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

UV/Visible 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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

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, IR Spectrum, UV/Visible spectrum, Gas Chromatography, Notes

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

Conia, 1954
Conia, J.-M., Alcoylation des cetones par l'intermediaire de l'amylate tertiaire de sodium (4^e Memoire). Cetones ethyleniques: II^e partie: Alcoylation en serie alicyclique, Bull. Soc. Chim. Fr., 1954, 21, 943-948. [all data]

Hoskovec, Grygarová, et al., 2005
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Rao B.R.R., 2002
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Bicchi, Frattini, et al., 1988
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Dwivedi, Khan, et al., 2004
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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]

Benzo, Gilardoni, et al., 2007
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]

Vagionas, Ngassapa, et al., 2007
Vagionas, K.; Ngassapa, O.; Runyoro, D.; Graikou, K.; Gortzi, O.; Chinou, I., Chemical analysis of edible aromatic plants growing in Tanzania, Food Chem., 2007, 105, 4, 1711-1717, https://doi.org/10.1016/j.foodchem.2007.05.029 . [all data]

Blagojevic, Radulovic, et al., 2006
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]

Antunes, Sevinate-Pinto, et al., 2004
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]

Javidnia, Miri, et al., 2004
Javidnia, K.; Miri, R.; Sadeghpour, H., Composition of the volatile oil of Achillea wilhelmsii C. Koch from Iran, DARU, 2004, 12, 2, 63-66, retrieved from http://www1.tums.ac.ir/daru/. [all data]

Stashenko, Jaramillo, et al., 2004
Stashenko, E.E.; Jaramillo, B.E.; Martínez, J.R., Comparison of different extraction methods for the analysis of volatile secondary metabolites of Lippia alba (Mill.) N.E. Brown, grown in Colombia, and evaluation of its in vitro antioxidant activity, J. Chromatogr. A, 2004, 1025, 1, 93-103, https://doi.org/10.1016/j.chroma.2003.10.058 . [all data]

Emilio Tomei, Manganelli, et al., 2003
Emilio Tomei, P.; Manganelli, R.E.U.; Flamini, G.; Cioni, P.L.; Morelli, I., Composition of the essential oil of Mentha microphylla from the Gennargentu Mountains (Sardinia, Italy), J. Agric. Food Chem., 2003, 51, 12, 3614-3617, https://doi.org/10.1021/jf026091w . [all data]

Javidnia, Miri, et al., 2003
Javidnia, K.; Miri, R.; Azarpira, A.; Tabaei, S.M.H., Composition of the essential oil of Stachys setifera C.A. Mey ssp. iranica growing in Iran, Flavour Fragr. J., 2003, 18, 4, 299-300, https://doi.org/10.1002/ffj.1165 . [all data]

Javidnia, Miri, et al., 2002
Javidnia, K.; Miri, R.; Safavi, F.; Azarpira, A.; Shafiee, A., Composition of the essential oil of Nepeta persica Boiss from Iran, Flavour Fragr. J., 2002, 17, 1, 20-22, https://doi.org/10.1002/ffj.1023 . [all data]

Aligiannis, Kalpoutzakis, et al., 2001
Aligiannis, N.; Kalpoutzakis, E.; Chinou, I.B.; Mitaku, S.; Gikas, E.; Tsarbopoulos, A., Composition and antimicrobial activity of the essential oils of five taxa of Sideritis from Greece, J. Agric. Food Chem., 2001, 49, 2, 811-815, https://doi.org/10.1021/jf001018w . [all data]

Guilliard, Delgado, et al., 2001
Guilliard, M.; Delgado, W.; Martínez, J.R.; Stashenko, E., Determination of the enantiomeric purity of carvone, main component of Colombian Lippia alba (Mill) oil by means of bidimensional gas chromatography (23rd International Symposium on Capillary Chromatography), 2001, retrieved from http://www.richrom.com/assets/CD23PDF/i01.pdf. [all data]

Skaltsa, Mavrommati, et al., 2001
Skaltsa, H.D.; Mavrommati, A.; Constantinidis, T., A chemotaxonomic investigation of volatile constituents in Stachys subsect. Swainsonianeae (Labiatae), Phytochemistry, 2001, 57, 2, 235-244, https://doi.org/10.1016/S0031-9422(01)00003-6 . [all data]

