Pulegone

Formula: C₁₀H₁₆O
Molecular weight: 152.2334
IUPAC Standard InChI: InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3/t8-/m0/s1
IUPAC Standard InChIKey: NZGWDASTMWDZIW-QMMMGPOBSA-N
CAS Registry Number: 89-82-7
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:
- Cyclohexanone, 5-methyl-2-(1-methylethylidene)-
- 5-Methyl-2-(1-methylethenylidene)cyclohexanone
Other names: Cyclohexanone, 5-methyl-2-(1-methylethylidene)-, (R)-; p-Menth-4(8)-en-3-one, (R)-(+)-; (+)-(R)-Pulegone; (+)-Pulegone; (R)-(+)-Pulegone; d-p-Menth-4(8)-en-3-one; d-Pulegone; p-Menth-4(8)-en-3-one; Pulegone, (d); 1-Isopropylidene-4-methyl-2-cyclohexanone; 1-Methyl-4-isopropylidene-3-cyclohexanone; 3-Methyl-6-isopropylidenecyclohexanone; 4(8)-p-Menthen-3-one, (R)-(+)-; Pulegon; (+)-4(8)-Para-menthen-3-one; 5-Methyl-2-(1-methylethylidene)cyclohexanone, (R)-; (1R)-(+)-p-Menth-4(8)-en-3-one; (R)-Pulegone; Cyclohexanone, 5-methyl-2-(1-methylethylidene)-, (5R)-; NSC 15334; β-Pulegone
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Normal alkane RI, non-polar column, temperature ramp

