Eicosanoic acid, methyl ester
- Formula: C21H42O2
- Molecular weight: 326.5570
- IUPAC Standard InChIKey: QGBRLVONZXHAKJ-UHFFFAOYSA-N
- CAS Registry Number: 1120-28-1
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: Methyl arachisate; Methyl eicosanoate; Arachidic acid methyl ester; Kemester 2050; Methyl aracidate; Methyl eicosenate; Methyl arachidate; methyl icosanoate
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Phase change data
Go To: Top, Gas Chromatography, References, Notes
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔvapH° | 28.90 ± 0.60 | kcal/mol | CGC | Chickos, Zhao, et al., 2004 | Based on data from 467. to 558. K.; AC |
ΔvapH° | 27.82 ± 0.36 | kcal/mol | N/A | van Genderen, van Miltenburg, et al., 2002 | AC |
ΔvapH° | 27.77 | kcal/mol | GC | Krop, Velzen, et al., 1997 | Based on data from 463. to 523. K.; AC |
Reduced pressure boiling point
Tboil (K) | Pressure (atm) | Reference | Comment |
---|---|---|---|
488.7 | 0.013 | Weast and Grasselli, 1989 | BS |
461.2 | 0.003 | Weast and Grasselli, 1989 | BS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
26.10 | 350. | N/A | van Genderen, van Miltenburg, et al., 2002 | AC |
23.4 ± 0.05 | 406. | N/A | van Genderen, van Miltenburg, et al., 2002 | AC |
18.4 | 498. | GC | Husain, Sarma, et al., 1993 | Based on data from 453. to 543. K.; AC |
22.1 | 465. | A,EST | Stephenson and Malanowski, 1987 | Based on data from 450. to 540. K. See also Rose and Schrodt, 1963.; AC |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
45.6 ± 2.4 | 314. | ME | Davies and Kybett, 1965 | Based on data from 311. to 318. K. See also Stephenson and Malanowski, 1987.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
17.8 | 319.2 | DSC | Chickos, Zhao, et al., 2004 | AC |
17.6 | 319.2 | N/A | King and Garner, 1936 | AC |
Gas Chromatography
Go To: Top, Phase change data, 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
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | OV-101 | 170. | 2295.6 | Kittiratanapiboon, Jeyashoke, et al., 1998 | 15. m/0.25 mm/0.2 μm, N2 |
Capillary | OV-101 | 175. | 2296.7 | Kittiratanapiboon, Jeyashoke, et al., 1998 | 15. m/0.25 mm/0.2 μm, N2 |
Capillary | OV-101 | 180. | 2297.8 | Kittiratanapiboon, Jeyashoke, et al., 1998 | 15. m/0.25 mm/0.2 μm, N2 |
Capillary | OV-101 | 185. | 2299. | Kittiratanapiboon, Jeyashoke, et al., 1998 | 15. m/0.25 mm/0.2 μm, N2 |
Capillary | OV-101 | 190. | 2300.2 | Kittiratanapiboon, Jeyashoke, et al., 1998 | 15. m/0.25 mm/0.2 μm, N2 |
Capillary | OV-101 | 195. | 2301.4 | Kittiratanapiboon, Jeyashoke, et al., 1998 | 15. m/0.25 mm/0.2 μm, N2 |
Capillary | OV-101 | 200. | 2302.7 | Kittiratanapiboon, Jeyashoke, et al., 1998 | 15. m/0.25 mm/0.2 μm, N2 |
Capillary | CP Sil 5 CB | 240. | 2312. | Hanai and Hong, 1989 | 30. m/0.25 mm/0.25 μm |
Packed | SE-30 | 200. | 2314. | Golovnya and Kuzmenko, 1977 | He, Chromosorb W (80-100 mesh); Column length: 1.5 m |
Packed | SE-30 | 200. | 2314. | Golovnya, Uralets, et al., 1976 | Gas Chrom Q (80-100 mesh); Column length: 1.5 m |
Kovats' RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | BP-1 | 2318. | Srivastava, Srivastava, et al., 2006 | 30. m/0.32 mm/0.25 μm, N2, 5. K/min, 220. C @ 3. min; Tstart: 60. C |
Kovats' RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | CP-Wax | 240. | 2617. | Hanai and Hong, 1989 | 25. m/0.25 mm/0.22 μm |
