1,3-Benzodioxole, 4-methoxy-6-(2-propenyl)-

Formula: C₁₁H₁₂O₃
Molecular weight: 192.2112
IUPAC Standard InChI: InChI=1S/C11H12O3/c1-3-4-8-5-9(12-2)11-10(6-8)13-7-14-11/h3,5-6H,1,4,7H2,2H3
IUPAC Standard InChIKey: BNWJOHGLIBDBOB-UHFFFAOYSA-N
CAS Registry Number: 607-91-0
Chemical structure:
This structure is also available as a 2d Mol file
Other names: Benzene, 5-allyl-1-methoxy-2,3-(methylenedioxy)-; Myristicin; 5-Allyl-1-methoxy-2,3-(methylenedioxy)benzene; 6-Allyl-4-methoxy-1,3-benzodioxole; Myristicine; 4-Methoxy-6-(2-propenyl)-1,3-benzodioxole; 1,3-Benzodioxole, 4-methoxy-6-(1-propenyl)-
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Normal alkane 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	DP-5	DP-5	DB-1	DB-5	DB-5
Column length (m)	30.	30.	50.	30.	30.
Carrier gas	Helium	Helium	Helium	Helium	Helium
Substrate
Column diameter (mm)	0.25	0.25	0.32	0.32	0.32
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	80.	80.	60.	35.	60.
T_end (C)	300.	300.	250.	200.	280.
Heat rate (K/min)	4.	4.	8.	2.	3.
Initial hold (min)	1.	1.
Final hold (min)	40.	40.
I	1516.	1516.	1492.	1519.	1509.
Reference	Vijayakumar, Duraipandiyan, et al., 2012	Vijayakumar, Duraipandiyan, et al., 2012	Misharina T., 2011	Pattiram, Lasekan, et al., 2011	Georgiou, Koutsaviti, et al., 2010
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-1	HP-5 MS	DB-1	HP-5MS	DB-5
Column length (m)	30.	30.	30.	60.	30.
Carrier gas	Helium	Helium	Helium	Helium	Nitrogen
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.25	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	50.	70.	50.	70.	40.
T_end (C)	265.	290.	220.	250.	250.
Heat rate (K/min)	2.5	5.	4.	3.	3.
Initial hold (min)	1.		2.		1.
Final hold (min)	20.	10.	2.		10.
I	1501.	1527.	1500.	1524.	1519.
Reference	Hajimahdipoor, Samadi, et al., 2010	Radulovic, Blagojevic, et al., 2010	Xu, Tang, et al., 2010	Males, Plazibat, et al., 2009	Rahimi-Nasrabadi, Gholivand, et al., 2009
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-5 MS	DB-5	HP-5	Col-Elite 5MS	DB-5
Column length (m)	30.	25.	30.	30.	30.
Carrier gas	Helium	Nitrogen	Helium	He	He
Substrate
Column diameter (mm)	0.25	0.22	0.25	0.25	0.25
Phase thickness (μm)	0.25	0.25	0.32	0.25	0.25
T_start (C)	50.	50.	60.	30.	60.
T_end (C)	280.	300.	250.	246.	300.
Heat rate (K/min)	4.	6.5	5.	3.	3.
Initial hold (min)		2.	30.
Final hold (min)		7.
I	1523.	1533.	1519.	1527.	1511.
Reference	Zhao, Zeng, et al., 2009	Chieng, Assim, et al., 2008	Yassa and Akhani, 2008	Gudaityte and Venskutonis R.P., 2007	Limberger, Scopel, et al., 2007
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	BPX-5	HP-5	HP-5	HP-5MS	HP-5
Column length (m)	50.	30.	30.	30.	25.
Carrier gas	He	He	N2	He	He