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	HP-5 MS	RTX-1	RTX-1	HP-5	HP-5 MS
Column length (m)	60.	60.	60.	30.	30.
Carrier gas	Helium	Helium	Helium	Helium	Helium
Substrate
Column diameter (mm)	0.25	0.22	0.22	0.25	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	40.	60.	60.	60.	50.
T_end (C)	250.	230.	230.	240.	180.
Heat rate (K/min)	3.	2.	2.	3.	2.
Initial hold (min)	1.
Final hold (min)	20.	5.	5.
I	1243.	1215.	1215.	1237.	1235.
Reference	Sardashti, Valizadeh, et al., 2013	Bendiabdellah, El Amine Dib, et al., 2012	Bendiabdellah, El Amine Dib, et al., 2012	Bertoli, Lepnardi, et al., 2011	Hammami, Kamoun, et al., 2011
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-5 MS	HP-5 MS	DB-5	5 % Phenyl methyl siloxane	DB-5 MS
Column length (m)	30.	30.	30.	60.	30.
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)	70.	70.	60.	90.	40.
T_end (C)	290.	290.	240.	225.	250.
Heat rate (K/min)	5.	5.	3.	3.	4.
Initial hold (min)					2.
Final hold (min)	10.	10.		3.	2.
I	1244.	1242.	1237.	1236.	1244.
Reference	Radulovic, Blagojevic, et al., 2010	Radulovic, Dordevic, et al., 2010	Alim, Goze, et al., 2009	Retta, Gattuso, et al., 2009	Su, Wang, et al., 2009
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	ZB-1	DB-5	HP-5MS	HP-5MS	DB-5
Column length (m)	30.	50.	30.	30.	30.
Carrier gas	Nitrogen	He	He	He	He
Substrate
Column diameter (mm)	0.25	0.32	0.25	0.25	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	45.	50.	60.	60.	70.
T_end (C)	230.	280.	280.	280.	310.
Heat rate (K/min)	3.	5.	3.	3.	3.
Initial hold (min)		2.			5.
Final hold (min)		10.			20.
I	1209.	1249.	1224.	1235.	1230.
Reference	Mierendorff, Stahl-Biskup, et al., 2008	Baranauskiene R., Bylaite E., et al., 2007	Basta, Pavlovic, et al., 2007	Bozin B., Mlmica-Dukic N., et al., 2007	Coelho, Grosso, et al., 2007
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	Col-Elite 5MS	DB-1	DB-1	HP-5 MS	HP-5MS
Column length (m)	30.	50.	60.	30.	30.
Carrier gas	He	He	He	Helium	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
T_start (C)	30.	95.	60.	60.	60.
T_end (C)	246.	240.	250.	280.	280.
Heat rate (K/min)	3.	4.	5.	3.	3.
Initial hold (min)
Final hold (min)
I	1211.	1231.	1222.	1237.	1203.
Reference	Gudaityte and Venskutonis R.P., 2007	Pala-Paul, Brophy, et al., 2007	Salehi, Fakhari, et al., 2007	Vagionas, Graikou, et al., 2007	Bozin, Mimicá-Dukic, et al., 2006
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-1	HP-5	DB-5	Methyl Silicone	DB-5
Column length (m)	60.	30.	30.	25.	25.
Carrier gas		Helium	He	N2
Substrate
Column diameter (mm)	0.25	0.32	0.25	0.3	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.15	0.15
T_start (C)	60.	40.	60.	50.	40.
T_end (C)	250.	240.	260.	210.	220.
Heat rate (K/min)	5.	4.	4.	2.	3.
Initial hold (min)			4.	5.	5.
Final hold (min)	10.	5.
I	1221.	1234.	1239.	1252.	1238.
Reference	Hadian, Sonboli, et al., 2006	Miyazawa and Kawata, 2006	Morteza-Semnani, Saeedi, et al., 2006	Tonzibo, Coffy, et al., 2006	Chagonda and Chalchat, 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	HP-5MS	HP-5MS	DB-5
Column length (m)	30.	30.	30.	30.	30.
Carrier gas	He	He		He	He
Substrate
Column diameter (mm)	0.25	0.32	0.2	0.25	0.25
Phase thickness (μm)	0.25	0.25		0.25	0.25
T_start (C)	60.	40.	60.	60.	60.
T_end (C)	240.	250.	280.	275.	220.
Heat rate (K/min)	3.	5.	3.	4.	3.
Initial hold (min)		0.5			4.
Final hold (min)		2.
I	1238.	1223.	1237.	1243.	1237.
Reference	Chaverri and Cicció, 2005	Özel, Gögüs, et al., 2005	Petrakis, Roussis, et al., 2005	Sajjadi and Ghannadi, 2005	Salehi, Sefidkon, et al., 2005
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-1	DB-5	DB-5	PE-5	HP-5MS
Column length (m)	60.	30.	30.	30.	30.
Carrier gas	He	He	He	H2	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.32	0.25
Phase thickness (μm)	0.25		0.25	0.25	0.25
T_start (C)	60.	40.	40.	60.	60.
T_end (C)	250.	240.	260.	230.	280.
Heat rate (K/min)	5.	4.	2.	5.	3.
Initial hold (min)			5.	2.
Final hold (min)	10.		20.	4.
I	1225.	1237.	1237.	1253.	1240.
Reference	Salehi, Sonboli, et al., 2005	Sefidkon and Jamzad, 2005	Senatore, Apostolides Arnold, et al., 2005	Singh, Raina, et al., 2005	Slavkovska, Couladis, et al., 2005
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	RTX-1	HP-5 MS	HP-5	HP-5	DB-5
Column length (m)	60.	30.	30.	30.	30.
Carrier gas	He	He	He	He	Helium
Substrate
Column diameter (mm)	0.25	0.25	0.32	0.25	0.25
Phase thickness (μm)	0.25	0.50	0.25	0.32
T_start (C)	60.	60.	60.	60.	60.
T_end (C)	25.	260.	260.	250.	240.
Heat rate (K/min)	5.	3.	5.	5.	2.
Initial hold (min)			2.	3.
Final hold (min)	10.	20.	13.		999.
I	1220.	1245.	1221.	1228.	1234.
Reference	Sonboli, Salehi, et al., 2005	Topçu, Barla, et al., 2005	Yayli, Yasar, et al., 2005	Aghel, Yamini, et al., 2004	Miyazawa, Fuhita, et al., 2004
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5	DB-1	DB-5	DB-5	RSL-200
Column length (m)	50.	50.	30.	60.	30.
Carrier gas	Helium	N2		He	H2
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.32	0.32
Phase thickness (μm)		0.25	0.25		0.25
T_start (C)	60.	95.	50.	50.	40.
T_end (C)	240.	240.	250.	220.	280.
Heat rate (K/min)	2.	4.	3.	3.	6.
Initial hold (min)			5.		5.
Final hold (min)	999.				5.
I	1234.	1230.	1237.	1249.	1230.
Reference	Miyazawa, Fujita, et al., 2004	Palá-Paúl, Velasco-Negueruela, et al., 2004	Sefidkon, Jamzad, et al., 2004	Edris, Shalaby, et al., 2003	Jirovetz, Buchbauer, et al., 2003
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	ZB-1	HP-5	5 % Phenyl methyl siloxane	BP-1	HP-5
Column length (m)	30.	60.	30.	25.	30.
Carrier gas	N2		He	N2
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.50	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	45.	40.	75.	60.	60.
T_end (C)	230.	250.	200.	220.	275.
Heat rate (K/min)	3.	5.	3.	5.	4.
Initial hold (min)		15.	4.		4.
Final hold (min)			8.	10.
I	1209.	1235.	1237.	1219.	1232.
Reference	Mierendorff, Stahl-Biskup, et al., 2003	Stashenko, Jaramillo, et al., 2003	Cicció and Gómez-Laurito, 2002	Das, Ram, et al., 2002	Lockwood, Asghari, et al., 2002
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5	OV-101	OV-1	BP-1	CBP-1
Column length (m)	30.	50.	25.	25.	30.
Carrier gas	He	He	H2	N2	He
Substrate
Column diameter (mm)	0.25	0.2	0.25	0.5	0.25
Phase thickness (μm)	0.25		0.25
T_start (C)	70.	50.	40.	60.	60.
T_end (C)	250.	250.	220.	220.	240.
Heat rate (K/min)	3.	2.	3.	5.	4.
Initial hold (min)	3.		5.
Final hold (min)	2.		5.	10.
I	1207.	1219.	1204.	1220.	1214.
Reference	Phatak and Heble, 2002	Orav and Kann, 2001	Oberhofer, Nikiforov, et al., 1999	Rao, Bhattacharya, et al., 1999	Lamarque, Maestri, et al., 1998
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary
Active phase	OV-101	OV-101
Column length (m)	30.	30.
Carrier gas	He	He
Substrate
Column diameter (mm)	0.5	0.5
Phase thickness (μm)	0.8	0.8
T_start (C)	40.	40.
T_end (C)	220.	220.
Heat rate (K/min)	2.	2.
Initial hold (min)
Final hold (min)
I	1215.	1215.
Reference	De Pooter and Schamp, 1986	De Pooter and Schamp, 1986
Comment	MSDC-RI	MSDC-RI

