Thujone

Formula: C₁₀H₁₆O
Molecular weight: 152.2334
IUPAC Standard InChI: InChI=1S/C10H16O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6-8H,4-5H2,1-3H3/t7-,8-,10+/m1/s1
IUPAC Standard InChIKey: USMNOWBWPHYOEA-MRTMQBJTSA-N
CAS Registry Number: 546-80-5
Chemical structure:
This structure is also available as a 2d Mol file
Species with the same structure:
- 3-Isothujone
Stereoisomers:
Other names: Bicyclo[3.1.0]hexan-3-one, 4-methyl-1-(1-methylethyl)-, [1S-(1α,4α,5α)]-; α-Thujone; Thujone, cis; 3-Thujanone, (1S,4R,5R)-(-)-; Thujon; 3-Thujanone, (-)-; l-Thujone; 4-Methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-one-, (1S,4R,5R)-; 3-Thujone; cis-Thujone; (Z)-Thujone; (-)-Thujone; Bicyclo(3.1.0)hexan-3-one, 4-methyl-1-(1-methylethyl)-, (1S,4R,5R)-; NSC 93742; (1S,4R,5R)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-one; 1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-one
Information on this page:
Other data available:
- Mass spectrum (electron ionization)
- Gas Chromatography
Options:
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Normal alkane RI, polar column, custom temperature program

Go To: Top, References, Notes

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

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	Innowax FSC	Innowax FSC	CP-Wax 52 CB	HP Innowax	Carbowax 20M
Column length (m)	60.	60.	50.	50.	30.
Carrier gas	Helium	Helium	Helium	Helium	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.20	0.25
Phase thickness (μm)	0.25	0.25	0.20	0.25	0.25
Program	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	60 0C (5 min) 3 0C/min -> 250 0C (20 min) 1 0C/min -> 255 0C	40 0C (5 min) 2 0C/min -> 270 0C -> 260 0C (20 min)	not specified
I	1430.	1430.	1426.	1430.	1420.
Reference	Polatoglu, Demirci, et al., 2010	Baser, Demirci, et al., 2009	Genisheva and Oliveira, 2009	Mancini, Arnold, et al., 2009	Hudaib and Aburjai, 2007
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-Innowax	HP-Innowax FSC	HP-Innowax FSC	HP-Innowax	Carbowax 20M
Column length (m)	50.	60.	60.	50.
Carrier gas	He	He	N2
Substrate
Column diameter (mm)	0.2	0.25	0.25	0.2
Phase thickness (μm)	0.2	0.25	0.25	0.2
Program	40C(5min) => 2C/min => 250C (15min) => 10C/min => 270C	60(10min) => 4C/min => 220C(10min) => 1C/min => 240C	60C(10min) => 4C/min => 220C (10min) => 1C/min => 240C	not specified	not specified
I	1430.	1430.	1437.	1430.	1477.
Reference	Senatore, Apostolides Arnold, et al., 2006	Suleimenov Y.M., Atazhanova G.A., et al., 2006	Demirci, Demirci, et al., 2005	Senatore, Apostolides Arnold, 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	Carbowax 20M	Innowax FSC	HP-Innowax FSC	HP-Innowax FSC	Innowax FSC
Column length (m)		60.	60.	60.	60.
Carrier gas		He	He	N2
Substrate
Column diameter (mm)		0.25	0.25	0.25	0.25
Phase thickness (μm)		0.25	0.25	0.25	0.25
Program	not specified	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	1405.	1430.	1430.	1437.	1438.
Reference	Vinogradov, 2004	Baser, Demirci, et al., 2003	Demirci, Baser, et al., 2003	Hüsnü Can Baser, Demirci, et al., 2002	Tunalier, Kirimer, et al., 2002
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-Innowax	HP-Innowax	Innowax FSC	NB-351	Supelcowax-10
Column length (m)	60.	60.	60.	25.	30.
Carrier gas	He	He	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.32	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.2
Program	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	60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C	40C(5min) => 4C/min => 170C => 8C/min => 240C (12min)	not specified
I	1430.	1430.	1430.	1446.	1435.
Reference	Baser, Demirci, et al., 2001	Gören, Demirci, et al., 2001	Tabanca N., Demirci F., et al., 2001	Kerrola, Galambosi, et al., 1994	Jean, Garneau, et al., 1993
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary
Active phase	Polyethylene Glycol
Column length (m)
Carrier gas
Substrate
Column diameter (mm)
Phase thickness (μm)
Program	not specified
I	1420.
Reference	Grundschober, 1991
Comment	MSDC-RI

