2-Cyclohexen-1-one, 3-methyl-6-(1-methylethyl)-

Formula: C₁₀H₁₆O
Molecular weight: 152.2334
IUPAC Standard InChI: InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9H,4-5H2,1-3H3
IUPAC Standard InChIKey: YSTPAHQEHQSRJD-UHFFFAOYSA-N
CAS Registry Number: 89-81-6
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:
- Isopiperitone
Stereoisomers:
- 2-Cyclohexen-1-one, 3-methyl-6-(1-methylethyl)-, (S)-
Other names: p-Menth-1-en-3-one; Piperitone; 3-Carvomenthenone; 1-Methyl-4-isopropyl-1-cyclohexen-3-one; 6-Isopropyl-3-methyl-2-cyclohexen-1-one; 3-Methyl-6-(1-methylethyl)-2-cyclohexen-1-one; 3-Methyl-6-isopropyl-2-cyclohexen-1-one; 6-isopropyl-3-methylcyclohex-2-enone
Information on this page:
Other data available:
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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	BP-20	CP Wax 52 CB	HP-Innowax	PEG-20M
Column length (m)	60.	50.	60.	30.	60.
Carrier gas	Helium	Helium	Helium	Helium	He
Substrate
Column diameter (mm)	0.22	0.22	0.25	0.25	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	60.	60.	40.	40.	90.
T_end (C)	230.	220.	220.	250.	225.
Heat rate (K/min)	2.	2.	3.	2.	3.
Initial hold (min)				5.
Final hold (min)	30.	20.			15.
I	1696.	1722.	1716.	1748.	1738.
Reference	Museli, Pau, et al., 2009	Ottavioli, Bighelli, et al., 2009	Chen, Chyau, et al., 2007	Formisano, Rigano, et al., 2007	Gil A., Van Baren C.M., et al., 2007
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	TC-FFAP	DB-Wax	DB-Wax	Carbowax 20M	CP-Wax
Column length (m)		60.	60.	60.	30.
Carrier gas	He			N2	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.25	0.32
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	60.	70.	70.	40.	40.
T_end (C)	220.	230.	230.	190.	180.
Heat rate (K/min)	3.	2.	2.	10.	5.
Initial hold (min)		2.	2.	2.	2.
Final hold (min)	30.	20.	20.	15.
I	1735.	1730.	1729.	1748.	1705.
Reference	Kurose, Okamura, et al., 2007	Lan Phi N.T., Nishiyama C., et al., 2006	Lan Phi N.T., Nishiyama C., et al., 2006	Babu and Kaul, 2005	Ka, Choi, 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	BP-20	DB-Wax	DB-Wax	DB-Wax
Column length (m)	30.	50.	60.	60.	60.
Carrier gas	He		He	He	Helium
Substrate
Column diameter (mm)	0.25	0.22	0.25	0.25	0.25
Phase thickness (μm)	0.25	0.25
T_start (C)	40.	60.	60.	60.	70.
T_end (C)	250.	220.	220.	220.	210.
Heat rate (K/min)	4.	2.	2.	2.	2.
Initial hold (min)			4.	4.
Final hold (min)	10.	20.			60.
I	1715.	1728.	1722.	1722.	1735.
Reference	Salehi, Sonboli, et al., 2005	Blanc, Muselli, et al., 2004	Jiang and Kubota, 2004	Jiang and Kubota, 2004	Mookdasanit, Tamura, 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	DB-Wax	PEG-20M	Carbowax 20M	CP-Wax 52CB
Column length (m)	50.	60.	50.	50.	50.
