9,12-Octadecadienoic acid (Z,Z)-

• Formula: C₁₈H₃₂O₂
• Molecular weight: 280.4455
• IUPAC Standard InChI: InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9- Copy

  
• IUPAC Standard InChIKey: OYHQOLUKZRVURQ-HZJYTTRNSA-N Copy
• CAS Registry Number: 60-33-3
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Stereoisomers:
  • Linoelaidic acid
• Other names: cis-9,cis-12-Octadecadienoic acid; cis,cis-Linoleic acid; Grape seed oil; Linoleic; Linoleic acid; Linolic acid; Polylin No. 515; Telfairic acid; Unifac 6550; 9,12-Octadecadienoic acid, cis,cis-; Leinoleic acid; 9,12-Linoleic acid; cis,cis-9,12-Octadecadienoic acid; Emersol 310; Emersol 315; Vespula pensylvanica b708568k063; 9-(Z), 12-(Z)-Octadecadienoic acid; Acide linoleique; Octadeca-9,12-dienoic acid, (cis,cis)-; (Z,Z)-9,12-Octadecadienoic acid; (Z,Z)-Octadeca-9, 12-dienoic acid; 9,12-Octadecadienoic acid (9Z,12Z)-; 9-cis,12-cis-Linoleic acid; 9Z,12Z-Linoleic acid; all-cis-9,12-Octadecadienoic acid; cis-Δ9,12-Octadecadienoic acid; Extra Linoleic 90; Polylin 515; 9,12-Octadecadienoic acid; Pamolyn 125 (Salt/Mix)
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• Information on this page:
  • Condensed phase thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Phase change data
  • Reaction thermochemistry data
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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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: Coblentz Society, Inc.

Condensed Phase Spectrum

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Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.

Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

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, temperature ramp

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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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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

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

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Richmond and Pombo-Villar, 1998
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Tret'yakov, 2007
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Sandoval-Montemayor, Garcia, et al., 2012
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Stojanovic, RAdulovic, et al., 2011
Stojanovic, I.Z.; RAdulovic, N.S.; Mitrovic, Y.L.J.; Stamenkovic, S.M.; Stojanovic, G.S., Volatile constituents of selected Parmeliaceae lichens, J. Serb. Chem. Soc., 2011, 76, 7, 987-994, https://doi.org/10.2298/JSC101004087S . [all data]

Radulovic, Blagojevic, et al., 2010
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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]

Xu, Tang, et al., 2010
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Kim and Chung, 2009
Kim, J.-S.; Chung, H.Y., GC-MS analysis of the volatile components in dried boxthorn (Lycium chimensis) Fruit, J. Korean Soc. Appl. Biol. Chem., 2009, 52, 5, 516-524, https://doi.org/10.3839/jksabc.2009.088 . [all data]

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Radulovic, N.S.; Blagojevic, P.D.; Palic, R.M.; Zlatkovic, B.K.; Stevanovic, B.M., Volatiles from vegetative organs of the paleoendemic resurrection plants Ramonda serbica Panc. and Ramonda nathaliae Panc. at Petrov, J. Serb. Chem. Soc., 2009, 74, 1, 35-44, https://doi.org/10.2298/JSC0901035R . [all data]

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Zhao, Zeng, et al., 2009
Zhao, C.; Zeng, Y.; Wan, M.; Li, R.; Liang, Y.; Li, C.; Zeng, Z.; Chau, F.-T., Comparative analysis of essential oils from eight herbal medicines with pungent flavor and cool nature by GC-MS and chemometric resolution methods, J. Sep. Sci., 2009, 32, 4, 660-670, https://doi.org/10.1002/jssc.200800484 . [all data]

Blazevic and Mastelic, 2008
Blazevic, I.; Mastelic, J., Free and bounded volatiles of rocket (Eruca sativa Mill.), Fravour Fragr. J., 2008, 23, 4, 278-285, https://doi.org/10.1002/ffj.1883 . [all data]