References

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

Sardashti, Valizadeh, et al., 2013
Sardashti, A.R.; Valizadeh, J.; Adhami, Y., Variations in the essential oil composition of Peroskia abrotonolides of different growth stage in Baluchestan, Middle-East J. Sci. Res., 2013, 13, 6, 781-784. [all data]

Bendiabdellah, El Amine Dib, et al., 2012
Bendiabdellah, A.; El Amine Dib, M.; Djabou, N.; Allali, H.; Tabti, B.; Costa, J.; Myseli, A., Biological activities and volatile cinstituents of Daucus muricatus L. from Algeria, Chem. Centr. J., 2012, 6, 48, 1-22. [all data]

Bertoli, Lepnardi, et al., 2011
Bertoli, A.; Lepnardi, M.; Krzyzanowska, J.; Oleszek, W.; Pistelli, L., Mentha longifolia in vitro cultures as safe source of flavouring ingradients, Acta Biochem. Polonica, 2011, 58, 4, 581-587. [all data]

Hammami, Kamoun, et al., 2011
Hammami, I.; Kamoun, N.; Rebai, A., Biocontrol of Botrytis cinerea with essential oil and methanol extract of Viola odorata flowers, Archives of Appl. Sci. Res., 2011, 3, 5, 44-51. [all data]

Radulovic, Blagojevic, et al., 2010
Radulovic, N.; Blagojevic, P.; Palic, R., Comparative study of the leaf volatiles of Arctostaphylos uva-ursi (L.) Spreng. and Vaccinium vitis-idaea L. (Ericaceae), Molecules, 2010, 15, 9, 6168-6185, https://doi.org/10.3390/molecules15096168 . [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]

