Eicosanoic acid
- Formula: C20H40O2
- Molecular weight: 312.5304
- IUPAC Standard InChIKey: VKOBVWXKNCXXDE-UHFFFAOYSA-N
- CAS Registry Number: 506-30-9
- 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: Arachic acid; Arachidic acid; Icosanoic acid; n-Eicosanoic acid; Arachidic acid (synthetic)
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Condensed phase thermochemistry data
Go To: Top, Phase change data, 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔcH°liquid | -12574.2 ± 1.5 | kJ/mol | Ccb | Adriaanse, Dekker, et al., 1965 | Hfusion=72.0 kJ/mol; Corresponding ΔfHºliquid = -1012.6 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
545.14 | 298.15 | Schaake, van Miltenburg, et al., 1982 | T = 80 to 355 K.; DH |
Phase change data
Go To: Top, Condensed phase thermochemistry data, 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:
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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tfus | 348.4 | K | N/A | Adriaanse, Dekker, et al., 1964 | Uncertainty assigned by TRC = 0.05 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 348.23 | K | N/A | Schaake, van Miltenburg, et al., 1982, 2 | Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 347.25 | K | N/A | Spizzichino, 1956 | Uncertainty assigned by TRC = 0.6 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ptriple | 1.99983×10-8 | bar | N/A | Spizzichino, 1956 | Uncertainty assigned by TRC = 1.0666×10-8 bar; TRC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
114.5 | 492. | A | Stephenson and Malanowski, 1987 | Based on data from 477. to 670. K.; AC |
125.5 | 392. | ME,TE | de Kruif, Schaake, et al., 1982 | Based on data from 380. to 404. K.; AC |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
148.4 | 305. to 323. | TPTD | Chattopadhyay and Ziemann, 2005 | Experimental values based on the TPTD method are often inconsistent with values determined using other experimental methods; AC |
199.6 ± 7.5 | 342. | ME | Davies and Malpass, 1961 | Based on data from 337. to 346. K. See also Cox and Pilcher, 1970.; AC |
200. ± 7.5 | 336.8 | V | Davies and Malpass, 1961, 2 | ALS |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
71.6 | 347.8 | DSC | Moreno, Cordobilla, et al., 2007 | AC |
69.2 | 348.2 | N/A | Domalski and Hearing, 1996 | AC |
Enthalpy of phase transition
ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
69.204 | 348.23 | crystaline, I | liquid | Schaake, van Miltenburg, et al., 1982 | DH |
Entropy of phase transition
ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
198.7 | 348.23 | crystaline, I | liquid | Schaake, van Miltenburg, et al., 1982 | DH |
Gas Chromatography
Go To: Top, Condensed phase thermochemistry data, 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
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5MS | 2365.3 | Andriamaharavo, 2014 | 30. m/0.25 mm/0.25 μm, He; Program: 60C (1 min) => 5 C/min => 210C => 10 C/min => 280C (15 min) |
Capillary | DB-5 | 2380. | Özel, Gögüs, et al., 2006 | Program: not specified |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5 MS | 2359. | Xu, Han, et al., 2012 | 30. m/0.25 mm/0.25 μm, 60. C @ 2. min, 15. K/min, 300. C @ 10. min |
Capillary | HP-5 MS | 2359. | Xu, Han, et al., 2009 | 30. m/0.25 mm/0.25 μm, Helium, 60. C @ 2. min, 15. K/min, 300. C @ 10. min |
Capillary | Methyl Silicone | 2359. | Vendramini and Trugo, 2000 | 50. m/0.25 mm/0.5 μm, H2, 40. C @ 0.5 min, 4. K/min; Tend: 260. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | 2380. | Karimi, Farmany, et al., 2011 | Program: not specified | |
Capillary | ZB-1 MS | 2366. | Al-Reza, Rahman, et al., 2009 | 30. m/0.25 mm/0.25 μm, Helium; Program: 50 0C 3 0C/min -> 150 0C (10 min) 10 0C/min -> 250 0C |
Lee's RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 377.8 | Donnelly, Abdel-Hamid, et al., 1993 | 30. m/0.32 mm/0.25 μm, He, 40. C @ 3. min, 8. K/min, 285. C @ 29.5 min |
References
Go To: Top, Condensed phase thermochemistry data, 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.
