Cyclohexanone, 2-methyl-5-(1-methylethenyl)-, trans-

Formula: C₁₀H₁₆O
Molecular weight: 152.2334
IUPAC Standard InChI: InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h8-9H,1,4-6H2,2-3H3/t8-,9-/m1/s1
IUPAC Standard InChIKey: AZOCECCLWFDTAP-RKDXNWHRSA-N
CAS Registry Number: 5948-04-9
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.
Stereoisomers:
Other names: p-Menth-8-en-2-one, trans-; trans-Dihydrocarvone; Carvone, Dihydro-, trans; p-Menth-8-en-2-one, E-; 5-Isopropenyl-2-methylcyclohexanone, trans; Dihydrocarvone; Cyclohexanone, 2-methyl-5-(1-methylethenyl)-, (2R,5R)-rel-; (2R,5R)-2-methyl-5-prop-1-en-2-ylcyclohexan-1-one
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Information on this page:
Other data available:
- Mass spectrum (electron ionization)
- Gas Chromatography
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Normal alkane RI, non-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	HP-1	DB-5 MS	HP-5 MS	OV-101	DB-5 MS
Column length (m)	30.	60.	30.	50.	60.
Carrier gas	Helium	Helium	Helium	Helium	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
T_start (C)	60.	40.	70.	70.	40.
T_end (C)	240.	250.	290.	220.	330.
Heat rate (K/min)	3.	5.	5.	2.	2.
Initial hold (min)		15.			12.
Final hold (min)		15.	10.		30.
I	1190.	1201.	1208.	1182.	1205.
Reference	Alizadeh, Khosh-Khui, et al., 2011	Mesa-Arango, Betancur-Galvis, et al., 2010	Radulovic, Dordevic, et al., 2010	Benites, Moiteiro, et al., 2009	Patil, Jayaprakasha, et al., 2009
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5 MS	CP Sil 5 CB	RTX-5 MS	HP-5	HP-5
Column length (m)	30.	30.	30.	30.	30.
Carrier gas	Helium	N2	He	N2	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
T_start (C)	40.	50.	45.	50.	50.
T_end (C)	250.	200.	210.	280.	280.
Heat rate (K/min)	4.	5.	3.	9.	9.
Initial hold (min)	2.			3.	3.
Final hold (min)	2.			3.	3.
I	1203.	1182.	1203.	1202.	1208.
Reference	Su, Wang, et al., 2009	Hnawia, Cabalion, et al., 2007	Hudaib and Aburjai, 2007	Abdelwahed, Hayder, et al., 2006	Abdelwahed, Hayder, et al., 2006
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	BP-1	DB-5	HP-5	HP-5	HP-5MS
Column length (m)	50.	30.	30.	60.	30.
Carrier gas	He	He	He	He	He
Substrate
Column diameter (mm)	0.22	0.25	0.25	0.32	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	60.	50.	50.	30.	60.
T_end (C)	220.	250.	300.	260.	275.
Heat rate (K/min)	2.	3.	5.	2.	15.
Initial hold (min)			5.	2.
Final hold (min)	20.	10.	5.	28.
I	1171.	1200.	1218.	1200.4	1200.
Reference	Boti, Muselli, et al., 2006	Havlik, Kokoska, et al., 2006	Figuérédo, Cabassu, et al., 2005	Leffingwell and Alford, 2005	Shams-Ardakani, Ghannadi, et al., 2005
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5	DB-5	DB-5	HP-5	HP-5
Column length (m)	30.	30.	60.	30.	60.
Carrier gas	He	He	He	Helium
Substrate
Column diameter (mm)	0.25	0.25	0.32	0.32	0.25
Phase thickness (μm)	0.25	0.25			0.25
T_start (C)	60.	60.	50.	70.	40.
T_end (C)	230.	240.	220.	210.	250.
Heat rate (K/min)	3.	4.	3.	2.	5.
Initial hold (min)					15.
Final hold (min)	20.			60.
I	1201.	1195.	1213.	1204.	1197.
Reference	Skoula and Grayer, 2005	Cabanillas, Lopez, et al., 2003	Edris, Shalaby, et al., 2003	Mookdasanit, Tamura, et al., 2003	Stashenko, Jaramillo, et al., 2003
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5	HP-5	HP-5	BP-1	HP-5
Column length (m)	30.	30.	30.	25.	30.
Carrier gas	He		N2	N2	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.33	0.25
Phase thickness (μm)	0.25	0.25	0.25	1.0	0.25
T_start (C)	60.	60.	60.	60.	60.
T_end (C)	240.	240.	220.	275.	275.
Heat rate (K/min)	3.	3.	5.	4.	4.
Initial hold (min)			10.
Final hold (min)
I	1202.	1210.	1202.	1199.	1202.
Reference	Kobaisy, Tellez, et al., 2002	Novak, Langbehn, et al., 2002	Gallori, Flamini, et al., 2001	Mohagheghzadeh, Shams-Ardakani, et al., 2000	Mohagheghzadeh, Shams-Ardakani, et al., 2000, 2
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary
Active phase	HP-5	HP-5
Column length (m)
Carrier gas
Substrate
Column diameter (mm)
Phase thickness (μm)
T_start (C)	40.	40.
T_end (C)	210.	210.
Heat rate (K/min)	2.	2.
Initial hold (min)
Final hold (min)
I	1197.	1197.
Reference	Collin, Deslauriers, et al., 1993	Collin, Deslauriers, et al., 1993
Comment	MSDC-RI	MSDC-RI

