(3S,3aR,3bR,4S,7R,7aR)-4-Isopropyl-3,7-dimethyloctahydro-1H-cyclopenta[1,3]cyclopropa[1,2]benzen-3-ol

Formula: C₁₅H₂₆O
Molecular weight: 222.3663
IUPAC Standard InChI: InChI=1S/C15H26O/c1-9(2)11-6-5-10(3)15-8-7-14(4,16)13(15)12(11)15/h9-13,16H,5-8H2,1-4H3
IUPAC Standard InChIKey: KONGRWVLXLWGDV-UHFFFAOYSA-N
CAS Registry Number: 23445-02-5
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:
- (3R,3aR,3bR,4S,7R,7aR)-4-Isopropyl-3,7-dimethyloctahydro-1H-cyclopenta[1,3]cyclopropa[1,2]benzen-3-ol
Stereoisomers:
Other names: Cubebol
Information on this page:
Other data available:
- Gas Chromatography
Options:
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Normal alkane RI, polar column, custom temperature program

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	Innowax FSC	HP Innowax FSP	Innowax FSC	Innowax FSC	HP-Innowax FSC
Column length (m)	60.	60.	60.	60.	60.
Carrier gas	Nitrogen	N2	He	He	N2
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
Program	60 0C (10 min) 1 0C/min -> 220 0C (10 min) 1 0C/min -> 240 0C	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C	60C(10min) => 4C/min >220C (10min) => 1C/min => 240C	60C(10min) => 4C/min >220C (10min) => 1C/min => 240C	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C
I	1957.	1957.	1957.	1957.	1957.
Reference	Kaya, Benirci, et al., 2007	Tabanca N., Demirci B., et al., 2007	Baser, Özek, et al., 2006	Baser, Özek, et al., 2006	Demirci B., Baser K.H.C., et al., 2006
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-Innowax FSC	HP-Innowax FSC	HP-Innowax FSC	HP-Innowax FSC	HP-Innowax FSC
Column length (m)	60.	60.	60.	60.	60.
Carrier gas	He	He	N2	N2	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
Program	60C(10min) => 4C/min => 220C (10min) => 1C/min => 240C	60(10min) => 4C/min => 220C(10min) => 1C/min => 240C	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C	60C(10min) => 4C/min => 220C (10min) => 1C/min => 240C	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C
I	1957.	1957.	1957.	1957.	1957.
Reference	Erdurak, Coskun, et al., 2006	Suleimenov Y.M., Atazhanova G.A., et al., 2006	Tunalier, Candan, et al., 2006	Demirci, Demirci, et al., 2005	Sezik E., Kocakulak E., et al., 2005
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-Innowax FSC	HP-Innowax FSC	HP-Innowax FSC	HP-Innowax FSC	HP-Innowax
Column length (m)	60.	60.	60.	60.	60.
Carrier gas	N2	He	He	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
Program	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C	60C (10min) => 4C/min => 220C (10min) => 1C/min => 240C	60 0C (10 min) 4 K/min -> 220 0C (10 min) 1 K/min -> 240 0C
I	1957.	1957.	1957.	1957.	1957.
Reference	Demirci, Paper, et al., 2004	Kivcak, Akay, et al., 2004	Kivcak, Akay, et al., 2004	Demirci, Baser, et al., 2003	Baser, Demirci, et al., 2002
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	Innowax	Innowax FSC	HP-Innowax	HP-Innowax FSC	Innowax
Column length (m)	60.	60.	60.	60.	60.
Carrier gas	He		He	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
Program	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C	60 0C (10 min) 10 K/min -> 220 0C (10 min) 1K/min -> 240 0C	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C	60C(10min) => 4C/min => 200C(10min) => 1C/min => 240C
I	1957.	1957.	1957.	1957.	1957.
Reference	Baser, Nuriddinov, et al., 2002	Tunalier, Kirimer, et al., 2002	Baser, Demirci, et al., 2001	Kirimer N., Tabanea N., et al., 2001	Özcan, Akgül, et al., 2001
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	Innowax FSC	HP-Innowax FSC	Innowax	Innowax FSC	Innowax FSC
Column length (m)	60.	60.	60.	60.	60.
Carrier gas	He		He	He	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
Program	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C	60 0C (10 min) 4 K/min -> 220 0C (10 min) 1 K/min -> 240 0C	60C(10 min) => 4C/min => 220C(10min) => 1C/min => 240C	60 0C (10 min) 4 0C/min -> 220 0C (10 min) 1 0C/min -> 240 0C
I	1957.	1957.	1957.	1957.	1957.
Reference	Tabanca N., Demirci F., et al., 2001	Tabanca, Kirimer, et al., 2001	Baser, Özek, et al., 2000	Kirimer, Tabanca, et al., 2000	Kirimer, Tabanca, et al., 1999
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary
Active phase	Innowax	DB-Wax
Column length (m)	60.	60.
Carrier gas		N2
Substrate
Column diameter (mm)	0.25
Phase thickness (μm)	0.25	0.25
Program	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C	not specified
I	1957.	1964.
Reference	Baser, Kürkcüoglu, et al., 1998	Weyerstahl, Marschall, et al., 1998
Comment	MSDC-RI	MSDC-RI

