1-Naphthalenol, 1,2,3,4,4a,7,8,8a-octahydro-1,6-dimethyl-4-(1-methylethyl)-, [1R-(1α,4β,4aβ,8aβ)]-

Formula: C₁₅H₂₆O
Molecular weight: 222.3663
IUPAC Standard InChI: InChI=1S/C15H26O/c1-10(2)12-7-8-15(4,16)14-6-5-11(3)9-13(12)14/h9-10,12-14,16H,5-8H2,1-4H3/t12-,13-,14-,15+/m0/s1
IUPAC Standard InChIKey: LHYHMMRYTDARSZ-ZQDZILKHSA-N
CAS Registry Number: 19435-97-3
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: (1R,4S,4aR,8aS)-4-Isopropyl-1,6-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-ol; 1β-Cadin-4-en-10-ol; δ-Cadinol; δ-Cadinol, (-)-; (-)-δ-Cadinol; (-)-Cedreanol; Cedreanol, (-)-; Torreyol; α-Muurolol; Amorphan-3-en-9-ol; 4-Isopropyl-1,6-dimethyl-1,2,3,4,4a,7,8,8a-octahydro-1-naphthalenol; 36564-42-8; Muurolol; Torreyol (α-muurolol); α-muurolol (torreyol)
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Information on this page:
Other data available:
- Mass spectrum (electron ionization)
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Van Den Dool and Kratz RI, 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-20M	HP-Innowax	HP-Innowax	DB-Wax	PEG
Column length (m)	50.	60.	30.	30.	30.
Carrier gas	He	He	He	He	N2
Substrate
Column diameter (mm)	0.2	0.25	0.25	0.25	0.32
Phase thickness (μm)	0.2	0.25	0.5	0.25	0.25
T_start (C)	70.	50.	60.	50.	50.
T_end (C)	180.	220.	260.	220.	220.
Heat rate (K/min)	4.	4.	3.	4.	2.
Initial hold (min)	4.	4.		4.	3.
Final hold (min)	15.	10.		20.	15.
I	2173.	2165.	2180.	2142.	2152.
Reference	Politeo, Jukic, et al., 2007	Quijano, Linares, et al., 2007	Saroglou, Marin, et al., 2007	Osorio, Alarcon, et al., 2006	Dob, Berramdane, et al., 2005
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-Wax	HP-Innowax	RTX-Wax	AT-Wax	AT-Wax
Column length (m)	60.	30.	30.	60.	60.
Carrier gas	He	He	He	He	He
Substrate
Column diameter (mm)	0.32	0.25	0.25	0.32	0.32
Phase thickness (μm)	0.25	0.5	0.25	0.25	0.25
T_start (C)	32.	60.	45.	65.	65.
T_end (C)	220.	260.	250.	250.	250.
Heat rate (K/min)	3.	3.	3.	2.	2.
Initial hold (min)			6.	10.	10.
Final hold (min)			10.	60.	60.
I	2205.	2180.	2166.	2167.	2167.
Reference	Brophy, Goldsack, et al., 2004	Skaltsa, Demetzos, et al., 2003	Mondello, Zappia, et al., 2002	Pino, Marbot, et al., 2002	Pino, Marbot, et al., 2001
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-Wax	DB-Wax	DB-Wax	DB-Wax	DB-Wax
Column length (m)	60.	60.	60.	60.	60.
Carrier gas	He	He	He	He	He
Substrate
Column diameter (mm)	0.50	0.53	0.53	0.53	0.53
Phase thickness (μm)	1.0	1.0	1.0
T_start (C)	60.	50.	50.	50.	50.
T_end (C)	225.	220.	220.	220.	220.
Heat rate (K/min)	3.	3.	3.	3.	3.
Initial hold (min)
Final hold (min)
I	2187.	2187.	2187.	2187.	2187.
Reference	Brophy, Goldsack, et al., 2000	Brophy, Goldsack, et al., 2000, 2	Brophy, Goldsack, et al., 2000, 3	Brophy, Goldsack, et al., 1999	Brophy, Goldsack, et al., 1999, 2
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	Innowax	Carbowax 20M	DB-Wax	DB-Wax	DB-Wax
Column length (m)	60.	25.	60.	60.	60.
Carrier gas	He	H2	He	He	He
Substrate
Column diameter (mm)	0.25	0.25	0.32	0.32	0.32
Phase thickness (μm)	0.25	0.3
T_start (C)	50.	50.	35.	65.	35.
T_end (C)	180.	200.	220.	225.	220.
Heat rate (K/min)	2.5	3.	3.	3.	3.
Initial hold (min)	5.	1.
Final hold (min)		20.
I	2150.	2192.	2208.	2187.	2187.
Reference	Stashenko, Cervantes, et al., 1999	Bicchi, Rubiolo, et al., 1998	Brophy, Forster, et al., 1998	Brophy, Goldsack, et al., 1998	Brophy, Goldsack, et al., 1998, 2
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-Wax	SP-1000	Supelcowax-10	DB-Wax	DB-Wax
Column length (m)	60.	85.	60.	60.	60.
Carrier gas	He	He	He
Substrate
Column diameter (mm)	0.32	0.5	0.25	0.25	0.25
Phase thickness (μm)			0.25	0.25	0.25
T_start (C)	65.	65.	60.	50.	50.
T_end (C)	225.	225.	230.	230.	230.
Heat rate (K/min)	3.	3.	5.	2.	2.
Initial hold (min)			5.
Final hold (min)			20.
I	2187.	2187.	2222.	2197.	2165.
Reference	Brophy, Goldsack, et al., 1997	Brophy, Goldsack, et al., 1997, 2	Granicher, Christen, et al., 1995	Shimoda, Shigematsu, et al., 1995	Shimoda, Shigematsu, et al., 1995
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary
Active phase	DB-Wax	DB-Wax	HP-FFAP	Carbowax 20M
Column length (m)	60.	60.	50.	50.
Carrier gas		He	He	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.25
Phase thickness (μm)	0.25	0.25
T_start (C)	50.	50.	60.	60.
T_end (C)	230.	230.	210.	180.
Heat rate (K/min)	2.	2.	3.	2.
Initial hold (min)				4.
Final hold (min)	60.	60.
I	2212.	2212.	2219.	2149.
Reference	Shiratsuchi, Shimoda, et al., 1994	Shiratsuchi, Shimoda, et al., 1994, 2	Chung, Eiserich, et al., 1993	Kawakami, Sachs, et al., 1990
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

