9,12,15-Octadecatrienoic acid, methyl ester, (Z,Z,Z)-
- Formula: C19H32O2
- Molecular weight: 292.4562
- IUPAC Standard InChIKey: DVWSXZIHSUZZKJ-YSTUJMKBSA-N
- CAS Registry Number: 301-00-8
- 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. - Stereoisomers:
- Other names: Linolenic acid, methyl ester; Methyl all-cis-9,12,15-octadecatrienoate; Methyl linolenate; cis,cis,cis-9,12,15-Octadecatrienoic acid, methyl ester; Methyl α-linolenate; Methyl linolenate, α; (Z,Z,Z)-9,12,15-Octadecatrienoic acid, methyl ester; [Z,Z,Z]-9,12,15-Octadecadienoic acid methyl ester; methyl (9Z,12Z,15Z)-9,12,15-octadecatrienoate
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Reaction thermochemistry data
Go To: Top, 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: 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
By formula: 3H2 + C19H32O2 = C19H38O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -85.40 ± 0.58 | kcal/mol | Chyd | Rogers and Siddiqui, 1975 | liquid phase; solvent: n-Hexane |
IR Spectrum
Go To: Top, Reaction 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 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
View scan of original (hardcopy) spectrum.
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Download spectrum in JCAMP-DX format.
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 | DOW CHEMICAL COMPANY |
Source reference | COBLENTZ NO. 2356 |
Date | Not specified, most likely prior to 1970 |
Name(s) | methyl (9Z,12Z,15Z)-9,12,15-octadecatrienoate |
State | SOLUTION (10% CCl4 FOR 5000-1330, 10% CS2 FOR 1330-625 CM-1) |
Instrument | Not specified, most likely a prism, grating, or hybrid spectrometer. |
Path length | 0.011 CM, 0.011 CM |
Resolution | 4 |
Sampling procedure | TRANSMISSION |
Data processing | DIGITIZED BY NIST FROM HARD COPY |
Gas Chromatography
Go To: Top, Reaction thermochemistry data, IR Spectrum, 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 | 200. | 2071.8 | Kittiratanapiboon, Jeyashoke, et al., 1998 | 15. m/0.25 mm/0.2 μm, N2 |
Capillary | CP Sil 5 CB | 240. | 2078. | Hanai and Hong, 1989 | 30. m/0.25 mm/0.25 μm |
Capillary | DB-1 | 240. | 2092. | Hanai and Hong, 1989 | 30. m/0.25 mm/0.25 μm |
Packed | SE-30 | 200. | 2079. | Golovnya and Kuzmenko, 1977 | He, Chromosorb W (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 | 2058. | Raina, Verma, et al., 2006 | 25. m/0.32 mm/0.25 μm, N2, 5. K/min, 220. C @ 13. min; Tstart: 60. C |
Kovats' RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | DB-Wax | 240. | 2590. | 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 | DB-5 | 2108. | Rout, Rao, et al., 2007 | 25. m/0.25 mm/0.25 μm, He, 2. K/min, 200. C @ 60. min; Tstart: 60. C |
Capillary | HP-5MS | 2105.4 | Zeng, Zhao, et al., 2007 | 30. m/0.25 mm/0.25 μm, He, 4. K/min; Tstart: 80. C; Tend: 300. C |
Capillary | SPB-1 | 2077. | Radulovic, Lazarevic, et al., 2006 | 30. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 5. K/min, 250. C @ 15. min |
Capillary | HP-5 | 2101. | Zhao, Wang X.Y., et al., 2006 | 30. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 10. K/min; Tend: 260. C |
Capillary | HP-1 | 2098. | Senatore, Rigano, et al., 2003 | 30. m/0.25 mm/0.33 μm, He, 40. C @ 5. min, 2. K/min, 260. C @ 20. min |
Capillary | BP-1 | 2073. | Tan, Wilkins, et al., 1989 | H2, 40. C @ 2. min, 4. K/min, 240. C @ 75. min; Column length: 12. m |
Capillary | OV-1 | 2069. | 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 |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-1 | 2084. | Sing, Smadja, et al., 1992 | 50. m/0.32 mm/1.05 μm, He; Program: 20C(0.5min) => 60C => 4C/min => 250C |
Normal alkane RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | LM-1 | 210. | 2078. | 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 | 2081. | 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 | SPB-1 | 2089. | Escalona-Arranz, Perez-Roses, et al., 2010 | 30. m/0.32 mm/0.25 μm, Helium, 30. C @ 3. min, 4. K/min, 250. C @ 10. min |
Capillary | OV-1 | 2076. | Hu, Liang, et al., 2010 | 30. m/0.25 mm/0.25 μm, Helium, 50. C @ 3. min, 5. K/min, 250. C @ 2. min |
Capillary | SPB-1 | 2073. | Lazarevic, Palic, et al., 2010 | 30. m/0.25 mm/0.25 μm, Helium, 50. C @ 3. min, 5. K/min, 250. C @ 15. min |
Capillary | HP-5 MS | 2113. | Vedernikov and Roschin, 2010 | 30. m/0.25 mm/0.25 μm, Helium, 5. K/min, 280. C @ 10. min; Tstart: 150. C |
