Safrole

Formula: C₁₀H₁₀O₂
Molecular weight: 162.1852
IUPAC Standard InChI: InChI=1S/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2,4-6H,1,3,7H2
IUPAC Standard InChIKey: ZMQAAUBTXCXRIC-UHFFFAOYSA-N
CAS Registry Number: 94-59-7
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: 1,3-Benzodioxole, 5-(2-propenyl)-; Benzene, 4-allyl-1,2-(methylenedioxy)-; m-Allylpyrocatechin methylene ether; Allylcatechol methylene ether; Allylpyrocatechol methylene ether; Rhyuno oil; Safrene; Safrol; Safrole MF; Shikimole; Shikomol; 1-Allyl-3,4-(methylenedioxy)benzene; 3,4-(Methylenedioxy)allylbenzene; 4-Allyl-1,2-(methylenedioxy)benzene; 5-Allyl-1,3-benzodioxole; (1,2-(Methylenedioxy)-4-allyl)benzene; 1,3-Benzodioxole, 5-allyl-; 4-Allylpyrocatechol formaldehyde acetal; 5-(2-Propenyl)-1,3-benzodioxole; Benzene, 1,2-methylenedioxy-4-allyl-; Rcra waste number U203; 3-(3,4-Methylenedioxyphenyl)prop-1-ene; 1,3-Benzodioxole, 5-(2-propen-1-yl)-; Allyldioxybenzene methylene ether; NSC 11831
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Normal alkane RI, non-polar column, temperature ramp

