Limonene

• Formula: C₁₀H₁₆
• Molecular weight: 136.2340
• IUPAC Standard InChI: InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3 Copy

  
• IUPAC Standard InChIKey: XMGQYMWWDOXHJM-UHFFFAOYSA-N Copy
• CAS Registry Number: 138-86-3
• 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:
  • Limonene
• Stereoisomers:
  • D-Limonene
  • Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (S)-
• Other names: Cyclohexene, 1-methyl-4-(1-methylethenyl)-; p-Mentha-1,8-diene; α-Limonene; Cajeputen; Cajeputene; Cinen; Cinene; Dipenten; Dipentene; Eulimen; Kautschin; Limonen; Nesol; p-Mentha-1,8(9)-diene; δ-1,8-Terpodiene; p-Mentha-1,8-diene, dl-; Acintene DP dipentene; Di-p-mentha-1,8-diene; DL-Limonene; Inactive limonene; 1-Methyl-4-isopropenyl-1-cyclohexene; 1,8(9)-p-Menthadiene; 4-Isopropenyl-1-methyl-1-cyclohexene; Acintene DP; Dipanol; UN 2052; Unitene; 4-Isopropenyl-1-methylcyclohexene; 1,8-p-Menthadiene; 1-Methyl-4-(1-methylethenyl)cyclohexene; 1-Methyl-4-isopropenylcyclohexene; (.+/-.)-Limonene; Achilles dipentene; 1-methyl-4-isopropenylcyclohex-1-ene; 1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene; Cyclohexene, 1-methyl-4-(1-methylethynyl); Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (.+/-.)-; (.+/-.)-Dipentene; (.+/-.)-α-Limonene; Flavor orange; Goldflush II; NSC 21446; Orange flavor; PC 560; D-Limonene; (+)-limonene; (+)-(4R)-limonene; ( R/ S)-limonene; (R)-(+)-Limonene; (R)-Limonene; (±)-limonene; Limonene [4R-(+), 4S-(-)]; δ-Limonene; 1-Limonene; 1-methyl-4-isopropenylcyclohex-1-ene (limonene); (S)-(-)-Limonene; Limonene+; Dipentene limonene
• Information on this page:
  • Normal alkane RI, polar column, custom temperature program
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
• Options:
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• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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Normal alkane RI, polar column, custom temperature program

Go To: Top, References, Notes

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

References

Go To: Top, Normal alkane RI, polar column, custom temperature program, 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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Wedge, Klun, et al., 2009
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Zellner, Amorim, et al., 2009
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Aicha, Ines, et al., 2008
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Beck, Higbee, et al., 2008
Beck, J.J.; Higbee, B.S.; Marrill, G.B.; Roitman, J.N., Comparison of volatile emissions from undamaged and mechanically damaged almonds, J, Sci. Food Argic., 2008, 88, 8, 1363-1368, https://doi.org/10.1002/jsfa.3224 . [all data]

Kaack and Christensen, 2008
Kaack, K.; Christensen, L.P., Effect of packing materials and storage time on volatile compounds in tea processes from flowers of black elder (Sambucus nigra L.), Eur. Food Res. Technol., 2008, 227, 4, 1259-1273, https://doi.org/10.1007/s00217-008-0844-8 . [all data]

Rodrigues, Caldera, et al., 2008
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Berard, Bianchi, et al., 2007
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Selli, 2007
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Tian, Zhang, et al., 2007
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Vichi, Guadayol, et al., 2007
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Viegas and Bassoli, 2007
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Baser K.H.C., Ozek G., et al., 2006
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Baser, Özek, et al., 2006
Baser, K.H.C.; Özek, G.; Özek, T.; Duran, A.; Duman, H., Composition of the essential oils of Rhabdosciadium oligocarpum (Post ex Boiss.) Hedge et Lamond and Rhabdosciadium microcalycinum Hand.-Mazz., Flavour Fragr. J., 2006, 21, 4, 650-655, https://doi.org/10.1002/ffj.1639 . [all data]

Demirci B., Baser K.H.C., et al., 2006
Demirci B.; Baser K.H.C.; Tabanca N.; Wedge D.E., Characterization of volatile constituents of Haplopappus greenei and studies on the antifungal activity against phytopathogens, J. Agric. Food Chem., 2006, 54, 8, 3146-3150, https://doi.org/10.1021/jf053222v . [all data]

Erdurak, Coskun, et al., 2006
Erdurak, C.S.; Coskun, M.; Demirci, B.; Baser, K.H.C., Composition of the essential oil of fruits and roots of Ferulago isaurica Pesmen and F. syriaca Boiss. (Umbelliferae) from Turkey, Flavour Fragr. J., 2006, 21, 1, 118-121, https://doi.org/10.1002/ffj.1540 . [all data]

Kürkçüoglu, Hüsnü Can Baser, et al., 2006
Kürkçüoglu, M.; Hüsnü Can Baser, K.; Iscan, G.; Malyer, H.; Kaynak, G., Composition and anticandidal activity of the essential oil of Chaerophyllum byzantinum Boiss., Flavour Fragr. J., 2006, 21, 1, 115-117, https://doi.org/10.1002/ffj.1539 . [all data]

Lorenzo, Loayza, et al., 2006
Lorenzo, D.; Loayza, I.; Dellacassa, E., Composition and chiral characterization of the essential oil of Buddleja tucumanensis from Bolivia, Flavour Fragr. J., 2006, 21, 1, 95-98, https://doi.org/10.1002/ffj.1526 . [all data]