References

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

Kaya, Benirci, et al., 2007
Kaya, A.; Benirci, B.; Baser, K.H.C., Micromorphology of glandular trichomes of Nepeta congesta Fisch. Mey. var. congesta (LAmiaceae) and chemical analysis of the essential oils, South African J. Botany, 2007, 73, 1, 29-34, https://doi.org/10.1016/j.sajb.2006.05.004 . [all data]

Tabanca N., Demirci B., et al., 2007
Tabanca N.; Demirci B.; Crockett S.L.; Baser K.H.C.; Wedge D.E., Chemical composition and antifungal activity of Arnica longifolia, Aster hesperius, and Chrysothamnus nauseosus essential oils, J. Agric. Food Chem., 2007, 55, 21, 8430-8435, https://doi.org/10.1021/jf071379c . [all data]

Baser, Özek, et al., 2006
Baser, K.H.C.; Özek, G.; Özek, T.; Duran, A.; Duman, H., Composition of the essential oils of Rhabdosciadium oligocarpum (Post ex Boiss.) Hedge et Lamond and Rhabdosciadium microcalycinum Hand.-Mazz., Flavour Fragr. J., 2006, 21, 4, 650-655, https://doi.org/10.1002/ffj.1639 . [all data]

Demirci B., Baser K.H.C., et al., 2006
Demirci B.; Baser K.H.C.; Tabanca N.; Wedge D.E., Characterization of volatile constituents of Haplopappus greenei and studies on the antifungal activity against phytopathogens, J. Agric. Food Chem., 2006, 54, 8, 3146-3150, https://doi.org/10.1021/jf053222v . [all data]

Erdurak, Coskun, et al., 2006
Erdurak, C.S.; Coskun, M.; Demirci, B.; Baser, K.H.C., Composition of the essential oil of fruits and roots of Ferulago isaurica Pesmen and F. syriaca Boiss. (Umbelliferae) from Turkey, Flavour Fragr. J., 2006, 21, 1, 118-121, https://doi.org/10.1002/ffj.1540 . [all data]

Suleimenov Y.M., Atazhanova G.A., et al., 2006
Suleimenov Y.M.; Atazhanova G.A.; Ozek T.; Demirci B.; Kulyyasov A.T.; Adekenov S.M.; Baser K.H.C., Essential oil composition of three species of Achillea from Kazakhstan, Chem. Nat. Compd. (Engl. Transl.), 2006, 37, 5, 447-450, https://doi.org/10.1023/A:1014471326724 . [all data]

Tunalier, Candan, et al., 2006
Tunalier, Z.; Candan, N.T.; Demirci, B.; Baser, K.H., The essential oil composition of Acroptilon repens (L.) DC. of Turkish origin, Flavour Fragr. J., 2006, 21, 3, 462-464, https://doi.org/10.1002/ffj.1670 . [all data]

Demirci, Demirci, et al., 2005
Demirci, B.; Demirci, F.; Dönmez, A.A.; Franz, G.; Paper, D.H.; Baser, K.H.C., Effects of Salvia essential oils on the chorioallantoic membrane (CAM) assay, Pharm. Biol., 2005, 43, 8, 666-671, https://doi.org/10.1080/13880200500383397 . [all data]

Sezik E., Kocakulak E., et al., 2005
Sezik E.; Kocakulak E.; Baser K.H.C.; Ozek T., Composition of the essential oils of Juniperus oxycedrus subsp macrocarpa from Turkey, Chem. Nat. Compd. (Engl. Transl.), 2005, 41, 3, 352-354, https://doi.org/10.1007/s10600-005-0149-0 . [all data]

Demirci, Paper, et al., 2004
Demirci, F.; Paper, D.H.; Demirci, F.; Hüsnü Can Baser, K.; Franz, G., Essential oil of Betula pendula Roth. buds, eCAM, 2004, 1, 3, 301-303. [all data]

Kivcak, Akay, et al., 2004
Kivcak, B.; Akay, S.; Demirci, B.; Baser, K.H.C., Chemical composition of essential oils from leaves and twigs of Pistacia lentiscus, Pistacia lentiscus var. chia, and Pistacia terebinthus from Turkey, Pharm. Biol, 2004, 42, 4-5, 360-366, https://doi.org/10.1080/13880200490519677 . [all data]

Demirci, Baser, et al., 2003
Demirci, B.; Baser, K.H.C.; Yildiz, B.; Bahcecioglu, Z., Composition of the essential oils of six endemic Salvia spp. from Turkey, Flavour Fragr. J., 2003, 18, 2, 116-121, https://doi.org/10.1002/ffj.1173 . [all data]

Baser, Demirci, et al., 2002
Baser, K.H.C.; Demirci, B.; Kirimer, N.; Satil, F.; Tumen, G., The essential oils of Thymus migricus and T. fedtschenkoi var. handelii from Turkey, Flavour Fragr. J., 2002, 17, 1, 41-45, https://doi.org/10.1002/ffj.1036 . [all data]

