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, 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° | -357.3 ± 2.4 | kJ/mol | Chyd | Rogers and Siddiqui, 1975 | liquid phase; solvent: n-Hexane |
Gas Chromatography
Go To: Top, Reaction thermochemistry 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 | 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, 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,
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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,
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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,
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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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Chemotaxonomically significant 2-ethyl substituted fatty acids from Stachys milanii Petrovic (Lamiaceae),
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Essential oil of Actinidia macrosperma, a catnip response kiwi endemic to China,
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Extractives from New Zealand unifloral honeys. 2. Degraded carotenoids and other substances from heather honey,
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Extractive compounds of Birch Buds (Betula pendula Roth.): I. Composition of fatty acids, hydrocarbons , and esters,
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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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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.,
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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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El-Shazly and Hussein, 2004
El-Shazly, A.M.; Hussein, K.T.,
Chemical analysis and biological activities of the essential oil of Teucrium leucocladum Boiss. (Lamiaceae),
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Baser, Özek, et al., 2004
Baser, K.H.C.; Özek, T.; Kirimer, N.; Deliorman, D.; Ergun, F.,
Composition of the essential oils of Galium aparine L. and Galium odoratum (L.) Scop. from Turkey,
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Erdemoglu, Sener, et al., 2003
Erdemoglu, N.; Sener, B.; Demirci, B.; Baser, K.H.C.,
The glycosidically bound volatile compounds of Taxus baccata,
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Castioni and Kapetanidis, 1996
Castioni, P.; Kapetanidis, I.,
Volatile constituents from Brunfelsia grandiflora ssp. grandiflora: qualitative analysis by GC-MS,
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Notes
Go To: Top, Reaction thermochemistry data, Gas Chromatography, References
- 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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