9,12-Octadecadienoic acid (Z,Z)-
- Formula: C18H32O2
- Molecular weight: 280.4455
- IUPAC Standard InChIKey: OYHQOLUKZRVURQ-HZJYTTRNSA-N
- CAS Registry Number: 60-33-3
- 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:
- Other names: cis-9,cis-12-Octadecadienoic acid; cis,cis-Linoleic acid; Grape seed oil; Linoleic; Linoleic acid; Linolic acid; Polylin No. 515; Telfairic acid; Unifac 6550; 9,12-Octadecadienoic acid, cis,cis-; Leinoleic acid; 9,12-Linoleic acid; cis,cis-9,12-Octadecadienoic acid; Emersol 310; Emersol 315; Vespula pensylvanica b708568k063; 9-(Z), 12-(Z)-Octadecadienoic acid; Acide linoleique; Octadeca-9,12-dienoic acid, (cis,cis)-; (Z,Z)-9,12-Octadecadienoic acid; (Z,Z)-Octadeca-9, 12-dienoic acid; 9,12-Octadecadienoic acid (9Z,12Z)-; 9-cis,12-cis-Linoleic acid; 9Z,12Z-Linoleic acid; all-cis-9,12-Octadecadienoic acid; cis-Δ9,12-Octadecadienoic acid; Extra Linoleic 90; Polylin 515; 9,12-Octadecadienoic acid; Pamolyn 125 (Salt/Mix)
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Condensed phase thermochemistry data
Go To: Top, IR Spectrum, Mass spectrum (electron ionization), 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -151.7 | kcal/mol | Chyd | Rogers, Hoyte, et al., 1978 |
IR Spectrum
Go To: Top, Condensed phase thermochemistry data, Mass spectrum (electron ionization), 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 by: Coblentz Society, Inc.
Condensed Phase Spectrum
Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.
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
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Owner | COBLENTZ SOCIETY Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | STANDARD OIL OF OHIO |
Source reference | COBLENTZ NO. 10104 |
Date | 1976/12/20 |
Name(s) | (9Z,12Z)-9,12-octadecadienoic acid LINOLEIC ACID |
State | LIQUID (NEAT) |
Instrument | PERKIN-ELMER 180 (GRATING) |
Instrument parameters | GRATING CHANGES AT 2000, 1000, 500, 250 CM-1 |
Path length | CAPILLARY, KBr CRYSTALS |
Resolution | 4 |
Sampling procedure | TRANSMISSION |
Data processing | DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS) |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, IR Spectrum, 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 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 | Japan AIST/NIMC Database- Spectrum MS-NW- 623 |
NIST MS number | 229327 |
Gas Chromatography
Go To: Top, Condensed phase thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), 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, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5MS | 2134. | Asuming, Beauchamp, et al., 2005 | 30. m/0.25 mm/0.25 μm, He, 50. C @ 10. min, 3. K/min, 250. C @ 5. min |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5MS | 2140. | Benkaci-Ali, Baaliouamer, et al., 2007 | 30. m/0.25 mm/0.25 μm, He, 60. C @ 8. min, 2. K/min, 250. C @ 30. min |
Capillary | DB-5 | 2130. | Wu, Zorn, et al., 2007 | 30. m/0.32 mm/0.25 μm, He, 40. C @ 2. min, 5. K/min, 250. C @ 5. min |