Substrate
Column diameter (mm)	0.22	0.25	0.25	0.25	0.25
Phase thickness (μm)	1.	0.32	0.25	0.25	0.25
T_start (C)	50.	60.	50.	60.	50.
T_end (C)	300.	250.	280.	280.	300.
Heat rate (K/min)	4.	5.	9.	3.	5.
Initial hold (min)	1.	30.	3.		5.
Final hold (min)	10.		3.
I	1563.	1519.	1565.	1518.	1519.
Reference	Rali, Wossa, et al., 2007	Yassa and Akhani, 2007	Abdelwahed, Hayder, et al., 2006	Bozin, Mimicá-Dukic, et al., 2006	Champagnat, Figueredo, et al., 2006
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-1	CP Sil 5 CB	HP-5	HP-1	DB-1
Column length (m)	30.	30.	30.	50.	25.
Carrier gas	He	N2	Helium	He	He
Substrate
Column diameter (mm)	0.25	0.25	0.32	0.2	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.5	0.25
T_start (C)	50.	60.	40.	60.	50.
T_end (C)	265.	300.	240.	250.	250.
Heat rate (K/min)	2.5	5.	4.	2.	3.
Initial hold (min)	1.	4.			3.
Final hold (min)	20.		5.	40.
I	1475.	1494.	1514.	1490.	1498.
Reference	Iranshahi, Amin, et al., 2006	Kurowska and Galazka, 2006	Miyazawa and Kawata, 2006	Valette, Fernandez, et al., 2006	Cégiéla-Carlioz, Bessière, et al., 2005
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-5MS	DB-1	DB-5	OV-101	DB-1
Column length (m)	30.	25.	30.	50.	50.
Carrier gas	He		He	He	N2
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.2	0.25
Phase thickness (μm)	0.32	0.25	0.25	0.5	0.25
T_start (C)	60.	60.	60.	50.	90.
T_end (C)	250.	180.	240.	250.	240.
Heat rate (K/min)	5.	3.	3.	2.	4.
Initial hold (min)	3.	10.
Final hold (min)		10.
I	1498.	1519.	1514.	1500.	1482.
Reference	Pourmortazavi, Ghadiri, et al., 2005	bin Jantan, Ayop, et al., 2004	Tellez, Khan, et al., 2004	Orav, Kailas, et al., 2003	Velasco-Negueruela, Pérez-Alonso, et al., 2003
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-5	RSL-200	DB-5	SPB-1	OV-101
Column length (m)	30.	30.	30.	50.	50.
Carrier gas	He	H2	He		He
Substrate
Column diameter (mm)	0.25	0.32	0.25	0.2	0.25
Phase thickness (μm)	0.32	0.25	0.25	0.33	0.25
T_start (C)	60.	40.	60.	60.	70.
T_end (C)	250.	280.	270.	260.	220.
Heat rate (K/min)	5.	6.	3.	4.	2.
Initial hold (min)	30.	5.			5.
Final hold (min)		5.
I	1525.	1502.	1523.	1491.	1478.
Reference	Yassa, Akhani, et al., 2003	Jirovetz, Buchbauer, et al., 2002	Palmeira, Conserva, et al., 2001	Choo, Wong, et al., 1999	Pateira, Nogueira, et al., 1999
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary
Active phase	DB-5	OV-101
Column length (m)	30.	25.
Carrier gas	He
Substrate
Column diameter (mm)	0.25	0.32
Phase thickness (μm)	0.25
T_start (C)	60.	50.
T_end (C)	240.	200.
Heat rate (K/min)	3.	5.
Initial hold (min)
Final hold (min)
I	1523.	1532.
Reference	Maia, Zohhbi, et al., 1998	Zollo, Biyiti, et al., 1998
Comment	MSDC-RI	MSDC-RI