References

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

Politeo, Jukic, et al., 2007
Politeo, O.; Jukic, M.; Milos, M., Chemical composition and antioxidant capacity of free volatile aglycones from basil (Ocimum basilicum L.) compared with its essential oil, Food Chem., 2007, 101, 1, 379-385, https://doi.org/10.1016/j.foodchem.2006.01.045 . [all data]

Quijano, Linares, et al., 2007
Quijano, C.E.; Linares, D.; Pino, J.A., Changes in volatile compounds of fermented cereza agria [Phyllanthus acidus (L.) Skeels] fruit, Flavour Fragr. J., 2007, 22, 5, 392-394, https://doi.org/10.1002/ffj.1810 . [all data]

Saroglou, Marin, et al., 2007
Saroglou, V.; Marin, P.D.; Rancic, A.; Veljic, M.; Skaltsa, H., Composition and antimicrobial activity of the essential oil of six Hypericum species from Serbia, Biochem. Syst. Ecol., 2007, 35, 3, 146-152, https://doi.org/10.1016/j.bse.2006.09.009 . [all data]

Osorio, Alarcon, et al., 2006
Osorio, C.; Alarcon, M.; Moreno, C.; Bonilla, A.; Barrios, J.; Garzon, C.; Duque, C., Characterization of Odor-Active Volatiles in Champa ( Campomanesia lineatifolia R. P.), J. Agric. Food Chem., 2006, 54, 2, 509-516, https://doi.org/10.1021/jf052098c . [all data]

Dob, Berramdane, et al., 2005
Dob, T.; Berramdane, T.; Chelgoum, C., Chemical composition of essential oil of Pinus halepensis Miller growing in Algeria, C.R. Chim., 2005, 8, 11-12, 1939-1945, https://doi.org/10.1016/j.crci.2005.05.007 . [all data]

Brophy, Goldsack, et al., 2004
Brophy, J.J.; Goldsack, R.J.; O'Sullivan, W., Chemistry of the Australian gymnosperms. Part VII. The leaf oils of the genus Actinostrobus, Biochem. Syst. Ecol., 2004, 32, 10, 867-873, https://doi.org/10.1016/j.bse.2004.05.001 . [all data]

