Methyleugenol

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/h4,6-8H,1,5H2,2-3H3
IUPAC Standard InChIKey: ZYEMGPIYFIJGTP-UHFFFAOYSA-N
CAS Registry Number: 93-15-2
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, 1,2-dimethoxy-4-(2-propenyl)-; Benzene, 4-allyl-1,2-dimethoxy-; Ent 21040; Eugenol methyl ether; Eugenyl methyl ether; Methyl eugenol ether; O-Methyleugenol; Veratrole methyl ether; 1-(3,4-Dimethoxyphenyl)-2-propene; 1-Allyl-3,4-dimethoxybenzene; 1,2-Dimethoxy-4-allylbenzene; 1,3,4-Eugenol methyl ether; 3,4-Dimethoxyallylbenzene; 4-Allyl-1,2-dimethoxybenzene; 4-Allylveratrole; 1,2-Dimethoxy-4-(2-propenyl)benzene; 4-Allyl-1,2-dimethyoxybenzene; Methyl eugenyl ether; o-Methyl eugenol ether; Benzene, 4-(2-propenyl)-1,2-dimethoxy; Eugenol methyl; Benzene, 1,2-dimethoxy-4-(2-propen-1-yl)-; NSC 209528
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Kovats' RI, non-polar column, temperature ramp

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

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5	HP-5MS	HP-5	BP-1	BP-1
Column length (m)	30.	30.	25.	25.	30.
Carrier gas	He	He		N2	N2
Substrate
Column diameter (mm)	0.26	0.25	0.2	0.32	0.32
Phase thickness (μm)	0.25	0.25	0.33	0.25	0.25
T_start (C)	60.	60.	60.	60.	60.
T_end (C)	246.	280.	240.	220.	220.
Heat rate (K/min)	3.	2.	3.	5.	5.
Initial hold (min)		8.
Final hold (min)		30.		13.	3.
I	1401.	1410.	1408.	1402.	1361.
Reference	Adams, González Elizondo, et al., 2006	Hazzit, Baaliouamer, et al., 2006	Oliveira, Leitao, et al., 2006	Raina, Verma, et al., 2006	Srivastava, Srivastava, et al., 2006
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	SE-30	HP-5
Column length (m)	30.	30.	30.	30.	30.
Carrier gas	Helium	He	He	He	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.25	0.25
Phase thickness (μm)	0.25	1.	0.25		0.25
T_start (C)	60.	40.	50.	60.	60.
T_end (C)	255.	250.	250.	240.	200.
Heat rate (K/min)	3.	5.	0.5	4.	4.
Initial hold (min)		1.	5.		1.
Final hold (min)			10.		15.
I	1403.	1415.	1407.	1371.	1404.
Reference	Medina, Lucero, et al., 2005	Bouzouita, Kachouri, et al., 2003	Viña and Murillo, 2003	Juliani, Koroch, et al., 2002	Juliani and Simon, 2002
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	BP-1	DB-5	DB-1	SE-54	DB-5
Column length (m)	25.	30.	30.	30.	30.
Carrier gas	N2	H2	He	He	He
Substrate
Column diameter (mm)	0.55	0.20	0.25	0.26	0.26
Phase thickness (μm)	0.25		0.25	0.25	0.25
T_start (C)	60.	60.	40.	60.	60.
T_end (C)	220.	240.	260.	246.	246.
Heat rate (K/min)	5.	3.	2.	3.	3.
Initial hold (min)			5.
Final hold (min)	15.		20.
I	1366.	1395.	1372.	1401.	1401.
Reference	Raina, Srivastava, et al., 2002	Moreira, Sousa, et al., 2001	Senatore and Rigano, 2001	Adams, 2000	Adams, 2000, 2
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	PTE-5	DB-5	SE-30	DB-5	DB-5
Column length (m)	60.	30.	25.	30.	30.
Carrier gas	H2	He	He
Substrate
Column diameter (mm)	0.32	0.26	0.2	0.25	0.25
Phase thickness (μm)	0.3	0.25
T_start (C)	60.	60.	60.	60.	60.
T_end (C)	285.	246.	180.	240.	240.
Heat rate (K/min)	4.3	3.	3.	3.	3.
Initial hold (min)			10.
Final hold (min)
I	1401.	1401.	1372.	1401.	1409.
Reference	Mitic and Dordevic, 2000	Adams, 1999	Jantan I. and Ahmad A.S., 1999	Lopes, Kato, et al., 1999	Lopes, Kato, et al., 1999
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-5MS	DB-5	DB-1	DB-1	DB-5
Column length (m)	30.	30.	60.	30.	30.
Carrier gas	He	He	He	He	He
Substrate
Column diameter (mm)	0.32	0.25	0.25	0.23	0.25
Phase thickness (μm)	0.25	0.25	0.25		0.25
T_start (C)	70.	60.	50.	50.	60.
T_end (C)	250.	240.	250.	200.	240.
Heat rate (K/min)	3.	4.	3.	3.	3.
Initial hold (min)	5.		5.
Final hold (min)			10.
I	1399.	1404.	1379.	1383.	1402.
Reference	Siani, Ramos, et al., 1999	da Silva, Zoghbi, et al., 1999	Bylaite, Venskutonis, et al., 1998	Fiorini, Fourasté, et al., 1997	Tellez, Estell, et al., 1997
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary
Active phase	DB-1	BP-1
Column length (m)	28.	50.
Carrier gas	He	H2
Substrate
Column diameter (mm)	0.25	0.33
Phase thickness (μm)	0.25
T_start (C)	50.	65.
T_end (C)	270.	220.
Heat rate (K/min)	4.	5.
Initial hold (min)	1.	2.
Final hold (min)
I	1375.	1376.
Reference	Saad, El-Sharkawy, et al., 1995	Ekundayo, Laakso, et al., 1988
Comment	MSDC-RI	MSDC-RI