Carrier gas		He	He	He	He
Substrate
Column diameter (mm)	0.2	0.25	0.2	0.22	0.30
Phase thickness (μm)	0.2			0.25	0.25
T_start (C)	50.	40.	70.	60.	40.
T_end (C)	220.	220.	220.	220.	220.
Heat rate (K/min)	4.	2.	2.	2.	3.
Initial hold (min)	5.				5.
Final hold (min)
I	1740.	1738.	1720.	1717.	1730.
Reference	Stashenko, Jaramillo, et al., 2003	Jiang and Kubota, 2001	Orav and Kann, 2001	Vernin, Lageot, et al., 2001	Chagonda, Makanda, et al., 2000
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-Innowax	BP-20	BP-20	DB-Wax	HP-Innowax FSC
Column length (m)	60.	25.	25.	60.	60.
Carrier gas	He	N2	H2	H2	He
Substrate
Column diameter (mm)	0.25	0.5	0.33	0.32	0.25
Phase thickness (μm)	0.25		0.5	0.25
T_start (C)	60.	60.	80.	60.	60.
T_end (C)	220.	200.	220.	220.	240.
Heat rate (K/min)		5.	5.	3.	4.
Initial hold (min)	10.				10.
Final hold (min)					10.
I	1748.	1740.	1744.	1714.	1748.
Reference	Kaya, Baser, et al., 1999	Rao, Bhattacharya, et al., 1999	Bignell, Dunlop, et al., 1998	Werkhoff, Güntert, et al., 1998	Baser, Kirimer, et al., 1997
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	BP-20	BP-20	BP-20	BP-20	BP-20
Column length (m)	25.	25.	25.	25.	25.
Carrier gas	H2	H2	H2	H2
Substrate
Column diameter (mm)	0.33	0.33	0.33	0.33	0.33
Phase thickness (μm)	0.5	0.5	0.5	0.5	0.5
T_start (C)	80.	80.	80.	80.	80.
T_end (C)	220.	220.	220.	220.	220.
Heat rate (K/min)	5.	5.	5.	5.	5.
Initial hold (min)
Final hold (min)
I	1744.	1744.	1744.	1744.	1744.
Reference	Bignell, Dunlop, et al., 1997	Bignell, Dunlop, et al., 1997, 2	Bignell, Dunlop, et al., 1997, 3	Bignell, Dunlop, et al., 1997, 4	Bignell, Dunlop, et al., 1997, 5
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	BP-20	DB-Wax	TC-Wax	Carbowax 20M	DB-Wax
Column length (m)	25.	30.	60.	45.	30.
Carrier gas	H2	N2		Hydrogen
Substrate
Column diameter (mm)	0.33	0.319	0.25	0.32	0.32
Phase thickness (μm)	0.5	0.25		1.0
T_start (C)	80.	60.	80.	60.	70.
T_end (C)	220.	300.	240.	200.	200.
Heat rate (K/min)	5.	8.	3.	2.	4.
Initial hold (min)			5.	5.	2.
Final hold (min)		15.
I	1744.	1739.	1737.	1699.	1745.
Reference	Bignell, Dunlop, et al., 1997, 6	Malizia, Molli, et al., 1996	Shuichi, Masazumi, et al., 1996	Kollmannsberger, Nitz, et al., 1992	Wyllie, Brophy, et al., 1990
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary
Active phase	Carbowax 20M	Carbowax 20M
Column length (m)	100.	100.
Carrier gas
Substrate
Column diameter (mm)	0.25	0.25
Phase thickness (μm)
T_start (C)	70.	70.
T_end (C)	170.	170.
Heat rate (K/min)	1.	1.
Initial hold (min)
Final hold (min)
I	1737.	1739.
Reference	Shibamoto and Jennings, 1977	Shibamoto and Jennings, 1977
Comment	MSDC-RI	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]

