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:
  • Kovats' RI, non-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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Kovats' RI, non-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, Kovats' RI, non-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.

de Marchese, de Heluani, et al., 2007
de Marchese, M.J.A.; de Heluani, C.S.; Catalán, C.A.N.; Griffin, C.A.; Vaughn, J.B., Jr.; Herz, W., Incisol, an alcohol with a novel sesquiterpene skeleton from Xenophyllum incisum, Biochem. Syst. Ecol., 2007, 35, 3, 169-175, https://doi.org/10.1016/j.bse.2006.10.006 . [all data]

Lima, Barros, et al., 2005
Lima, M.A.S.; Barros, M.C.P.; Pinheiro, S.M.; do Nascimento, R.F.; de Abreu Matos, F.J.; Silveira, E.R., Volatile compositions of two Asteraceae from the north-east of Brazil: Ageratum conyzoides and Acritopappus confertus (Eupatorieae), Flavour Fragr. J., 2005, 20, 6, 559-561, https://doi.org/10.1002/ffj.1483 . [all data]

Tuberoso, Kowalczyk, et al., 2005
Tuberoso, C.I.G.; Kowalczyk, A.; Coroneo, V.; Russo, M.T.; Dessì, S.; Cabras, P., Chemical Composition and Antioxidant, Antimicrobial, and Antifungal Activities of the Essential Oil of Achillea ligustica All., J. Agric. Food Chem., 2005, 53, 26, 10148-10153, https://doi.org/10.1021/jf0518913 . [all data]

Dwivedi, Khan, et al., 2004
Dwivedi, S.; Khan, M.; Srivastava, S.K.; Syamasunnder, K.V.; Srivastava, A., Essential oil composition of different accessions of Mentha × piperita L. grown on the northern plains of India, Flavour Fragr. J., 2004, 19, 5, 437-440, https://doi.org/10.1002/ffj.1333 . [all data]

Riu-Aumatell, Castellari, et al., 2004
Riu-Aumatell, M.; Castellari, M.; López-Tamames, E.; Galassi, S.; Buxaderas, S., Characterisation of volatile compounds of fruit juices and nectars by HS/SPME and GC/MS, Food Chem., 2004, 87, 4, 627-637, https://doi.org/10.1016/j.foodchem.2003.12.033 . [all data]

Sibanda, Chigwada, et al., 2004
Sibanda, S.; Chigwada, G.; Poole, M.; Gwebu, E.T.; Noletto, J.A.; Schmidt, J.M.; Rea, A.I.; Setzer, W.N., Composition and bioactivity of the leaf essential oil of Heteropyxis dehniae from Zimbabwe, J. Ethnopharmacol., 2004, 92, 1, 107-111, https://doi.org/10.1016/j.jep.2004.02.010 . [all data]

Araújo, Silveira, et al., 2003
Araújo, E.C.C.; Silveira, E.R.; Lima, M.A.S.; Neto, M.A.; de Andrade, I.L.; Lima, M.A.A.; Santiago, G.M.P.; Mesquita, A.L.M., Insecticidal activity and chemical composition of volatile oils from Hyptis martiusii Benth, J. Agric. Food Chem., 2003, 51, 13, 3760-3762, https://doi.org/10.1021/jf021074s . [all data]

Raina, Srivastava, et al., 2003
Raina, V.K.; Srivastava, S.K.; Aggarwal, K.K.; Syamasunder, K.V.; Khanuja, S.P.S., Essential oil composition of Cymbopogon martinii from different places in India, Flavour Fragr. J., 2003, 18, 4, 312-315, https://doi.org/10.1002/ffj.1222 . [all data]

Rao, Kaul, et al., 2003
Rao, B.R.R.; Kaul, P.N.; Syamasundar, K.V.; Ramesh, S., Comparative composition of decanted and recovered essential oils of Eucalyptus citriodora Hook, Flavour Fragr. J., 2003, 18, 2, 133-135, https://doi.org/10.1002/ffj.1157 . [all data]

Shellie and Marriott, 2003
Shellie, R.A.; Marriott, P.J., Comprehensive two-dimensional gas chromatography-mass spectrometry analysis of Pelargonium graveolens essential oil using rapid scanning quadrupole mass spectrometry, Analyst, 2003, 128, 7, 879-883, https://doi.org/10.1039/b304371a . [all data]

Wongpornchai, Sriseadka, et al., 2003
Wongpornchai, S.; Sriseadka, T.; Choonvisase, S., Identification and quantitation of the rice aroma compound, 2-acetyl-1-pyrroline, in bread flowers (Vallaris glabra Ktze), J. Agric. Food Chem., 2003, 51, 2, 457-462, https://doi.org/10.1021/jf025856x . [all data]

Bruce, Cork, et al., 2002
Bruce, T.J.; Cork, A.C.; Hall, D.R.; Dunkelblum, E., Laboratory and field evaluation of floral odours from African marigold, Tagetes erecta, and sweet pea, Lathyrus odoratus, as kairomones for the cotton bollworm Helicoverpa armigera, 2002, retrieved from http://phero.net/iobc/samos/bulletin/bruce.pdf. [all data]

El-Shazly, Dorai, et al., 2002
El-Shazly, A.; Dorai, G.; Wink, M., Chemical composition and biological activity of the essential oils of Senecio aegyptus var. discoideus Boiss., Z. Naturforsch., 2002, 57c, 434-439. [all data]

Bizzo, Lopes, et al., 2001
Bizzo, H.R.; Lopes, D.; Abdala, R.V.; Pimentel, F.A.; de Souza, J.A.; Pereira, M.V.G.; Bergter, L.; Guimaraes, E.F., Sarisan from leaves of Piper affinis hispidinervum C. DC (long pepper), Flavour Fragr. J., 2001, 16, 2, 113-115, https://doi.org/10.1002/ffj.957 . [all data]