Alim, Goze, et al., 2009
Alim, A.; Goze, I.; Cetin, A.; Atas, A.; Vural, N.; Donmez, E., Antimicrobial activity of the essential oil of Cyclotrichimun niveum (Boiss.) Manden. Et Scheng, African J. Microbiol. Res., 2009, 3, 8, 422-425. [all data]

Retta, Gattuso, et al., 2009
Retta, D.; Gattuso, M.; Gattuso, S.; Lira, P. Di Leo; van Baren, C.; Ferraro, G.; Bandoni A., Essential oil composition of Achyrocline flaccida (Weinm.) DC. (Asteraceae) from different locations of Argentina, Biochem. Systematics Ecol., 2009, 36, 12, 877-881, https://doi.org/10.1016/j.bse.2008.11.001 . [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]

Mierendorff, Stahl-Biskup, et al., 2008
Mierendorff, H.-G.; Stahl-Biskup, E.; Posthumus, M.A.; van Beek, T.A., Composition of commercial Cape chamomile oil (Eriocephalus punctuatus / Eriocephalus tenuifolius), 2008, retrieved from http://www.chemische-analysen-hamburg.de/Publikationen?Cape_Chamomile_Oil/. [all data]

Baranauskiene R., Bylaite E., et al., 2007
Baranauskiene R.; Bylaite E.; Venskutonis R.P., Flavor retention of peppermint (Mentha piperita L.) essential oil spray-dried in modified starches during encapsulation and storage, J. Agric. Food Chem., 2007, 55, 8, 3027-3036, https://doi.org/10.1021/jf062508c . [all data]

Basta, Pavlovic, et al., 2007
Basta, A.; Pavlovic, M.; Couladis, M.; Tzakou, O., Essential oil composition of the flowerheads of Chrysanthemum coronarium L. from Greece, Flavour Fragr. J., 2007, 22, 3, 197-200, https://doi.org/10.1002/ffj.1781 . [all data]

Bozin B., Mlmica-Dukic N., et al., 2007
Bozin B.; Mlmica-Dukic N.; Samojlik I.; Jovin E., Antimicrobial and antioxidant properties of rosemary and sage (Rosmarinus officinalis L. and Salvia officinalis L., lamiaceae) essential oils, J. Agric. Food Chem., 2007, 55, 19, 7879-7885, https://doi.org/10.1021/jf0715323 . [all data]

Coelho, Grosso, et al., 2007
Coelho, J.A.; Grosso, C.; Pereira, A.P.; Burillo, J.; Urieta, J.S.; Figueiredo, A.C.; Barroso, J.G.; Mendes, R.L.; Palavra, A.M.F., Supercritical carbon dioxide extraction of volatiles from Satureja fruticosa Béguinot, Flavour Fragr. J., 2007, 22, 5, 438-442, https://doi.org/10.1002/ffj.1819 . [all data]

Gudaityte and Venskutonis R.P., 2007
Gudaityte, O.; Venskutonis R.P., Chemotypes of Achillea millefolium transferred from 14 different locations in Lithuania to the controlled environment, Biochem. Syst. Ecol., 2007, 35, 9, 582-592, https://doi.org/10.1016/j.bse.2007.03.016 . [all data]

Pala-Paul, Brophy, et al., 2007
Pala-Paul, J.; Brophy, J.J.; Perez-Alonso, M.J.; Usano, J.; Soria, S.C., Essential oil composition of the different parts of Eryngium corniculatum Lam. (Apiaceae) from Spain, J. Chromatogr. A, 2007, 1175, 2, 289-293, https://doi.org/10.1016/j.chroma.2007.10.061 . [all data]

Salehi, Fakhari, et al., 2007
Salehi, P.; Fakhari, A.R.; Ebrahimi, S.N.; Heydari, R., Rapid essential oil screening of Rosmarinus officinalis L. by hydrodistillation-headspace solvent microextraction, Flavour Fragr. J., 2007, 22, 4, 280-285, https://doi.org/10.1002/ffj.1793 . [all data]

Vagionas, Graikou, et al., 2007
Vagionas, K.; Graikou, K.; Ngassapa, O.; Runyoro, D.; Chinou, I., Composition and antimicrobial activity of the essential oils of three Satureja species growing in Tansania, Food Chem., 2007, 103, 2, 319-324, https://doi.org/10.1016/j.foodchem.2006.07.051 . [all data]