Capillary | HP-5 MS | 2100. | 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-5MS | 2125. | Calyecac-cortero, Cibrian-Tovar, et al., 2007 | 30. m/0.32 mm/0.25 μm, N2, 50. C @ 1. min, 1. K/min; Tend: 200. C |
Capillary | RTX-5 MS | 2098. | Edris, Chizzola, et al., 2007 | 30. m/0.25 mm/0.25 μm, He, 60. C @ 2. min, 2. K/min, 200. C @ 10. min |
Capillary | Elite-5MS | 2096. | Tava, Pecetti, et al., 2007 | 30. m/0.32 mm/0.5 μm, He, 40. C @ 5. min, 4. K/min, 280. C @ 10. min |
Capillary | HP-101 | 2081. | Mastelic, Jerkovic, et al., 2006 | 25. m/0.2 mm/0.2 μm, He, 70. C @ 2. min, 3. K/min, 200. C @ 15. min |
Capillary | DB-5 | 2099. | Rout, Naik, et al., 2006 | 30. m/0.25 mm/0.25 μm, He, 2. K/min, 200. C @ 60. min; Tstart: 60. C |
Capillary | DB-5 | 2096. | Rout, Misra, et al., 2005 | 25. m/0.25 mm/0.25 μm, He, 2. K/min, 200. C @ 80. min; Tstart: 60. C |
Capillary | HP-5 | 2073. | 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 | 2098. | 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 | BP-5 | 2082. | Ardakani, Mosaddegh, et al., 2003 | He, 3. K/min; Column length: 25. m; Column diameter: 0.33 mm; Tstart: 50. C; Tend: 275. C |
Capillary | DB-5 | 2099. | Senatore and Bruno, 2003 | 30. m/0.25 mm/0.25 μm, 40. C @ 5. min, 2. K/min; Tend: 260. C |
Capillary | DB-5 | 2098. | Tellez, Khan, et al., 2002 | 30. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 60. C; Tend: 240. C |
Capillary | OV-101 | 2078. | Ehrhardt, Osterroht, et al., 1980 | Hydrogen, 60. C @ 0.5 min, 4. K/min; Column length: 30. m; Column diameter: 0.35 mm; Tend: 270. C |
Capillary | OV-101 | 2078. | Ehrhardt, Osterroht, et al., 1980 | Hydrogen, 60. C @ 0.5 min, 4. K/min; Column length: 30. m; Column diameter: 0.35 mm; Tend: 270. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | VF-5 | 2108. | Shivashankar, Roy, et al., 2012 | 30. m/0.25 mm/0.25 μm, Helium; Program: 50 0C (2 min) 3 0C/min -> 200 0C (3 min) 10 0C/min -> 220 0C (8 min) |
Capillary | VF-5 | 2098. | Shivashankar, Roy, et al., 2012 | 30. m/0.25 mm/0.25 μm, Helium; Program: not specified |
Capillary | HP-5 MS | 2047. | Grzeszczuk, Wesolowska, et al., 2011 | 30. m/0.25 mm/0.25 μm, Helium; Program: 40 0C (5 min) 30 0C/min -> 60 0C 6 0C/min -> 230 0C (10 min) |
Capillary | RTx-1 | 2081. | Dib, Bendahou, et al., 2010 | 60. m/0.22 mm/0.25 μm, Helium; Program: not specified |
Capillary | HP-5 MS | 2098. | Vedernikov and Roschin, 2010 | 30. m/0.25 mm/0.25 μm, Helium; Program: not specified |
Capillary | HP-5 | 2095. | Maggi, Bilek, et al., 2009 | 25. m/0.32 mm/0.17 μm, Helium; Program: 60 0C (5 min) 4 0C/min -> 220 0C 11 0C/min -> 280 0C |
Capillary | OV-1 | 2080. | El-Shazly and Hussein, 2004 | He; Column length: 15. m; Column diameter: 0.317 mm; Program: 50C(4min) => 4C/min => 90C => 10C/min => 300C(10min) |
Normal alkane RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Supelcowax-10 | 2508. | Calyecac-cortero, Cibrian-Tovar, et al., 2007 | 30. m/0.32 mm/0.25 μm, N2, 50. C @ 1. min, 1. K/min; Tend: 200. C |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Innowax FSC | 2583. | Baser, Özek, et al., 2004 | 60. m/0.25 mm/0.25 μm, He; Program: 60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C |
Capillary | HP-Innowax FSC | 2583. | Erdemoglu, Sener, et al., 2003 | 60. m/0.25 mm/0.25 μm, He; Program: 60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C |
Capillary | Supelcowax 10 | 2550. | Castioni and Kapetanidis, 1996 | 60. m/0.25 mm/0.25 μm, Helium; Program: 60 0C (10 min) 2 0C/min -> 80 0C 3 0C/min -> 100 0C 4 0C/min -> 220 0C (30 min) |
Capillary | Supelcowax 10 | 2558. | Castioni and Kapetanidis, 1996 | 60. m/0.25 mm/0.25 μm, Helium; Program: not specified |
References
Go To: Top, Reaction thermochemistry data, IR Spectrum, Gas Chromatography, 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]
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
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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
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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
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Raina, Verma, et al., 2006
Raina, V.K.; Verma, S.C.; Dhawan, S.; Khan, M.; Ramesh, S.; Singh, S.C.; Yadav, A.; Srivastava, S.K.,
Essential oil composition of Murraya exotica from the plains of northern India,