Go To: Top, References, Notes

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-5	DB-5 MS	DB-5
Column length (m)	30.	30.	30.	30.	30.
Carrier gas	Helium	Helium	Helium	Helium	Helium
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)	80.	80.	50.	60.	50.
T_end (C)	300.	300.	250.	240.	250.
Heat rate (K/min)	4.	4.	2.	3.	5.
Initial hold (min)	1.	1.			2.
Final hold (min)	40.	40.
I	1327.	1327.	1287.	1287.	1287.
Reference	Vijayakumar, Duraipandiyan, et al., 2012	Vijayakumar, Duraipandiyan, et al., 2012	Ho, Wang, et al., 2010	Silva, Pott, et al., 2010	Ho, Wang, 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	HP-5 MS	DB-5MS	DB-5	ZB-5
Column length (m)	30.	30.	30.	30.	30.
Carrier gas	Helium	Helium	He	He
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.	50.	60.	60.	60.
T_end (C)	280.	230.	240.	300.	220.
Heat rate (K/min)	4.	3.	3.	3.	4.
Initial hold (min)		10.			5.
Final hold (min)		10.			20.
I	1289.	1286.	1286.	1278.	1296.
Reference	Zhao, Zeng, et al., 2009	Adams, Beauchamp, et al., 2007	Da Silva J.K.R., Sousa P.J.C., et al., 2007	Limberger, Scopel, et al., 2007	Mohottalage, Tabacchi, et al., 2007
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	BP-1	DB-5	FSOT-RSL-200	CP Sil 5 CB	SPB-5
Column length (m)	50.	30.	30.	25.	30.
Carrier gas	He	Hydrogen	Hydrogen	H2	He
Substrate
Column diameter (mm)	0.22	0.25	0.32	0.25	0.25
Phase thickness (μm)	0.25	0.25	0.25		0.25
T_start (C)	60.	70.	40.	50.	60.
T_end (C)	220.	280.	280.	230.	250.
Heat rate (K/min)	2.	4.	6.	3.	4.
Initial hold (min)		4.	5.		2.
Final hold (min)	20.		5.		20.
I	1260.	1285.	1285.	1267.	1285.
Reference	Boti, Muselli, et al., 2006	Pino, Marbot, et al., 2006	Schmidt, Jirovetz, et al., 2006	Tesso, König, et al., 2006	Pino, Marbot, et al., 2005
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-1	HP-5	DB-5	DB-5	DB-5MS
Column length (m)	25.	25.	30.	30.	30.
Carrier gas		H2	He	He	He
Substrate
Column diameter (mm)	0.25	0.32	0.25	0.25	0.25
Phase thickness (μm)	0.25	0.52	0.25	0.25	0.25
T_start (C)	60.	40.	60.	60.	60.
T_end (C)	180.	240.	300.	240.	240.
Heat rate (K/min)	3.	4.	3.	3.	3.
Initial hold (min)	10.
Final hold (min)	10.
I	1289.	1287.	1287.	1286.	1284.
Reference	bin Jantan, Ayop, et al., 2004	Simic, Sokovic, et al., 2004	Tirillini, Pellegrino, et al., 2004	da Silva, Luz, et al., 2003	Taveira, de Lima, et al., 2003
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	RSL-200	DB-5	DB-5MS	DB-5	DB-5
Column length (m)	30.	30.	30.	30.	30.
Carrier gas	H2	He	He	He	He
Substrate
Column diameter (mm)	0.32	0.25	0.25	0.25	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	40.	60.	60.	60.	60.
T_end (C)	280.	240.	240.	240.	240.
Heat rate (K/min)	6.	3.	3.	3.	3.
Initial hold (min)	5.
Final hold (min)	5.
I	1280.	1286.	1287.	1287.	1290.
Reference	Jirovetz, Buchbauer, et al., 2002	Maia, da Silva, et al., 2002	Maia, Zoghbi, et al., 2002	Zoghbi, Andrade, et al., 2002	Maia, Zoghbi, et al., 2000
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	SE-30	SPB-1	HP-1	OV-101	DB-5
Column length (m)	25.	50.	25.	50.	30.
Carrier gas	He		H2	N2
Substrate
Column diameter (mm)	0.2	0.2	0.32	0.2	0.32
Phase thickness (μm)		0.33	0.17		1.
T_start (C)	60.	60.	40.	80.	40.
T_end (C)	230.	260.	260.	200.	200.
Heat rate (K/min)	3.	4.	3.	1.	3.
Initial hold (min)			5.		5.
Final hold (min)				20.
I	1286.	1264.	1267.	1295.	1291.
Reference	Ali N.A.M. and Jantan, 1999	Choo, Wong, et al., 1999	Lopes, Koketsu, et al., 1999	Menon, Chacko, et al., 1999	Meynier, Novelli, et al., 1999
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	SE-30	DB-5MS	DB-5	HP-1	OV-101
Column length (m)	25.	30.	30.	25.	50.
Carrier gas	He	He	He	Helium
Substrate
Column diameter (mm)	0.2	0.25	0.25	0.32	0.22
Phase thickness (μm)		0.25	0.25	0.25
T_start (C)	60.	60.	60.	60.	80.
T_end (C)	230.	240.	240.	220.	200.
Heat rate (K/min)	3.	3.	3.	4.	2.
Initial hold (min)	10.			2.
Final hold (min)				20.
I	1286.	1290.	1285.	1259.	1278.
Reference	Mohd and Jantan, 1999	Zoghbi, Andrade, et al., 1999	Maia, Zohhbi, et al., 1998	Thanh, Dung, et al., 1996	Egolf and Jurs, 1993
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary
Active phase	CP Sil 8 CB
Column length (m)	25.
Carrier gas
Substrate
Column diameter (mm)	0.20
Phase thickness (μm)
T_start (C)	60.
T_end (C)	230.
Heat rate (K/min)	3.
Initial hold (min)	10.
Final hold (min)
I	1293.
Reference	Jantan and Goh, 1990
Comment	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]

Ho, Wang, et al., 2010
Ho, C.-L.; Wang, E.I.-C.; Yu, H.-T.; Yu, H.-M.; Su, Y.-C., Composition amd antioxidant activities of essential oils of different tissues from Cryptomeria japonica D. Don, Quarterly J. Chin. Forestry, 2010, 32, 1, 63-76. [all data]

Silva, Pott, et al., 2010
Silva, D.B.; Pott, A.; Oliveira, D.C.R., Analyses of the headspace volatile constituents of aerial parts (leaves and stems), flowers and fruits of Bidens gardneri Bak. and Bidens sulphurea (Cav.) Sch. Bip. using solid-phase microextraction, J. Essen. Oil Res., 2010, 22, 6, 560-563, https://doi.org/10.1080/10412905.2010.9700400 . [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]

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]

Adams, Beauchamp, et al., 2007
Adams, R.P.; Beauchamp, P.S.; Dev, V.; Dutz, S.M., New Natural Products Isolated from One-Seeded Juniperus of the Southwestern United States: Isolation and Occurence of 2-Ethenyl-3-methyl Phanol and Its Derivatives, J. Essent. Oil Res., 2007, 19, 2, 146-152, https://doi.org/10.1080/10412905.2007.9699247 . [all data]

