Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-

Formula: C₁₀H₁₄O
Molecular weight: 150.2176
IUPAC Standard InChI: InChI=1S/C10H14O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-8H,5H2,1-3H3
IUPAC Standard InChIKey: DCSCXTJOXBUFGB-UHFFFAOYSA-N
CAS Registry Number: 80-57-9
Chemical structure:
This structure is also available as a 2d Mol file
Stereoisomers:
- Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-, (1S)-
- D-Verbenone
Other names: 2-Pinen-4-one; Berbenone; Verbenone; 4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one
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Other data available:
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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	HP-Innowax	Innowax FSC	Innowax FSC	DB-Wax	HP-Innowax FSC
Column length (m)	60.	60.	60.	60.	60.
Carrier gas	Helium	Helium	Helium	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	not specified	60 0C (10 min) 4 0C/min -> 220 0C (10 min) 1 0C/min -> 240 0C	60 0C (10 min) 4 0C/min -> 220 0C (10 min) 1 0C/min -> 240 0C	40C(3min) => 2C/min => 150C => 4C/min => 200C (20min)	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C
I	1733.	1725.	1725.	1714.	1725.
Reference	Feng, Cui, et al., 2011	Polatoglu, Demirci, et al., 2010	Baser, Demirci, et al., 2009	Seo, Kim, et al., 2007	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	Innowax FSC	Carbowax 20M
Column length (m)	60.	60.	60.	60.
Carrier gas		He	He	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.25
Phase thickness (μm)	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	not specified
I	1724.	1725.	1725.	1726.	1730.
Reference	Tabanca, Demirci, et al., 2006	Sezik E., Kocakulak E., et al., 2005	Viljoen, Subramoney, et al., 2005	Baser, Özek, et al., 2004	Vinogradov, 2004
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	HP-Innowax FSC	HP-Innowax FSC	HP-Innowax
Column length (m)	60.	60.	60.	60.	60.
Carrier gas	He	He	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	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(40min)	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C
I	1725.	1725.	1725.	1725.	1725.
Reference	Baser, Demirci, et al., 2003	Demirci, Baser, et al., 2003	Kaya, Demirci, et al., 2003	Kürkcüoglu, Demirci, et al., 2003	Viljoen, van Vuuren, et al., 2003
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-Innowax	Innowax FSC	Innowax	HP-Innowax	HP-Innowax
Column length (m)	60.	60.	60.	60.	60.
Carrier gas	He	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	60 0C (10 min) 4 K/min -> 220 0C (10 min) 1 K/min -> 240 0C	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	60 0C (10 min) 4 K/min -> 220 0C (10 min) 1 K/min -> 240 0C
I	1725.	1725.	1725.	1725.	1725.
Reference	Baser, Demirci, et al., 2002	Baser, Demirei, et al., 2002	Baser, Nuriddinov, et al., 2002	Baser, Demirci, et al., 2001	Gören, Demirci, et al., 2001
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	HP-Wax	Innowax	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	50 0C 3 K/min -> 200 0C 8 K/min -> 280 0C	60 0C (10 min) 4 K/min -> 220 0C (10 min) 1 K/min -> 240 0C	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C
I	1725.	1725.	1735.	1725.	1726.
Reference	Kirimer N., Tabanea N., et al., 2001	Tabanca, Kirimer, et al., 2001	Usubillaga, Aparicio, et al., 2001	Baser, Özek, et al., 2000	Baser, Kürkcüoglu, et al., 1998
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary
Active phase	DB-Wax	DB-Wax	Carbowax 20M
Column length (m)	60.	60.
Carrier gas	N2	He
Substrate
Column diameter (mm)		0.25
Phase thickness (μm)	0.25
Program	not specified	45C(4min) => 30C/min => 60C (5min) => 3C/min => 220C(40min)	not specified
I	1716.	1724.	1730.
Reference	Weyerstahl, Marschall, et al., 1998	Ziegleder, 1998	Shibamoto, 1987
Comment	MSDC-RI	MSDC-RI	MSDC-RI

References

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

Feng, Cui, et al., 2011
Feng, T.; Cui, J.-J.; Xiao, Z.-B.; Tian, H.-X.; Yi, F.-P.; Ma, X., Chemical composition od essential oil from the peel of Chinese Torreya grandis Frt, Org. Chem. International, 2011, 2011, 1-5, https://doi.org/10.1155/2011/187372 . [all data]

Polatoglu, Demirci, et al., 2010
Polatoglu, K.; Demirci, F.; Demirci, B.; Goren, N.; Baser, K.H.C., Antimicrobial activity and essential oil composition of a new T. argyrophyllum (C. Koch) Tvzel var. argyrophyllium chemotype, J. Oleo Sci., 2010, 59, 6, 307-313, https://doi.org/10.5650/jos.59.307 . [all data]

Baser, Demirci, et al., 2009
Baser, K.H.C.; Demirci, B.; Kurkcuoglu, M.; Satin, F.; Tumen, G., Comparative morphological and phytochemical charactertization of Salvia cadmica and S. smyrnaea, Pak. J. Bot., 2009, 41, 4, 1545-1555. [all data]

Seo, Kim, et al., 2007
Seo, H.-Y.; Kim, J.-H.; Song, H.-P.; Kim, D.-H.; Byun, M.-W.; Kwon, J.-H.; Kima, K.-S., Effects of gamma irradiation on the yields of volatile extracts of Angelica gigas Nakai, Radiat. Phys. Chem., 2007, 76, 11-12, 1869-1874, https://doi.org/10.1016/j.radphyschem.2007.03.020 . [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]