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]
Schaake, van Miltenburg, et al., 1982
Schaake, R.C.F.; van Miltenburg, J.C.; De Kruif, C.G.,
Thermodynamic properties of the normal alkanoic acids. II. Molar heat capacities of seven even-numbered normal alkanoic acids,
J. Chem. Thermodynam., 1982, 14, 771-778. [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]
Schaake, van Miltenburg, et al., 1982, 2
Schaake, R.C.F.; van Miltenburg, J.C.; De Kruif, C.G.,
Thermodynamic properties of the normal alkanoic acids. II. Molar heat capacities of seven even-numbered normal alkanoic acids.,
J. Chem. Thermodyn., 1982, 14, 771-8. [all data]
Spizzichino, 1956
Spizzichino, C.,
Contribution a l'etude des tensions de vapeur et des chaleurs de vaporisation des acides gras, esters methyliques et alcools gras a des pressions inferieures a 1 mm de mercure,
J. des Recherches du C.N.R.S., 1956, 34, 1-24. [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]
de Kruif, Schaake, et al., 1982
de Kruif, C.G.; Schaake, R.C.F.; van Miltenburg, J.C.; van der Klauw, K.; Blok, J.G.,
Thermodynamic properties of the normal alkanoic acids III. Enthalpies of vaporization and vapour pressures of 13 normal alkanoic acids,
The Journal of Chemical Thermodynamics, 1982, 14, 8, 791-798, https://doi.org/10.1016/0021-9614(82)90176-8
. [all data]
Chattopadhyay and Ziemann, 2005
Chattopadhyay, Sulekha; Ziemann, Paul J.,
Vapor Pressures of Substituted and Unsubstituted Monocarboxylic and Dicarboxylic Acids Measured Using an Improved Thermal Desorption Particle Beam Mass Spectrometry Method,
Aerosol Science and Technology, 2005, 39, 11, 1085-1100, https://doi.org/10.1080/02786820500421547
. [all data]
Davies and Malpass, 1961
Davies, Mansel; Malpass, V.E.,
212. Heats of sublimation of straight-chain monocarboxylic acids,
J. Chem. Soc., 1961, 1048, https://doi.org/10.1039/jr9610001048
. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]
Davies and Malpass, 1961, 2
Davies, M.; Malpass, V.E.,
Heats of sublimation of straight-chain monocarboxylic acids,
J. Chem. Soc., 1961, 1048-10. [all data]
Moreno, Cordobilla, et al., 2007
Moreno, Evelyn; Cordobilla, Raquel; Calvet, Teresa; Cuevas-Diarte, M.A.; Gbabode, Gabin; Negrier, Philippe; Mondieig, Denise; Oonk, Harry A.J.,
Polymorphism of even saturated carboxylic acids from n-decanoic to n-eicosanoic acid,
New J. Chem., 2007, 31, 6, 947, https://doi.org/10.1039/b700551b
. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [all data]
Andriamaharavo, 2014
Andriamaharavo, N.R.,
Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2014. [all data]
Özel, Gögüs, et al., 2006
Özel, M.Z.; Gögüs, F.; Lewis, A.C.,
Determination of Teucrium chamaedrys volatiles by using direct thermal desorption-comprehensive two-dimensional gas chromatography-time-of-flight mass spectrometry,
J. Chromatogr. A, 2006, 1114, 1, 164-169, https://doi.org/10.1016/j.chroma.2006.02.036
. [all data]
Xu, Han, et al., 2012
Xu, L.-L.; Han, T.; Wu, J.-Z.; Zhang, Q.-Y.; Zhang, H.; Huang, B.-K.; Rahman, K.,
Comparative research of chemical constituents, antifungal and antitumor properties of ether extracts of Panax ginseng and its endophytic fungus, 2012, retrieved from http://www.thefreelibrary.com/Comparative .... [all data]
Xu, Han, et al., 2009
Xu, L.-L.; Han, T.; Wu, J.-Z.; Zhang, Q.-Y.; Zhang, H.; Huang, B.-K.; Rahman, K.,
Comparative research of chemical constituents, antifungal and antitumor properties of ether extracts of Panax ginseng and its endophytic fungus,
Phytomedicine: Int. J. Phytotherapy Phytopharmacology, 2009, 16, 6-7, 609-616, https://doi.org/10.1016/j.phymed.2009.03.014
. [all data]
Vendramini and Trugo, 2000
Vendramini, A.L.; Trugo, L.C.,
Chemical composition of acerola fruit (Malpighia punicifolia L.) at three stages of maturity,
Food Chem., 2000, 71, 2, 195-198, https://doi.org/10.1016/S0308-8146(00)00152-7
. [all data]
Karimi, Farmany, et al., 2011
Karimi, H.; Farmany, A.; Noorizadeh, H.,
Prediction of linear retention index of Teucrium chamaedrys volatiles in GCxGC-TOF/MS by linear model,
World Appl. Sci. J., 2011, 15, 8, 1086-1088. [all data]
Al-Reza, Rahman, et al., 2009
Al-Reza, S.M.; Rahman, A.; Kang, S.C.,
Chemical composition and inhibitory effect of essentiasl oil and organic extracts of Cestrum nocturnum L. om food-borne pathogens,
Int. J. Food Sci. Technol., 2009, 44, 6, 1176-1182, https://doi.org/10.1111/j.1365-2621.2009.01939.x
. [all data]
Donnelly, Abdel-Hamid, et al., 1993
Donnelly, J.R.; Abdel-Hamid, M.S.; Jeter, J.L.; Gurka, D.F.,
Application of gas chromatographic retention properties to the identification of environmental contaminants,
J. Chromatogr., 1993, 642, 1-2, 409-415, https://doi.org/10.1016/0021-9673(93)80106-I
. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas Chromatography, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid Ptriple Triple point pressure Tfus Fusion (melting) point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfusH Enthalpy of fusion ΔsubH Enthalpy of sublimation ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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