Bozin, Mimicá-Dukic, et al., 2006
Bozin, B.; Mimicá-Dukic, N.; Simin, N.; Anackov, G., Characterization of the volatile composition of essential oils of some lamiaceae spices and the antimicrobial and antioxidant activities of the entire oils, J. Agric. Food Chem., 2006, 54, 5, 1822-1828, https://doi.org/10.1021/jf051922u . [all data]

Hadian, Sonboli, et al., 2006
Hadian, J.; Sonboli, A.; Ebrahimi, S.N.; Mirjalili, M.H., Essential oil composition of Nepeta satureioides from Iran, Chem. Nat. Compd. (Engl. Transl.), 2006, 42, 2, 175-177, https://doi.org/10.1007/s10600-006-0071-0 . [all data]

Miyazawa and Kawata, 2006
Miyazawa, M.; Kawata, J., Identification of the Key Aroma Compounds in Dried Roots of Rubia cordifolia, L. Oleo Sci., 2006, 55, 1, 37-39, https://doi.org/10.5650/jos.55.37 . [all data]

Morteza-Semnani, Saeedi, et al., 2006
Morteza-Semnani, K.; Saeedi, M.; Akbarsadeh, M.; Moshiri, K., The essential oil composition of Onosma microcarpum DC., Flavour Fragr. J., 2006, 21, 2, 314-316, https://doi.org/10.1002/ffj.1597 . [all data]

Tonzibo, Coffy, et al., 2006
Tonzibo, Z.F.; Coffy, A.A.; Chalachat, J.C.; N'guessan, Y.T., Chemical composition of essential oils of Hoslundia opposita Vahl. from Ivory Coast., Flavour Fragr. J., 2006, 21, 5, 789-791, https://doi.org/10.1002/ffj.1715 . [all data]

Chagonda and Chalchat, 2005
Chagonda, L.S.; Chalchat, J.-C., The essential oil of the fruit of Garcinia huillensis Welw. ex. Oliv. from Zimbabwe, Flavour Fragr. J., 2005, 20, 3, 313-315, https://doi.org/10.1002/ffj.1420 . [all data]

Chaverri and Cicció, 2005
Chaverri, C.; Cicció, J.F., Essential oil of trees of the genus Ocotea (Lauraceae) in Costa Rica. I. Ocotea brenesii, Rev. Biol. Trop., 2005, 53, 3-4, 431-436, https://doi.org/10.15517/rbt.v53i3-4.14611 . [all data]

Özel, Gögüs, et al., 2005
Özel, M.Z.; Gögüs, F.; Hamilton, J.F.; Lewis, A.C., Analysis of volatile components from Ziziphora taurica subsp. taurica by steam distillation, superheated-water extraction, and direct thermal desorption with GC×GC-TOFMS, Anal. Bioanal. Chem., 2005, 382, 1, 115-119, https://doi.org/10.1007/s00216-005-3156-x . [all data]

Petrakis, Roussis, et al., 2005
Petrakis, P.V.; Roussis, V.; Papadimitriou, D.; Vagias, C.; Tsitsimpikou, C., The effect of terpenoid extracts from 15 pine species on the feeding behavioural sequence of the late instars of the pine processionary caterpillar Thaumetopoea pityocampa, Behav. Processes, 2005, 69, 3, 303-322, https://doi.org/10.1016/j.beproc.2004.12.008 . [all data]

Sajjadi and Ghannadi, 2005
Sajjadi, S.-E.; Ghannadi, A., Essential oil of the Persian sage, Salvia rhytidea Benth., Acta Pharm. Sin., 2005, 55, 321-326. [all data]

Salehi, Sefidkon, et al., 2005
Salehi, P.; Sefidkon, F.; Bazzaz Tolami, L.; Sonboli, A., Essential oil composition of Salvia palaestina Benth. from Iran, Flavour Fragr. J., 2005, 20, 5, 525-527, https://doi.org/10.1002/ffj.1448 . [all data]

Salehi, Sonboli, et al., 2005
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Sefidkon and Jamzad, 2005
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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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