Da Silva J.K.R., Sousa P.J.C., et al., 2007
Da Silva J.K.R.; Sousa P.J.C.; Andrade E.H.A.; Maia JGS, Antioxidant capacity and cytotoxicity of essential oil and methanol extract of Aniba canellia (HBK) Mez, J. Agric. Food Chem., 2007, 55, 23, 9422-9426, https://doi.org/10.1021/jf071928e . [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]

Mohottalage, Tabacchi, et al., 2007
Mohottalage, S.; Tabacchi, R.; Guerin, P.M., Components from Sri Lankan Piper betle L. leaf oil and their analogues showing toxicity against the housefly, Musca domestica, Flavour Fragr. J., 2007, 22, 2, 130-138, https://doi.org/10.1002/ffj.1770 . [all data]

Boti, Muselli, et al., 2006
Boti, J.B.; Muselli, A.; Tomi, F.; Koukoua, G.; N'Guessan, T.Y.; Costa, J.; Casanova, J., Combined analysis of Cymbopogon giganteus Chiov. leaf oil from Ivory Coast by GC/RI, GC/MS and ¹³C-NMR, C.R. Chim., 2006, 9, 1, 164-168, https://doi.org/10.1016/j.crci.2005.10.003 . [all data]

Pino, Marbot, et al., 2006
Pino, J.A.; Marbot, R.; Payo, A.; Chao, D.; Herrera, P., Aromatic Plants from Western Cuba VII. Composition of the Leaf Oil of Psidium wrightii KRug et Urb., Lantana involucrata L., Cinnamonum montanum (Sw.) Berchtold et J. Persl. and Caesalpinia violacea (Mill.) Standley, J. Essent. Oil. Res., 2006, 18, 2, 170-174, https://doi.org/10.1080/10412905.2006.9699058 . [all data]

Schmidt, Jirovetz, et al., 2006
Schmidt, E.; Jirovetz, L.; Buchbauer, G.; Eller, G.A.; Stoilova, I.; Krastanov, A.; Stoyanova, A.; Geisseler, M., Composition and antioxidant activities of the essential oil of cinnamon (Cinnamomum zeylanicum Blume) leaves from Sri Lanka, Jeobp, 2006, 9, 2, 170-182. [all data]

Tesso, König, et al., 2006
Tesso, H.; König, W.A.; Son, P.T.; Giang, P.M., Composition of the essential oil of flowers of Chloranthus spicatus (Thunb.) Makino, Flavour Fragr. J., 2006, 21, 4, 592-597, https://doi.org/10.1002/ffj.1528 . [all data]

Pino, Marbot, et al., 2005
Pino, J.A.; Marbot, R.; Rosado, A.; Vázquez, C., Volatile constituents of genipap (Genipa americana L.) fruit from Cuba, Flavour Fragr. J., 2005, 20, 6, 583-586, https://doi.org/10.1002/ffj.1491 . [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]

Simic, Sokovic, et al., 2004
Simic, A.; Sokovic, M.D.; Ristic, M.; Grujic-Jovanovic, S.; Vukojevic, J.; Marin, P.D., The chemical composition of some Lauraceae essential oils and their antifungal activities, Phytother. Res., 2004, 18, 9, 713-717, https://doi.org/10.1002/ptr.1516 . [all data]

Tirillini, Pellegrino, et al., 2004
Tirillini, B.; Pellegrino, R.; Bini, L.M., Essential oil composition of Stachys sylvatica L. from Italy, Flavour Fragr. J., 2004, 19, 4, 330-332, https://doi.org/10.1002/ffj.1308 . [all data]

da Silva, Luz, et al., 2003
da Silva, J.D.; Luz, A.I.R.; da Silva, M.H.L.; Andrade, E.H.A.; Soghbi, M.G.B.; Maia, J.G.S., Essential oils of the leaves and stems of four Psidium spp., Flavour Fragr. J., 2003, 18, 3, 240-243, https://doi.org/10.1002/ffj.1219 . [all data]

Taveira, de Lima, et al., 2003
Taveira, F.S.N.; de Lima, W.N.; Andrade, E.H.A.; Maia, J.G.S., Seasonal essential oil variation of Aniba canelilla, Biochem. Syst. Ecol., 2003, 31, 1, 69-75, https://doi.org/10.1016/S0305-1978(02)00088-1 . [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]

