; Raj, M.K.; Ignacimunthu, S., Phytochemical analysis and in vitro antimicrobial activity of Illicium griffithii Hook f. Thoms extracts, Asian Pacific J. Tropical Diseases, 2012, 2, 3, 190-199, https://doi.org/10.1016/S2222-1808(12)60045-0 . [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]

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]

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]

Al-Reza, Rahman, et al., 2009
Al-Reza, S.M.; Rahman, A.; Kang, S.C., Chemical composition and inhibitory effect of essentiasl oil and organic extracts of Cestrum nocturnum L. om food-borne pathogens, Int. J. Food Sci. Technol., 2009, 44, 6, 1176-1182, https://doi.org/10.1111/j.1365-2621.2009.01939.x . [all data]

Zhao, Li, et al., 2008
Zhao, Y.; Li, J.; Xu, Y.; Duan, H.; Fan, W.; Zhao, G., EXtraction, preparation and identification of volatile compounds in Changyu XO brandy, Chinese J. Chromatogr., 2008, 26, 2, 212-222, https://doi.org/10.1016/S1872-2059(08)60014-0 . [all data]

Ansorena, Gimeno, et al., 2001
Ansorena, D.; Gimeno, O.; Astiasarán, I.; Bello, J., Analysis of volatile compounds by GC-MS of a dry fermented sausage: chorizo de Pamplona, Food Res. Int., 2001, 34, 1, 67-75, https://doi.org/10.1016/S0963-9969(00)00133-2 . [all data]

Teai, Claude-Lafontaine, et al., 2001
Teai, T.; Claude-Lafontaine, A.; Schippa, C.; Cozzolino, F., Volatile compounds in fresh pulp of pineapple (Ananas comosus [L.] Merr.) from French Polynesia, J. Essent. Oil Res., 2001, 13, 5, 314-318, https://doi.org/10.1080/10412905.2001.9712222 . [all data]

Ibarz, Ferreira, et al., 2006
Ibarz, M.J.; Ferreira, V.; Hernández-Orte, P.; Loscos, N.; Cacho, J., Optimization and evaluation of a procedure for the gas chromatographic-mass spectrometric analysis of the aromas generated by fast acid hydrolysis of flavor precursors extracted from grapes, J. Chromatogr. A, 2006, 1116, 1-2, 217-229, https://doi.org/10.1016/j.chroma.2006.03.020 . [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]

Loscos, Hernandez-Orte, et al., 2009
Loscos, N.; Hernandez-Orte, P.; Cacho, J.; Ferreira, V., Fate of grape flavor precursors during storage on yeast lees, J. Agric. Food Chem., 2009, 57, 12, 5468-5479, https://doi.org/10.1021/jf804057q . [all data]

Loskos, Hernandez-Orte, et al., 2007
Loskos, N.; Hernandez-Orte, P.; Cacho, J.; Ferreira, V., Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions, J. Agric. Food Chem., 2007, 55, 16, 6674-6684, https://doi.org/10.1021/jf0702343 . [all data]

Notes

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Symbols used in this document:

T_boil Boiling point
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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