Capillary | DB-Wax | 240. | 2646. | Hanai and Hong, 1989 | 25. m/0.25 mm/0.22 μm |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5 | 2339. | Fokialakis, Melliou, et al., 2003 | 30. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 60. C; Tend: 280. C |
Capillary | DB-1 | 2310. | Johnson, Urso, et al., 1997 | 30. m/0.2 mm/0.25 μm, 50. C @ 2. min, 5. K/min, 300. C @ 5. min |
Capillary | DB-1 | 2310. | Johnson, Urso, et al., 1997 | 30. m/0.2 mm/0.25 μm, 50. C @ 2. min, 5. K/min, 300. C @ 5. min |
Capillary | Ultra-1 | 2311.59 | Richmond and Pombo-Villar, 1997 | 25. m/0.32 mm/0.52 μm, 15. K/min, 320. C @ 10. min; Tstart: 35. C |
Capillary | OV-1 | 2302. | Tan, Holland, et al., 1988 | He, 8. K/min, 280. C @ 10. min; Column length: 25. m; Column diameter: 0.32 mm; Tstart: 40. C |
Capillary | DB-5 | 2329. | Rostad and Pereira, 1986 | 30. m/0.26 mm/0.25 μm, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5 | 2332. | Isidorov, Krajewska, et al., 2001 | 30. m/0.25 mm/0.25 μm, He; Program: 50C => 6C/min => 100C => 4C/min => 280C |
Capillary | DB-1 | 2311. | Peng, 2000 | 15. m/0.53 mm/1. μm, He; Program: 40C(3min) => 8C/min => 200(1min) => 5C/min => 300C(25min) |
Van Den Dool and Kratz RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 2638. | Peng, 2000 | 15. m/0.53 mm/1. μm, He, 40. C @ 3. min, 5. K/min, 220. C @ 30. min |
Capillary | HP-Wax | 2640. | Peng, 2000 | 15. m/0.53 mm/1. μm, He, 40. C @ 3. min, 5. K/min, 220. C @ 30. min |
Normal alkane RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | DB-1 | 200. | 2311. | Aryusuk and Krisnangkura, 2003 | |
Capillary | LM-1 | 210. | 2317. | Filho and Lancas, 1995 | 30. m/0.25 mm/0.25 μm, Hydrogen |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | RTx-1 | 2311. | Dib, Bendahou, et al., 2010 | 60. m/0.22 mm/0.25 μm, Helium, 2. K/min, 230. C @ 35. min; Tstart: 60. C |
Capillary | HP-5 MS | 2335. | Vedernikov and Roschin, 2010 | 30. m/0.25 mm/0.25 μm, Helium, 5. K/min, 280. C @ 10. min; Tstart: 150. C |
Capillary | DB-1 | 2305. | Guy and Vernin, 1996 | He, 70. C @ 5. min, 3. K/min; Column length: 30. m; Column diameter: 0.25 mm; Tend: 300. C |
Capillary | DB-5 | 2333. | Wang, Jin, et al., 1992 | 30. m/0.25 mm/0.215 μm, N2, 50. C @ 4. min, 6. K/min, 300. C @ 20. min |
Capillary | Ultra-1 | 2309. | Okumura, 1991 | 25. m/0.32 mm/0.25 μm, He, 3. K/min; Tstart: 80. C; Tend: 260. C |
Packed | SE-30 | 2313. | Horning, Casparrini, et al., 1969 | Gas Chrom P, 2. K/min; Column length: 3.7 m; Tstart: 145. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Siloxane, 5 % Ph | 2307. | VOC BinBase, 2012 | Program: not specified |
Capillary | Polydimethyl siloxane, 5 % phenyl | 2307. | Skogerson, Wohlgemuth, et al., 2011 | Program: not specified |
Capillary | RTx-1 | 2312. | Dib, Bendahou, et al., 2010 | 60. m/0.22 mm/0.25 μm, Helium; Program: not specified |
Capillary | HP-5 MS | 2324. | Vedernikov and Roschin, 2010 | 30. m/0.25 mm/0.25 μm, Helium; Program: not specified |
Capillary | DB-5 | 2329. | Wang, Jin, et al., 1992 | 30. m/0.25 mm/0.215 μm, N2; Program: not specified |
Lee's RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5MS | 376.90 | Chen, Keeran, et al., 2002 | 30. m/0.25 mm/0.5 μm, 40. C @ 1. min, 10. K/min; Tend: 310. C |
Capillary | DB-5MS | 380.64 | Chen, Keeran, et al., 2002 | 30. m/0.25 mm/0.5 μm, 40. C @ 1. min, 4. K/min; Tend: 310. C |
