4-Isopropyl-6-methyl-1-methylene-1,2,3,4-tetrahydronaphthalene

Formula: C₁₅H₂₀
Molecular weight: 200.3193
IUPAC Standard InChI: InChI=1S/C15H20/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h5,7,9-10,13H,4,6,8H2,1-3H3
IUPAC Standard InChIKey: KFYISTOZYAKAPV-UHFFFAOYSA-N
CAS Registry Number: 50277-34-4
Chemical structure:
This structure is also available as a 2d Mol file
Other names: Naphthalene, 1,2,3,4-tetrahydro-6-methyl-1-methylene-4-(1-methylethyl)-; β-Calacorene; Calacorene B
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Other data available:
- Gas Chromatography
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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	HP-5	HP-5	RTX-1	RTX-1	HP-5
Column length (m)	30.	30.	60.	60.	30.
Carrier gas	Nitrogen	Hydrogen	Helium	Helium	Helium
Substrate
Column diameter (mm)	0.25	0.25	0.22	0.22	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	50.	70.	60.	60.	50.
T_end (C)	280.	290.	230.	230.	280.
Heat rate (K/min)	5.	5.	2.	2.	9.
Initial hold (min)	1.				3.
Final hold (min)	1.		30.	30.	3.
I	1548.	1571.	1548.	1566.	1560.
Reference	Tekaya-Karoui, Boughalleb, et al., 2011	Radulovic, Dordevic, et al., 2010	Museli, Pau, et al., 2009	Museli, Pau, et al., 2009	Aicha, Ines, et al., 2008
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	RTX-1	DB-5	DB-5	HP-1	DB-5
Column length (m)	60.	30.	30.	30.	30.
Carrier gas	He	He	Helium	He	Helium
Substrate
Column diameter (mm)	0.22	0.26	0.26	0.25	0.26
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	60.	60.	60.	60.	60.
T_end (C)	230.	240.	290.	240.	290.
Heat rate (K/min)	2.	3.	3.	2.	3.
Initial hold (min)
Final hold (min)	35.			20.
I	1548.	1563.	1563.	1527.	1563.
Reference	Paolini, Tomi, et al., 2008	Bos, Woerdenbag, et al., 2007	Elfami, Bos, et al., 2007	Hachicha, Skanji, et al., 2007	Elfami, Komar, et al., 2006
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-5	BP-1	DB-5	DB-1	DB-5
Column length (m)	30.	50.	30.	50.	30.
Carrier gas	He	He	Hydrogen	N2	He
Substrate
Column diameter (mm)	0.25	0.22	0.25	0.25	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	50.	60.	70.	90.	60.
T_end (C)	300.	220.	280.	240.	240.
Heat rate (K/min)	5.	2.	4.	4.	3.
Initial hold (min)	5.		4.
Final hold (min)	5.	20.
I	1562.	1549.	1564.	1548.	1565.
Reference	Figuérédo, Cabassu, et al., 2006	Lesueur, Ban, et al., 2006	Pino, Marbot, et al., 2006	Velasco-Negueruela, Pérez-Alonso, et al., 2006	Chaverri and Cicció, 2005
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-5MS	DB-5MS	DB-5	DB-1	DB-5
Column length (m)	30.	30.	30.	50.	30.
Carrier gas	He	He	He	N2	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.25	0.32