Skaltsa, Demetzos, et al., 2003
Skaltsa, H.D.; Demetzos, C.; Lazari, D.; Sokovic, M., Essential oil analysis and antimicrobial activity of eight Stachys species from Greece, Phytochemistry, 2003, 64, 3, 743-752, https://doi.org/10.1016/S0031-9422(03)00386-8 . [all data]

Mondello, Zappia, et al., 2002
Mondello, L.; Zappia, G.; Cotroneo, A.; Bonaccorsi, I.; Chowdhury, J.U.; Yusuf, M.; Dugo, G., Studies on the essential oil-bearing plants of Bangladesh. Part VIII. Composition of some Ocimum oils O. basilicum L. var. purpurascens; O. sanctum L. green; O. sanctum L. purple; O. americanum L., citral type; O. americanum L., camphor type, Flavour Fragr. J., 2002, 17, 5, 335-340, https://doi.org/10.1002/ffj.1108 . [all data]

Pino, Marbot, et al., 2002
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]

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]

Brophy, Goldsack, et al., 2000
Brophy, J.J.; Goldsack, R.J.; Forster, P.I., Essential oils of the genus Lophostemon (Myrtaceae), Flavour Fragr. J., 2000, 15, 1, 17-20, https://doi.org/10.1002/(SICI)1099-1026(200001/02)15:1<17::AID-FFJ859>3.0.CO;2-D . [all data]

Brophy, Goldsack, et al., 2000, 2
Brophy, J.; Goldsack, R.J.; Bean, A.R.; Forster, P.I.; Lepschi, B.J., Leaf essential oils of the genus Leptospermum (Myrtaceae) in eastern Australia. Part 6. Leptospermum polygalifolium and allies, Flavour Fragr. J., 2000, 15, 4, 271-277, https://doi.org/10.1002/1099-1026(200007/08)15:4<271::AID-FFJ910>3.0.CO;2-E . [all data]

Brophy, Goldsack, et al., 2000, 3
Brophy, J.J.; Goldsack, R.J.; Punruckvong, A.; Bean, A.R.; Forster, P.I.; Lepschi, B.J.; Doran, J.C.; Rozefelds, A.C., Leaf essential oils of the genus Leptospermum (Myrtaceae) in eastern Australia. Part 7. Leptospermum petersonii, L. liversidgei and allies, Flavour Fragr. J., 2000, 15, 5, 342-351, https://doi.org/10.1002/1099-1026(200009/10)15:5<342::AID-FFJ924>3.0.CO;2-V . [all data]

Brophy, Goldsack, et al., 1999
Brophy, J.J.; Goldsack, R.J.; Punruckvong, A.; Forster, P.I., The leaf essential oils of Pilidiostigma (Myrtaceae), Flavour Fragr. J., 1999, 14, 2, 143-146, https://doi.org/10.1002/(SICI)1099-1026(199903/04)14:2<143::AID-FFJ798>3.0.CO;2-P . [all data]

Brophy, Goldsack, et al., 1999, 2
Brophy, J.J.; Goldsack, R.J.; Bean, A.R.; Forster, P.I.; Lepschi, B.J., Leaf essential oils of the genus Leptospermum (Myrtaceae) in eastern Australia. Part 5. Leptospermum continentale and allies, Flavour Fragr. J., 1999, 14, 2, 98-104, https://doi.org/10.1002/(SICI)1099-1026(199903/04)14:2<98::AID-FFJ797>3.0.CO;2-V . [all data]

Stashenko, Cervantes, et al., 1999
Stashenko, E.E.; Cervantes, M.; Combariza, Y.; Fuentes, H.; Martínez, J.R., HRGC/FID and HRGC/MSD analysis of the secondary metabolites obtained by different extraction methods from Lepechinia schiedeana, an in vitro evaluation of its antioxidant activity, J. Hi. Res. Chromatogr., 1999, 22, 6, 343-349, https://doi.org/10.1002/(SICI)1521-4168(19990601)22:6<343::AID-JHRC343>3.0.CO;2-J . [all data]

Bicchi, Rubiolo, et al., 1998
Bicchi, C.; Rubiolo, P.; Marschall, H.; Weyerstahl, P.; Laurent, R., Constituents of Artemisia roxburghiana Besser essential oil, Flavour Fragr. J., 1998, 13, 1, 40-46, https://doi.org/10.1002/(SICI)1099-1026(199801/02)13:1<40::AID-FFJ688>3.0.CO;2-Z . [all data]