Capillary | DB-5 | 2131. | Wu, Zorn, et al., 2007 | 30. m/0.32 mm/0.25 μm, He, 40. C @ 2. min, 5. K/min, 250. C @ 5. min |
Capillary | HP-5MS | 2095.2 | Zeng, Zhao, et al., 2007 | 30. m/0.25 mm/0.25 μm, He, 4. K/min; Tstart: 80. C; Tend: 300. C |
Capillary | HP-5MS | 2104. | Saroglou, Dorizas, et al., 2006 | 30. m/0.25 mm/0.25 μm, He, 60. C @ 5. min, 4. K/min; Tend: 280. C |
Capillary | HP-5MS | 2144. | Saroglou, Dorizas, et al., 2006 | 30. m/0.25 mm/0.25 μm, He, 60. C @ 5. min, 4. K/min; Tend: 280. C |
Capillary | HP-5MS | 2170. | Vujisic L., Vuckovic I., et al., 2006 | 30. m/0.25 mm/0.25 μm, H2, 4.3 K/min; Tstart: 50. C; Tend: 285. C |
Capillary | CP Sil 5 CB | 2095. | Ziegenbein, Hanssen, et al., 2006 | H2, 10. K/min; Column length: 25. m; Column diameter: 0.25 mm; Tstart: 80. C; Tend: 270. C |
Capillary | CP Sil 5 CB | 2095. | Ziegenbein, Hanssen, et al., 2006, 2 | 25. m/0.25 mm/0.4 μm, He, 10. K/min; Tstart: 80. C; Tend: 270. C |
Capillary | DB-5 | 2173. | Alves, Pinto, et al., 2005 | 30. m/0.25 mm/0.25 μm, H2, 5. K/min, 270. C @ 20. min; Tstart: 35. C |
Capillary | SE-30 | 2156. | Tundis, Passalacqua, et al., 2005 | 30. m/0.25 mm/0.25 μm, He, 60. C @ 3. min, 16. K/min, 280. C @ 10. min |
Capillary | DB-5 | 2126. | Wu, Zorn, et al., 2005 | 30. m/0.32 mm/0.25 μm, He, 40. C @ 2. min, 5. K/min, 250. C @ 5. min |
Capillary | HP-5 | 2159. | Javidnia, Miri, et al., 2004 | He, 3. K/min; Column length: 30. m; Column diameter: 0.25 mm; Tstart: 60. C; Tend: 260. C |
Capillary | Optima 5 | 2114. | Chosson, Vérité, et al., 2003 | 25. m/0.25 mm/0.25 μm, He, 3. K/min, 280. C @ 20. min; Tstart: 60. C |
Capillary | HP-5MS | 2130. | Lalel, Singh, et al., 2003 | 60. m/0.25 mm/0.25 μm, He, 40. C @ 1. min, 3. K/min, 310. C @ 20. min |
Capillary | HP-5 | 2152. | Skaltsa, Demetzos, et al., 2003 | 30. m/0.25 mm/0.25 μm, He, 60. C @ 5. min, 4. K/min; Tend: 280. C |
Capillary | CP Sil 5 CB | 2113. | Pino, Marbot, et al., 2002 | 30. m/0.25 mm/0.25 μm, H2, 60. C @ 10. min, 2. K/min, 280. C @ 40. min |
Capillary | CP Sil 5 CB | 2113. | Pino, Marbot, et al., 2002, 2 | 50. m/0.32 mm/0.4 μm, He, 60. C @ 10. min, 3. K/min, 280. C @ 60. min |
Capillary | Ultra-1 | 2106. | Richmond and Pombo-Villar, 1998 | 25. m/0.32 mm/0.52 μm, He, 15. K/min, 320. C @ 10. min; Tstart: 35. C |
Capillary | CP Sil 5 CB | 2112. | Montanarella, Bos, et al., 1986 | N2, 4. K/min; Column length: 25. m; Column diameter: 0.22 mm; Tstart: 70. C; Tend: 295. C |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | VF-5MS | 2145.8 | Tret'yakov, 2007 | 30. m/0.25 mm/0.25 μm, He; Program: Multi-step temperature program; T(initial)=60C; T(final)=270C |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5 MS | 2179. | Sandoval-Montemayor, Garcia, et al., 2012 | 25. m/0.20 mm/0.30 μm, Helium, 40. C @ 2. min, 10. K/min, 260. C @ 20. min |
Capillary | HP-5 MS | 2113. | 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 | 2147. | Miyazawa, Marumoto, et al., 2011 | 30. m/0.25 mm/0.25 μm, Helium, 4. K/min, 260. C @ 5. min; Tstart: 40. C |
Capillary | DB-5 MS | 2128. | Stojanovic, RAdulovic, et al., 2011 | 30. m/0.25 mm/0.25 μm, Helium, 5. K/min, 290. C @ 10. min; Tstart: 70. C |
