Cubenol

Formula: C₁₅H₂₆O
Molecular weight: 222.3663
IUPAC Standard InChI: InChI=1S/C15H26O/c1-10(2)13-6-5-12(4)15(16)8-7-11(3)9-14(13)15/h9-10,12-14,16H,5-8H2,1-4H3/t12-,13+,14+,15-/m0/s1
IUPAC Standard InChIKey: COGPRPSWSKLKTF-YJNKXOJESA-N
CAS Registry Number: 21284-22-0
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.
Stereoisomers:
Other names: 1-Isopropyl-4,7-dimethyl-1,3,4,5,6,8a-hexahydro-4a(2H)-naphthalenol-, [1S-(1α,4β,4aβ,8aα)]-; (-)-Cubenol; 10βH-Cadin-4-en-1-ol
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Other data available:
- Mass spectrum (electron ionization)
- Gas Chromatography
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Van Den Dool and Kratz 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	CP-Sil PONA GB	DB-5	RTX-1	RTX-1	ZB-5
Column length (m)	100.	30.	60.	60.	30.
Carrier gas	He		He	He	He
Substrate
Column diameter (mm)	0.25	0.22	0.22	0.22	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	140.	60.	60.	60.	50.
T_end (C)	230.	240.	230.	230.	250.
Heat rate (K/min)	5.	3.	2.	2.	3.
Initial hold (min)	10.	2.
Final hold (min)	25.		35.	35.
I	1651.	1647.	1631.	1631.	1642.
Reference	Cunicao, Lopes, et al., 2007	Martins, Santos, et al., 2007	Paolini J., Costa J., et al., 2007	Paolini, Muselli, et al., 2007	Simoniatto, Bonani, et al., 2007
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5	DB-5	DB-5	BP-1	DB-5
Column length (m)	30.	30.	30.	50.	50.
Carrier gas	He	N2	N2	He	N2
Substrate
Column diameter (mm)	0.25	0.32	0.25	0.22	0.2
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.32
T_start (C)	60.	60.	60.	60.	60.
T_end (C)	240.	240.	240.	220.	220.
Heat rate (K/min)	3.	3.	3.	2.	5.
Initial hold (min)		3.	3.		3.
Final hold (min)		5.	3.	20.	5.
I	1642.	1641.	1642.	1620.	1642.
Reference	Telascrea, de Araujo, et al., 2007	Dob, Dahmane, et al., 2006	Dob, Dahmane, et al., 2006, 2	Gonny, Cavaleiro, et al., 2006	Masoudi, Esmaeili, et al., 2006
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	SPB-1	DB-1	DB-1	DB-5	RTX-1
Column length (m)	30.	30.	30.	25.	60.
Carrier gas	He	N2		N2	He
Substrate
Column diameter (mm)	0.2	0.32	0.32	0.25	0.22
Phase thickness (μm)	0.2	0.25	0.25	0.25	0.25
T_start (C)	70.	50.	50.	75.	60.
T_end (C)	220.	260.	250.	210.	230.
Heat rate (K/min)	3.	2.	2.	3.	2.
Initial hold (min)		3.	8.	10.
Final hold (min)	15.	5.		1.	35.
I	1605.	1640.	1604.	1645.	1631.
Reference	Salgueiro L.R., Pinto E., et al., 2006	Dob T., Berramdane T., et al., 2005	Dob, Dahmane, et al., 2005	bin Jantan, Yalvema, et al., 2005	Paolini, Costa, 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-5	HP-1	RSL-200	RTX-1
Column length (m)	30.	30.	25.	30.	60.
Carrier gas	He	He	He	H2	He
Substrate
Column diameter (mm)	0.25	0.25	0.32	0.32	0.22
Phase thickness (μm)	0.25	0.26	0.17	0.25	0.25
T_start (C)	60.	60.	50.	40.	60.
T_end (C)	250.	210.	200.	280.	230.
Heat rate (K/min)	4.	3.	3.	6.	2.
Initial hold (min)	2.			5.
Final hold (min)	20.			5.	45.
I	1642.	1623.	1604.	1647.	1634.
Reference	Pino, Mesa, et al., 2005	Sati and Mathela, 2005	Fernández-Ocaña, Gómez-Rodríguez, et al., 2004	Ngassoum, Ousmaila, et al., 2004	Cavalli, Tomi, et al., 2003
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	RTX-5	HP-5	HP-5MS	DB-5	HP-1
Column length (m)	30.	30.	30.	30.	24.
Carrier gas	He	He		He	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	0.17
T_start (C)	45.	60.	50.	60.	60.
T_end (C)	250.	280.	280.	260.	250.
Heat rate (K/min)	3.	3.	3.	4.	4.
Initial hold (min)	6.		5.		2.
Final hold (min)					20.
I	1651.	1642.	1642.	1642.	1625.
Reference	Shellie, Marriott, et al., 2003	Tzakou, Couladis, et al., 2003	Demetzos, Angelopoulou, et al., 2002	Javidnia, Miri, et al., 2002	Nath, Sarma, et al., 2002
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	CP Sil 5 CB	CP Sil 5 CB	HP-5	HP-5	DB-5
Column length (m)	30.	50.	30.	30.	30.
Carrier gas	H2	He	He	He	H2
Substrate
Column diameter (mm)	0.25	0.32	0.25	0.25	0.25
Phase thickness (μm)	0.25	0.4	0.25	0.25	0.25
T_start (C)	60.	60.	60.	60.	60.
T_end (C)	280.	280.	260.	380.	240.
Heat rate (K/min)	2.	3.	3.	3.	3.
Initial hold (min)	10.	10.
Final hold (min)	40.	60.	10.
I	1619.	1619.	1641.	1640.	1644.
Reference	Pino, Marbot, et al., 2002	Pino, Marbot, et al., 2002, 2	Couladis, Baziou, et al., 2001	Couladis, Tsortanidou, et al., 2001	Nogueira, Bittrich, et al., 2001
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary
Active phase	CP Sil 5 CB	DB-5	DB-5	CBP-1
Column length (m)	50.	30.	30.	30.
Carrier gas	He	He	He	He
Substrate
Column diameter (mm)	0.32	0.25	0.25	0.25
Phase thickness (μm)	0.4	0.25	0.25
T_start (C)	60.	60.	60.	60.
T_end (C)	280.	240.	240.	240.
Heat rate (K/min)	3.	3.	3.	4.
Initial hold (min)	10.	2.	2.
Final hold (min)	60.
I	1618.	1641.	1641.	1632.
Reference	Pino, Marbot, et al., 2001	Maia, de Paula, et al., 2000	Maia, de Paula, et al., 2000	Zunino, Lopez, et al., 2000
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