References

Go To: Top, Kovats' RI, non-polar column, temperature ramp, Notes

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]

Hazzit, Baaliouamer, et al., 2006
Hazzit, M.; Baaliouamer, A.; Faleiro, M.L.; Miguel, M.G., Composition of the Essential Oils of Thymus and Origanum Species from Algeria and Their Antioxidant and Antimicrobial Activities, J. Agric. Food Chem., 2006, 54, 17, 6314-6321, https://doi.org/10.1021/jf0606104 . [all data]

Oliveira, Leitao, et al., 2006
Oliveira, D.R.; Leitao, G.G.; Santos, S.S.; Bizzo, H.R.; Lopes, D.; Alviano, C.S.; Alviano, D.S.; Leitao, S.G., Ethnopharmacological study of two Lippia species from Oriximina, Brazil, J. Ethnopharmacol., 2006, 108, 1, 103-108, https://doi.org/10.1016/j.jep.2006.04.018 . [all data]

Raina, Verma, et al., 2006
Raina, V.K.; Verma, S.C.; Dhawan, S.; Khan, M.; Ramesh, S.; Singh, S.C.; Yadav, A.; Srivastava, S.K., Essential oil composition of Murraya exotica from the plains of northern India, Flavour Fragr. J., 2006, 21, 1, 140-142, https://doi.org/10.1002/ffj.1547 . [all data]

Srivastava, Srivastava, et al., 2006
Srivastava, A.K.; Srivastava, S.K.; Syamsundar, K.V., Volatile composition of Curcuma angustifolia Roxb. rhizome from central and southern India, Flavour Fragr. J., 2006, 21, 3, 423-426, https://doi.org/10.1002/ffj.1680 . [all data]