Capillary | HP-5 MS | 2136. | Radulovic, Blagojevic, et al., 2010 | 30. m/0.25 mm/0.25 μm, Helium, 5. K/min, 290. C @ 10. min; Tstart: 70. C |
Capillary | HP-5 MS | 2133. | Radulovic, Dordevic, et al., 2010 | 30. m/0.25 mm/0.25 μm, Helium, 5. K/min, 290. C @ 10. min; Tstart: 70. C |
Capillary | DB-1 | 2109. | Xu, Tang, et al., 2010 | 30. m/0.25 mm/0.25 μm, Helium, 50. C @ 2. min, 4. K/min, 220. C @ 2. min |
Capillary | HP-5 MS | 2135. | Kim and Chung, 2009 | 30. m/0.25 mm/0.25 μm, Helium, 35. C @ 5. min, 2. K/min, 195. C @ 30. min |
Capillary | HP-5 MS | 2136. | Radulovic, Blagojevic, et al., 2009 | 30. m/0.25 mm/0.25 μm, Helium, 5. K/min, 290. C @ 10. min; Tstart: 70. C |
Capillary | HP-5 MS | 2113. | 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 | HP-5 MS | 2154. | Zhao, Zeng, et al., 2009 | 30. m/0.25 mm/0.25 μm, Helium, 4. K/min; Tstart: 50. C; Tend: 280. C |
Capillary | HP-101 | 2111. | Blazevic and Mastelic, 2008 | 25. m/0.20 mm/0.25 μm, Helium, 70. C @ 2. min, 3. K/min; Tend: 200. C |
Capillary | HP-101 | 2130. | Blazevic and Mastelic, 2008 | 25. m/0.20 mm/0.25 μm, Helium, 70. C @ 2. min, 3. K/min; Tend: 200. C |
Capillary | HP-5 MS | 2146. | Szarka, Hethelyi, et al., 2008 | 30. m/0.25 mm/0.25 μm, Helium, 60. C @ 1. min, 10. K/min, 280. C @ 7. min |
Capillary | HP-5MS | 2144. | Ferhat, Meklati, et al., 2007 | 30. m/0.25 mm/0.25 μm, He, 60. C @ 8. min, 2. K/min, 250. C @ 15. min |
Capillary | HP-5MS | 2156. | Ferhat, Tigrine-Kordjani, et al., 2007 | 30. m/0.25 mm/0.25 μm, He, 60. C @ 8. min, 2. K/min, 250. C @ 15. min |
Capillary | HP-5 | 2136. | Ristic, Krivokuca-Dokic, et al., 2007 | 30. m/0.25 mm/0.25 μm, Helium, 4. K/min; Tstart: 40. C; Tend: 260. C |
Capillary | HP-5 | 2122. | Miyazawa and Kawata, 2006 | 30. m/0.32 mm/0.25 μm, Helium, 4. K/min, 240. C @ 5. min; Tstart: 40. C |
Capillary | HP-5 MS | 2156. | Tigrine-Kordiani, Meklati, et al., 2006 | 30. m/0.25 mm/0.25 μm, Helium, 60. C @ 8. min, 2. K/min, 250. C @ 15. min |
Capillary | SPB-5 | 2132. | Pino, Marbot, et al., 2005 | 30. m/0.25 mm/0.25 μm, He, 60. C @ 2. min, 4. K/min, 250. C @ 20. min |
Capillary | HP-5 | 2150. | Saeidnia, Gohari, et al., 2005 | He, 5. K/min; Column length: 30. m; Column diameter: 0.25 mm; Tstart: 60. C; Tend: 240. C |
Capillary | SPB-1 | 2107. | Wong and Tan, 2005 | 50. m/0.2 mm/0.33 μm, He, 50. C @ 3. min, 4. K/min, 220. C @ 30. min |
Capillary | HP-5 | 2128. | N/A | 30. m/0.32 mm/0.25 μm, Helium, 40. C @ 2. min, 5. K/min, 250. C @ 5. min |
Capillary | HP-5 | 2130. | N/A | 30. m/0.32 mm/0.25 μm, Helium, 40. C @ 2. min, 5. K/min, 250. C @ 5. min |
Capillary | HP-5 | 2131. | N/A | 30. m/0.32 mm/0.25 μm, Helium, 40. C @ 2. min, 5. K/min, 250. C @ 5. min |
Capillary | HP-5 | 2140. | N/A | 30. m/0.32 mm/0.25 μm, Helium, 40. C @ 2. min, 5. K/min, 250. C @ 5. min |
Capillary | DB-5 | 2123. | Miyazawa, Fuhita, et al., 2004 | Helium, 2. K/min, 240. C @ 999. min; Column length: 30. m; Column diameter: 0.25 mm; Tstart: 60. C |