References

Go To: Top, Van Den Dool and Kratz RI, non-polar column, temperature ramp, Notes

Cunicao, Lopes, et al., 2007
Cunicao, M.M.; Lopes, A.R.; Côcco, L.C.; Yamamoto, C.I.; Plocharski, R.C.B.; Miguel, M.D.; Junior, A.G.; Auer, C.G.; Miguel, O.G., Phytochemical and antibacterial evaluation of essential oils from Ottonia Martiana Miq. (Piperaceae), J. Braz. Chem. Soc., 2007, 18, 1, 184-188, https://doi.org/10.1590/S0103-50532007000100021 . [all data]

Martins, Santos, et al., 2007
Martins, F.T.; Santos, M.H.; Polo, M.; Barbosa, L.C.A., Effects of the interactions among macronutrients, plant age and photoperiod in the composition of Hyptis suaveolens (L.) Poit essential oil from Alfenas (MG), Brazil, Flavour Fragr. J., 2007, 22, 2, 123-129, https://doi.org/10.1002/ffj.1769 . [all data]

Paolini J., Costa J., et al., 2007
Paolini J.; Costa J.; Bernardini A.F., Analysis of the essential oil from the roots of Eupatorium cannabinum subsp corsicum (L.) by GC, GC-MS and C-13-NMR, Phytochem. Anal., 2007, 18, 3, 235-244, https://doi.org/10.1002/pca.977 . [all data]