Medina, Lucero, et al., 2005
Medina, A.L.; Lucero, M.E.; Holguin, F.O.; Estell, R.E.; Posakony, J.J.; Simon, J.; O'Connell, M.A., Composition and antimicrobial activity of Anemopsis californica leaf oil, J. Agric. Food Chem., 2005, 53, 22, 8694-8698, https://doi.org/10.1021/jf0511244 . [all data]

Bouzouita, Kachouri, et al., 2003
Bouzouita, N.; Kachouri, F.; Hamdi, M.; Chaabouni, M.M., Antimicrobial activity of essential oils from Tunisian aromatic plants, Flavour Fragr. J., 2003, 18, 5, 380-383, https://doi.org/10.1002/ffj.1200 . [all data]

Viña and Murillo, 2003
Viña, A.; Murillo, E., Essential oil composition from twelve varieties of basil (Ocimum spp) grown in Columbia, J. Braz. Chem. Soc., 2003, 14, 5, 744-749, https://doi.org/10.1590/S0103-50532003000500008 . [all data]

Juliani, Koroch, et al., 2002
Juliani, H.R., Jr.; Koroch, A.R.; Juliani, H.R.; Trippi, V.S.; Zygadlo, J.A., Intraespecific variation in leafoils of Lippia junelliana (mold.) tronc, Biochem. Syst. Ecol., 2002, 30, 2, 163-170, https://doi.org/10.1016/S0305-1978(01)00067-9 . [all data]

Juliani and Simon, 2002
Juliani, H.R.; Simon, J.E., Antioxidant acitivity of basil in Trends in new crops and new uses, Janick,J.; Whipkey,A., ed(s)., ASHA Press, Alexandria, Va, 2002, 575-579. [all data]

Raina, Srivastava, et al., 2002
Raina, V.K.; Srivastava, S.K.; Jain, N.; Ahmad, A.; Syamasundar, K.V.; Aggarwal, K.K., Essential oil composition of Curcuma longa L. cv. Roma from the plains of northern India, Flavour Fragr. J., 2002, 17, 2, 99-102, https://doi.org/10.1002/ffj.1053 . [all data]

Moreira, Sousa, et al., 2001
Moreira, D.L.; Sousa, P.O.; Pereira, N.A.; Cardoso, G.L., Effect of leaf essential oil from Piper solmsianum C.DC. in mice behaviour, An. Acad. Bras. Cienc., 2001, 73, 1, 1-7, https://doi.org/10.1590/S0001-37652001000100004 . [all data]

Senatore and Rigano, 2001
Senatore, F.; Rigano, D., Essential oil of two Lippia spp. (Verbenaceae) growing wild in Guatemala, Flavour Fragr. J., 2001, 16, 3, 169-171, https://doi.org/10.1002/ffj.972 . [all data]

Adams, 2000
Adams, R.P., Systematics of smooth leaf margin Juniperus of the western hemisphere based on leaf essential oils and RAPD DNA fingerprinting, Biochem. Syst. Ecol., 2000, 28, 2, 149-162, https://doi.org/10.1016/S0305-1978(99)00047-2 . [all data]

Adams, 2000, 2
Adams, R.P., The serrate leaf margined Juniperus (Section Sabina) of the western hemisphere: systematics and evolution based on leaf essential oils and Random Amplified Polymorphic DNAs (RAPDs), Biochem. Syst. Ecol., 2000, 28, 10, 975-989, https://doi.org/10.1016/S0305-1978(00)00022-3 . [all data]

Mitic and Dordevic, 2000
Mitic, V.; Dordevic, S., Essential oil composition of Hyssopus Officinalis L. cultivated in Serbia, Facta Univ. Phys. Chem. Technol., 2000, 2, 2, 105-108. [all data]

Adams, 1999
Adams, R.P., Systematics of multi-seeded eastern hemisphere Juniperus based on leaf essential oils and RAPD DNA fingerprinting, Biochem. Syst. Ecol., 1999, 27, 7, 709-725, https://doi.org/10.1016/S0305-1978(99)00016-2 . [all data]