Capillary | DB-5 | 2123. | Miyazawa, Fujita, et al., 2004 | Helium, 2. K/min, 240. C @ 999. min; Column length: 50. m; Column diameter: 0.25 mm; Tstart: 60. C |
Capillary | DB-5 | 2119. | Senatore, Rigano, et al., 2004 | 30. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 2. K/min, 250. C @ 20. min |
Capillary | HP-1 | 2107. | Lopes, Koketsu, et al., 1999 | 25. m/0.32 mm/0.17 μm, H2, 40. C @ 5. min, 3. K/min; Tend: 260. C |
Capillary | OV-101 | 2125. | Sugisawa, Nakamura, et al., 1990 | Nitrogen, 2. K/min; Column length: 50. m; Column diameter: 0.25 mm; Tstart: 70. C; Tend: 200. C |
Capillary | OV-101 | 2125. | Sugisawa, Nakamura, et al., 1990 | Nitrogen, 2. K/min; Column length: 50. m; Column diameter: 0.25 mm; Tstart: 80. C; Tend: 200. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-1 | 2130. | Xu, Tang, et al., 2010 | 30. m/0.25 mm/0.25 μm, Helium; Program: not specified |
Capillary | HP-5 MS | 2104. | Mancini, Arnold, et al., 2009 | 30. m/0.25 mm/0.25 μm, Helium; Program: 40 0C (5 min) 2 0C/min -> 270 0C -> 260 0C (20 min) |
Capillary | RTX-5 MS | 2097. | Mebazaa, Mahmoudi, et al., 2009 | 30. m/0.25 mm/0.25 μm, Helium; Program: 50 0C (5 min) 2 0C/min -> 100 0C (5 min) 5 0C/min -> 300 0C |
Capillary | DB-1 | 2125. | Mendes, Trindade, et al., 2009 | 30. m/0.25 mm/0.25 μm, Hydrogen; Program: 45 0C 3 0C/min -> 175 0C 15 0C/min -> 300 0C (10 min) |
Capillary | DB-5 | 2130. | Nivinsliene, Butkiene, et al., 2007 | 50. m/0.32 mm/0.25 μm, Helium; Program: 60 0C (1 min) 5 0C/min -> 160 0C 10 0C/min -> 250 0C |
Capillary | HP-5 | 2152. | Ristic, Krivokuca-Dokic, et al., 2007 | 30. m/0.25 mm/0.25 μm, Helium; Program: not specified |
Capillary | HP-5 | 2118. | Yasar, Üçüncü, et al., 2005 | 30. m/0.25 mm/0.25 μm, He; Program: 60C(5min) => 3C/min => 120C (2min) => 2C/min => 200C (2min) => 3C/min => 320C |
Capillary | 2115. | El-Shazily, Hafez, et al., 2004 | Program: not specified | |
Capillary | Ultra-1 | 2105. | Richmond and Pombo-Villar, 1998 | 25. m/0.32 mm/0.52 μm, He; Program: not specified |
Normal alkane RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | TC-Wax | 3215. | Miyazawa, Kurose, et al., 2001 | He, 4. K/min, 250. C @ 47. min; Column length: 60. m; Column diameter: 0.25 mm; Tstart: 80. C |
Capillary | DB-Wax | 3168. | Hatsuko, Kazuko, et al., 1992 | He, 60. C @ 10. min, 3. K/min; Column length: 30. m; Column diameter: 0.25 mm; Tend: 240. C |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Innowax | 3157. | Noorizadeh, Farmany, et al., 2011 | 60. m/0.25 mm/0.33 μm; Program: not specified |
Capillary | HP Innowax | 3157. | Noorizadeh and Farmany, 2010 | 60. m/0.25 mm/0.33 μm; Program: not specified |
Capillary | HP Innowax | 3160. | Mancini, Arnold, et al., 2009 | 50. m/0.20 mm/0.25 μm, Helium; Program: 40 0C (5 min) 2 0C/min -> 270 0C -> 260 0C (20 min) |
Capillary | DB-Wax | 3176. | Hatsuko, Kazuko, et al., 1992 | He; Column length: 30. m; Column diameter: 0.25 mm; Program: not specified |
References
Go To: Top, Condensed phase thermochemistry 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.