Capillary | DB-1 | 390.6 | Johnson, Urso, et al., 1997 | 30. m/0.2 mm/0.25 μm, 50. C @ 2. min, 5. K/min, 300. C @ 5. min |
Capillary | DB-1 | 390.6 | Johnson, Urso, et al., 1997 | 30. m/0.2 mm/0.25 μm, 50. C @ 2. min, 5. K/min, 300. C @ 5. min |
Capillary | DB-5 | 379.61 | Wang, Jin, et al., 1992 | 30. m/0.25 mm/0.215 μm, N2, 50. C @ 4. min, 6. K/min, 300. C @ 20. min |
Capillary | DB-5 | 378.87 | Rostad and Pereira, 1986 | 30. m/0.26 mm/0.25 μm, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min |
Lee's RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Polydimethyl siloxanes | 378.87 | Eckel and Kind, 2003 | Program: not specified |
Capillary | DB-5 | 378.87 | Wang, Jin, et al., 1992 | 30. m/0.25 mm/0.215 μm, N2; Program: not specified |
References
Go To: Top, Phase change data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Chickos, Zhao, et al., 2004
Chickos, James S.; Zhao, Hui; Nichols, Gary,
The vaporization enthalpies and vapor pressures of fatty acid methyl esters C18, C21 to C23, and C25 to C29 by correlation -- gas chromatography,
Thermochimica Acta, 2004, 424, 1-2, 111-121, https://doi.org/10.1016/j.tca.2004.05.020
. [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]
Krop, Velzen, et al., 1997
Krop, Hildo B.; Velzen, Martin J.M.v.; Parsons, John R.; Govers, Harrie A.J.,
Determination of environmentally relevant physical-chemical properties of some fatty acid esters,
J Amer Oil Chem Soc, 1997, 74, 3, 309-315, https://doi.org/10.1007/s11746-997-0142-9
. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Husain, Sarma, et al., 1993
Husain, Sajid; Sarma, P. Nageswara; Swamy, G.Y.S.K.; Devi, K. Sita,
Determination of physicochemical properties of some fatty acid methyl esters by gas liquid chromatography,
J Am Oil Chem Soc, 1993, 70, 2, 149-155, https://doi.org/10.1007/BF02542618
. [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]
Davies and Kybett, 1965
Davies, M.; Kybett, B.,
Sublimation and vaporization heats of long-chain alcohols,
Trans. Faraday Soc., 1965, 61, 1608. [all data]
King and Garner, 1936
King, A. Millicent; Garner, William E.,
297. The heats of crystallisation of methyl and ethyl esters of monobasic fatty acids,
J. Chem. Soc., 1936, 1372, https://doi.org/10.1039/jr9360001372
. [all data]
Kittiratanapiboon, Jeyashoke, et al., 1998
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
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]
Golovnya and Kuzmenko, 1977
Golovnya, R.V.; Kuzmenko, T.E.,
Thermodynamic evaluation of the interaction of fatty acid methyl esters with polar and non-polar stationary phases, based on their retention indices,
Chromatographia, 1977, 10, 9, 545-548, https://doi.org/10.1007/BF02262915
. [all data]
Golovnya, Uralets, et al., 1976
Golovnya, R.V.; Uralets, V.P.; Kuzmenko, T.E.,
Characterization of fatty acid methyl esters by gas chromatography on siloxane liquid phases,
J. Chromatogr., 1976, 121, 1, 118-121, https://doi.org/10.1016/S0021-9673(00)82312-2
. [all data]
Srivastava, Srivastava, et al., 2006
Srivastava, A.K.; Srivastava, S.K.; Syamsundar, K.V.,
Volatile composition of Curcuma angustifolia Roxb. rhizome from central and southern India,
Flavour Fragr. J., 2006, 21, 3, 423-426, https://doi.org/10.1002/ffj.1680
. [all data]
Fokialakis, Melliou, et al., 2003
Fokialakis, N.; Melliou, E.; Magiatis, P.; Harvala, C.; Mitaku, S.,
Composition of the steam volatiles of six Euphorbia spp. from Greece,
