Undecanoic acid, methyl ester

• Formula: C₁₂H₂₄O₂
• Molecular weight: 200.3178
• IUPAC Standard InChI: InChI=1S/C12H24O2/c1-3-4-5-6-7-8-9-10-11-12(13)14-2/h3-11H2,1-2H3 Copy

  
• IUPAC Standard InChIKey: XPQPWPZFBULGKT-UHFFFAOYSA-N Copy
• CAS Registry Number: 1731-86-8
• 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.
• Other names: Methyl undecanoate; Methyl undecylenate; n-Undecanoic acid methyl ester; Methyl ester of undecanoic acid; methyl n-undecanoate
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• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Enthalpy of vaporization

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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Gas Phase Spectrum

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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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Van Den Dool and Kratz RI, polar column, temperature ramp

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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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References

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

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

Adriaanse, Dekker, et al., 1965
Adriaanse, N.; Dekker, H.; Coops, J., Heats of combustion of normal saturated fatty acids and their methyl esters, Rec. Trav. Chim. Pays/Bas, 1965, 84, 393-407. [all data]

Urry and Huyer, 1953
Urry, W.H.; Huyer, E.S., J. Am. Chem. Soc., 1953, 75, 4876. [all data]

Adriaanse, Dekker, et al., 1964
Adriaanse, N.; Dekker, H.; Coops, J., Some Physical Constants of Normal, Saturated Fatty Acids and Their Methyl Esters, Recl. Trav. Chim. Pays-Bas, 1964, 83, 557. [all data]

van Genderen, van Miltenburg, et al., 2002
van Genderen, Aad C.G.; van Miltenburg, J. Cees; Blok, Jacobus G.; van Bommel, Mark J.; van Ekeren, Paul J.; van den Berg, Gerrit J.K.; Oonk, Harry A.J., Liquid--vapour equilibria of the methyl esters of alkanoic acids: vapour pressures as a function of temperature and standard thermodynamic function changes, Fluid Phase Equilibria, 2002, 202, 1, 109-120, https://doi.org/10.1016/S0378-3812(02)00097-3 . [all data]

Chickos, Hosseini, et al., 1995
Chickos, James S.; Hosseini, Sarah; Hesse, Donald G., Determination of vaporization enthalpies of simple organic molecules by correlations of changes in gas chromatographic net retention times, Thermochimica Acta, 1995, 249, 41-62, https://doi.org/10.1016/0040-6031(95)90670-3 . [all data]

Mansson, Sellers, et al., 1977
Mansson, M.; Sellers, P.; Stridh, G.; Sunner, S., Enthalpies of vaporization of some 1-substituted n-alkanes, J. Chem. Thermodyn., 1977, 9, 91. [all data]

Månsson, Sellers, et al., 1977
Månsson, M.; Sellers, P.; Stridh, G.; Sunner, S., Enthalpies of vaporization of some 1-substituted n-alkanes, The Journal of Chemical Thermodynamics, 1977, 9, 1, 91-97, https://doi.org/10.1016/0021-9614(77)90202-6 . [all data]

Baccanari, Novinski, et al., 1968
Baccanari, D.P.; Novinski, J.A.; Pan, Y.; Yevitz, M.M.; Swain, H.A., Jr., Heats of sublimation and vaporization at 25° of long chain fatty acids and methyl esters, Trans. Faraday Soc., 1968, 64, 1201. [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Rose and Schrodt, 1963
Rose, Arthur; Schrodt, Verle N., Correlation and Prediction of Vapor Pressures of Homologs. Use of Structure Parameters and Gas Chromatography Data., J. Chem. Eng. Data, 1963, 8, 1, 9-13, https://doi.org/10.1021/je60016a002 . [all data]

Hanai and Hong, 1989
Hanai, T.; Hong, C., Structure-retention correlation in CGC, J. Hi. Res. Chromatogr., 1989, 12, 5, 327-332, https://doi.org/10.1002/jhrc.1240120517 . [all data]

Haken and Korhonen, 1984
Haken, J.K.; Korhonen, I.O.O., Gas chromatography of homologous esters. XXV. Capillary column studies of monochlorinated C₅-C₁8 n-carboxylic esters, J. Chromatogr., 1984, 298, 89-100, https://doi.org/10.1016/S0021-9673(01)92697-4 . [all data]

Shashkova, Znamenskaia, et al., 1969
Shashkova, A.A.; Znamenskaia, A.P.; Pas'ko, L.Ya., Investigation of esters of odd series halohenated acids with Kovats indices, Gazovaya Khromatografiya, 1969, 9, 40-47. [all data]

Ohnishi and Shibamoto, 1984
Ohnishi, S.; Shibamoto, T., Volatile compounds from heated beef fat and beef fat with glycine, J. Agric. Food Chem., 1984, 32, 5, 987-992, https://doi.org/10.1021/jf00125a008 . [all data]

Krupcik, Matisova, et al., 1982
Krupcik, J.; Matisova, E.; Garaj, J.; Sojak, L.; Brezkin, V.G., Contribution of adsorption to retention data in glass capillary gas chromatography. Part. I. Polar stationary phases, Chromatographia, 1982, 16, 1, 166-168, https://doi.org/10.1007/BF02258890 . [all data]