Rogers, Hoyte, et al., 1978
Rogers, D.W.; Hoyte, O.P.A.; Ho, R.K.C.,
Heats of hydrogenation of large molecules. Part 2. Six unsaturated and polyunsaturated fatty acids,
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Asuming, Beauchamp, et al., 2005
Asuming, W.A.; Beauchamp, P.S.; Descalzo, J.T.; Dev, B.C.; Dev, V.; Frost, S.; Ma, C.W.,
Essential oil composition of four Lomatium Raf. species and their chemotaxonomy,
Biochem. Syst. Ecol., 2005, 33, 1, 17-26, https://doi.org/10.1016/j.bse.2004.06.005
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Benkaci-Ali, Baaliouamer, et al., 2007
Benkaci-Ali, F.; Baaliouamer, A.; Meklati, B.Y.; Chemat, F.,
Chemical composition of seed essential oils from Algerian Nigella sativa extracted by microwave and hydrodistillation,
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Wu, Zorn, et al., 2007
Wu, S.; Zorn, H.; Krings, U.; Berger, R.G.,
Volatiles from submerged and surface-cultured beefsteak fungus, Fistulina hepatica,
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Zeng, Zhao, et al., 2007
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,
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Saroglou, Dorizas, et al., 2006
Saroglou, V.; Dorizas, N.; Kypriotakis, Z.; Skaltsa, H.D.,
Analysis of the essential oil composition of eight Anthemis species from Greece,
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Vujisic L., Vuckovic I., et al., 2006
Vujisic L.; Vuckovic I.; Tesevic V.; Dokovic D.; Ristic M.S.; Janackovic P.; Milosavljevic S.,
Comparative examination of the essential oils of Anthemis ruthenica and A-arvensis wild-growing in Serbia,
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Ziegenbein, Hanssen, et al., 2006
Ziegenbein, F.C.; Hanssen, H.-P.; König, W.A.,
Secondary metabolites from Ganoderma lucidum and Spongiporus leucomallellus,
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Ziegenbein, Hanssen, et al., 2006, 2
Ziegenbein, F.C.; Hanssen, H.-P.; König, W.A.,
Chemical constituents of the essential oils of three wood-rotting fungi,
Flavour Fragr. J., 2006, 21, 5, 813-816, https://doi.org/10.1002/ffj.1732
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Alves, Pinto, et al., 2005
Alves, R.J.V.; Pinto, A.C.; da Costa, A.V.M.; Rezende, C.M.,
Zizyphus mauritiana Lam. (Rhamnaceae) and the chemical composition of its floral fecal odor,
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Tundis, Passalacqua, et al., 2005
Tundis, R.; Passalacqua, N.G.; Peruzzi, L.; Statti, G.A.; Bonesi, M.; Loizzo, M.R.; Conforti, F.; Cesca, G.; Menichini, F.,
Comparative chemical variability of the non-polar extracts from Senecio cineraria group (Asteraceae),
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Wu, Zorn, et al., 2005
Wu, S.; Zorn, H.; Krings, U.; Berger, R.G.,
Characteristic Volatiles from Young and Aged Fruiting Bodies of Wild Polyporus sulfureus (Bull.:Fr.) Fr.,
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Javidnia, Miri, et al., 2004
Javidnia, K.; Miri, R.; Kamalinejad, M.; Sarkarzadeh, H.; Jamalian, A.,
Chemical composition of the essential oils of Anthemis altissima L. grown in Iran,
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Chosson, Vérité, et al., 2003
Chosson, E.; Vérité, P.; Blanckaert, A.; Seguin, E.; Litaudon, M.; Sévenet, T.,
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Lalel, Singh, et al., 2003
Lalel, H.J.D.; Singh, Z.; Chye Tan, S.,
Glycosidically-bound aroma volatile compounds in the skin and pulp of 'Kensington Pride' mango fruit at different stages of maturity,
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Skaltsa, Demetzos, et al., 2003
Skaltsa, H.D.; Demetzos, C.; Lazari, D.; Sokovic, M.,
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Pino, Marbot, et al., 2002
Pino, J.A.; Marbot, R.; Bello, A.,
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Pino, Marbot, et al., 2002, 2
Pino, J.A.; Marbot, R.; Vázquez, C.,
Characterization of volatile in Cosa Rican Guava [Psidium friedrichsthalianum (Berg) Niedenzu] fruit,
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Notes
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