References

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

Alizadeh, Khosh-Khui, et al., 2011
Alizadeh, A.; Khosh-Khui, M.; Javidnia, K.; Firuzi, O.; Jokar, S.M., Chemical composition of the essential oil, total phenolic content and antioxidant activity in Origanum maiorana L. (Lamiaceae) cultivated in Iran, Adv. Environ. Biol., 2011, 5, 8, 2326-2331. [all data]

Mesa-Arango, Betancur-Galvis, et al., 2010
Mesa-Arango, A.C.; Betancur-Galvis, L.; Montiel, J.; Bueno, J.G.; Baena, A.; Duran, D.C.; Martinez, J.R.; Stashenko, E.E., Antifungal activity and chemical composition of the essential oils of Lippia alba (Miller) N.E. Brown grown in different regions of Colombia, J. Essential Oil Res., 2010, 22, 6, 568-574, https://doi.org/10.1080/10412905.2010.9700402 . [all data]

Radulovic, Dordevic, et al., 2010
Radulovic, N.; Dordevic, N.; Markovic, M.; Palic, R., Volatile constituents of Glechoma Hirsuta Waldst. Kit. and G. Hederacea L. (Lamiaceae), Bull. Chem. Soc. Ethiop., 2010, 24, 1, 67-76, https://doi.org/10.4314/bcse.v24i1.52962 . [all data]

Benites, Moiteiro, et al., 2009
Benites, J.; Moiteiro, C.; Miguel, G.; Rojo, L.; Lopez, J.; Venancio, F.; Ramalho, L.; Feio, S.; Dandlen, S.; Casanova, H.; Torres, I., Composition and biological activity of the essential oil of Peruvial Lantana camara, J. Chilean Chem. Soc., 2009, 54, 4, 379-384, https://doi.org/10.4067/S0717-97072009000400012 . [all data]

Patil, Jayaprakasha, et al., 2009
Patil, J.R.; Jayaprakasha, G.K.; Murthy, K.N.C.; Tichy, S.E.; Chetti, M.B.; Patil, B.S., Apoptosis-mediated proliferation inhibition of human colon cancer cells by volatile principles of Citrus auratifolia, Food Chem., 2009, 114, 4, 1351-1358, https://doi.org/10.1016/j.foodchem.2008.11.033 . [all data]

Su, Wang, et al., 2009
Su, Y.; Wang, C.; Yinlong, G., Analysis of volatile compounds from Mentha hapioealyx Briq. by GC-MS based on accurate mass measurements and retention indices, Acta Chem. Sinica, 2009, 67, 6, 546-554. [all data]

Hnawia, Cabalion, et al., 2007
Hnawia, E.; Cabalion, P.; Raunicher, I.; Waikedre, J.; Patissou, J.; Buchbauer, G.; Menut, C., The leaf essential oil of Murraya crenulata (Turcz.) Oliver from New Caledonia, Flavour Fragr. J., 2007, 22, 1, 32-34, https://doi.org/10.1002/ffj.1745 . [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]

Abdelwahed, Hayder, et al., 2006
Abdelwahed, A.; Hayder, N.; Kilani, S.; Mahmoud, A.; Chibani, J.; Hammami, M.; Chekir-Ghedira, L.; Ghedira, K., Chemical composition and antimicrobial activity of essential oils from Tunisian Pituranthos tortuosus (Coss.) Maire, Flavour Fragr. J., 2006, 21, 1, 129-133, https://doi.org/10.1002/ffj.1542 . [all data]

Boti, Muselli, et al., 2006
Boti, J.B.; Muselli, A.; Tomi, F.; Koukoua, G.; N'Guessan, T.Y.; Costa, J.; Casanova, J., Combined analysis of Cymbopogon giganteus Chiov. leaf oil from Ivory Coast by GC/RI, GC/MS and ¹³C-NMR, C.R. Chim., 2006, 9, 1, 164-168, https://doi.org/10.1016/j.crci.2005.10.003 . [all data]