Paolini, Muselli, et al., 2007
Paolini, J.; Muselli, A.; Bernardini, A.-F.; Bighelli, A.; Casanova, J.; Costa, J., Thymol derivatives from essential oil of Doronicum corsicum L., Flavour Fragr. J., 2007, 22, 6, 479-487, https://doi.org/10.1002/ffj.1824 . [all data]

Simoniatto, Bonani, et al., 2007
Simoniatto, E.; Bonani, V.F.L.; Morel, A.F.; Poppi, N.R.; Raposo, J.L., Jr.; Stuker, C.Z.; Peruzzo, G.M.; Peres, M.T.L.P.; Hess, S.C., Chemical composition and evaluation of antibacterial and antioxidant activities of the essential oil of Croton urucurana Baillon (Euphorbiaceae) stem bark, J. Braz. Chem., 2007, 18, 5, 879-885, https://doi.org/10.1590/S0103-50532007000500002 . [all data]

Telascrea, de Araujo, et al., 2007
Telascrea, M.; de Araujo, C.C.; Marques, M.O.M.; Facanali, R.; de Moraes, P.L.R.; Cavalheiro, A.J., Essential oil from leaves of Cryptocarya mandioccana Meisner (Lauraceae): Composition and intraspecific chemical variability, Biochem. Syst. Ecol., 2007, 35, 4, 222-232, https://doi.org/10.1016/j.bse.2006.09.015 . [all data]

Dob, Dahmane, et al., 2006
Dob, T.; Dahmane, D.; Chelghoum, C., Essential oil composition of Juniperus oxycedrus growing in Algeria, Pharm. Biol., 2006, 44, 1, 1-6, https://doi.org/10.1080/13880200500530922 . [all data]

Dob, Dahmane, et al., 2006, 2
Dob, T.; Dahmane, D.; Agli, M.; Chelghoum, C., Essential oil composition of Lavandula stoechas from Algeria, Pharm. Biol., 2006, 44, 1, 60-64, https://doi.org/10.1080/13880200500496421 . [all data]

Gonny, Cavaleiro, et al., 2006
Gonny, M.; Cavaleiro, C.; Salgueiro, L.; Casanova, J., Analysis of Juniperus communis subsp. alpina needle, berry, wood and root oils by combination of GC, GC/MS and ¹³C-NMR, Flavour Fragr. J., 2006, 21, 1, 99-106, https://doi.org/10.1002/ffj.1527 . [all data]

Masoudi, Esmaeili, et al., 2006
Masoudi, S.; Esmaeili, A.; Khalilzadeh, M.A.; Rustaiyan, A.; Moazami, N.; Akhgar, M.R.; Varavipoor, M., Volatile constituents of Dorema aucheri Boiss., Seseli libanotis (L.) W. D. Koch var. armeniacum bordz. and Conium maculatum L. three Umbelliferae herbs growing wild in Iran, Flavour Fragr. J., 2006, 21, 5, 801-804, https://doi.org/10.1002/ffj.1722 . [all data]

Salgueiro L.R., Pinto E., et al., 2006
Salgueiro L.R.; Pinto E.; Goncalves M.J.; Costa I.; Palmeira A.; Cavaleiro C.; Pina-Vaz C.; Rodrigues A.G.; Martinez-De-Oliveira J., Antifungal activity of the essential oil of Thymus capitellatus against Candida, Aspergillus and dermatophyte strains, Flavour Fragr. J., 2006, 21, 5, 749-753, https://doi.org/10.1002/ffj.1610 . [all data]

Dob T., Berramdane T., et al., 2005
Dob T.; Berramdane T.; Chelghoum C., Analysis of essential oil from the needles of Pinus pinaster growing in Algeria, Chem. Nat. Compd. (Engl. Transl.), 2005, 41, 5, 545-548, https://doi.org/10.1007/s10600-005-0202-z . [all data]