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	60.	60.	60.	95.	60.
T_end (C)	200.	280.	220.	240.	280.
Heat rate (K/min)	4.	3.	4.	4.	3.
Initial hold (min)	30.	30.	5.
Final hold (min)
I	1554.	1532.	1566.	1553.	1548.
Reference	Gauvin and Smadja, 2005	Marongiu, Piras, et al., 2005	Morteza-Semnani, Akbarzadeh, et al., 2005	Pala-Paul, Perez-Alonso, et al., 2005	Tzakou and Constantinidis, 2005
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	BP-1	DB-1	DB-5	HP-5MS	HP-5MS
Column length (m)	50.	30.	25.	30.	30.
Carrier gas		N2	Nitrogen	He	He
Substrate
Column diameter (mm)	0.22	0.25	0.25	0.25	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	60.	50.	60.	60.	60.
T_end (C)	220.	200.	240.	280.	280.
Heat rate (K/min)	2.	5.	3.	3.	4.
Initial hold (min)
Final hold (min)	20.
I	1548.	1547.	1560.	1559.	1563.
Reference	Blanc, Muselli, et al., 2004	Fekam Boyom, Fotio, et al., 2004	JAvidnia, Mojab, et al., 2004	Couladis, Özcan, et al., 2003	Ghasemi, Asghari, et al., 2003
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	HP-5	HP-5
Column length (m)	30.	30.	30.	25.	25.
Carrier gas	He	He	N2	H2	H2
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.32	0.32
Phase thickness (μm)	0.25	0.25	0.25	0.53	0.53
T_start (C)	60.	60.	40.	40.	40.
T_end (C)	280.	280.	230.	280.	280.
Heat rate (K/min)	3.	3.	2.	4.	4.
Initial hold (min)
Final hold (min)	30.
I	1548.	1542.	1550.	1557.	1566.
Reference	Marongiu, Porcedda, et al., 2003	Pitarokili, Tzakou, et al., 2003	Rotman, Ahumada, et al., 2003	Velickovic, Randjelovic, et al., 2003	Velickovic, Randjelovic, et al., 2003
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	5 % Phenyl methyl siloxane	PTE-5	DB-5	HP-1	HP-5
Column length (m)	30.	60.	30.	50.	30.
Carrier gas	He	H2	He	N2	H2
Substrate
Column diameter (mm)	0.25	0.32	0.25	0.25	0.25
Phase thickness (μm)	0.25	0.30	0.25	0.25	0.25
T_start (C)	75.	60.	35.	90.	40.
T_end (C)	200.	285.	280.	220.	280.
Heat rate (K/min)	3.	4.3	3.	3.	4.
Initial hold (min)	4.		2.
Final hold (min)	8.		15.
I	1566.	1563.	1574.	1549.	1563.
Reference	Cicció and Gómez-Laurito, 2002	Gudzic, Djokovic, et al., 2002	Krauze-Baranowska, Mardarowicz, et al., 2002	Priestap, van Baren, et al., 2002	Velickovic, Randjelovic, et al., 2002
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary
Active phase	DB-5	DB-1	DB-5
Column length (m)	30.	60.	30.
Carrier gas	He	N2	He
Substrate
Column diameter (mm)	0.25	0.248	0.32
Phase thickness (μm)	0.25	0.25
T_start (C)	60.	60.	60.
T_end (C)	240.	220.	250.
Heat rate (K/min)	3.	3.	3.
Initial hold (min)		5.
Final hold (min)		22.
I	1541.	1554.	1554.
Reference	Zoghbi, Andrade, et al., 2002	Bailac, Dellacasa, et al., 2001	Abreu and Noronha, 1997
Comment	MSDC-RI	MSDC-RI	MSDC-RI