References

Go To: Top, Normal alkane RI, non-polar column, temperature ramp, Notes

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]

Misharina T., 2011
Misharina T., Headspace analysis of aroma compounds using porous adsorbents, Chemistry Chem. Technol., 2011, 5, 3, 347-354. [all data]

Pattiram, Lasekan, et al., 2011
Pattiram, P.D.; Lasekan, O.; Tan, C.P.; Zaidul, I.S.M., Identification of the aroma-active constituents of the essential oils of Water Dropwort (Oenanthe javanica) and Kacip Fatimah (Labisia pumilia), Int. Food Res. J., 2011, 18, 3, 1021-1026. [all data]

Georgiou, Koutsaviti, et al., 2010
Georgiou, C.; Koutsaviti, A.; Bazos, I.; Tzakou, O., Chemical composition of Echinophora tenuifolia subsp. sibthorpiana essential oil from Greece, Rec. Nat. Prod., 2010, 4, 3, 167-170. [all data]

Hajimahdipoor, Samadi, et al., 2010
Hajimahdipoor, H.; Samadi, N.; Mozaffarian, V.; Rahimifard, N.; Shoeibi, Sh.; Pirali, H.M., Chemical composition and antimicrobial activity of Oliveria decumbens volatile oil from west of Iran, J. of Medicinal Plants, 2010, 9, Suppl. # 6., 39-44. [all data]

Radulovic, Blagojevic, et al., 2010
Radulovic, N.; Blagojevic, P.; Palic, R., Comparative study of the leaf volatiles of Arctostaphylos uva-ursi (L.) Spreng. and Vaccinium vitis-idaea L. (Ericaceae), Molecules, 2010, 15, 9, 6168-6185, https://doi.org/10.3390/molecules15096168 . [all data]

Xu, Tang, et al., 2010
Xu, X.; Tang, Z.; Liang, Y., Comparative analysis of plant essential oils by GC-MS coupled with integrated chemometric resolution methods, Anal. Methods, 2010, 2, 4, 359-367, https://doi.org/10.1039/b9ay00213h . [all data]

Males, Plazibat, et al., 2009
Males, Z.; Plazibat, M.; Bucar, F., Essential oil of Portanschlagiella ramosissima from Croatia, a rich source of myristicin, Croat. Chem. Acta, 2009, 82, 4, 725-728. [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]

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]

Chieng, Assim, et al., 2008
Chieng, T.C.; Assim, Z.B.; Fasihuddin, B.A., Toxicity and antitermite activities of the essential oils from Piper sarmentosum, The Malaysian J. Anal. Sci., 2008, 12, 1, 234-239. [all data]

Yassa and Akhani, 2008
Yassa, N.; Akhani, H., The essential oils composition in two species of the genus Eriocycla Lindl. (Apiaceae) from Iran, 2008, retrieved from http://biology.ut.ac.ir/members/akhani/PdfReprintNumber/27.pdf. [all data]

Gudaityte and Venskutonis R.P., 2007
Gudaityte, O.; Venskutonis R.P., Chemotypes of Achillea millefolium transferred from 14 different locations in Lithuania to the controlled environment, Biochem. Syst. Ecol., 2007, 35, 9, 582-592, https://doi.org/10.1016/j.bse.2007.03.016 . [all data]

Limberger, Scopel, et al., 2007
Limberger, R.P.; Scopel, M.; Sobral, M.; Henriques, A.T., Comparative analysis of volatiles from Drimys brasiliensis Miers and D. angustifolia Miers (Winteraceae) from Southern Brazil, Biochem. Syst. Ecol., 2007, 35, 3, 130-137, https://doi.org/10.1016/j.bse.2006.09.007 . [all data]

Rali, Wossa, et al., 2007
Rali, T.; Wossa, S.W.; Leach, D.N.; Waterman, P.G., Volatile chemical constituents of Piper aduncum L and Piper gibbilimbum C. DC (Piperaceae) from Papua New Guinea, Molecules, 2007, 12, 3, 389-394, https://doi.org/10.3390/12030389 . [all data]

Yassa and Akhani, 2007
Yassa, N.; Akhani, H., The essential oils composition in two species of the genus Eriocycla Lindl. (Apiaceae) from Iran, 2007, retrieved from http://biology.ut.ac.ir/members/akhani/PdfReprintNumber/27.pdf. [all data]

