Isopulegol

Formula: C₁₀H₁₈O
Molecular weight: 154.2493
IUPAC Standard InChI: InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h8-11H,1,4-6H2,2-3H3/t8-,9+,10-/m0/s1
IUPAC Standard InChIKey: ZYTMANIQRDEHIO-AEJSXWLSSA-N
CAS Registry Number: 89-79-2
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:
- Cyclohexanol, 5-methyl-2-(1-methylethenyl)-
Stereoisomers:
Other names: Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, [1R-(1α,2β,5α)]-; p-Menth-8-en-3-ol, (1R,3R,4S)-(-)-; (-)-Isopulegol; L-isopulegol; 2-Isopropenyl-5-methylcyclohexanol-, (1R-(1alpha,2beta,5alpha))-; p-Menth-8(9)-en-3-ol; (1R,2S,5R)-5-Methyl-2-(prop-1-en-2-yl)cyclohexanol
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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	DB-1 MS	BP-1	DB-1	HP-5	HP-5
Column length (m)	30.	50.	60.	30.	25.
Carrier gas	Helium			He	He
Substrate
Column diameter (mm)	0.25	0.22	0.25	0.25	0.2
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.33
T_start (C)	40.	60.	70.	60.	60.
T_end (C)	250.	220.	230.	220.	240.
Heat rate (K/min)	6.	2.	2.	5.	3.
Initial hold (min)	1.		2.	10.
Final hold (min)	4.	20.	20.		7.
I	1127.	1130.	1148.	1148.	1143.
Reference	Seo, Kim, et al., 2009	Boti, Yao, et al., 2006	Lan Phi N.T., Nishiyama C., et al., 2006	Pintore G., Chessa M., et al., 2006	Duarte, Figueira, et al., 2005
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	Methyl Silicone	HP-5MS	PE-5	RSL-200	DB-5
Column length (m)	12.5	30.	30.	30.	30.
Carrier gas	He	He	H2	H2	H2
Substrate
Column diameter (mm)	0.25	0.25	0.32	0.32	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	50.	60.	60.	40.	60.
T_end (C)	270.	280.	230.	280.	280.
Heat rate (K/min)	4.	3.	5.	6.	4.
Initial hold (min)		5.	2.	5.	10.
Final hold (min)			4.	5.	40.
I	1144.	1142.	1165.	1145.	1146.
Reference	Ricci, Fraternale, et al., 2005	Setzer, Noletto, et al., 2005	Singh, Raina, et al., 2005	Jirovetz, Buchbauer, et al., 2003	Pino, Marbot, et al., 2003
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-5	DB-5	HP-5	BP-5	RSL-200
Column length (m)	60.	30.	30.	50.	60.
Carrier gas		N2	N2	H2	H2
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.25	0.32
Phase thickness (μm)	0.25	0.25	0.25	1.	0.25
T_start (C)	40.	50.	50.	60.	40.
T_end (C)	250.	250.	250.	270.	250.
Heat rate (K/min)	5.	4.	4.	6.	6.
Initial hold (min)	15.		5.
Final hold (min)
I	1146.	1146.	1146.	1156.	1129.
Reference	Stashenko, Jaramillo, et al., 2003	Farah, Fechtal, et al., 2002	Farah, Fechtal. M., et al., 2002	Doimo, 2001	Jirovetz, Puschmann, et al., 2000
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	OV-101	OV-1	BP-1	BP-1	DB-5
Column length (m)	50.	25.	25.	25.	30.
Carrier gas	N2	H2	N2	N2
Substrate
Column diameter (mm)	0.2	0.25	0.50	0.50	0.25
Phase thickness (μm)		0.25
T_start (C)	80.	40.	60.	60.	40.
T_end (C)	200.	220.	220.	220.	210.
Heat rate (K/min)	1.	3.	5.	5.	2.
Initial hold (min)		5.			2.
Final hold (min)	20.	5.			33.
I	1146.	1122.	1147.	1148.	1152.
Reference	Menon, Chacko, et al., 1999	Oberhofer, Nikiforov, et al., 1999	Rajeswara, Kaul, et al., 1996	Rajeswara, Kaul, et al., 1996	Sohounhloue, Dangou, et al., 1996
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary
Active phase	DB-1	DB-1	OV-101
Column length (m)	60.	60.	50.
Carrier gas	He	He	N2
Substrate
Column diameter (mm)	0.25	0.25	0.25
Phase thickness (μm)	0.25	0.25
T_start (C)	70.	70.	80.
T_end (C)	270.	270.	200.
Heat rate (K/min)	2.5	2.5	2.
Initial hold (min)	5.	5.
Final hold (min)
I	1146.	1146.	1137.
Reference	Tirado, Stashenko, et al., 1995	Tirado, Stashenko, et al., 1995	Sugisawa, Yamamoto, et al., 1989
Comment	MSDC-RI	MSDC-RI	MSDC-RI