References

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

Tekaya-Karoui, Boughalleb, et al., 2011
Tekaya-Karoui, A.; Boughalleb, N.; Hammami, S.; Ben Jannet, H.; Mighri, Z., Chemical composition and antifungal activity of volatile components from woody terminal branches and roots of Tetraclinis articulate (Vahl.) Masters growing in Tunisia, Afr. J. Plant Sci., 2011, 5, 2, 115-122. [all data]

Radulovic, Dordevic, et al., 2010
Radulovic, N.S.; Dordevic, N.D.; Palic, R.M., Volatiles of Pleurospermum austriacum (L.) Hoffm. (Apiaceae), J. Serbian Chem. Soc., 2010, 75, 12, 1-11, https://doi.org/10.2298/JSC100323127R . [all data]

Museli, Pau, et al., 2009
Museli, A.; Pau, M.; Desjobert, J.-M.; Foddai, M.; Usai, M.; Costa, J., Volatile constituents of Achllea ligustica All. by HS-SPME/GC/GC-MS. Comparison with essential oils obtained by hydrodistillation from Corsica and Sardinia, Chromatographia, 2009, 69, 5/6, 575-585, https://doi.org/10.1365/s10337-008-0939-1 . [all data]

Aicha, Ines, et al., 2008
Aicha, N.; Ines, S.; Mohamed, B.S.; Ines, B.; Soumaya, K.; Kamel, G.; Mohamed, N.; Imed, C.; Mohamed, H.; Leila, C.-G., Chemical composition, mutagenic and antimutagenic activities of essential oils from (Tunisian) Artemisia campestris and Artemisia herba-alba, J. Ess. Oil Res., 2008, 20, 5, 471-477. [all data]

Paolini, Tomi, et al., 2008
Paolini, J.; Tomi, P.; Bernardini, A.-F.; Bradesi, P.; Casanova, J.; Kaloustian, J., Detailed analysis of the essential oil from Cistus albidus L. by combination of GC/RI, GC/MS and 13C-NMR spectroscopy, N.Z. J. Agric. Res., 2008, 22, 14, 1270-1278. [all data]

Bos, Woerdenbag, et al., 2007
Bos, R.; Woerdenbag, H.J.; Kayser, O.; Quax, W.J.; Ruslan, K.; Elfami, Essential oil constituents of Piper cubeba L. fils. from Indonesia, J. Essent. Oil Res., 2007, 19, 1, 14-17, https://doi.org/10.1080/10412905.2007.9699217 . [all data]

Elfami, Bos, et al., 2007
Elfami; Bos, R.; Ruslan, K.; Woerdenbag, H.J.; Kayser, P.; Quax, W.J., Essential Oil Constituents of Piper cubeba from Indonesia, 2007, 53-60. [all data]

Hachicha, Skanji, et al., 2007
Hachicha, S.F.; Skanji, T.; Barrek, S.; Ghrabi, Z.G.; Zarrouk, H., Composition of the essential oil of Teucrium ramosissimum Desf. (Lamiaceae) from Tunisia, Flavour Fragr. J., 2007, 22, 2, 101-104, https://doi.org/10.1002/ffj.1764 . [all data]

Elfami, Komar, et al., 2006
Elfami, R.B.; Komar, R.; Woerdenbag, H.J.; Kayser, P.; Quax, W.J., Essential oil constituents of Piper cubeba from Indonesia, 2006, retrieved from http://dissertations.ub.rug.nl/FILES/facultiew/science/2006/elfahmi/05_c5.pdf. [all data]

Figuérédo, Cabassu, et al., 2006
Figuérédo, G.; Cabassu, P.; Chalchat, J.-C.; Pasquier, B., Studies of Mediterranean oregano populations. VIII. Chemical composition of essential oils of oreganos of various origins, Flavour Fragr. J., 2006, 21, 1, 134-139, https://doi.org/10.1002/ffj.1543 . [all data]

Lesueur, Ban, et al., 2006
Lesueur, D.; Ban, N.K.; Bighelli, A.; Muselli, A.; Casanova, J., Analysis of the root oil of Fokienia hodginsii (Dunn) Henry et Thomas (Cupressaceae) by GC, GC-MS and ¹³C-NMR, Flavour Fragr. J., 2006, 21, 1, 171-174, https://doi.org/10.1002/ffj.1557 . [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]

Velasco-Negueruela, Pérez-Alonso, et al., 2006
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 volatiles from the fruits of Ammodaucus leucotrichus subsp. leucotrichus and subsp. nanocarpus grown in North Africa and the Canary Islands, respectively, J. Chromatogr. A, 2006, 1108, 2, 273-275, https://doi.org/10.1016/j.chroma.2006.01.031 . [all data]

Chaverri and Cicció, 2005
Chaverri, C.; Cicció, J.F., Essential oil of trees of the genus Ocotea (Lauraceae) in Costa Rica. I. Ocotea brenesii, Rev. Biol. Trop., 2005, 53, 3-4, 431-436, https://doi.org/10.15517/rbt.v53i3-4.14611 . [all data]