Abdelwahed, Hayder, et al., 2006
Abdelwahed, A.; Hayder, N.; Kilani, S.; Mahmoud, A.; Chibani, J.; Hammami, M.; Chekir-Ghedira, L.; Ghedira, K., Chemical composition and antimicrobial activity of essential oils from Tunisian Pituranthos tortuosus (Coss.) Maire, Flavour Fragr. J., 2006, 21, 1, 129-133, https://doi.org/10.1002/ffj.1542 . [all data]

Bozin, Mimicá-Dukic, et al., 2006
Bozin, B.; Mimicá-Dukic, N.; Simin, N.; Anackov, G., Characterization of the volatile composition of essential oils of some lamiaceae spices and the antimicrobial and antioxidant activities of the entire oils, J. Agric. Food Chem., 2006, 54, 5, 1822-1828, https://doi.org/10.1021/jf051922u . [all data]

Champagnat, Figueredo, et al., 2006
Champagnat, P.; Figueredo, G.; Chalchat, J.-C.; Bessiere, J.-M., Essential oil composition of Vetiveria nigritana from Mali, J. Essent. Oil Res., 2006, 18, 6, 647-649, https://doi.org/10.1080/10412905.2006.9699193 . [all data]

Iranshahi, Amin, et al., 2006
Iranshahi, M.; Amin, G.; Sourmaghi, M.S.; Shafiee, A.; Hadjiakhoondi, A., Sulphur-containing compounds in the essential oil of the root of Ferula persica Willd. var. persica, Flavour Fragr. J., 2006, 21, 2, 260-261, https://doi.org/10.1002/ffj.1574 . [all data]

Kurowska and Galazka, 2006
Kurowska, A.; Galazka, I., Essential oil composition of the parsley seed of cultivars marketed in Poland, Flavour Fragr. J., 2006, 21, 1, 143-147, https://doi.org/10.1002/ffj.1548 . [all data]

Miyazawa and Kawata, 2006
Miyazawa, M.; Kawata, J., Identification of the Key Aroma Compounds in Dried Roots of Rubia cordifolia, L. Oleo Sci., 2006, 55, 1, 37-39, https://doi.org/10.5650/jos.55.37 . [all data]

Valette, Fernandez, et al., 2006
Valette, L.; Fernandez, X.; Poulain, S.; Lizzani-Cuvelier, L.; Loiseau, A.-M., Chemical composition of the volatile extracts from Brassica oleracea L. var. botrytis 'Romanesco' cauliflower seeds, Flavour Fragr. J., 2006, 21, 1, 107-110, https://doi.org/10.1002/ffj.1530 . [all data]

Cégiéla-Carlioz, Bessière, et al., 2005
Cégiéla-Carlioz, P.; Bessière, J.-M.; David, B.; Mariotte, A.-M.; Gibbons, S.; Dijoux-Franca, M.-G., Modulation of multi-drug resistance (MDR) in Staphylococcus aureus by Osha (Ligusticum porteri L., Apiaceae) essential oil compounds, Flavour Fragr. J., 2005, 20, 6, 671-675, https://doi.org/10.1002/ffj.1584 . [all data]

Pourmortazavi, Ghadiri, et al., 2005
Pourmortazavi, S.M.; Ghadiri, M.; Hajimirsadeghi, S.S., Supercritical fluid extraction of volatile components from Bunium persicum Boiss. (black cumin) and Mespilus germanica L. (medlar) seeds, J. Food Comp. Anal., 2005, 18, 5, 439-446, https://doi.org/10.1016/j.jfca.2004.01.003 . [all data]

bin Jantan, Ayop, et al., 2004
bin Jantan, I.; Ayop, N.; Mohd Ali, N.A.; Ahmad, A.S.; Yalvema, M.F.; Muhammad, K.; Azizi, A.R., The essential oils of Cinnamomum rhyncophyllum Miq. as natural sources of benzyl benzoate, safrole and methyl (E)-cinnamate, Flavour Fragr. J., 2004, 19, 3, 260-262, https://doi.org/10.1002/ffj.1301 . [all data]