Moore and Brown, 1976
Moore, B.P.; Brown, W.V., 3,4,5-Trimethoxybenzylhydrazine - an efficient subtraction reagent for aldehydes and ketones in gas chromatography, J. Chromatogr., 1976, 121, 2, 279-284, https://doi.org/10.1016/S0021-9673(00)85024-4 . [all data]

Pino, Mesa, et al., 2005
Pino, J.A.; Mesa, J.; Muñoz, Y.; Martí, M.P.; Marbot, R., Volatile components from mango (Mangifera indica L.) cultivars, J. Agric. Food Chem., 2005, 53, 6, 2213-2223, https://doi.org/10.1021/jf0402633 . [all data]

van den Dool and Kratz, 1963
van den Dool, H.; Kratz, P. Dec., A generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography, J. Chromatogr., 1963, 11, 463-471, https://doi.org/10.1016/S0021-9673(01)80947-X . [all data]

Tret'yakov, 2007
Tret'yakov, K.V., Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2007. [all data]

Eri, Khoo, et al., 2000
Eri, S.; Khoo, B.K.; Lech, J.; Hartman, T.G., Direct thermal desorption-gas chromatography and gas chromatography-mass spectrometry profiling of hop (Humulus lupulus L.) essential oils in support of varietal characterization, J. Agric. Food Chem., 2000, 48, 4, 1140-1149, https://doi.org/10.1021/jf9911850 . [all data]

Peng, 2000
Peng, C.T., Prediction of retention indices. V. Influence of electronic effects and column polarity on retention index, J. Chromatogr. A, 2000, 903, 1-2, 117-143, https://doi.org/10.1016/S0021-9673(00)00901-8 . [all data]

Ledauphin, Saint-Clair, et al., 2004
Ledauphin, J.; Saint-Clair, J.-F.; Lablanquie, O.; Guichard, H.; Founier, N.; Guichard, E.; Barillier, D., Identification of trace volatile compounds in freshly distilled calvados and cognac using preparative separations coupled with gas chromatography-mass spectrometry, J. Agric. Food Chem., 2004, 52, 16, 5124-5134, https://doi.org/10.1021/jf040052y . [all data]

Chen, Kuo, et al., 1986
Chen, C.-C.; Kuo, M.-C.; Liu, S.-E.; Wu, C.-M., Volatile components of salted and pickled prunes (Prunus mume Sieb. et Zucc.), J. Agric. Food Chem., 1986, 34, 1, 140-144, https://doi.org/10.1021/jf00067a038 . [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]

Dickschat, Bode, et al., 2005
Dickschat, J.S.; Bode, H.B.; Kroppenstedt, R.M.; Müller, R.; Schulz, S., Biosynthesis of iso-fatty acids in myxobacteria, Org. Biomol. Chem., 2005, 3, 15, 2824-2831, https://doi.org/10.1039/b504889c . [all data]

Ledauphin, Guichard, et al., 2003
Ledauphin, J.; Guichard, H.; Saint-Clair, J.-F.; Picoche, B.; Barillier, D., Chemical and sensorial aroma characterization of freshly distilled calvados. 2. Identification of volatile compounds and key odorants, J. Agric. Food Chem., 2003, 51, 2, 433-442, https://doi.org/10.1021/jf020373e . [all data]

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Guy and Vernin, 1996
Guy, I.; Vernin, G., Minor compounds from Cistus ladaniferus L. essential oil from esterel. 2. Acids and phenols, J. Essent. Oil Res., 1996, 8, 4, 455-462, https://doi.org/10.1080/10412905.1996.9700666 . [all data]

Okumura, 1991
Okumura, T., retention indices of environmental chemicals on methyl silicone capillary column, Journal of Environmental Chemistry (Japan), 1991, 1, 2, 333-358, https://doi.org/10.5985/jec.1.333 . [all data]

VOC BinBase, 2012
VOC BinBase, The volatile compound BinBase (VOC BinBase), 2012, retrieved from http://fiehnlab.ucdavis.edu/projects/VocBinBase and http://binbase.sourceforge.net. [all data]

Skogerson, Wohlgemuth, et al., 2011
Skogerson, K.; Wohlgemuth, G.; Fiehn, O., VocBinNase, 2011, retrieved from http://fiehnlab.ucdavis.edu/projects//VocBinBase. [all data]

Weyerstahl, Marschall, et al., 1998
Weyerstahl, P.; Marschall, H.; Weirauch, M.; Thefeld, K.; Surburg, H., Constituents of commercial Labdanum oil, Flavour Fragr. J., 1998, 13, 5, 295-318, https://doi.org/10.1002/(SICI)1099-1026(1998090)13:5<295::AID-FFJ751>3.0.CO;2-I . [all data]

Waggott and Davies, 1984
Waggott, A.; Davies, I.W., Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]

Notes

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

• Symbols used in this document:
  

  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔcH°liquid	Enthalpy of combustion of liquid 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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