References

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

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]

Genisheva and Oliveira, 2009
Genisheva, Z.; Oliveira, J.M., Monoterpenic characterization of white cultivars from Vinhos Verdes appelation of origin (North Portugal), J. Inst. Brewing, 2009, 115, 4, 308-317, https://doi.org/10.1002/j.2050-0416.2009.tb00386.x . [all data]

Mancini, Arnold, et al., 2009
Mancini, E.; Arnold, N.A.; De Martino, L.; De Feo, V.; Formisano, C.; Rigano, D.; Senatore, F., Chemical composition and phytotoxic effects of essential oils of Salvia hierosolymitana Boiss. and Salvia multicaulis Vahl. var. simplicifolia Boiss. growing wild in Lebanon, Molecules, 2009, 14, 11, 4725-4736, https://doi.org/10.3390/molecules14114725 . [all data]

Hudaib and Aburjai, 2007
Hudaib, M.; Aburjai, T., Volatile components of Thymus vulgaris L. from wild-growing and cultivated plants in Jordan, Flavour Fragr. J., 2007, 22, 4, 322-327, https://doi.org/10.1002/ffj.1800 . [all data]

Senatore, Apostolides Arnold, et al., 2006
Senatore, F.; Apostolides Arnold, N.; Piozzi, F.; Formisano, C., Chemical composition of the essential oil of Salvia microstegia Boiss. et Balansa growing wild in Lebanon, J. Chromatogr. A, 2006, 1108, 2, 276-278, https://doi.org/10.1016/j.chroma.2006.01.066 . [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]

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]

Senatore, Apostolides Arnold, et al., 2004
Senatore, F.; Apostolides Arnold, N.; Piozzi, F., Chemical composition of the essential oil of Salvia multicaulis Vahl. var. simplicifolia Boiss. growing wild in Lebanon, J. Chromatogr. A, 2004, 1052, 1-2, 237-240, https://doi.org/10.1016/j.chroma.2004.08.095 . [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]

Hüsnü Can Baser, Demirci, et al., 2002
Hüsnü Can Baser, K.; Demirci, B.; Femirci, F.; Kocak, S.; Akinci, C.; Malyer, H.; Güleryüz, G., Composition and antimicrobial activity of the essential oil of Achellea multifida, Planta Medica, 2002, 68, 10, 941-943, https://doi.org/10.1055/s-2002-34923 . [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]

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]

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]

Kerrola, Galambosi, et al., 1994
Kerrola, K.; Galambosi, B.; Kallio, H., Volatile components and odor intensity of four phenotypes of hyssop (Hyssopus officinalis L.), J. Agric. Food Chem., 1994, 42, 3, 776-781, https://doi.org/10.1021/jf00039a035 . [all data]

Jean, Garneau, et al., 1993
Jean, F.-I.; Garneau, F.-X.; Collin, G.J.; Bouhajib, M.; Zamir, L.O., The essential oil and glycosidically bound volatile compounds of Taxus canadensis marsh, J. Essent. Oil Res., 1993, 5, 1, 7-11, https://doi.org/10.1080/10412905.1993.9698163 . [all data]

Grundschober, 1991
Grundschober, F., The identification of individual components in flavourings and flavoured foods, Z. Lebensm. Unters. Forsch., 1991, 192, 6, 530-534, https://doi.org/10.1007/BF01202508 . [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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