Suleimenov Y.M., Atazhanova G.A., et al., 2006
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]

Tabanca, Demirci, et al., 2006
Tabanca, N.; Demirci, B.; Ozek, T.; Kirimer, N.; Can Baser, K.H.; Bedir, E.; Khan, I.A.; Wedge, D.E., Gas chromatographic-mass spectrometric analysis of essential oils from Pimpinella species gathered from Central and Northern Turkey, J. Chromatogr. A, 2006, 1117, 2, 194-205, https://doi.org/10.1016/j.chroma.2006.03.075 . [all data]

Tabanca, Demirci, et al., 2006, 2
Tabanca, N.; Demirci, B.; Can Baser, K.H.; Aytac, Z.; Ekici, M.; Khan, S.I.; Jacob, M.R.; Wedge, D.E., Chemical Composition and Antifungal Activity of Salvia macrochlamys and Salvia recognita Essential Oils, J. Agric. Food Chem., 2006, 54, 18, 6593-6597, https://doi.org/10.1021/jf0608773 . [all data]

Tosun, Kürkcüoglu, et al., 2006
Tosun, A.; Kürkcüoglu, M.; Dogan, E.; Duman, H.; Baser, K.H.C., Essential oil composition of Seseli petraeum M. Bieb. and Seseli andronakii Woron. growing in Turkey, Flavour Fragr. J., 2006, 21, 2, 257-259, https://doi.org/10.1002/ffj.1572 . [all data]

Vichi, Guadayol, et al., 2006
Vichi, S.; Guadayol, J.M.; Caixach, J.; López-Tamames, E.; Buxaderas, S., Monoterpene and sesquiterpene hydrocarbons of virgin olive oil by headspace solid-phase microextraction coupled to gas chromatography/mass spectrometry, J. Chromatogr. A, 2006, 1125, 1, 117-123, https://doi.org/10.1016/j.chroma.2006.05.029 . [all data]

Berlinet, Ducruet, et al., 2005
Berlinet, C.; Ducruet, V.; Brillouet, J.-M.; Reynes, M.; Brat, P., Evolution of aroma compounds from orange juice stored in polyethylene terephthalate (PET), Food Addit. Contam., 2005, 22, 2, 185-195, https://doi.org/10.1080/02652030500037860 . [all data]

Demirci, Demirci, et al., 2005
Demirci, B.; Demirci, F.; Baser, K.H.C., Headspace-SPME and hydrodistillation of two fragrant Artemisia sp., Flavour Fragr. J., 2005, 20, 4, 395-398, https://doi.org/10.1002/ffj.1426 . [all data]

Demirci, Demirci, et al., 2005, 2
Demirci, B.; Demirci, F.; Dönmez, A.A.; Franz, G.; Paper, D.H.; Baser, K.H.C., Effects of Salvia essential oils on the chorioallantoic membrane (CAM) assay, Pharm. Biol., 2005, 43, 8, 666-671, https://doi.org/10.1080/13880200500383397 . [all data]

Editorial paper, 2005
Editorial paper, Solid Phase Microextraction (SPME) Application Guide, The Reporter Europe (Supelco), 2005, 16, 5, 12-12. [all data]

Giuseppe, Manuela, et al., 2005
Giuseppe, Z.; Manuela, G.; Marta, B.; Vincenzo, G., Application of artificial neural network on mono- and sesquiterpenes compounds determined by headspace solid-phase microextraction-gas chromatography-mass spectrometry for the Piedmont ricotta cheese traceability, J. Chromatogr. A, 2005, 1071, 1-2, 247-253, https://doi.org/10.1016/j.chroma.2004.11.083 . [all data]

Jales, Maia, et al., 2005
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Mattheis, Buchanan, et al., 1992
Mattheis, J.P.; Buchanan, D.A.; Fellman, J.K., Volatile compounds emitted by sweet cherries (Prunus avium Cv. Bing) during fruit development and ripening, J. Agric. Food Chem., 1992, 40, 3, 471-474, https://doi.org/10.1021/jf00015a022 . [all data]

Peng, Yang, et al., 1991
Peng, C.T.; Yang, Z.C.; Ding, S.F., Prediction of rentention idexes. II. Structure-retention index relationship on polar columns, J. Chromatogr., 1991, 586, 1, 85-112, https://doi.org/10.1016/0021-9673(91)80028-F . [all data]

Vernin, 1991
Vernin, G., Volatile constituents of the essential oil of Santolina chamaecyparissus L., J. Essent. Oil Res., 1991, 3, 1, 49-53, https://doi.org/10.1080/10412905.1991.9697907 . [all data]

Binder and Flath, 1989
Binder, R.G.; Flath, R.A., Volatile components of pineapple guava, J. Agric. Food Chem., 1989, 37, 3, 734-736, https://doi.org/10.1021/jf00087a034 . [all data]

Shibamoto, 1987
Shibamoto, T., Retention Indices in Essential Oil Analysis in Capillary Gas Chromatography in Essential Oil Analysis, Sandra, P.; Bicchi, C., ed(s)., Hutchig Verlag, Heidelberg, New York, 1987, 259-274. [all data]

MacLeod and Pieris, 1981
MacLeod, A.J.; Pieris, N.M., Volatile flavor components of beli fruit (Aegle marmelos) and a processed product, J. Agric. Food Chem., 1981, 29, 6, 1262-1264, https://doi.org/10.1021/jf00108a040 . [all data]

Notes

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