Dob, Dahmane, et al., 2005
Dob, T.; Dahmane, D.; Berramdane, T.; Chelghoum, C., Chemical composition of the essential oil of Artemisia campestris L. from Algeria, Pharm. Biol., 2005, 43, 6, 512-514, https://doi.org/10.1080/13880200500220664 . [all data]

bin Jantan, Yalvema, et al., 2005
bin Jantan, I.; Yalvema, M.F.; Ayop, N.; Ahmad, A.S., Constituents of the essential oils of Cinnamomum sintoc Blume from a mountain forest of Peninsular Malaysia, Flavour Fragr. J., 2005, 20, 6, 601-604, https://doi.org/10.1002/ffj.1495 . [all data]

Paolini, Costa, et al., 2005
Paolini, J.; Costa, J.; Bernardini, A., Analysis of the essential oil from aerial parts of Eupatorium cannabinum subsp. corsicum (L.) by gas chromatography with electron impact and chemical ionization mass spectrometry, J. Chromatogr. A, 2005, 1076, 1-2, 170-178, https://doi.org/10.1016/j.chroma.2005.03.131 . [all data]

Pino, Mesa, et al., 2005
Pino, J.A.; Mesa, J.; Muñoz, Y.; Martí, M.P.; Marbot, R., Volatile components from mango (Mangifera indica L.) cultivars, J. Agric. Food Chem., 2005, 53, 6, 2213-2223, https://doi.org/10.1021/jf0402633 . [all data]

Sati and Mathela, 2005
Sati, S.; Mathela, C.S., Essential oil composition of Valeriana hardwickii var. arnottiana from the Himalayas, Flavour Fragr. J., 2005, 20, 3, 299-301, https://doi.org/10.1002/ffj.1415 . [all data]

Fernández-Ocaña, Gómez-Rodríguez, et al., 2004
Fernández-Ocaña, A.M.; Gómez-Rodríguez, M.V.; Velasco-Negueruela, A.; Camacho-Simarro, A.M.; Fernández-López, C.; Altarejos, J., In vivo antifungal activity of the essential oil of Bupleurum gibraltarium against plasmopara halstedii in sunflower, J. Agric. Food Chem., 2004, 52, 21, 6414-6417, https://doi.org/10.1021/jf040219n . [all data]

Ngassoum, Ousmaila, et al., 2004
Ngassoum, M.B.; Ousmaila, H.; Ngamo, L.T.; Maponmetsem, P.M.; Jirovetz, L.; Buchbauer, G., Aroma compounds of essential oils of two varieties of the spice plant Ocimum canum Sims from northern Cameroon, J. Food Comp. Anal., 2004, 17, 2, 197-204, https://doi.org/10.1016/j.jfca.2003.08.002 . [all data]

Cavalli, Tomi, et al., 2003
Cavalli, J.-F.; Tomi, F.; Bernardini, A.-F.; Casanova, J., Composition and chemical variability of the bark oil of Cedrelopsis grevei H. Baillon from Madagascar, Flavour Fragr. J., 2003, 18, 6, 532-538, https://doi.org/10.1002/ffj.1263 . [all data]

Shellie, Marriott, et al., 2003
Shellie, R.; Marriott, P.; Zappia, G.; Mondello, L.; Dugo, G., Interactive use of linear retention indices on polar and apolar columns with an MS-Library for reliable characterization of Australian tea tree and other Melaleuca sp. oils, J. Essent. Oil Res., 2003, 15, 5, 305-312, https://doi.org/10.1080/10412905.2003.9698597 . [all data]

Tzakou, Couladis, et al., 2003
Tzakou, O.; Couladis, M.; Slavkovska, V.; Mimica-Dukic, N.; Jancic, R., The essential oil composition of Salvia brachyodon Vandas, Flavour Fragr. J., 2003, 18, 1, 2-4, https://doi.org/10.1002/ffj.1132 . [all data]

Demetzos, Angelopoulou, et al., 2002
Demetzos, C.; Angelopoulou, D.; Perdetzoglou, D., A comparative study of the essential oils of Cistus salviifolius in several populations of Crete (Greece), Biochem. Syst. Ecol., 2002, 30, 7, 651-665, https://doi.org/10.1016/S0305-1978(01)00145-4 . [all data]

