Bicyclo[3.1.0]hexan-2-ol, 2-methyl-5-(1-methylethyl)-, (1α,2α,5α)-

Formula: C₁₀H₁₈O
Molecular weight: 154.2493
IUPAC Standard InChI: InChI=1S/C10H18O/c1-7(2)10-5-4-9(3,11)8(10)6-10/h7-8,11H,4-6H2,1-3H3
IUPAC Standard InChIKey: KXSDPILWMGFJMM-UHFFFAOYSA-N
CAS Registry Number: 17699-16-0
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.
Species with the same structure:
- Bicyclo[3.1.0]hexan-2-ol, 2-methyl-5-(1-methylethyl)-
Stereoisomers:
Other names: (1R,2R,5S)-5-Isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol; trans-Sabinene hydrate (trans for Me vs IP); trans-Sabinene hydrate; trans-Sabinene hydroxide; Sabinene hydrate, trans; 5-Isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol, (1α,2α,5α)-; (1α,2α,5α)-2-Methyl-5-(1-methylethyl)bicyclo(3.1.0)hexan-2-ol; trans-4-Thujanol; cis-Sabinene hydrate (cis for OH vs IP); 15826-83-2; cis-Sabinene hydrate; trans-Sabinenhydrate; Sabinene hydrate-cis; cis-Sabinene hydroxide
Information on this page:
Other data available:
- Mass spectrum (electron ionization)
- Gas Chromatography
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Normal alkane 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	RTX-Wax	HP-Innowax	PEG-20M	HP-Innowax	Supelcowax-10
Column length (m)	60.	30.	60.	30.	30.
Carrier gas	Helium	N2	He	He	He
Substrate
Column diameter (mm)	0.22	0.25	0.25	0.25	0.2
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.2
T_start (C)	60.	50.	90.	60.	70.
T_end (C)	230.	240.	225.	240.	220.
Heat rate (K/min)	2.	5.	3.	2.	3.
Initial hold (min)		1.
Final hold (min)	30.	4.	15.	20.	15.
I	1440.	1466.	1463.	1450.	1464.
Reference	Museli, Pau, et al., 2009	Cheraif, Ben Jannet, et al., 2007	Gil A., Van Baren C.M., et al., 2007	Hachicha, Skanji, et al., 2007	Pinto, Salgueiro, et al., 2007
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	AT-Wax	BP-20	DB-Wax	DB-Wax	DB-Wax
Column length (m)	60.	50.	60.	30.	60.
Carrier gas	He	He		He	Nitrogen
Substrate
Column diameter (mm)	0.25	0.22	0.25	0.25	0.32
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.50
T_start (C)	60.	60.	70.	50.	35.
T_end (C)	200.	220.	230.	180.	235.
Heat rate (K/min)	4.	2.	2.	3.	2.
Initial hold (min)			2.		4.
Final hold (min)	20.	20.	20.	40.	30.
I	1458.	1454.	1467.	1463.	1489.
Reference	Borges, Rojas, et al., 2006	Fanciullino, Tomi, et al., 2006	Lan Phi N.T., Nishiyama C., et al., 2006	Lee, Umano, et al., 2005	Qian and Wang, 2005
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-Wax	Supelcowax-10	Supelcowax-10	SW-10	Supelcowax-10
Column length (m)	60.	50.	50.	50.	30.
Carrier gas	N2	He	He	He	He
Substrate
Column diameter (mm)	0.25	0.2	0.2	0.20	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	70.	70.	70.	50.	60.
T_end (C)	230.	230.	230.	230.	240.
Heat rate (K/min)	2.	2.	2.	2.	4.
Initial hold (min)	2.
Final hold (min)	20.
I	1463.	1460.	1460.	1460.	1467.