Gauvin and Smadja, 2005
Gauvin, A.; Smadja, J., Essential oil composition of four Psiadia species from Reunion Island: A chemotaxonomic study, Biochem. Syst. Ecol., 2005, 33, 7, 705-714, https://doi.org/10.1016/j.bse.2004.12.013 . [all data]

Marongiu, Piras, et al., 2005
Marongiu, B.; Piras, A.; Porcedda, S.; Scorciapino, A., Chemical composition of the essential oil and supercritical CO₂ extract of Commiphora myrrha (Nees) Engl. and of Acorus calamus L., J. Agric. Food Chem., 2005, 53, 20, 7939-7943, https://doi.org/10.1021/jf051100x . [all data]

Morteza-Semnani, Akbarzadeh, et al., 2005
Morteza-Semnani, K.; Akbarzadeh, M.; Rostami, B., The essential oil composition of Teucrium chamaedrys L. from Iran, Flavour Fragr. J., 2005, 20, 5, 544-546, https://doi.org/10.1002/ffj.1479 . [all data]

Pala-Paul, Perez-Alonso, et al., 2005
Pala-Paul, J.; Perez-Alonso, M.J.; Velasco-Negueruela, A.; Vadare, J.; Villa, A.M.; Sanz, J.; Brophy, J.J., Essential oil composition of the different parts of Eryngium bourgatii Gouan from Spain, J. Chromatogr. A, 2005, 1074, 1-2, 235-239, https://doi.org/10.1016/j.chroma.2005.03.036 . [all data]

Tzakou and Constantinidis, 2005
Tzakou, O.; Constantinidis, T., Chemotaxonomic significance of volatile compounds in Thymus samius and its related species Thymus atticus and Thymus parnassicus, Biochem. Syst. Ecol., 2005, 33, 11, 1131-1140, https://doi.org/10.1016/j.bse.2005.03.008 . [all data]

Blanc, Muselli, et al., 2004
Blanc, M.-C.; Muselli, A.; Bradesi, P.; Casanova, J., Chemical composition and variability of the essential oil of Inula graveolens from Corsica, Flavour Fragr. J., 2004, 19, 4, 314-319, https://doi.org/10.1002/ffj.1304 . [all data]

Fekam Boyom, Fotio, et al., 2004
Fekam Boyom, F.; Fotio, D.; Amvam Zollo, P.H.; Agnaniet, H.; Menut, C.; Bessière, J.M., Aromatic plants of tropical Central Africa. Part XLIV. Volatile components from Pseudocedrela kotschyi (Schweinf.) harms growing in Cameroon, Flavour Fragr. J., 2004, 19, 1, 9-11, https://doi.org/10.1002/ffj.1254 . [all data]

JAvidnia, Mojab, et al., 2004
JAvidnia, K.; Mojab, F.; Mojahedi, S.A., Chemical constituents of the essential oil of Stachys lavandulifolia Vahl from Iran, Iranian J. Pharm. Res., 2004, 3, 61-63. [all data]

Couladis, Özcan, et al., 2003
Couladis, M.; Özcan, M.; Tzakou, O.; Akgül, A., Comparative essential oil composition of various parts of the turpentine tree (Pistacia terebinthus L) growing wild in Turkey, J. Sci. Food Agric., 2003, 83, 2, 136-138, https://doi.org/10.1002/jsfa.1295 . [all data]

Ghasemi, Asghari, et al., 2003
Ghasemi, N.; Asghari, G.; Ardakani, M.S.; Siahpoush, A., Characterization of volatile constituents from aerial parts of varthemia persica DC (var. persica), Iran. J. Pharm. Res., 2003, 2, 241-243. [all data]

Marongiu, Porcedda, et al., 2003
Marongiu, B.; Porcedda, S.; Caredda, A.; de Gioannis, B.; Vargiu, L.; la Colla, P., Extraction of Juniperus oxycedrus ssp. Oxycedrus essential oil by supercritical carbon dioxide: influence of some process parameters and biological activity, Flavour Fragr. J., 2003, 18, 5, 390-397, https://doi.org/10.1002/ffj.1224 . [all data]