Ottavioli, Bighelli, et al., 2009
Ottavioli, J.; Bighelli, A.; Casanova, J.; Bang, B.T.; Y., GC (retention indices), GC-MS, and 13C NMR of two citral-rich Cymbopogon leaf oils: C. Flexuosus and C. tortilis, Spectroscopy Lett., 2009, 42, 8, 506-512, https://doi.org/10.1080/00387010903022350 . [all data]

Chen, Chyau, et al., 2007
Chen, C.-C.; Chyau, C.-C.; Hseu, TY.-H., Production of a COX-2 inhibitor, 2,4,5-trimethoxybenzaldehyde, with submerged cultured Antrodia camphorata, Lett. Appl. Microbiol., 2007, 44, 4, 387-392, https://doi.org/10.1111/j.1472-765X.2006.02087.x . [all data]

Formisano, Rigano, et al., 2007
Formisano, C.; Rigano, D.; Napolitano, F.; Senatore, F.; Arnold, N.A.; Piozzi, F.; Rosselli, S., Volatile constituents of Calamintha ariganifolia Boiss. growing wild in Lebanon, Natural Product Communications, 2007, 2, 12, 1253-1256. [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]

Kurose, Okamura, et al., 2007
Kurose, K.; Okamura, D.; Yatagai, M., Composition of the essential oils from the leaves of nine Pinus species and the cones of three of Pinus species, Flavour Fragr. J., 2007, 22, 1, 10-20, https://doi.org/10.1002/ffj.1609 . [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]

Babu and Kaul, 2005
Babu, K.G.D.; Kaul, V.K., Variation in essential oil composition of rose-scented geranium (Pelargonium sp.) distilled by different distillation techniques, Flavour Fragr. J., 2005, 20, 2, 222-231, https://doi.org/10.1002/ffj.1414 . [all data]

Ka, Choi, et al., 2005
Ka, M.-H.; Choi, E.H.; Chun, H.-S.; Lee, K.-G., Antioxidative Activity of Volatile Extracts Isolated from Angelica tenuissimae Roots, Peppermint Leaves, Pine Needles, and Sweet Flag Leaves, J. Agric. Food Chem., 2005, 53, 10, 4124-4129, https://doi.org/10.1021/jf047932x . [all data]

Salehi, Sonboli, et al., 2005
Salehi, P.; Sonboli, A.; Eftekhar, F.; Nejad-Ebrahimi, S.; Yousefzadi, M., Essential Oil Composition, Antibacterial and Antioxidant Activity of the Oil and Various Extracts of Ziziphora clinopodioides subsp. rigida (BOISS.) RECH. f. from Iran, Biol. Pharm. Bull., 2005, 28, 10, 1892-1896, https://doi.org/10.1248/bpb.28.1892 . [all data]

Blanc, Muselli, et al., 2004
Blanc, M.-C.; Muselli, A.; Bradesi, P.; Casanova, J., Chemical composition and variability of the essential oil of Inula graveolens from Corsica, Flavour Fragr. J., 2004, 19, 4, 314-319, https://doi.org/10.1002/ffj.1304 . [all data]

Jiang and Kubota, 2004
Jiang, L.; Kubota, K., Differences in the volatile components and their odor characteristics of green and ripe fruits and dried pericarp of Japanese pepper (Xanthoxylum piperitum DC.), J. Agric. Food Chem., 2004, 52, 13, 4197-4203, https://doi.org/10.1021/jf030663a . [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]

Stashenko, Jaramillo, et al., 2003
Stashenko, E.E.; Jaramillo, B.E.; Martínez, J.R., Comparación de la composición química y de la actividad antioxidante in vitro de los metabolitos secundarios volátiles de plantas de la familia verbenaceae, Rev. Acad. Colomb. Cienc. Exactas Fis. Nat., 2003, 27, 105, 579-597. [all data]

Jiang and Kubota, 2001
Jiang, L.; Kubota, K., Formation by mechanical stimulus of the flavor compounds in young leaves of Japanese pepper (Xanthoxylum piperitum DC.), J. Agric. Food Chem., 2001, 49, 3, 1353-1357, https://doi.org/10.1021/jf001166m . [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]

Vernin, Lageot, et al., 2001
Vernin, G.; Lageot, C.; Gaydou, E.M.; Parkanyi, C., Analysis of the essential oil of Lippia graveolens HBK from El Salvador, Flavour Fragr. J., 2001, 16, 3, 219-226, https://doi.org/10.1002/ffj.984 . [all data]

Chagonda, Makanda, et al., 2000
Chagonda, L.S.; Makanda, C.; Chalchat, J.-C., The essential oils of wild and cultivated Cymbopogon validus (Stapf) Stapf ex Burtt Davy and Elionurus muticus (Spreng.) Kunth from Zimbabwe, Flavour Fragr. J., 2000, 15, 2, 100-104, https://doi.org/10.1002/(SICI)1099-1026(200003/04)15:2<100::AID-FFJ874>3.0.CO;2-Y . [all data]

Kaya, Baser, et al., 1999
Kaya, A.; Baser, K.H.C.; Tümen, G.; Koca, F., The essential oil of Acinos suaveolens (Sm.) G. Don fil. Acinos arvensis (Lam.) Dandy and Acinos rotundifolius Pers. growing wild in Turkey, Flavour Fragr. J., 1999, 14, 1, 60-64, https://doi.org/10.1002/(SICI)1099-1026(199901/02)14:1<60::AID-FFJ785>3.0.CO;2-0 . [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]