Jantan I. and Ahmad A.S., 1999
Jantan I.; Ahmad A.S., Oleoresins of three pinus species from malaysian pine plantations, ASEAN Review of BiodiversityEnvironment Conservation, 1999, November-December, 1-9. [all data]

Lopes, Kato, et al., 1999
Lopes, N.P.; Kato, M.J.; Andrade, E.H.A.; Maia, J.G.S.; Yoshida, M.; Planchart, A.R.; Katzin, A.M., Antimalarial use of volatile oil from leaves of Virola surinamensis (Rol.) Warb. by Waiãpi Amazon Indians, J. Ethnopharmacol., 1999, 67, 3, 313-319, https://doi.org/10.1016/S0378-8741(99)00072-0 . [all data]

Siani, Ramos, et al., 1999
Siani, A.C.; Ramos, M.F.S.; Menezes-de-Lima, O., Jr.; Ribeiro-dos-Santos, R.; Fernadez-Ferreira, E.; Soares, R.O.A.; Rosas, E.C.; Susunaga, G.S.; Guimarães, A.C.; Zoghbi, M.G.B.; Henriques, M.G.M.O., Evaluation of anti-inflammatory-related activity of essential oils from the leaves and resin of species of Protium, J. Ethnopharmacol., 1999, 66, 1, 57-69, https://doi.org/10.1016/S0378-8741(98)00148-2 . [all data]

da Silva, Zoghbi, et al., 1999
da Silva, M.H.L.; Zoghbi, M.G.B.; Andrade, E.H.A.; Maia, J.G.S., The essential oils of Peperomia pellucida Kunth and P. circinnata link var. circinnata, Flavour Fragr. J., 1999, 14, 5, 312-314, https://doi.org/10.1002/(SICI)1099-1026(199909/10)14:5<312::AID-FFJ835>3.0.CO;2-B . [all data]

Bylaite, Venskutonis, et al., 1998
Bylaite, E.; Venskutonis, R.P.; Roozen, J.P., Influence of harvesting time on the composition of volatile components in different anatomical parts of lovage (Levisticum officinale Koch.), J. Agric. Food Chem., 1998, 46, 9, 3735-3740, https://doi.org/10.1021/jf9800559 . [all data]

Fiorini, Fourasté, et al., 1997
Fiorini, C.; Fourasté, I.; David, B.; Bessière, J.M., Composition of the flower, leaf, and stem essential oils from Laurus nobilis L., Flavour Fragr. J., 1997, 12, 2, 91-93, https://doi.org/10.1002/(SICI)1099-1026(199703)12:2<91::AID-FFJ623>3.0.CO;2-3 . [all data]

Tellez, Estell, et al., 1997
Tellez, M.R.; Estell, R.E.; Fredrickson, E.L.; Havstad, K.M., Essential oil of Dyssodia acerosa DC., J. Agric. Food Chem., 1997, 45, 8, 3276-3278, https://doi.org/10.1021/jf9701502 . [all data]

Saad, El-Sharkawy, et al., 1995
Saad, H.-E.A.; El-Sharkawy, S.H.; Halim, A.F., Essential oils of Daucus carota ssp. maximus, Pharm. Acta Helv., 1995, 70, 1, 79-84, https://doi.org/10.1016/0031-6865(94)00054-Y . [all data]

Ekundayo, Laakso, et al., 1988
Ekundayo, O.; Laakso, I.; Adegbola, R.-M.; Oguntimein, B.; Sofowora, A.; Hiltunen, R., Essential oil constituents of Ashanti pepper (Piper guineense) fruits (berries), J. Agric. Food Chem., 1988, 36, 5, 880-882, https://doi.org/10.1021/jf00083a001 . [all data]

Notes

Go To: Top, Kovats' RI, non-polar column, temperature ramp, References

Symbols used in this document:

T_end Final temperature

T_start Initial temperature
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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