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Ferhat, Meklati, et al., 2007
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Wong and Tan, 2005
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Mancini, E.; Arnold, N.A.; De Martino, L.; De Feo, V.; Formisano, C.; Rigano, D.; Senatore, F., Chemical composition and phytotoxic effects of essential oils of Salvia hierosolymitana Boiss. and Salvia multicaulis Vahl. var. simplicifolia Boiss. growing wild in Lebanon, Molecules, 2009, 14, 11, 4725-4736, https://doi.org/10.3390/molecules14114725 . [all data]

Mebazaa, Mahmoudi, et al., 2009
Mebazaa, R.; Mahmoudi, A.; Fouchet, M.; Dos Santos, M.; Kamissoko, F.; Nafti, A.; Ben Cheikh, R.; Rega, B.; Camel, V., Characterization of volatile compounds in Tunisian fenugreek seeds, Food Chem., 2009, 115, 4, 1326-1336, https://doi.org/10.1016/j.foodchem.2009.01.066 . [all data]

Mendes, Trindade, et al., 2009
Mendes, M.D.; Trindade, H.; Figueiredo, A.C.; Pedro, L.G.; Barroso, J.G., Chaerophyllum azoricun Trel. grown in the Azores archipelago, Portugal: evaluation of the genetic diversity using molecular markers and comparison with volatile oils profiles, Flavour Fragr. J., 2009, 24, 5, 259-265, https://doi.org/10.1002/ffj.1939 . [all data]

Nivinsliene, Butkiene, et al., 2007
Nivinsliene, O.; Butkiene, R.; Gudalevic, A.; Mockute, D.; Meskauskiene, V.; Grigaliunaite, B., Influence of urban environment on chemical composition of Tilia cordata essential oil, Chemija, 2007, 18, 1, 44-49. [all data]

Yasar, Üçüncü, et al., 2005
Yasar, A.; Üçüncü, O.; Güleç, C.; Inceer, H.; Ayaz, S.; Yayh, N., GC-MS analysis of chloroform extracts in flowers, stems, and roots of Tripleurospermum callosum, Pharm. Biol., 2005, 43, 2, 108-112, https://doi.org/10.1080/13880200590919384 . [all data]

El-Shazily, Hafez, et al., 2004
El-Shazily, A.M.; Hafez, S.S.; Wink, M., Comparative study of the essential oils and extracts of Achillea fragrantissima (Forssk.) Sch. Bip. and Achillea santolina L. (Asteraceae) from Egypt, Pharmazie, 2004, 59, 226-230. [all data]

Miyazawa, Kurose, et al., 2001
Miyazawa, M.; Kurose, K.; Itoh, A.; Hiraoka, N., Comparison of the essential oils of Glehnia littoralis from Northern and Southern Japan, J. Agric. Food Chem., 2001, 49, 11, 5433-5436, https://doi.org/10.1021/jf010219c . [all data]

Hatsuko, Kazuko, et al., 1992
Hatsuko, S.; Kazuko, H.; Masayoshi, K.; Yoshiaki, I., Improvement of quality of likorine extract by heat treatment, J. Food Sci. Technol., 1992, 39, 11, 976-983, https://doi.org/10.3136/nskkk1962.39.976 . [all data]

Noorizadeh, Farmany, et al., 2011
Noorizadeh, H.; Farmany, A.; Noorizadeh, M., Quantitative structure-retention relationships analysis of retention index of essential oils, Quim. Nova, 2011, 34, 2, 242-249, https://doi.org/10.1590/S0100-40422011000200014 . [all data]

Noorizadeh and Farmany, 2010
Noorizadeh, H.; Farmany, A., Exploration of linear and nonlinear modeling techniques to predict of retention index of essential oils, J. Chin. Chem. Soc., 2010, 1268-1277. [all data]

Notes

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

• Symbols used in this document:
  

  ΔfH°liquid

  Enthalpy of formation of liquid at standard conditions

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