Maia, da Silva, et al., 2002
Maia, J.G.S.; da Silva, M.H.L.; Andrade, E.H.A.; Zoghbi, M.G.B.; Carreira, L.M.M., Essential oils from Astronium urundeuva (Allemao) Engl. and A. fraxinifolium Schott ex Spreng., Flavour Fragr. J., 2002, 17, 1, 72-74, https://doi.org/10.1002/ffj.1046 . [all data]

Maia, Zoghbi, et al., 2002
Maia, J.G.S.; Zoghbi, M.G.B.; Andrade, E.H.A.; da Silva, M.H.L.; Luz, A.I.R.; da Silva, J.D., Essential oils composition of Eupatorium species growing wild in the Amazon, Biochem. Syst. Ecol., 2002, 30, 11, 1071-1077, https://doi.org/10.1016/S0305-1978(02)00059-5 . [all data]

Zoghbi, Andrade, et al., 2002
Zoghbi, M.G.B.; Andrade, E.H.A.; da Silva, M.H.; Maia, J.G.S.; Luz, A.I.R.; da Silva, J.D., Chemical variation in the essential oils of Hyptis crenata Pohl ex Benth., Flavour Fragr. J., 2002, 17, 1, 5-8, https://doi.org/10.1002/ffj.1031 . [all data]

Maia, Zoghbi, et al., 2000
Maia, J.G.S.; Zoghbi, M.G.B.; Andrade, E.H.A.; da Silva, M.H.L., Essential oils from Conobea scoparioides (Cham. Schltdl.) Benth., Flavour Fragr. J., 2000, 15, 6, 413-414, https://doi.org/10.1002/1099-1026(200011/12)15:6<413::AID-FFJ931>3.0.CO;2-H . [all data]

Ali N.A.M. and Jantan, 1999
Ali N.A.M.; Jantan, I., Essential oil of cinnamomum tahijanum kost. from sarawak, ASEAN Review of BiodiversityEnvironment Conservation, 1999, November-December, 1-4. [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]

Lopes, Koketsu, et al., 1999
Lopes, D.; Koketsu, M.; Carauta, J.P.P.; de Oliveira, R.R.; Kaplan, M.A.C., Chemical composition of Pourouma guianensis Aublet essential oils, Flavour Fragr. J., 1999, 14, 4, 233-236, https://doi.org/10.1002/(SICI)1099-1026(199907/08)14:4<233::AID-FFJ813>3.0.CO;2-L . [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]

Meynier, Novelli, et al., 1999
Meynier, A.; Novelli, E.; Chissolinim, R.; Zanardi, E.; Gandemer, G., Volatile compounds of commercial Milano salami, Meat Sci., 1999, 51, 2, 175-183, https://doi.org/10.1016/S0309-1740(98)00122-3 . [all data]

Mohd and Jantan, 1999
Mohd, N.A.; Jantan, I., Essential oil of cinnamomum tahijanum Kost. from Sarawak, 1999, retrieved from http://www.arbec.com.my/pdf/art5novdec99.pdf. [all data]

Zoghbi, Andrade, et al., 1999
Zoghbi, M.G.B.; Andrade, E.H.A.; Maia, J.G.S., Volatile constituents from leaves and flowers of Alpinia speciosa K. Schum. and A. purpurata (Viell.) Schum., Flavour Fragr. J., 1999, 14, 6, 411-414, https://doi.org/10.1002/(SICI)1099-1026(199911/12)14:6<411::AID-FFJ854>3.0.CO;2-U . [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]

Thanh, Dung, et al., 1996
Thanh, L.; Dung, N.X.; Bighetti, A.; Casanova, J.; Leclercq, P.A., Combination of cCapillary GC, GC/MS and 13C-NMR for the Characterization of the Rhizome Oil of Piper betle L. (Piperaceae) from Vietnam, Spectroscopy, 1996, 13, 2, 131-136, https://doi.org/10.1155/1997/397354 . [all data]

Egolf and Jurs, 1993
Egolf, L.M.; Jurs, P.C., Quantitative structure-retention and structure-odor intensity relationships for a diverse group of odor-active compounds, Anal. Chem., 1993, 65, 21, 3119-3126, https://doi.org/10.1021/ac00069a027 . [all data]

Jantan and Goh, 1990
Jantan, I.; Goh, S.H., The essential oils of Cinnamomum mollissimum as natural sources of safrole and benzyl benzoate, J. Tropical Forest Sci., 1990, 2, 3, 252-259. [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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