Tellez, Khan, et al., 2004
Tellez, M.R.; Khan, I.A.; Schaneberg, B.T.; Crockett, S.L.; Rimando, A.M.; Kobaisy, M., Steam distillation-solid-phase microextraction for the detection of Ephedra sinica in herbal preparations, J. Chromatogr. A, 2004, 1025, 1, 51-56, https://doi.org/10.1016/S0021-9673(03)01035-5 . [all data]

Orav, Kailas, et al., 2003
Orav, A.; Kailas, T.; Jegorova, A., Composition of the essential oil of dill, celery, and parsley from Estonia, Proc. Est. Acad. Sci. Chem., 2003, 52, 4, 147-154. [all data]

Velasco-Negueruela, Pérez-Alonso, et al., 2003
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 Rutheopsis herbanica (Bolle) Hans. Kunk., gathered in Fuerteventura (Canary Islands), J. Chromatogr. A, 2003, 984, 1, 159-162, https://doi.org/10.1016/S0021-9673(02)01742-9 . [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]

Jirovetz, Buchbauer, et al., 2002
Jirovetz, L.; Buchbauer, G.; Ngassoum, M.B.; Geissler, M., Aroma compound analysis of Piper nigrum and Piper guineense essential oils from Cameroon using solid-phase microextraction-gas chromatography, solid-phase microextraction-gas chromatography-mass spectrometry and olfactometry, J. Chromatogr. A, 2002, 976, 1-2, 265-275, https://doi.org/10.1016/S0021-9673(02)00376-X . [all data]

Palmeira, Conserva, et al., 2001
Palmeira, S.F., Jr.; Conserva, L.M.; Andrade, E.H.A.; Guilhon, G.M.S.P., Analysis by GC-MS of the hexane extract of the aerial parts of Aristolochia acutifolia Duchtr., Flavour Fragr. J., 2001, 16, 2, 85-88, https://doi.org/10.1002/1099-1026(200103/04)16:2<85::AID-FFJ948>3.0.CO;2-2 . [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]

Pateira, Nogueira, et al., 1999
Pateira, L.; Nogueira, T.; Antunes, A.; Venancio, F.; Tavares, R.; Capelo, J., Two chemotypes of Crithmum maritimum L. from Portugal, Flavour Fragr. J., 1999, 14, 5, 333-343, https://doi.org/10.1002/(SICI)1099-1026(199909/10)14:5<333::AID-FFJ839>3.0.CO;2-V . [all data]

Maia, Zohhbi, et al., 1998
Maia, J.G.S.; Zohhbi, M.G.B.; Andrade, E.H.A.; Santos, A.S.; da Silva, M.H.L.; Luz, A.I.R.; Bastos, C.N., Constituents of the essential oil of Piper aduncum L. growing wild in the Amazon region, Flavour Fragr. J., 1998, 13, 4, 269-272, https://doi.org/10.1002/(SICI)1099-1026(1998070)13:4<269::AID-FFJ744>3.0.CO;2-A . [all data]

Zollo, Biyiti, et al., 1998
Zollo, P.H.A.; Biyiti, L.; Tchoumbougnang, F.; Menut, C.; Lamaty, G.; Bouchet, Ph., Aromatic plants of tropical central Africa. Part XXXII. Chemical composition and antifungal activity of thirteen essential oils from aromatic plants of Cameroon, Flavour Fragr. J., 1998, 13, 2, 107-114, https://doi.org/10.1002/(SICI)1099-1026(199803/04)13:2<107::AID-FFJ701>3.0.CO;2-G . [all data]

Notes

Go To: Top, Normal alkane 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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