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Rout, Rao, et al., 2007
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Composition of essential oil, concrete, absolute, wax and headspace volatiles of Murrarya paniculata (Linn.) Jack flowers,
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Essential oil of Actinidia macrosperma, a catnip response kiwi endemic to China,
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Volatile components of Centaurea cineraria L. subsp. umbrosa (lacaita) Pign. and Centaurea napifolia L. (Asteraceae), two species growing wild in Sicily,
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Tan, Wilkins, et al., 1989
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Extractives from New Zealand unifloral honeys. 2. Degraded carotenoids and other substances from heather honey,
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Identification of FAMEs using ECL values and a three-dimensional Kovats retention index system,
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Chemical constituents of Tamarindus indica L. leaves,
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Hu, Liang, et al., 2010
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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,
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Edris, A.E.; Chizzola, R.; Franz, C.,
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Tava, Pecetti, et al., 2007
Tava, A.; Pecetti, L.; Ricci, M.; Pagnotta, M.A.; Russi, L.,
Volatile compounds from leaves and flowers of Bituminaria bituminosa (L.) Stirt. (Fabaceae) from Italy,
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Mastelic, Jerkovic, et al., 2006
Mastelic, J.; Jerkovic, I.; Mesic, M.,
Volatile constituents from flowers, leaves, bark and wood of Prunus mahaleb L.,
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Rout, Naik, et al., 2006
Rout, P.K.; Naik, S.N.; Rao, Y.R.,
Composition of the concrete, absolute, headspace and essential oil of the flowers of Michelia champaca Linn.,
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Rout, Misra, et al., 2005
Rout, P.K.; Misra, R.; Sahoo, S.; Sree, A.; Rao, Y.R.,
Extraction of kewda (Pandanus fascicularis Lam.) flowers with hexane: composition of concrete, absolute and wax,
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Senatore, Rigano, et al., 2004
Senatore, F.; Rigano, D.; de Fusco, R.; Bruno, M.,
Composition of the essential oil from flowerheads of Chrysanthemum coronarium L. (Asteraceae) growing wild in Southern Italy,
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Ardakani, Mosaddegh, et al., 2003
Ardakani, M.S.; Mosaddegh, M.; Shafaati, A.,
Volatile constituents from the aerial parts of Verbena Officinalis L. (Vervain),
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Senatore and Bruno, 2003
Senatore, F.; Bruno, M.,
Composition of the essential oil of Pallenis spinosa (L.) Cass. (Asteraceae),
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Tellez, Khan, et al., 2002
Tellez, M.R.; Khan, I.A.; Kobaisy, M.; Schrader, K.K.; Dayan, F.E.; Osbrink, W.,
Composition of the essential oil of Lepidium meyenii (Walp.),
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Ehrhardt, Osterroht, et al., 1980
Ehrhardt, M.; Osterroht, C.; Petrick, G.,
Fatty-acid methyl esters dissolved in seawater and associated with suspended particulate material,
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Shivashankar, Roy, et al., 2012
Shivashankar, S.; Roy, T.K.; Moorthy, P.N.R.,
Headspace solid phase micro extraction and GC/MS analysis of the volatile components in seed and cake of Azadirachta indica A. juss,
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Grzeszczuk, Wesolowska, et al., 2011
Grzeszczuk, M.; Wesolowska, A.; Jadczak, D.; Jakubowska, B.,
Nutritional value of Chili edible flowers,
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Maggi, Bilek, et al., 2009
Maggi, F.; Bilek, T.; Lucarini, D.; Papa, F.; Sagratini, G.; Vittori, S.,
Melittis melissophyllum L. subsp. melissophylum (Lamiaceae) from central Italy: A new source of a mushrrom-like flavour,
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Notes
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- Symbols used in this document:
ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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