Baser, Nuriddinov, et al., 2002
Baser, K.H.C.; Nuriddinov, H.R.; Ozek, T.; Demirci, A.B.; Azcan, N.; Nigmatullaev, A.M., Essential oil of Arischrada korolkowii from the Chatkal mountains of Uzbekistan, Chem. Nat. Compd. (Engl. Transl.), 2002, 38, 1, 51-53, https://doi.org/10.1023/A:1015729731464 . [all data]

Tunalier, Kirimer, et al., 2002
Tunalier, Z.; Kirimer, N.; Baser, K.H.C., The composition of essential oils from various parts of Juniperus foetidissima, Chem. Nat. Compd. (Engl. Transl.), 2002, 38, 1, 43-47, https://doi.org/10.1023/A:1015725630556 . [all data]

Baser, Demirci, et al., 2001
Baser, K.H.C.; Demirci, B.; Tabanca, N.; Özek, T.; Gören, N., Composition of the essential oils of Tanacetum armenum (DC.) Schultz Bip., T. balsamita L., T. chiliophyllum (Fisch. Mey.) Schultz Bip. var. chiliophyllum and T. haradjani (Rech. fil.) Grierson and the enantiomeric distribution of camphor and carvone, Flavour Fragr. J., 2001, 16, 3, 195-200, https://doi.org/10.1002/ffj.977 . [all data]

Kirimer N., Tabanea N., et al., 2001
Kirimer N.; Tabanea N.; Demirci B.; Baser K.H.C.; Duman H.; Aytac Z., The essential oil of a new Sideritis species: Sideritis ozturkii Aytac and Aksoy, Chem. Nat. Compd. (Engl. Transl.), 2001, 37, 3, 234-237, https://doi.org/10.1023/A:1012561806033 . [all data]

Özcan, Akgül, et al., 2001
Özcan, M.; Akgül, A.; Bascr, K.H.C.; Özck, T.; Tabanca, N., Essential oil composition of sea fennel (Crithmum maritimum) form Turkey, Nahrung/Food, 2001, 45, 5, 353-356, https://doi.org/10.1002/1521-3803(20011001)45:5<353::AID-FOOD353>3.0.CO;2-4 . [all data]

Tabanca N., Demirci F., et al., 2001
Tabanca N.; Demirci F.; Ozek T.; Tumen G.; Baser K.H.C., Composition and antimicrobial activity of the essential oil of Origanum x dolichosiphon P. H. Davis, Chem. Nat. Compd. (Engl. Transl.), 2001, 37, 3, 238-241, https://doi.org/10.1023/A:1012513922871 . [all data]

Tabanca, Kirimer, et al., 2001
Tabanca, N.; Kirimer, N.; Can Baser, K.H., The composition of essential oils from two varieties of Sideritis erythrantha var. erythrantha and var. cedretorum, Turk. J. Chem., 2001, 25, 201-208. [all data]

Baser, Özek, et al., 2000
Baser, K.H.C.; Özek, T.; Demirci, B.; Duman, H., Composition of the essential oil of Prangos heyniae H. Duman et M. F. Watson, a new endemic from Turkey, Flavour Fragr. J., 2000, 15, 1, 47-49, https://doi.org/10.1002/(SICI)1099-1026(200001/02)15:1<47::AID-FFJ869>3.0.CO;2-9 . [all data]

Kirimer, Tabanca, et al., 2000
Kirimer, N.; Tabanca, N.; Özek, T.; Tümen, G.; Baser, K.H.C., Essential oils of annual Sideritis species growing in Turkey, Pharm. Biol., 2000, 38, 2, 106-111, https://doi.org/10.1076/1388-0209(200004)3821-1FT106 . [all data]

Kirimer, Tabanca, et al., 1999
Kirimer, N.; Tabanca, N.; Ozek, T.; Basher, K.H.C.; Tumen, G., Composition of essential oils from two endemic Sideritis species of Turkey, Chem. Natural Comp., 1999, 35, 1, 61-64, https://doi.org/10.1007/BF02238211 . [all data]

Baser, Kürkcüoglu, et al., 1998
Baser, K.H.C.; Kürkcüoglu, M.; Aytac, Z., Composition of the essential oil of Salvia euphratica Montbret ex Bentham var. euphratica from Turkey, Flavour Fragr. J., 1998, 13, 1, 63-64, https://doi.org/10.1002/(SICI)1099-1026(199801/02)13:1<63::AID-FFJ694>3.0.CO;2-Z . [all data]

Weyerstahl, Marschall, et al., 1998
Weyerstahl, P.; Marschall, H.; Thefeld, K.; Subba, G.C., Constituents of the essential oil from the rhizomes of Hedychium gardnerianum Roscoe, Flavour Fragr. J., 1998, 13, 6, 377-388, https://doi.org/10.1002/(SICI)1099-1026(199811/12)13:6<377::AID-FFJ755>3.0.CO;2-F . [all data]

Notes

Go To: Top, Normal alkane RI, polar column, custom temperature program, References

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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