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 Copy

  
• IUPAC Standard InChIKey: NZGWDASTMWDZIW-QMMMGPOBSA-N Copy
• 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
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• 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
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • UV/Visible spectrum
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Condensed phase thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

Phase change data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos

IR Spectrum

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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

Gas Phase Spectrum

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Additional Data

Mass spectrum (electron ionization)

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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

Spectrum

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Additional Data

Gas Chromatography

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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

Kovats' RI, non-polar column, isothermal

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Kovats' RI, non-polar column, temperature ramp

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Kovats' RI, non-polar column, custom temperature program

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Van Den Dool and Kratz RI, polar column, temperature ramp

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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Normal alkane RI, polar column, temperature ramp

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Normal alkane RI, polar column, custom temperature program

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References

Go To: Top, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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Rojas and Usubillaga, 2000
Rojas, L.B.; Usubillaga, A., Composition of the essential oil fo Satureja brownei (SW.) Briq. from Venezuela, Flavour Fragr. J., 2000, 15, 1, 21-22, https://doi.org/10.1002/(SICI)1099-1026(200001/02)15:1<21::AID-FFJ861>3.0.CO;2-G . [all data]

Stojanovic, Palic, et al., 2000
Stojanovic, G.; Palic, R.; Alagic, S.; Zekovic, Z., Chemical composition and antimicrobial activity of the essential oil and CO₂ extracts of semi-oriental tobacco, Otlja, Flavour Fragr. J., 2000, 15, 5, 335-338, https://doi.org/10.1002/1099-1026(200009/10)15:5<335::AID-FFJ921>3.0.CO;2-W . [all data]

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Benzo, M.; Gilardoni, G.; Gandini, C.; Caccialanza, G.; Finzi, P.V.; Vidari, G.; Abdo, S.; Layedra, P., Determination of the threshold odor concentration of main odorants in essential oils using gas chromatography-olfactometry incremental dilution technique, J. Chromatogr. A, 2007, 1150, 1-2, 131-135, https://doi.org/10.1016/j.chroma.2007.02.031 . [all data]

Castilho, Liu, et al., 2007
Castilho, P.; Liu, K.; Rodrigues, A.I.; Feio, S.; Tomi, F.; Casanova, J., Composition and antimicrobial activity of the essential oil of Clinopodium ascendens (Jordan) Sampaio from Madeira, Flavour Fragr. J., 2007, 22, 2, 139-144, https://doi.org/10.1002/ffj.1771 . [all data]

Saroglou, Marin, et al., 2007
Saroglou, V.; Marin, P.D.; Rancic, A.; Veljic, M.; Skaltsa, H., Composition and antimicrobial activity of the essential oil of six Hypericum species from Serbia, Biochem. Syst. Ecol., 2007, 35, 3, 146-152, https://doi.org/10.1016/j.bse.2006.09.009 . [all data]

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Blagojevic, P.; Radulovic, N.; Palic, R.; Stojanovic, G., Chemical composition of the essential oils of Serbian wild-growing Srtemisia absinthium and Artemisia vulgaris, J. Agric. Food Chem., 2006, 54, 13, 4780-4789, https://doi.org/10.1021/jf060123o . [all data]

Javidnia, Miri, et al., 2006
Javidnia, K.; Miri, R.; Banani, A., Volatile oil constituents of Haplophyllum tuberculatum (Forssk.) A. Juss. (Rutaceae) from Iran, J. Essent. Oil Res., 2006, 18, 4, 355-356, https://doi.org/10.1080/10412905.2006.9699111 . [all data]

Pavlovic, Tzakou, et al., 2006
Pavlovic, M.; Tzakou, O.; Petrakis, P.V.; Couladis, M., The essential oil of Hypericum perforatum L., Hypericum tetrapterum Fries and Hypericum olympicum L. growing in Greece, Flavour Fragr. J., 2006, 21, 1, 84-87, https://doi.org/10.1002/ffj.1521 . [all data]

Saroglou, Dorizas, et al., 2006
Saroglou, V.; Dorizas, N.; Kypriotakis, Z.; Skaltsa, H.D., Analysis of the essential oil composition of eight Anthemis species from Greece, J. Chromatogr. A, 2006, 1104, 1-2, 313-322, https://doi.org/10.1016/j.chroma.2005.11.087 . [all data]

Agnihotri, Agarwal, et al., 2005
Agnihotri, V.K.; Agarwal, S.G.; Dhar, P.L.; Thappa, R.K.; Baleshwar; Kapahi, B.K.; Saxena, R.K.; Qazi, G.N., Essential oil composition of Mentha pulegium L. growing wild in the north-western Himalayas India, Flavour Fragr. J., 2005, 20, 6, 607-610, https://doi.org/10.1002/ffj.1497 . [all data]

Paolini, Costa, et al., 2005
Paolini, J.; Costa, J.; Bernardini, A., Analysis of the essential oil from aerial parts of Eupatorium cannabinum subsp. corsicum (L.) by gas chromatography with electron impact and chemical ionization mass spectrometry, J. Chromatogr. A, 2005, 1076, 1-2, 170-178, https://doi.org/10.1016/j.chroma.2005.03.131 . [all data]

Pino, Mesa, et al., 2005
Pino, J.A.; Mesa, J.; Muñoz, Y.; Martí, M.P.; Marbot, R., Volatile components from mango (Mangifera indica L.) cultivars, J. Agric. Food Chem., 2005, 53, 6, 2213-2223, https://doi.org/10.1021/jf0402633 . [all data]

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Antunes, T.; Sevinate-Pinto, I.; Barroso, J.G.; Cavaleiro, C.; Salgueiro, L.R., Micromorphology of trichomes and composition of essential oil of Teucrium capitatum, Flavour Fragr. J., 2004, 19, 4, 336-340, https://doi.org/10.1002/ffj.1310 . [all data]

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Bruni, Bianchi, et al., 2007
Bruni, R.; Bianchi, A.; Bellardi, M.G., Essential oil composition of Agastache anethiodora Britton (Lamiaceae) infected by cucumber mosaic virus (CMV), Flavour Fragr. J., 2007, 22, 1, 66-70, https://doi.org/10.1002/ffj.1760 . [all data]

Cardeal, da Silva, et al., 2006
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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
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Pontes, Marques, et al., 2007
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Tabanca N., Demirci B., et al., 2007
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Demirci B., Baser K.H.C., et al., 2006
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Suleimenov Y.M., Atazhanova G.A., et al., 2006
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Baser, Demirci, et al., 2002
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Baser, Nuriddinov, et al., 2002
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Tabanca, Kirimer, et al., 2001
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Kirimer, Tabanca, et al., 2000
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Baser, Kürkcüoglu, et al., 1998
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Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References

• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  Tboil	Boiling point
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔvapH°	Enthalpy of vaporization at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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