9,12,15-Octadecatrienoic acid, methyl ester, (Z,Z,Z)-

• Formula: C₁₉H₃₂O₂
• Molecular weight: 292.4562
• IUPAC Standard InChI: InChI=1S/C19H32O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19(20)21-2/h4-5,7-8,10-11H,3,6,9,12-18H2,1-2H3/b5-4-,8-7-,11-10- Copy

  
• IUPAC Standard InChIKey: DVWSXZIHSUZZKJ-YSTUJMKBSA-N Copy
• CAS Registry Number: 301-00-8
• 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:
  • 9,12,15-Octadecatrienoic acid, methyl ester
• Other names: Linolenic acid, methyl ester; Methyl all-cis-9,12,15-octadecatrienoate; Methyl linolenate; cis,cis,cis-9,12,15-Octadecatrienoic acid, methyl ester; Methyl α-linolenate; Methyl linolenate, α; (Z,Z,Z)-9,12,15-Octadecatrienoic acid, methyl ester; [Z,Z,Z]-9,12,15-Octadecadienoic acid methyl ester; methyl (9Z,12Z,15Z)-9,12,15-octadecatrienoate
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
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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

Phase change 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 as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Reduced pressure boiling point

Enthalpy of vaporization

Reaction 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

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

3 +  =

By formula: 3H₂ + C₁₉H₃₂O₂ = C₁₉H₃₈O₂

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, isothermal

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Kovats' RI, non-polar column, temperature ramp

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Kovats' RI, polar column, isothermal

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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, isothermal

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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.

Rogers and Siddiqui, 1975
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Lipkind, Dmitry; Kapustin, Yaroslav; Umnahanant, Patamaporn; Chickos, James S., The vaporization enthalpies and vapor pressures of a series of unsaturated fatty acid methyl esters by correlation gas chromatography, Thermochimica Acta, 2007, 456, 2, 94-101, https://doi.org/10.1016/j.tca.2007.02.008 . [all data]

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Kittiratanapiboon, K.; Jeyashoke, N.; Krisnangkura, K., The relationship of Kováts retention indices and equivalent chain lengths of fatty acid methyl esters on a methyl silicone capillary column, J. Chromatogr. Sci., 1998, 36, 7, 361-364, https://doi.org/10.1093/chromsci/36.7.361 . [all data]

Hanai and Hong, 1989
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Zeng, Y.-X.; Zhao, C.-X.; Liang, Y.-Z.; Yang, H.; Fang, H.-Z.; Yi, L.-Z.; Zeng, Z.-D., Comparative analysis of volatile components from Clematis species growing in China, Anal. Chim. Acta., 2007, 595, 1-2, 328-339, https://doi.org/10.1016/j.aca.2006.12.022 . [all data]

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Zhao, Wang X.Y., et al., 2006
Zhao, Y.P.; Wang X.Y.; Wang, Z.C.; Lu Y.; Fu, C.X.; Chen, S.Y., Essential oil of Actinidia macrosperma, a catnip response kiwi endemic to China, Journal of Zhejiang University SCIENCE B, 2006, 7, 9, 708-712, https://doi.org/10.1631/jzus.2006.B0708 . [all data]

Senatore, Rigano, et al., 2003
Senatore, F.; Rigano, D.; de Fusco, R.; Bruno, M., Volatile components of Centaurea cineraria L. subsp. umbrosa (lacaita) Pign. and Centaurea napifolia L. (Asteraceae), two species growing wild in Sicily, Flavour Fragr. J., 2003, 18, 3, 248-251, https://doi.org/10.1002/ffj.1179 . [all data]

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Tan, S.-T.; Holland, P.T.; Wilkins, A.L.; Molan, P.C., Extractives from New Zealand honeys. 1. White clovers, manuka, and kanuka unifloral honeys, J. Agric. Food Chem., 1988, 36, 3, 453-460, https://doi.org/10.1021/jf00081a012 . [all data]