Frizzo, Serafini, et al., 2001
Frizzo, C.D.; Serafini, L.A.; Dellacassa, E.; Lorenzo, D.; Moyna, P., Essential oil of Baccharis uncinella DC. from Southern Brazil, Flavour Fragr. J., 2001, 16, 4, 286-288, https://doi.org/10.1002/ffj.998 . [all data]

Moreira, Sousa, et al., 2001
Moreira, D.L.; Sousa, P.O.; Pereira, N.A.; Cardoso, G.L., Effect of leaf essential oil from Piper solmsianum C.DC. in mice behaviour, An. Acad. Bras. Cienc., 2001, 73, 1, 1-7, https://doi.org/10.1590/S0001-37652001000100004 . [all data]

Novak, Zitterl-Eglseer, et al., 2001
Novak, J.; Zitterl-Eglseer, K.; Deans, S.G.; Franz, C.M., Essential oils of different cultivars of Cannabis sativa L. and their antimicrobial activity, Flavour Fragr. J., 2001, 16, 4, 259-262, https://doi.org/10.1002/ffj.993 . [all data]

Dickens J.C., 2000
Dickens J.C., Sexual maturation and temporal variation of neural responses in adult Colorado potato beetles to volatiles emitted by potato plants, J. Chem. Ecol., 2000, 26, 5, 1265-1279, https://doi.org/10.1023/A:1005492229377 . [all data]

Khouri, Usubillaga, et al., 2000
Khouri, N.; Usubillaga, A.; Rojas, L.B.; Galarraga, F., The essential oil of Espeletia weddellii Sch. Bip. ex Wedd., Flavour Fragr. J., 2000, 15, 4, 263-265, https://doi.org/10.1002/1099-1026(200007/08)15:4<263::AID-FFJ907>3.0.CO;2-Q . [all data]

Rao, Rout, et al., 2000
Rao, Y.R.; Rout, P.K.; Jena, K.S.; Sahu, S.B., Composition of essential oil of citronella (Cymbopogon winterianus jowitt) grown in coastal Orissa, Fafai J., 2000, 2, 4, 29-31. [all data]

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]

Adams, 1998
Adams, R.P., The essential oils and chemotaxonomy of Juniperus sect. Juniperus, Biochem. Syst. Ecol., 1998, 26, 6, 637-645, https://doi.org/10.1016/S0305-1978(98)00020-9 . [all data]

Andrade, Santos, et al., 1998
Andrade, E.H.A.; Santos, A.S.; Zoghbi, M.G.B.; Maia, J.G.S., Volatile constituents of fruits of Astrocarium vulgare Mart. and Bactris gasipaes H.B.K. (Arecaceae), Flavour Fragr. J., 1998, 13, 3, 151-153, https://doi.org/10.1002/(SICI)1099-1026(199805/06)13:3<151::AID-FFJ712>3.0.CO;2-E . [all data]

Santos, Andrade, et al., 1998
Santos, A.S.; Andrade, E.H.A.; Zoghbi, M.G.B.; Maia, J.G.S., Volatile constituents of fruits of Annona glabra L. from Brazil, Flavour Fragr. J., 1998, 13, 3, 148-150, https://doi.org/10.1002/(SICI)1099-1026(199805/06)13:3<148::AID-FFJ711>3.0.CO;2-Y . [all data]

Machado, Militao, et al., 1995
Machado, S.M.F.; Militao, J.S.L.T.; Facundo, V.A.; Ribeiro, A.; de Morais, S.M.; de Alencar, J.W.; Filho, R.B., Essential Oil of Conyza sumatrensis (Retz) Walk, J. Essent. Oil Res., 1995, 7, 1, 83-84, https://doi.org/10.1080/10412905.1995.9698470 . [all data]

MacLeod, MacLeod, et al., 1988
MacLeod, A.J.; MacLeod, G.; Subramanian, G., Volatile aroma constituents of orange, Phytochemistry, 1988, 27, 7, 2185-2188, https://doi.org/10.1016/0031-9422(88)80123-7 . [all data]

Okamoto, Ellison, et al., 1981
Okamoto, R.A.; Ellison, B.O.; Kepner, R.E., Volatile terpenes in Sequoia sempervirens foliage. Changes in composition during maturation, J. Agric. Food Chem., 1981, 29, 2, 324-326, https://doi.org/10.1021/jf00104a026 . [all data]

Ramsey, Lee, et al., 1980
Ramsey, J.D.; Lee, T.D.; Osselton, M.D.; Moffat, A.C., Gas-liquid chromatographic retention indices of 296 non-drug substances on SE-30 or OV-1 likely to be encountered in toxicological analyses, J. Chromatogr., 1980, 184, 2, 185-206, https://doi.org/10.1016/S0021-9673(00)85641-1 . [all data]

Malingré and Maarse, 1974
Malingré, T.M.; Maarse, H., Composition of the essential oil of Mentha aquatica, Phytochemistry, 1974, 13, 8, 1531-1535, https://doi.org/10.1016/0031-9422(74)80322-5 . [all data]

Minyard, Tumlinson, et al., 1967
Minyard, J.P.; Tumlinson, J.H.; Thompson, A.C.; Hedin, P.A., Constituents of the cotton bud. The carbonyl compounds, J. Agric. Food Chem., 1967, 15, 3, 517-524, https://doi.org/10.1021/jf60151a021 . [all data]

Notes

Go To: Top, Kovats' RI, non-polar column, custom temperature program, References

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