References

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

Seo, Kim, et al., 2009
Seo, S.-M.; Kim, J.; Lee, S.-G.; Shin, C.-H.; Shin, S.-C.; Park, I.-K., Fumigant antitermitic activity of plant essential oils and components from Aiowan (Trachyspermum ammi), Allspice (Pimenta dioica), Caraway (Carum carvi), Dill (Anethum graveolens), Geranium (Pelargonium graveolens), and Litsea (Litsea cubeba( oils against Japanese termite (Reticulitermes speratus Kolbe), J. Agric. Food Chem., 2009, 57, 15, 6596-6602. [all data]

Boti, Yao, et al., 2006
Boti, J.B.; Yao, P.A.; Koukoua, G.; N'Guessan, T.Y.; Casanova, J., Components and chemical variability of Isolona campanulata Engler Diels leaf oil, Flavour Fragr. J., 2006, 21, 1, 166-170, https://doi.org/10.1002/ffj.1555 . [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]

Pintore G., Chessa M., et al., 2006
Pintore G.; Chessa M.; Manconi P.; Zanetti S.; Deriu A.; Tirillini B., Chemical composition and antimicrobial activities of essential oil of stachys glutinosa L. from Sardinia, Natural Product Communications, 2006, 1, 12, 1133-1136. [all data]

Duarte, Figueira, et al., 2005
Duarte, M.C.T.; Figueira, G.M.; Sartoratto, A.; Rehder, V.L.G.; Delarmelina, C., Anti-Candida activity of Brazilian medicinal plants, J. Ethnopharmacol., 2005, 97, 2, 305-311, https://doi.org/10.1016/j.jep.2004.11.016 . [all data]

Ricci, Fraternale, et al., 2005
Ricci, D.; Fraternale, D.; Giamperi, L.; Bucchini, A.; Epifano, F.; Burini, G.; Curini, M., Chemical composition, antimicrobial and antioxidant activity of the essential oil of Teucrium marum (Lamiaceae), J. Ethnopharmacol., 2005, 98, 1-2, 195-200, https://doi.org/10.1016/j.jep.2005.01.022 . [all data]

Setzer, Noletto, et al., 2005
Setzer, W.N.; Noletto, J.A.; Lawton, R.O.; Haber, W.A., Leaf essential oil composition of five Zanthoxylum species from Monteverde, Costa Rica, Molecular Diversity, 2005, 9, 1-3, 3-13, https://doi.org/10.1007/s11030-005-1298-6 . [all data]

Singh, Raina, et al., 2005
Singh, A.K.; Raina, V.K.; Naqvi, A.A.; Patra, N.K.; Kumar, B.; Ram, P.; Khanuja, S.P.S., Essential oil composition and chemoarrays of menthol mint (Mentha arvensis L. f. piperascens Malinvaud ex. Holmes) cultivars, Flavour Fragr. J., 2005, 20, 3, 302-305, https://doi.org/10.1002/ffj.1417 . [all data]

Jirovetz, Buchbauer, et al., 2003
Jirovetz, L.; Buchbauer, G.; Shafi, M.P.; Leela, N.K., Analysis of the essential oils of the leaves, stems, rhizomes and roots of the medicinal plant Alpinia galanga from southern India, Acta Pharm. Hung., 2003, 53, 73-81. [all data]

Pino, Marbot, et al., 2003
Pino, J.A.; Marbot, R.; Fuentes, V., Characterization of volatiles in Bullock's heart (Annona reticulata L.) fruit cultivars from Cuba, J. Agric. Food Chem., 2003, 51, 13, 3836-3839, https://doi.org/10.1021/jf020733y . [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]