Werkhoff, Güntert, et al., 1998
Werkhoff, P.; Güntert, M.; Krammer, G.; Sommer, H.; Kaulen, J., Vacuum headspace method in aroma research: flavor chemistry of yellow passion fruits, J. Agric. Food Chem., 1998, 46, 3, 1076-1093, https://doi.org/10.1021/jf970655s . [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]

Bignell, Dunlop, et al., 1997
Bignell, C.M.; Dunlop, P.J.; Brophy, J.J.; Fookes, C.J.R., Volatile leaf oils of some South-Western and Southern Australian species of the genus Eucalyptus (Series I). Part XIV: Subgenus Monocalyptus, Flavour Fragr. J., 1997, 12, 3, 177-183, https://doi.org/10.1002/(SICI)1099-1026(199705)12:3<177::AID-FFJ626>3.0.CO;2-9 . [all data]

Bignell, Dunlop, et al., 1997, 2
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 I). Part XV: Subgenus symphyomyrtus, section bisectaria, series levispermae, Flavour Fragr. J., 1997, 12, 3, 185-193, https://doi.org/10.1002/(SICI)1099-1026(199705)12:3<185::AID-FFJ627>3.0.CO;2-B . [all data]

Bignell, Dunlop, et al., 1997, 3
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 I). Part XVI: Subgenus symphyomyrtus, section bisectaria, series cneorifoliae, series porantherae and series falcatae, Flavour Fragr. J., 1997, 12, 261-267. [all data]

Bignell, Dunlop, et al., 1997, 4
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 I). Part XVII: Subgenus symphyomyrtus (i) section bisectaria, series calycogonae and (ii) section dumaria, series dumosae, series rigentes and series ovulares, Flavour Fragr. J., 1997, 12, 269-275. [all data]

Bignell, Dunlop, et al., 1997, 5
Bignell, C.M.; Dunlop, P.J.; Brophy, J.J., Volatile leaf oils of some Queensland and Norther Australian species of the genus Eucalyptus (Series II) Part II. Subgenera (a) Blakella, (b) Corymbia, (c) Unnamed, (d) Idiogenes, (e) Monocalyptus and (f) Symphyomyrtus, Flavour Fragr. J., 1997, 12, 4, 277-284, https://doi.org/10.1002/(SICI)1099-1026(199707)12:4<277::AID-FFJ642>3.0.CO;2-B . [all data]

Bignell, Dunlop, et al., 1997, 6
Bignell, C.M.; Dunlop, P.J.; Brophy, J.J., Volatile leaf oils of some south-western and southern Australian speices of the genus Eucalyptus (Series I). Part XVIII. A. Subgenus monocalyptus. B. Subgenus Symphyomyrtus: (i) section Guilfoyleanae; (ii) section bisectaria, series accedentes, series occidentales, series levispermae, series loxophlebae, series macrocarpae, series orbifoliae, series calycogonae; (iii) section dumaria, series incrassatae and series ovulares, Flavour Fragr. J., 1997, 12, 423-432. [all data]

Malizia, Molli, et al., 1996
Malizia, R.A.; Molli, J.S.; Cardell, D.A.; Retamar, J.A., Volatile constituents of the essential oil of Nepeta cataria L. grown in Cordoba Province (Argentina), J. Essent. Oil Res., 1996, 8, 5, 565-567, https://doi.org/10.1080/10412905.1996.9700691 . [all data]

Shuichi, Masazumi, et al., 1996
Shuichi, H.; Masazumi, N.; Hiromu, K.; Kiyoshi, F., Comparison of volatile compounds berween the crude drugs, Onji-tsutsu and Onji-niki, Nippon nogei kagaku kaishi, 1996, 70, 2, 151-160. [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]

Wyllie, Brophy, et al., 1990
Wyllie, S.G.; Brophy, J.J.; Sarafis, V.; Hobbs, M., Volatile Components of the Fruit of Pistacia Lentiscus, J. Food. Sci., 1990, 55, 5, 1325-1326, https://doi.org/10.1111/j.1365-2621.1990.tb03926.x . [all data]

Shibamoto and Jennings, 1977
Shibamoto, T.; Jennings, W.G., The volatile composition of the leaf oil of California Juniper (J. californica Carr.) in Proceedings of VII International Congress of Essential Oils, October 7-11, 1977, Kyoto, Japan, 1977, 413-418. [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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