Pitarokili, Tzakou, et al., 2003
Pitarokili, D.; Tzakou, O.; Loukis, A.; Harvala, C., Volatile metabolites from Salvia fruticosa as antifungal agents in soilborne pathogens, J. Agric. Food Chem., 2003, 51, 11, 3294-3301, https://doi.org/10.1021/jf0211534 . [all data]

Rotman, Ahumada, et al., 2003
Rotman, A.; Ahumada, O.; Demo, M.S.; Oliva, M.M.; Turina, A.V.; López, M.L.; Zygadlo, J.A., Aromatic plants from Yungas. Part III. Composition and antimicrobial activity of Myrrhinium atropurpureum Schott var. octandrum Bentham essential oil, Flavour Fragr. J., 2003, 18, 3, 211-214, https://doi.org/10.1002/ffj.1189 . [all data]

Velickovic, Randjelovic, et al., 2003
Velickovic, D.T.; Randjelovic, N.V.; Ristic, M.S.; Velickovic, A.S.; Smelcerovic, A.A., Chemical constituents and antimicrobial activity of the ethanol extracts obtained from the flower, leaf, and stem of Salvia officinalis L., J. Serb. Chem. Soc., 2003, 68, 1, 17-24, https://doi.org/10.2298/JSC0301017V . [all data]

Cicció and Gómez-Laurito, 2002
Cicció, J.F.; Gómez-Laurito, J., Volatile constituents of the leaves of Siparuna thecaphora (Siparunaceae) from Turrialba, Costa Rica, Rev. Biol. Trop., 2002, 50, 3/4, 963-967. [all data]

Gudzic, Djokovic, et al., 2002
Gudzic, B.; Djokovic, D.; Vajs, V.; Palic, R.; Stojanovic, G., Composition and antimicrobial activity of the essential oil of Hypericum maculatum Crantz, Flavour Fragr. J., 2002, 17, 5, 392-394, https://doi.org/10.1002/ffj.1112 . [all data]

Krauze-Baranowska, Mardarowicz, et al., 2002
Krauze-Baranowska, M.; Mardarowicz, M.; Wiwart, M.; Poblocka, L.; Dynowska, M., Antifungal activity of the essential oils from some species of the genus Pinus, Z. Naturforsch., 2002, 57c, 478-482. [all data]

Priestap, van Baren, et al., 2002
Priestap, H.A.; van Baren, C.M.; Lira, P.D.L.; Prado, H.J.; Neugebauer, M.; Mayer, R.; Bandoni, A.L., Essential oils from aerial parts of Aristolochia gibertii Hook., Flavour Fragr. J., 2002, 17, 1, 69-71, https://doi.org/10.1002/ffj.1044 . [all data]

Velickovic, Randjelovic, et al., 2002
Velickovic, D.T.; Randjelovic, N.V.; Ristic, M.S.; Smelcerovic, A.A.; Velickovic, A.S., Chemical composition and antimicrobial action of the ethanol extracts of Salvia pratensis L., Salvia glutinosa L. and Salvia aethiopis L., J. Serb. Chem. Soc., 2002, 67, 10, 639-646, https://doi.org/10.2298/JSC0210639V . [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]

Bailac, Dellacasa, et al., 2001
Bailac, P.N.; Dellacasa, A.D.; Bernasconi, H.O.; Ponzi, M.I.; Firpo, N.H., Essential oil of female plants of Baccharis coridifolia De Candole, J. Essent. Oil Res., 2001, 13, 1, 23-24, https://doi.org/10.1080/10412905.2001.9699593 . [all data]

Abreu and Noronha, 1997
Abreu, P.M.; Noronha, R.G., Volatile constituents of the rhizomes of Aframomum alboviolaceum (Ridley) K. Schum. from Guinea-Bissau, Flavour Fragr. J., 1997, 12, 2, 79-83, https://doi.org/10.1002/(SICI)1099-1026(199703)12:2<79::AID-FFJ617>3.0.CO;2-7 . [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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