Flavour Fragr. J., 2003, 18, 1, 39-42, https://doi.org/10.1002/ffj.1148
. [all data]
Johnson, Urso, et al., 1997
Johnson, C.I.; Urso, A.; Geleta, L.,
Broad spectrum analysis of municipal and industrial effluents discharged into the Peace, Athabasca and Slave river basins: characterization of effluent samples, 1994 - Volume 1 of 2, Northern River Basins Study Project Report No. 121, Norther River Basins Study, Edmonton, Alberta, 1997, 27. [all data]
Richmond and Pombo-Villar, 1997
Richmond, R.; Pombo-Villar, E.,
Short communication. Gas chromatography-mass spectrometry coupled with pseudo-Sadtler retention indices, for the identification of components in the essential oil of Curcuma longa L.,
J. Chromatogr. A, 1997, 760, 2, 303-308, https://doi.org/10.1016/S0021-9673(96)00802-3
. [all data]
Tan, Holland, et al., 1988
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]
Rostad and Pereira, 1986
Rostad, C.E.; Pereira, W.E.,
Kovats and Lee retention indices determined by gas chromatography/mass spectrometry for organic compounds of environmental interest,
J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 6, 328-334, https://doi.org/10.1002/jhrc.1240090603
. [all data]
Isidorov, Krajewska, et al., 2001
Isidorov, V.A.; Krajewska, U.; Dubis, E.N.; Jdanova, M.A.,
Partition coefficients of alkyl aromatic hydrocarbons and esters in a hexane-acetonitrile system,
J. Chromatogr. A, 2001, 923, 1-2, 127-136, https://doi.org/10.1016/S0021-9673(01)00929-3
. [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]
Aryusuk and Krisnangkura, 2003
Aryusuk, K.; Krisnangkura, K.,
Prediction of gas chromatographic retention times of capillary columns of different inside diameters,
J. Sep. Sci., 2003, 26, 18, 1688-1692, https://doi.org/10.1002/jssc.200301505
. [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]
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]
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]
Wang, Jin, et al., 1992
Wang, X.; Jin, Z.; Xu, X.,
Analysis of fatty acids in bacteria by using gas chromatographic retention indices,
Chin. J. Chromatogr., 1992, 10, 2, 92-94. [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]
Horning, Casparrini, et al., 1969
Horning, M.G.; Casparrini, G.; Horning, E.C.,
The use of gas phase analytical methods for the analysis of phospholipids,
J. Chromatogr. Sci., 1969, 7, 5, 267-275, https://doi.org/10.1093/chromsci/7.5.267
. [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]
Chen, Keeran, et al., 2002
Chen, P.H.; Keeran, W.S.; Van Ausdale, W.A.; Schindler, D.R.; Roberts, D.W.,
Application of Lee retention indices to the confirmation of tentatively identified compounds from GC/MS analysis of environmental samples, Technical paper, Analytical Services Division, Environmental ScienceEngineering, Inc, PO Box 1703, Gainesville, FL 32602, 2002, 11. [all data]
Eckel and Kind, 2003
Eckel, W.P.; Kind, T.,
Use of boiling point-Lee retention index correlation for rapid review of gas chromatography-mass spectrometry data,
Anal. Chim. Acta., 2003, 494, 1-2, 235-243, https://doi.org/10.1016/j.aca.2003.08.003
. [all data]
Notes
Go To: Top, Phase change data, Gas Chromatography, References
- Symbols used in this document:
Tboil Boiling point ΔfusH Enthalpy of fusion ΔsubH Enthalpy of sublimation 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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