Tabanca, Demirci, et al., 2006
Tabanca, N.; Demirci, B.; Ozek, T.; Kirimer, N.; Can Baser, K.H.; Bedir, E.; Khan, I.A.; Wedge, D.E., Gas chromatographic-mass spectrometric analysis of essential oils from Pimpinella species gathered from Central and Northern Turkey, J. Chromatogr. A, 2006, 1117, 2, 194-205, https://doi.org/10.1016/j.chroma.2006.03.075 . [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]

Viljoen, Subramoney, et al., 2005
Viljoen, A.M.; Subramoney, S.; van Vuuren, S.F.; Baser, K.H.C.; Demirci, B., The composition, geographical variation and antimicrobial activity of Lippia javanica (Verbenaceae) leaf essential oils, J. Ethnopharmacol., 2005, 96, 1-2, 271-277, https://doi.org/10.1016/j.jep.2004.09.017 . [all data]

Baser, Özek, et al., 2004
Baser, K.H.C.; Özek, T.; Kirimer, N.; Deliorman, D.; Ergun, F., Composition of the essential oils of Galium aparine L. and Galium odoratum (L.) Scop. from Turkey, J. Essent. Oil Res., 2004, 16, 4, 305-307, https://doi.org/10.1080/10412905.2004.9698728 . [all data]

Vinogradov, 2004
Vinogradov, B.A., Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]

Baser, Demirci, et al., 2003
Baser, K.H.C.; Demirci, B.; Dekebo, A.; Dagne, E., Essential oils of some Boswellia spp., myrrh and opopanax, Flavour Fragr. J., 2003, 18, 2, 153-156, https://doi.org/10.1002/ffj.1166 . [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]

Kaya, Demirci, et al., 2003
Kaya, A.; Demirci, B.; Baser, K.H.C., The essential oil of Seseli tortuosum L. growing in Turkey, Flavour Fragr. J., 2003, 18, 2, 159-161, https://doi.org/10.1002/ffj.1162 . [all data]

Kürkcüoglu, Demirci, et al., 2003
Kürkcüoglu, M.; Demirci, B.; Tabanca, N.; Özek, T.; Baser, K.H.C., The essential oil of Achillea falcata L., Flavour Fragr. J., 2003, 18, 3, 192-194, https://doi.org/10.1002/ffj.1176 . [all data]

Viljoen, van Vuuren, et al., 2003
Viljoen, A.; van Vuuren, S.; Ernst, E.; Klepser, M.; Demirci, B.; Baser, H.; van Wyk, B.-E., Osmitopsis asteriscoides (Asteraceae)-the antimicrobial activity and essential oil composition of a Cape-Dutch remedy, J. Ethnopharmacol., 2003, 88, 2-3, 137-143, https://doi.org/10.1016/S0378-8741(03)00191-0 . [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, Demirei, et al., 2002
Baser, K.H.C.; Demirei, B.; Özek, T.; Akalin, E.; Özhatay, N., Micro-distilled volatile compounds from Ferulago species growing in Western Turkey, Pharm. Biol., 2002, 40, 6, 466-471, https://doi.org/10.1076/phbi.40.6.466.8439 . [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]

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]

Gören, Demirci, et al., 2001
Gören, N.; Demirci, B.; Baser, K.H.C., Composition of the essential oils of Tanacetum spp. from Turkey, Flavour Fragr. J., 2001, 16, 3, 191-194, https://doi.org/10.1002/ffj.976 . [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]

Tabanca, Kirimer, et al., 2001
Tabanca, N.; Kirimer, N.; Demirci, B.; Demirci, F.; Can Baser, K.H., Composition and antimicrobial activity of the essential oils of Micromeria cristata subsp. phrygia and the enantiomeric distribution of borneol, J. Agric. Food Chem., 2001, 49, 9, 4300-4303, https://doi.org/10.1021/jf0105034 . [all data]

Usubillaga, Aparicio, et al., 2001
Usubillaga, A.; Aparicio, R.; Romero, M.; Rojas, L.B.; Khouri, N., Volatile constituents from the leaves of four Libanothamus species from the Venezuelan Andes, Flavour Fragr. J., 2001, 16, 3, 209-211, https://doi.org/10.1002/ffj.981 . [all data]

Baser, Özek, et al., 2000
Baser, K.H.C.; Özek, T.; Demirci, B.; Duman, H., Composition of the essential oil of Glaucosciadium cordifolium (Boiss.) Burtt et Davis from Turkey, Flavour Fragr. J., 2000, 15, 1, 45-46, https://doi.org/10.1002/(SICI)1099-1026(200001/02)15:1<45::AID-FFJ867>3.0.CO;2-L . [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.; Weirauch, M.; Thefeld, K.; Surburg, H., Constituents of commercial Labdanum oil, Flavour Fragr. J., 1998, 13, 5, 295-318, https://doi.org/10.1002/(SICI)1099-1026(1998090)13:5<295::AID-FFJ751>3.0.CO;2-I . [all data]

Ziegleder, 1998
Ziegleder, G., Volatile and odorous compounds in unprinted paperboard, Packag. Technol. Sci., 1998, 11, 5, 231-239, https://doi.org/10.1002/(SICI)1099-1522(1998090)11:5<231::AID-PTS437>3.0.CO;2-A . [all data]

Shibamoto, 1987
Shibamoto, T., Retention Indices in Essential Oil Analysis in Capillary Gas Chromatography in Essential Oil Analysis, Sandra, P.; Bicchi, C., ed(s)., Hutchig Verlag, Heidelberg, New York, 1987, 259-274. [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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