Reference	Choi, 2004	Orav, Stulova, et al., 2004	Orav, Stulova, et al., 2004	Raal, Paaver, et al., 2004	Cabanillas, Lopez, et al., 2003
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-Wax	Innowax	DB-Wax	DB-Wax	BP-20
Column length (m)	60.	60.	60.	60.	50.
Carrier gas	Helium	He	N2	He	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.25	0.22
Phase thickness (μm)			0.25	0.25	0.25
T_start (C)	70.	60.	70.	40.	60.
T_end (C)	210.	220.	230.	200.	230.
Heat rate (K/min)	2.	4.	2.	2.	2.
Initial hold (min)		10.	2.	2.
Final hold (min)	60.	10.	20.		35.
I	1467.	1474.	1453.	1459.	1458.
Reference	Mookdasanit, Tamura, et al., 2003	Suleimenov, Atazharova, et al., 2003	Tu, Onishi, et al., 2003	Umano, Hagi, et al., 2002	Lota, de Rocca Serra, et al., 2001
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	PEG-20M	Supelcowax-10	BP-20	DB-Wax	Supelcowax-10
Column length (m)	50.	60.	25.	60.	30.
Carrier gas	He	He	Nitrogen	He	He
Substrate
Column diameter (mm)	0.2	0.25	0.50	0.25	0.25
Phase thickness (μm)		0.25	0.25	0.25
T_start (C)	70.	60.	60.	40.	60.
T_end (C)	220.	280.	200.	200.	240.
Heat rate (K/min)	2.	4.	5.	2.	4.
Initial hold (min)				2.
Final hold (min)
I	1461.	1470.	1470.	1467.	1467.
Reference	Orav and Kann, 2001	Korány, Mednyánszky, et al., 2000	Mallavarapu, Rao, et al., 2000	Umano, Hagi, et al., 2000	Labuckas, Zygadlo, et al., 1999
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-Wax	BP-20	BP-20	HP-Innowax	HP-Innowax FSC
Column length (m)	60.	25.	25.	60.	60.
Carrier gas	He	N2	H2	He	He
Substrate
Column diameter (mm)	0.25	0.5	0.33	0.25	0.25
Phase thickness (μm)	0.25		0.5	0.25	0.25
T_start (C)	60.	60.	80.	50.	60.
T_end (C)	240.	200.	220.	220.	220.
Heat rate (K/min)	4.	5.	5.	5.	4.
Initial hold (min)				5.	10.
Final hold (min)					10.
I	1464.	1465.	1476.	1444.	1474.
Reference	Ngassoum, Yonkeu, et al., 1999	Rao, Bhattacharya, et al., 1999	Bignell, Dunlop, et al., 1998	Stashenko, Cervantes, et al., 1998	Tümen, Baser, et al., 1998
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-Innowax FSC	Supelcowax-10	Carbowax 20M	Carbowax 20M	FFAP
Column length (m)	60.	60.	60.	45.	50.
Carrier gas	He	He	He	Hydrogen
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.32
Phase thickness (μm)		0.25	0.25	1.0
T_start (C)	60.	40.	50.	60.	50.
T_end (C)	240.	200.	150.	200.	180.
Heat rate (K/min)	4.	3.	2.	2.	10.
Initial hold (min)	10.	3.	10.	5.	1.
Final hold (min)	10.	30.	20.
I	1474.	1467.	1463.	1464.	1484.
Reference	Baser, Kirimer, et al., 1997	Wong and Lai, 1996	Tirado, Stashenko, et al., 1995	Kollmannsberger, Nitz, et al., 1992	Brophy, Davies, et al., 1989
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary
Active phase	Carbowax 20M
Column length (m)	25.
Carrier gas
Substrate
Column diameter (mm)	0.30
Phase thickness (μm)
T_start (C)	40.
T_end (C)	220.
Heat rate (K/min)	2.
Initial hold (min)	5.
Final hold (min)
I	1462.
Reference	Nykanen, 1986
Comment	MSDC-RI