Yin, Xiu, et al., 2001
Yin, W.; Xiu, Z.; Aijin, H., Analysis of the volatile components in trogopterorum feces by capillary gas chromatography and gas chromatography/mass spectrometry, Fenxi Huaxue, 2001, 29, 2, 195-198. [all data]

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Baldovini, N.; Ristorcelli, D.; Tomi, F.; Casanova, J., Infraspecific variability of the essential oil of Calamintha nepeta from Corsica (France), Flavour Fragr. J., 2000, 15, 1, 50-54, https://doi.org/10.1002/(SICI)1099-1026(200001/02)15:1<50::AID-FFJ871>3.0.CO;2-F . [all data]

Skaltsa, Lazari, et al., 2000
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Mirza and Sefidkon, 1999
Mirza, M.; Sefidkon, F., Essential oil composition of two Salvia species from Iran, Salvia nemorosa L. and Salvia reuterana Boiss., Flavour Fragr. J., 1999, 14, 4, 230-232, https://doi.org/10.1002/(SICI)1099-1026(199907/08)14:4<230::AID-FFJ816>3.0.CO;2-L . [all data]

Warthen, Lee, et al., 1997
Warthen, J.D.; Lee, C.-J.; Jang, E.B.; Lance, D.R.; McInnis, D.O., Volatile, potential attractants from ripe coffee fruit for female Mediterranean fruit fly, J. Chem. Ecol., 1997, 23, 7, 1891-1900, https://doi.org/10.1023/B:JOEC.0000006458.02342.61 . [all data]

Píry, Príbela, et al., 1995
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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
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
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Suleimenov Y.M.; Atazhanova G.A.; Ozek T.; Demirci B.; Kulyyasov A.T.; Adekenov S.M.; Baser K.H.C., Essential oil composition of three species of Achillea from Kazakhstan, Chem. Nat. Compd. (Engl. Transl.), 2006, 37, 5, 447-450, https://doi.org/10.1023/A:1014471326724 . [all data]

Baser, Demirci, et al., 2002
Baser, K.H.C.; Demirci, B.; Kirimer, N.; Satil, F.; Tumen, G., The essential oils of Thymus migricus and T. fedtschenkoi var. handelii from Turkey, Flavour Fragr. J., 2002, 17, 1, 41-45, https://doi.org/10.1002/ffj.1036 . [all data]

Baser, Nuriddinov, et al., 2002
Baser, K.H.C.; Nuriddinov, H.R.; Ozek, T.; Demirci, A.B.; Azcan, N.; Nigmatullaev, A.M., Essential oil of Arischrada korolkowii from the Chatkal mountains of Uzbekistan, Chem. Nat. Compd. (Engl. Transl.), 2002, 38, 1, 51-53, https://doi.org/10.1023/A:1015729731464 . [all data]

Tabanca, Kirimer, et al., 2001
Tabanca, N.; Kirimer, N.; Demirci, B.; Demirci, F.; Can Baser, K.H., Composition and antimicrobial activity of the essential oils of Micromeria cristata subsp. phrygia and the enantiomeric distribution of borneol, J. Agric. Food Chem., 2001, 49, 9, 4300-4303, https://doi.org/10.1021/jf0105034 . [all data]

Kirimer, Tabanca, et al., 2000
Kirimer, N.; Tabanca, N.; Özek, T.; Tümen, G.; Baser, K.H.C., Essential oils of annual Sideritis species growing in Turkey, Pharm. Biol., 2000, 38, 2, 106-111, https://doi.org/10.1076/1388-0209(200004)3821-1FT106 . [all data]

Baser, Kürkcüoglu, et al., 1998
Baser, K.H.C.; Kürkcüoglu, M.; Aytac, Z., Composition of the essential oil of Salvia euphratica Montbret ex Bentham var. euphratica from Turkey, Flavour Fragr. J., 1998, 13, 1, 63-64, https://doi.org/10.1002/(SICI)1099-1026(199801/02)13:1<63::AID-FFJ694>3.0.CO;2-Z . [all data]

Notes

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