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 boiling point
  • 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
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Normal boiling point

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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

References

Go To: Top, Normal boiling point, Notes

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

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Ipatieff, Germain, et al., 1952
Ipatieff, V.N.; Germain, J.E.; Thompson, W.W.; Pines, H., The Terpene Series XII. Cyclic Isomerization of Limonene. Proof of the Structure of A New Bicycloterpene, J. Org. Chem., 1952, 17, 272-85. [all data]

Lecat, 1943
Lecat, M., Azeotropes of Ethyl Urethane and other Azeotropes, C. R. Hebd. Seances Acad. Sci., 1943, 217, 273. [all data]

Anonymous, 1942
Anonymous, R., , Am. Pet. Inst. Res. Proj. 6, Natl. Bur. Stand., 1942. [all data]

Kafuku, Nozoe, et al., 1931
Kafuku, K.; Nozoe, T.; Hata, C., Bull. Chem. Soc. Jpn., 1931, 6, 40. [all data]

Richter and Wolff, 1930
Richter, F.; Wolff, W., Chem. Ber., 1930, 63, 1721. [all data]

Treibs and Schmidt, 1928
Treibs, W.; Schmidt, H., Oxidation of Reactive Methylene Groups, Chem. Ber., 1928, 61B, 459-65. [all data]

Uchida, 1916
Uchida, S., The Essential Oil of Sugi (Cryptomeria japonica) Leaves, J. Am. Chem. Soc., 1916, 38, 687-98. [all data]

Delepine, 1910
Delepine, M., Bull. Soc. Chim. Fr., 1910, 7, 468. [all data]

Bacon, 1909
Bacon, R.F., Philippine J. Sci., 1909, 4, 93. [all data]

Kay and Perkin, 1906
Kay, F.W.; Perkin, W.H., Experiments on the synthesis of the terpenes: viii synthesis of the optically active modifications of delta(3)-p-menthenol(8) and delta(3.8(9)) -p-menthadiene, J. Chem. Soc., 1906, 89, 839-56. [all data]

Wallach, 1888
Wallach, O., Justus Liebigs Ann. Chem., 1888, 245, 191. [all data]

Wallach, 1887
Wallach, O., Justus Liebigs Ann. Chem., 1887, 239, 1-54. [all data]

Notes

Go To: Top, Normal boiling point, References

• Symbols used in this document:
  

  Tboil

  Boiling point

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