Brophy, Forster, et al., 1998
Brophy, J.J.; Forster, P.I.; Goldsack, R.J., Esssential oils of some Australian monimiaceae, Flavour Fragr. J., 1998, 13, 4, 273-276, https://doi.org/10.1002/(SICI)1099-1026(1998070)13:4<273::AID-FFJ745>3.0.CO;2-O . [all data]

Brophy, Goldsack, et al., 1998
Brophy, J.J.; Goldsack, R.J.; Forster, P.I.; Bean, A.R.; Clarkson, J.R.; Lepschi, B.J., Leaf essential oils of the genus Leptospermum (Myrtaceae) in Eastern Australia. Part 1. Leptospermum brachyandrum and Leptospermum pallidum groups, Flavour Fragr. J., 1998, 13, 1, 19-25, https://doi.org/10.1002/(SICI)1099-1026(199801/02)13:1<19::AID-FFJ679>3.0.CO;2-9 . [all data]

Brophy, Goldsack, et al., 1998, 2
Brophy, J.J.; Goldsack, R.J.; Bean, A.R.; Forster, P.I.; Lepschi, B.J., Leaf essential oils of the genus Leptospermum (Myrtaceae) in eastern Australia. Part 2. Leptospermum blakelyi and allies, Flavour Fragr. J., 1998, 13, 5, 353-358, https://doi.org/10.1002/(SICI)1099-1026(1998090)13:5<353::AID-FFJ759>3.0.CO;2-1 . [all data]

Brophy, Goldsack, et al., 1997
Brophy, J.J.; Goldsack, R.J.; Forster, P.I., The essential oils of the Australian species of Rhodomyrtus (Myrtaceae), Flavour Fragr. J., 1997, 12, 2, 103-108, https://doi.org/10.1002/(SICI)1099-1026(199703)12:2<103::AID-FFJ621>3.0.CO;2-B . [all data]

Brophy, Goldsack, et al., 1997, 2
Brophy, J.J.; Goldsack, R.J.; Forster, P.I., The leaf essential oils of the Australian species of Rhodamnia (Myrtaceae), Flavour Fragr. J., 1997, 12, 5, 345-354, https://doi.org/10.1002/(SICI)1099-1026(199709/10)12:5<345::AID-FFJ658>3.0.CO;2-6 . [all data]

Granicher, Christen, et al., 1995
Granicher, F.; Christen, P.; Kapetanidis, I., Essential oils from normal and hairy roots of valeriana officinalis var. sambucifolia, Phytochemistry, 1995, 40, 5, 1421-1424, https://doi.org/10.1016/0031-9422(95)00492-P . [all data]

Shimoda, Shigematsu, et al., 1995
Shimoda, M.; Shigematsu, H.; Shiratsuchi, H.; Osajima, Y., Comparison of the odor concentrates by SDE and adsorptive column method from green tea infusion, J. Agric. Food Chem., 1995, 43, 6, 1616-1620, https://doi.org/10.1021/jf00054a037 . [all data]

Shiratsuchi, Shimoda, et al., 1994
Shiratsuchi, H.; Shimoda, M.; Imayoshi, K.; Noda, K.; Osajima, Y., Off-flavor compounds in spray-dried skim milk powder, J. Agric. Food Chem., 1994, 42, 6, 1323-1327, https://doi.org/10.1021/jf00042a014 . [all data]

Shiratsuchi, Shimoda, et al., 1994, 2
Shiratsuchi, H.; Shimoda, M.; Imayoshi, K.; Noda, K.; Osajima, Y., Volatile flavor compounds in spray-dried skim milk powder, J. Agric. Food Chem., 1994, 42, 4, 984-988, https://doi.org/10.1021/jf00040a028 . [all data]

Chung, Eiserich, et al., 1993
Chung, T.Y.; Eiserich, J.P.; Shibamoto, T., Volatile compounds isolated from edible Korean chamchwi (Aster scaber Thunb), J. Agric. Food Chem., 1993, 41, 10, 1693-1697, https://doi.org/10.1021/jf00034a033 . [all data]

Kawakami, Sachs, et al., 1990
Kawakami, M.; Sachs, R.M.; Shibamoto, T., Volatile constituents of essential oils obtained from newly developed tea tree (Melaleuca alternifolia) clones, J. Agric. Food Chem., 1990, 38, 8, 1657-1661, https://doi.org/10.1021/jf00098a007 . [all data]

Notes

Go To: Top, Van Den Dool and Kratz RI, 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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