Havlik, Kokoska, et al., 2006
Havlik, J.; Kokoska, L.; Vasickova, S.; Valterova, I., Chemical composition of essential oil from the seeds of Nigella arvensis L. and assessment of its actimicrobial activity, Flavour Fragr. J., 2006, 21, 4, 713-717, https://doi.org/10.1002/ffj.1713 . [all data]

Figuérédo, Cabassu, et al., 2005
Figuérédo, G.; Cabassu, P.; Chalchat, J.-C.; Pasquier, B., Studies of Mediterranean oregano populations- V. Chemical composition of essential oils of oregano: Origanum syriacum L. var. bevanii (Holmes) Ietswaart, O. syriacum L. var. sinaicum (Boiss.) Ietswaart, and O. syriacum L. var. syriacum from Lebanon and Israel, Flavour Fragr. J., 2005, 20, 164-168. [all data]

Leffingwell and Alford, 2005
Leffingwell, J.C.; Alford, E.D., Volatile constituents of Perique tobacco, Electron. J. Environ. Agric. Food Chem., 2005, 4, 2, 899-915. [all data]

Shams-Ardakani, Ghannadi, et al., 2005
Shams-Ardakani, M.; Ghannadi, A.; Badr, P.; Mohagheghzadeh, A., Biotransformation of terpenes and related compounds by suspension culture of Glycyrrhiza glabra L. (Papilionaceae), Flavour Fragr. J., 2005, 20, 2, 141-144, https://doi.org/10.1002/ffj.1401 . [all data]

Skoula and Grayer, 2005
Skoula, M.; Grayer, R.J., Volatile oils of Coridothymus capitatus, Satureja thymbra, Satureja spinosa and Thymbra calostachya (Lamiaceae) from Crete, Flavour Fragr. J., 2005, 20, 6, 573-576, https://doi.org/10.1002/ffj.1489 . [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]

Edris, Shalaby, et al., 2003
Edris, A.E.; Shalaby, A.S.; Fadel, H.M.; Abdel-Wahab, M.A., Evaluation of a chemotype of spearmint (Mentha spicata L.) grown in Siwa Oasis, Egypt, Eur. Food Res. Technol., 2003, 218, 1, 74-78, https://doi.org/10.1007/s00217-003-0802-4 . [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]

Kobaisy, Tellez, et al., 2002
Kobaisy, M.; Tellez, M.R.; Dayan, F.E.; Duke, S.O., Phytotoxicity and volatile constituents from leaves of Callicarpa japonica Thunb., Phytochemistry, 2002, 61, 1, 37-40, https://doi.org/10.1016/S0031-9422(02)00207-8 . [all data]

Novak, Langbehn, et al., 2002
Novak, J.; Langbehn, J.; Pank, F.; Franz. C.M., Essential oil compounds in a historical sample of marjoram (Origanum majorana L., Lamiaceae), Flavour Fragr. J., 2002, 17, 3, 175-180, https://doi.org/10.1002/ffj.1077 . [all data]

Gallori, Flamini, et al., 2001
Gallori, S.; Flamini, G.; Bilia, A.R.; Morelli, I.; Landini, A.; Vincieri, F.F., Chemical composition of some traditional herbal drug preparations: essential oil and aromatic water of costmary (Balsamita suaveolens Pers.), J. Agric. Food Chem., 2001, 49, 12, 5907-5910, https://doi.org/10.1021/jf0107656 . [all data]

Mohagheghzadeh, Shams-Ardakani, et al., 2000
Mohagheghzadeh, A.; Shams-Ardakani, M.; Ghannadi, A., Linalol-rich essential oil of Zataria multiflora Boiss. (Lamiaceae), Flavour Fragr. J., 2000, 15, 2, 119-122, https://doi.org/10.1002/(SICI)1099-1026(200003/04)15:2<119::AID-FFJ878>3.0.CO;2-V . [all data]

Mohagheghzadeh, Shams-Ardakani, et al., 2000, 2
Mohagheghzadeh, A.; Shams-Ardakani, M.; Ghannadi, A., Volatile constituents of callus and flower-bearing tops of Zataria multiflora Boiss. (Lamiaceae), Flavour Fragr. J., 2000, 15, 6, 373-376, https://doi.org/10.1002/1099-1026(200011/12)15:6<373::AID-FFJ923>3.0.CO;2-9 . [all data]

Collin, Deslauriers, et al., 1993
Collin, G.J.; Deslauriers, H.; Pageau, N.; Gagnon, M., Essential oil of Tansy (Tanacetum vulgare L.) of Canadian origin, J. Essent. Oil Res., 1993, 5, 6, 629-638, https://doi.org/10.1080/10412905.1993.9698296 . [all data]

Notes

Go To: Top, Normal alkane RI, non-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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