References

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

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]

Cheraif, Ben Jannet, et al., 2007
Cheraif, I.; Ben Jannet, H.; Hammami, M.; Khouja, M.L.; Mighri, Z., Chemical composition and antimicrobial activity of essential oils of Cupressus arizonica Greene, Biochem. Syst. Ecol., 2007, 35, 12, 813-820, https://doi.org/10.1016/j.bse.2007.05.009 . [all data]

Gil A., Van Baren C.M., et al., 2007
Gil A.; Van Baren C.M.; Lira P.M.D.L.; Bandoni A.L., Identification of the genotype from the content and composition of the essential oil of lemon verbena (Aloysia citriodora Palau), J. Agric. Food Chem., 2007, 55, 21, 8664-8669, https://doi.org/10.1021/jf0708387 . [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]

Pinto, Salgueiro, et al., 2007
Pinto, E.; Salgueiro, L.R.; Cavaleiro, C.; Palmeira, A.; Goncalves, M.J., In vitro susceptibility of some species of yeasts and filamentous fungi to essential oils of Salvia of?cinalis, Ind. Crops Prod., 2007, 26, 2, 135-141, https://doi.org/10.1016/j.indcrop.2007.02.004 . [all data]

Borges, Rojas, et al., 2006
Borges, R.; Rojas, L.B.; Cegarra, J.A.; Usubillaga, A., Study of the essential oils from the leaves and flowers of Lepechinia conferta (Benth) Epl., Flavour Fragr. J., 2006, 21, 1, 155-157, https://doi.org/10.1002/ffj.1550 . [all data]

Fanciullino, Tomi, et al., 2006
Fanciullino, A.-L.; Tomi, F.; Luro, F.; Desjobert, J.M.; Casanova, J., Chemical variability of peel and leaf oils of mandarins, Flavour Fragr. J., 2006, 21, 2, 359-367, https://doi.org/10.1002/ffj.1658 . [all data]

Lan Phi N.T., Nishiyama C., et al., 2006
Lan Phi N.T.; Nishiyama C.; Choi H.-S.; Sawamura M., Evaluation of aroma characteristic compounds of Citrus natsudaidai Hayata (Natsudaidai) cold-pressed peel oil, Biosci. Biotechnol. Biochem., 2006, 70, 8, 1832-1838, https://doi.org/10.1271/bbb.50705 . [all data]

Lee, Umano, et al., 2005
Lee, S.-J.; Umano, K.; Shibamoto, T.; Lee, K.-G., Identification of volatile components in basil (Ocimum basilicum L.) and thyme leaves (Thymus vulgaris L.) and their antioxidant properties, Food Chem., 2005, 91, 1, 131-137, https://doi.org/10.1016/j.foodchem.2004.05.056 . [all data]

Qian and Wang, 2005
Qian, M.C.; Wang, Y., Seasonal Variations of Volatile Composition and Odor Activity Value of Marion (Rubus spp. hyb) and Thornless Evergreen (R.laciniatus L.) Blackberries, J. Food. Sci., 2005, 70, 1, c13-c20, https://doi.org/10.1111/j.1365-2621.2005.tb09013.x . [all data]

Choi, 2004
Choi, H.-S., Aroma evaluation of an aquatic herb, changpo (Acorus calamus Var. angustatus Bess), by AEDA and SPME, J. Agric. Food Chem., 2004, 52, 26, 8099-8104, https://doi.org/10.1021/jf040239p . [all data]

Orav, Stulova, et al., 2004
Orav, A.; Stulova, I.; Kailas, T.; Müürisepp, M., Effect of storage on the essential oil composition of piper nigrum L. fruits of different ripening states, J. Agric. Food Chem., 2004, 52, 9, 2582-2586, https://doi.org/10.1021/jf030635s . [all data]

Raal, Paaver, et al., 2004
Raal, A.; Paaver, U.; Arak, E.; Orav, A., Content and composition of the essential oil of Thymus serpyllum L. growing wild in Estonia, Medicina (Kaunas), 2004, 40, 8, 795-800. [all data]

Cabanillas, Lopez, et al., 2003
Cabanillas, C.M.; Lopez, M.L.; Daniele, G.; Zygadlo, J.A., Essential oil composition of Aloysia polystachya (Griseb.) Moldenke under rust disease, Flavour Fragr. J., 2003, 18, 5, 446-448, https://doi.org/10.1002/ffj.1249 . [all data]