Farah, Fechtal, et al., 2002
Farah, A.; Fechtal, M.; Chaouch, A., Effet de l'hybridation interspécifique sur la teneur et la composition chimique des huiles essentielles d'eucalyptus cultivés au Maroc, Biotechnol. Agron. Soc. Environ., 2002, 6, 3, 163-169. [all data]

Farah, Fechtal. M., et al., 2002
Farah, A.; Fechtal. M.; Chaouch, A.; Zrira, S., The essential oils of Eucalyptus camaldulensis and its natural hybrid (clone 583) from Morocco, Flavour Fragr. J., 2002, 17, 5, 395-397, https://doi.org/10.1002/ffj.1114 . [all data]

Doimo, 2001
Doimo, L., Iso-citrals and iso-geraniols in lemon-myrtle (Backhousia citriodora F. Muell.) essential oils, J. Essent. Oil Res., 2001, 13, 4, 236-237, https://doi.org/10.1080/10412905.2001.9699680 . [all data]

Jirovetz, Puschmann, et al., 2000
Jirovetz, L.; Puschmann, C.; Stojanova, A.; Metodiev, S.; Buchbauer, G., Analysis of the essential oil volatiles of Douglas fir (Pseudotsuga menziesii) from Bulgaria, Flavour Fragr. J., 2000, 15, 6, 434-437, https://doi.org/10.1002/1099-1026(200011/12)15:6<434::AID-FFJ935>3.0.CO;2-0 . [all data]

Menon, Chacko, et al., 1999
Menon, A.N.; Chacko, S.; Narayanan, C.S., Free and glycosidically bound volatiles of cardamom (Eletteria cardamomum Maton var. miniscula Burkill), Flavour Fragr. J., 1999, 14, 1, 65-68, https://doi.org/10.1002/(SICI)1099-1026(199901/02)14:1<65::AID-FFJ789>3.0.CO;2-A . [all data]

Oberhofer, Nikiforov, et al., 1999
Oberhofer, B.; Nikiforov, A.; Buchbauer, G.; Jirovetz, L.; Bicchi, C., Investigation of the alteration of the composition of various essential oils used in aroma lamp applications, Flavour Fragr. J., 1999, 14, 5, 293-299, https://doi.org/10.1002/(SICI)1099-1026(199909/10)14:5<293::AID-FFJ829>3.0.CO;2-T . [all data]

Rajeswara, Kaul, et al., 1996
Rajeswara, B.R.; Kaul, P.N.; Bhattacharya, A.K.; Mallavarapu, G.R.; Ramesh, S., Yield and chemical composition of the essential oils of three Cymbopogon species suffering from iron chlorosis, Flavour Fragr. J., 1996, 11, 5, 289-293, https://doi.org/10.1002/(SICI)1099-1026(199609)11:5<289::AID-FFJ590>3.0.CO;2-7 . [all data]

Sohounhloue, Dangou, et al., 1996
Sohounhloue, D.K.; Dangou, J.; Gnomhossou, B.; Garneau, F.-X.; Gagnon, H.; Jean, F.-I., Leaf oils of three Eucalyptus species from Benin: E. torelliana F. Muell., E. citriodora Hook. and E. tereticornis Smith, J. Essent. Oil Res., 1996, 8, 1, 111-113, https://doi.org/10.1080/10412905.1996.9700571 . [all data]

Tirado, Stashenko, et al., 1995
Tirado, C.B.; Stashenko, E.E.; Combariza, M.Y.; Martinez, J.R., Comparative study of Colombian citrus oils by high-resolution gas chromatography and gas chromatography-mass spectrometry, J. Chromatogr. A, 1995, 697, 1-2, 501-513, https://doi.org/10.1016/0021-9673(94)00955-9 . [all data]

Sugisawa, Yamamoto, et al., 1989
Sugisawa, H.; Yamamoto, M.; Tamura, H.; Takagi, N., The comparison of volatile components in peel oil from four species of navel orange, Nippon Shokuhin Kogio Gakkaishi, 1989, 36, 6, 455-462, https://doi.org/10.3136/nskkk1962.36.6_455 . [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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