9,12-Octadecadienoic acid (Z,Z)-, methyl ester
- Formula: C19H34O2
- Molecular weight: 294.4721
- IUPAC Standard InChI: InChI=1S/C19H34O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19(20)21-2/h7-8,10-11H,3-6,9,12-18H2,1-2H3/b8-7-,11-10-
- IUPAC Standard InChIKey: WTTJVINHCBCLGX-NQLNTKRDSA-N
- CAS Registry Number: 112-63-0
- Chemical structure:
This structure is also available as a 2d Mol file - Stereoisomers:
- Other names: Linoleic acid, methyl ester; Methyl cis,cis-9,12-octadecadienoate; Methyl linoleate; Methyl 9-cis,12-cis-octadecadienoate; 9,12-Octadecadienoic acid, methyl ester, (Z,Z); cis-9,cis-12-Octadecadienoic acid, methyl ester; cis-Linoleic acid methyl ester; Methyl (Z,Z)-9,12-octadecadienoate; (Z,Z)-9,12-octadecadienoic acid methyl ester; (9Z,12Z)-Octadecadienoic acid methyl ester; 9,12-Octadecadienoic acid (9Z,12Z)-, methyl ester; Methyl linolate; methyl (Z,Z)-9,12-octadienoate; Natural methyl linoleate
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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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°liquid | -144.57 | kcal/mol | Chyd | Rogers and Siddiqui, 1975 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -2794.00 ± 0.37 | kcal/mol | Ccb | Freedman, Bagby, et al., 1989 | Corresponding ΔfHºliquid = -154.33 kcal/mol (simple calculation by NIST; no Washburn corrections) |
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
Reduced pressure boiling point
| Tboil (K) | Pressure (atm) | Reference | Comment |
|---|---|---|---|
| 465.2 | 0.005 | Aldrich Chemical Company Inc., 1990 | BS |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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| Temperature (K) | A | B | C | Reference | Comment |
|---|---|---|---|---|---|
| 439.7 to 479. | 3.82275 | 2066.995 | -116.87 | Althouse and Triebold, 1944 | Coefficents calculated by NIST from author's data. |
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
+ 2
=
By formula: C19H34O2 + 2H2 = C19H38O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -58.60 ± 0.39 | kcal/mol | Chyd | Rogers and Siddiqui, 1975 | liquid phase; solvent: n-Hexane |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
- SOLUTION (10% CCl4 FOR 4000-1220, 10% CS2 FOR 1220-450 CM-1) VS SOLVENT; CARY 90 (GRATING); 2 cm-1 resolution
- SOLUTION (10% CS2 FOR 5000-2380 AND 1390-625, 10% C2Cl4 FOR 2380-1390 CM-1); PERKIN-ELMER; DIGITIZED BY NIST FROM HARD COPY; 4 cm-1 resolution
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
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
| Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
|---|---|
| Origin | NIST Mass Spectrometry Data Center |
| NIST MS number | 333205 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Rogers and Siddiqui, 1975
Rogers, D.W.; Siddiqui, N.A.,
Heats of hydrogenation of large molecules. I. Esters of unsaturated fatty acids,
J. Phys. Chem., 1975, 79, 574-577. [all data]
Freedman, Bagby, et al., 1989
Freedman, B.; Bagby, M.O.; Khoury, H.,
Correlation of heats of combustion with empirical formulas for fatty alcohols,
J. Am. Oil Chem. Soc., 1989, 66, 595-596. [all data]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Althouse and Triebold, 1944
Althouse, Paul M.; Triebold, Howard O.,
Physical Constants of Methyl Esters of Commonly Occurring Fatty Acids Vapor Pressure,
Ind. Eng. Chem. Anal. Ed., 1944, 16, 10, 605-606, https://doi.org/10.1021/i560134a003
. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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