Javidnia, Miri, et al., 2002
Javidnia, K.; Miri, R.; Kamalinejad, M.; Nasiri, A., Composition of the essential oil of Salvia mirzayanii Rech. f. Esfand from Iran, Flavour Fragr. J., 2002, 17, 6, 465-467, https://doi.org/10.1002/ffj.1128 . [all data]

Nath, Sarma, et al., 2002
Nath, S.C.; Sarma, K.K.; Vajezikova, I.; Leclercq, P.A., Comparison of volatile inflorescence oils and taxonomy of certain Cymbopogon taxa described as Cymbopogon flexuosus (Nees ex Steud.) Wats., Biochem. Syst. Ecol., 2002, 30, 2, 151-162, https://doi.org/10.1016/S0305-1978(01)00066-7 . [all data]

Pino, Marbot, et al., 2002
Pino, J.A.; Marbot, R.; Bello, A., Volatile compounds of Psidium salutare (H.B.K.) Berg. fruit, J. Agric. Food Chem., 2002, 50, 18, 5146-5148, https://doi.org/10.1021/jf0116303 . [all data]

Pino, Marbot, et al., 2002, 2
Pino, J.A.; Marbot, R.; Vázquez, C., Characterization of volatile in Cosa Rican Guava [Psidium friedrichsthalianum (Berg) Niedenzu] fruit, J. Agric. Food Chem., 2002, 50, 21, 6023-6026, https://doi.org/10.1021/jf011456i . [all data]

Couladis, Baziou, et al., 2001
Couladis, M.; Baziou, P.; Petrakis, P.V.; Harvala, C., Essential oil composition of Hypericum perfoliatum L. growing in different locations in Greece, Flavour Fragr. J., 2001, 16, 3, 204-206, https://doi.org/10.1002/ffj.979 . [all data]

Couladis, Tsortanidou, et al., 2001
Couladis, M.; Tsortanidou, V.; Francisco-Ortega, J.; Santos-Guerra, A.; Harvala, C., Composition of the essential oils of Argyranthemum species growing in the Canary Islands, Flavour Fragr. J., 2001, 16, 2, 103-106, https://doi.org/10.1002/ffj.954 . [all data]

Nogueira, Bittrich, et al., 2001
Nogueira, P.C.L.; Bittrich, V.; Shepherd, G.J.; Lopes, A.V.; Marsaioli, A.J., The ecological and taxonomic importance of flower volatiles of Clusia species (Guttiferae), Phytochemistry, 2001, 56, 5, 443-452, https://doi.org/10.1016/S0031-9422(00)00213-2 . [all data]

Pino, Marbot, et al., 2001
Pino, J.A.; Marbot, R.; Vázquez, C., Characterization of volatiles in strawberry guava (Psidium cattleianum Sabine) fruit, J. Agric. Food Chem., 2001, 49, 12, 5883-5887, https://doi.org/10.1021/jf010414r . [all data]

Maia, de Paula, et al., 2000
Maia, B.H.L.N.S.; de Paula, J.R.; Sant'Ana, J.; da Silva, M.F.G.F.; Fernandes, J.B.; Vieira, P.C.; Costa, M.S.S.; Ohashi, O.S.; Silva, J.N.M., Essential oils of Toona and Cedrela species (Meliaceae): Taxonomic and ecological implications, J. Braz. Chem. Soc., 2000, 11, 6, 629-639, https://doi.org/10.1590/S0103-50532000000600012 . [all data]

Zunino, Lopez, et al., 2000
Zunino, M.P.; Lopez, M.L.; Faillacik, S.M.; Lopez, A.G.; Espinar, L.A.; Zygadlo, J.A., Essential oil of Baccharis cordobensis Heering, Flavour Fragr. J., 2000, 15, 3, 151-152, https://doi.org/10.1002/1099-1026(200005/06)15:3<151::AID-FFJ884>3.0.CO;2-E . [all data]

Notes

Go To: Top, Van Den Dool and Kratz 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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