Mookdasanit, Tamura, et al., 2003
Mookdasanit, J.; Tamura, H.; Yoshizawa T.; Tokunaga T.; Nakanishi, K., Trace Volatile Compounds in Essential Oil of Citrus Sudachi by Means of Modified Solvent Extraction Method, Food Sci Technol. Res., 2003, 9, 1, 54-61, https://doi.org/10.3136/fstr.9.54 . [all data]

Suleimenov, Atazharova, et al., 2003
Suleimenov, E.M.; Atazharova, G.A.; Demirchi, B.; Baser, K.H.C.; Adekenov, S.M., Essential oil composition of Artemisia Lercheana and A. Sieversiana of Kazakhstan flora in Recent problems of development of new medicines of natural origin, Proceedings of symposium, St.Petersburg - Pushkin, 2003, 382-385. [all data]

Tu, Onishi, et al., 2003
Tu, N.T.M.; Onishi, Y.; Son, U.S.; Ogawa, E.; Ukeda, H.; Sawamura, M., Characteristic odour components of Citrus inflata Hort. Ex Tanaka (Mochiyu) cold-pressed peel oil, Flavour Fragr. J., 2003, 18, 5, 454-459, https://doi.org/10.1002/ffj.1252 . [all data]

Umano, Hagi, et al., 2002
Umano, K.; Hagi, Y.; Shibamoto, T., Volatile chemicals identified in extracts from newly hybrid citrus, dekopon (Shiranuhi mandarin Suppl. J.), J. Agric. Food Chem., 2002, 50, 19, 5355-5359, https://doi.org/10.1021/jf0203951 . [all data]

Lota, de Rocca Serra, et al., 2001
Lota, M.-L.; de Rocca Serra, D.; Tomi, F.; Casanova, J., Chemical variability of peel and leaf essential oils of 15 species of mandarins, Biochem. Syst. Ecol., 2001, 29, 1, 77-104, https://doi.org/10.1016/S0305-1978(00)00029-6 . [all data]

Orav and Kann, 2001
Orav, A.; Kann, J., Determination of peppermint and orange aroma compounds in food and beverages, Proc. Est. Acad. Sci. Chem., 2001, 50, 4, 217-225. [all data]

Korány, Mednyánszky, et al., 2000
Korány, K.; Mednyánszky, Zs.; Amtmann, M., Preliminary results of a recognition method visualizing the aroma and fragrance features, Acta Aliment., 2000, 29, 2, 187-198, https://doi.org/10.1556/AAlim.29.2000.2.9 . [all data]

Mallavarapu, Rao, et al., 2000
Mallavarapu, G.R.; Rao, L.; Ramesh, S., Volatile constituents of the leaf and fruit oils of Murraya koenigii Spreng., L. Ess. Oil Res., 2000, 12, 6, 766-768, https://doi.org/10.1080/10412905.2000.9712211 . [all data]

Umano, Hagi, et al., 2000
Umano, K.; Hagi, Y.; Nakahara, K.; Shoji, A.; Shibamoto, T., Volatile chemicals identified in extracts from leaves of Japanese mugwort (Artemisia princeps Pamp.), J. Agric. Food Chem., 2000, 48, 8, 3463-3469, https://doi.org/10.1021/jf0001738 . [all data]

Labuckas, Zygadlo, et al., 1999
Labuckas, D.O.; Zygadlo, J.A.; Faillaci, S.M.; Espinar, L.A., Constituents of the volatile oil of Porophyllum obscurum (Spreng.) D.C., Flavour Fragr. J., 1999, 14, 2, 107-108, https://doi.org/10.1002/(SICI)1099-1026(199903/04)14:2<107::AID-FFJ799>3.0.CO;2-E . [all data]

Ngassoum, Yonkeu, et al., 1999
Ngassoum, M.B.; Yonkeu, S.; Jirovetz, L.; Buchbauer, G.; Schmaus, G.; Hammerschmidt, F.-J.H., Chemical composition of essential oils of Lantana camara leaves and flowers from Cameroon and Madagascar, Flavour Fragr. J., 1999, 14, 4, 245-250, https://doi.org/10.1002/(SICI)1099-1026(199907/08)14:4<245::AID-FFJ819>3.0.CO;2-X . [all data]

