9,12,15-Octadecatrienoic acid, methyl ester, (Z,Z,Z)-
- Formula: C19H32O2
- Molecular weight: 292.4562
- IUPAC Standard InChI: InChI=1S/C19H32O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19(20)21-2/h4-5,7-8,10-11H,3,6,9,12-18H2,1-2H3/b5-4-,8-7-,11-10-
- 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
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
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IR Spectrum
Go To: Top, 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
View scan of original (hardcopy) spectrum.
View image of digitized spectrum (can be printed in landscape orientation).
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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 |
Mass spectrum (electron ionization)
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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.
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 | 333199 |
Gas Chromatography
Go To: Top, 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, 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, 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.
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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Comparative analysis of volatile components from Clematis species growing in China,
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Radulovic, Lazarevic, et al., 2006
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Chemotaxonomically significant 2-ethyl substituted fatty acids from Stachys milanii Petrovic (Lamiaceae),
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Zhao, Wang X.Y., et al., 2006
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Essential oil of Actinidia macrosperma, a catnip response kiwi endemic to China,
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Senatore, Rigano, et al., 2003
Senatore, F.; Rigano, D.; de Fusco, R.; Bruno, M.,
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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Tan, Holland, et al., 1988
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Extractives from New Zealand honeys. 1. White clovers, manuka, and kanuka unifloral honeys,
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Filho and Lancas, 1995
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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
Hu, C.-D.; Liang, Y.-Z.; Guo, F.-Q.; Li, X.-R.; Wang, W.-P.,
Determination of essential oil composition from Osmanthus fragrans tea by GC-MS combined with a chemometric resolution method,
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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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Zhao, Zeng, et al., 2009
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Calyecac-cortero, H.G.; Cibrian-Tovar, J.; Soto-Hernandez, M.; Garcia-Velasco, R.,
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Edris, Chizzola, et al., 2007
Edris, A.E.; Chizzola, R.; Franz, C.,
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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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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),
Iran. J. Pharm. Res., 2003, 2, 39-42. [all data]
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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. [all data]
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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. [all data]
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,
Chem. Bull. of Politechnika Univ. Timisoara, Romania, 2012, 57(71), 1, 1-6. [all data]
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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. [all data]
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),
Biochem. Syst. Ecol., 2004, 32, 7, 665-674, https://doi.org/10.1016/j.bse.2003.12.009
. [all data]
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,
J. Essent. Oil Res., 2004, 16, 4, 305-307, https://doi.org/10.1080/10412905.2004.9698728
. [all data]
Erdemoglu, Sener, et al., 2003
Erdemoglu, N.; Sener, B.; Demirci, B.; Baser, K.H.C.,
The glycosidically bound volatile compounds of Taxus baccata,
Chem. Nat. Compd. (Engl. Transl.), 2003, 39, 2, 195-198, https://doi.org/10.1023/A:1024870031960
. [all data]
Castioni and Kapetanidis, 1996
Castioni, P.; Kapetanidis, I.,
Volatile constituents from Brunfelsia grandiflora ssp. grandiflora: qualitative analysis by GC-MS,
Scientia Pharmaceutica, 1996, 64, 83-91. [all data]
Notes
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