Sing, Smadja, et al., 1992
Sing, A.S.C.; Smadja, J.; Brevard, H.; Maignial, L.; Chaintreau, A.; Marion, J.-P., Volatile constituents of faham (Jumellea fragrans (Thou.) Schltr.), J. Agric. Food Chem., 1992, 40, 4, 642-646, https://doi.org/10.1021/jf00016a024 . [all data]

Filho and Lancas, 1995
Filho, N.R.A.; Lancas, F.M., Identification of FAMEs using ECL values and a three-dimensional Kovats retention index system, J. High Resol. Chromatogr., 1995, 18, 3, 167-170, https://doi.org/10.1002/jhrc.1240180306 . [all data]

Dib, Bendahou, et al., 2010
Dib, M.A.; Bendahou, M.; Bendiabdellah, A.; Djabou, N.; Allali, H.; Tabti, B.; Paolini, J.; Costa, J., Partial chemical composition and antimicrobial activity of Daucus crinitus Desf. extracts, Grasas y Aceites, 2010, 61, 3, 271-278, https://doi.org/10.3989/gya.122609 . [all data]

Escalona-Arranz, Perez-Roses, et al., 2010
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Hu, Liang, et al., 2010
Hu, C.-D.; Liang, Y.-Z.; Guo, F.-Q.; Li, X.-R.; Wang, W.-P., Determination of essential oil composition from Osmanthus fragrans tea by GC-MS combined with a chemometric resolution method, Molecules, 2010, 15, 5, 3683-3693, https://doi.org/10.3390/molecules15053683 . [all data]

Lazarevic, Palic, et al., 2010
Lazarevic, J.S.; Palic, R.V.M.; Radulovic, N.S.; Ristic, N.R.; Stojanovic, G.S., Chemical composition and screening of the antimicrobial and antioxidative acrivity of extracts of Stachys species, J. Serb. Chem. Soc., 2010, 75, 10, 1347-1359, https://doi.org/10.2298/JSC100601117L . [all data]

Vedernikov and Roschin, 2010
Vedernikov, D.N.; Roschin, V.I., Extractive compounds of Birch Buds (Betula pendula Roth.): I. Composition of fatty acids, hydrocarbons , and esters, Rus. J. Bioorg. Chem., 2010, 36, 7, 894-898, https://doi.org/10.1134/S1068162010070174 . [all data]

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]

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Calyecac-cortero, H.G.; Cibrian-Tovar, J.; Soto-Hernandez, M.; Garcia-Velasco, R., Aislamento e identificacion de volatiles de Physalis philadelphica LAM. (Isolation and identification of Physalis philadelphica LAM. volatiles), Agrociencia, 2007, 41, 337-346. [all data]

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Edris, A.E.; Chizzola, R.; Franz, C., Isolation and characterization of the volatile aroma compounds from the concrete headspace and the absolute of Jasminum sambac (L.) Ait. (Oleaceae) flowers grown in Egypt, Eur. Food Res. Technol., 2007, https://doi.org/10.1007/s00217-007-0623-y . [all data]

Tava, Pecetti, et al., 2007
Tava, A.; Pecetti, L.; Ricci, M.; Pagnotta, M.A.; Russi, L., Volatile compounds from leaves and flowers of Bituminaria bituminosa (L.) Stirt. (Fabaceae) from Italy, Flavour Fragr. J., 2007, 22, 5, 363-370, https://doi.org/10.1002/ffj.1806 . [all data]

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Mastelic, J.; Jerkovic, I.; Mesic, M., Volatile constituents from flowers, leaves, bark and wood of Prunus mahaleb L., Flavour Fragr. J., 2006, 21, 2, 306-313, https://doi.org/10.1002/ffj.1596 . [all data]

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Baser, K.H.C.; Özek, T.; Kirimer, N.; Deliorman, D.; Ergun, F., Composition of the essential oils of Galium aparine L. and Galium odoratum (L.) Scop. from Turkey, J. Essent. Oil Res., 2004, 16, 4, 305-307, https://doi.org/10.1080/10412905.2004.9698728 . [all data]

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Notes

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

• Symbols used in this document:
  

  Tboil	Boiling point
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

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