Rao, Bhattacharya, et al., 1999
Rao, B.R.R.; Bhattacharya, A.K.; Mallavarapu, G.R.; Ramesh, S., Volatile constituents of different parts of cornmint (Mentha arvensis L.), Flavour Fragr. J., 1999, 14, 5, 262-264, https://doi.org/10.1002/(SICI)1099-1026(199909/10)14:5<262::AID-FFJ766>3.0.CO;2-6 . [all data]

Bignell, Dunlop, et al., 1998
Bignell, C.M.; Dunlop, P.J.; Brophy, J.J., Volatile leaf oils of some South-Western and Southern Australian species of the genus Eucalyptus (Series 1). Part XIX, Flavour Fragr. J., 1998, 13, 2, 131-139, https://doi.org/10.1002/(SICI)1099-1026(199803/04)13:2<131::AID-FFJ710>3.0.CO;2-X . [all data]

Stashenko, Cervantes, et al., 1998
Stashenko, E.E.; Cervantes, M.; Combariza, Y.; Martínez, J.R., HRGC-FID-MSD Analysis of the Secondary Metabolites Obtained by Different Extraction Methods from Lepechinia schiedeana, and Evaluation of its Antioxidant Activity in vitro in 20th International Symposium on Capillary Chromatography, 1998, 1-11. [all data]

Tümen, Baser, et al., 1998
Tümen, G.; Baser, K.H.C.; Demirci, B.; Ermin, N., The essential oils of Satureja coerulea Janka and Thymus aznavourii Velen., Flavour Fragr. J., 1998, 13, 1, 65-67, https://doi.org/10.1002/(SICI)1099-1026(199801/02)13:1<65::AID-FFJ695>3.0.CO;2-Q . [all data]

Baser, Kirimer, et al., 1997
Baser, K.H.C.; Kirimer, N.; Duman, H., Composition of the essential oil of Micromeria dolichodontha P. H. Davis, Flavour Fragr. J., 1997, 12, 4, 289-291, https://doi.org/10.1002/(SICI)1099-1026(199707)12:4<289::AID-FFJ640>3.0.CO;2-A . [all data]

Wong and Lai, 1996
Wong, K.C.; Lai, F.Y., Volatile constituents from the fruits of four Syzygium species grown in Malaysia, Flavour Fragr. J., 1996, 11, 1, 61-66, https://doi.org/10.1002/(SICI)1099-1026(199601)11:1<61::AID-FFJ539>3.0.CO;2-1 . [all data]

Tirado, Stashenko, et al., 1995
Tirado, C.B.; Stashenko, E.E.; Combariza, M.Y.; Martinez, J.R., Comparative study of Colombian citrus oils by high-resolution gas chromatography and gas chromatography-mass spectrometry, J. Chromatogr. A, 1995, 697, 1-2, 501-513, https://doi.org/10.1016/0021-9673(94)00955-9 . [all data]

Kollmannsberger, Nitz, et al., 1992
Kollmannsberger, H.; Nitz, S.; Drawert, F., UBer die Aromastoffzusammensetzung von Hochdruckextrakten. I. Pfeffer (Piper nigrum, Var. muntok), Z. Lebensm. Unters Forsch., 1992, 194, 6, 545-551, https://doi.org/10.1007/BF01185481 . [all data]

Brophy, Davies, et al., 1989
Brophy, J.J.; Davies, N.W.; Southwell, I.A.; Stiff, I.A.; Williams, L.R., Gas chromatographic quality control for oil of Melaleuca terpinen-4-ol type (Australian tea tree), J. Agric. Food Chem., 1989, 37, 5, 1330-1335, https://doi.org/10.1021/jf00089a027 . [all data]

Nykanen, 1986
Nykanen, I., High Resolution Gas Chromatographic - Mass Spectrometric determination of the Flavour Composition of Wild Majoram (Origanum vulgare L.) Cultivated in Finland, Z. Lebensm Unters Forsch, 1986, 183, 4, 267-272, https://doi.org/10.1007/BF01087742 . [all data]

Notes

Go To: Top, Normal alkane 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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