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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Normal alkane RI, non-polar column, temperature ramp
Go To: Top, 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
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | HP-5 MS | HP-5 MS | RTx-1 | HP-5 MS | DB-5 MS |
| Column length (m) | 30. | 30. | 60. | 30. | 30. |
| Carrier gas | Helium | Helium | Helium | Helium | Helium |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.25 | 0.22 | 0.25 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
| Tstart (C) | 60. | 150. | 60. | 70. | 60. |
| Tend (C) | 230. | 280. | 230. | 290. | 240. |
| Heat rate (K/min) | 3. | 5. | 2. | 5. | 3. |
| Initial hold (min) | |||||
| Final hold (min) | 5. | 35. | 10. | ||
| I | 2098. | 2081. | 2083. | 2098. | 2087. |
| Reference | Pripdeevech and Saansoomchai, 2013 | Vedernikov, Shabanova, et al., 2011 | Dib, Bendahou, et al., 2010 | Radulovic, Dordevic, et al., 2010 | Silva, Pott, et al., 2010 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | HP-5 MS | DB-1 | HP-5 MS | DB-5 | HP-5 MS |
| Column length (m) | 30. | 30. | 30. | 30. | 30. |
| Carrier gas | Helium | Helium | Helium | Nitrogen | Helium |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
| Tstart (C) | 150. | 50. | 35. | 40. | 50. |
| Tend (C) | 280. | 220. | 195. | 230. | 280. |
| Heat rate (K/min) | 5. | 4. | 2. | 2. | 4. |
| Initial hold (min) | 2. | 5. | |||
| Final hold (min) | 10. | 2. | 30. | ||
| I | 2107. | 2070. | 2090. | 2096. | 2094. |
| Reference | Vedernikov and Roschin, 2010 | Xu, Tang, et al., 2010 | Kim and Chung, 2009 | Scrivanti, Anton, et al., 2009 | Zhao, Zeng, et al., 2009 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | VF-5MS | DB-5 MS | RTX-5 MS | HP-5MS | DB-5 |
| Column length (m) | 30. | 30. | 30. | 30. | 30. |
| Carrier gas | Helium | Helium | He | He | He |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
| Tstart (C) | 240. | 50. | 60. | 60. | 60. |
| Tend (C) | 320. | 300. | 200. | 250. | 320. |
| Heat rate (K/min) | 20. | 5. | 2. | 2. | 10. |
| Initial hold (min) | 1. | 5. | 2. | 8. | |
| Final hold (min) | 5. | 10. | 15. | 4. | |
| I | 2110. | 2094. | 2089. | 2088. | 2091. |
| Reference | Kowalski, 2008 | Noudogbessi, Yedomonhan, et al., 2008 | Edris, Chizzola, et al., 2007 | Ferhat, Tigrine-Kordjani, et al., 2007 | Smelcerovic, Spiteller, et al., 2007 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | HP-5MS | DB-5MS | DB-5 | DB-5 | DB-1 |
| Column length (m) | 30. | 30. | 30. | 30. | 30. |
| Carrier gas | He | He | He | He | He |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
| Tstart (C) | 40. | 60. | 60. | 40. | 50. |
| Tend (C) | 260. | 280. | 200. | 250. | 265. |
| Heat rate (K/min) | 4. | 3. | 2. | 4. | 2.5 |
| Initial hold (min) | 2. | 1. | |||
| Final hold (min) | 30. | 60. | 10. | 20. | |
| I | 2093.3 | 2079. | 2092. | 2091. | 2087. |
| Reference | Zizovic, Stamenic, et al., 2007 | Maronigiu, Piras, et al., 2006 | Rout, Naik, et al., 2006 | Shen X., Gao Y., et al., 2006 | Khanavi, Ghasemian, et al., 2005 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | DB-5 | HP-5 | HP-5 | HP-5 | HP-5 |
| Column length (m) | 25. | 30. | 30. | 30. | 30. |
| Carrier gas | He | He | Helium | Helium | Helium |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.25 | 0.32 | 0.32 | 0.32 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | |
| Tstart (C) | 60. | 60. | 40. | 40. | 40. |
| Tend (C) | 200. | 240. | 250. | 250. | 250. |
| Heat rate (K/min) | 2. | 5. | 5. | 5. | 5. |
| Initial hold (min) | 2. | 2. | 2. | ||
| Final hold (min) | 80. | 5. | 5. | 5. | |
| I | 2090. | 2092. | 2075. | 2076. | 2079. |
| Reference | Rout, Misra, et al., 2005 | Saeidnia, Gohari, et al., 2005 | N/A | N/A | N/A |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | HP-5 | DB-5 | DB-5 | DB-5 | DB-5 |
| Column length (m) | 30. | 30. | 50. | 30. | 30. |
| Carrier gas | Helium | Helium | Helium | He | |
| Substrate | |||||
| Column diameter (mm) | 0.32 | 0.25 | 0.25 | 0.25 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | ||
| Tstart (C) | 40. | 60. | 60. | 40. | 40. |
| Tend (C) | 250. | 240. | 240. | 250. | 260. |
| Heat rate (K/min) | 5. | 2. | 2. | 2. | 2. |
| Initial hold (min) | 2. | 5. | 5. | ||
| Final hold (min) | 5. | 999. | 999. | 20. | |
| I | 2079. | 2088. | 2088. | 2094. | 2097. |
| Reference | N/A | Miyazawa, Fuhita, et al., 2004 | Miyazawa, Fujita, et al., 2004 | Senatore, Rigano, et al., 2004 | Senatore and Bruno, 2003 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | DB-5 | SPB-5 | DB-5 | DB-5 | OV-101 |
| Column length (m) | 25. | 30. | 30. | 30. | 30. |
| Carrier gas | He | Helium | He | He | Hydrogen |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.35 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | |
| Tstart (C) | 40. | 60. | 60. | 60. | 60. |
| Tend (C) | 280. | 250. | 240. | 270. | 270. |
| Heat rate (K/min) | 3. | 4. | 3. | 3. | 4. |
| Initial hold (min) | 5. | 2. | 0.5 | ||
| Final hold (min) | 5. | 20. | |||
| I | 2096. | 2090. | 2092. | 2098. | 2073. |
| Reference | Merle, Blázquez, et al., 2002 | Pino, Marbot, et al., 2002 | Tellez, Khan, et al., 2002 | Palmeira, Conserva, et al., 2001 | Ehrhardt, Osterroht, et al., 1980 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary |
|---|---|
| Active phase | OV-101 |
| Column length (m) | 30. |
| Carrier gas | Hydrogen |
| Substrate | |
| Column diameter (mm) | 0.35 |
| Phase thickness (μm) | |
| Tstart (C) | 60. |
| Tend (C) | 270. |
| Heat rate (K/min) | 4. |
| Initial hold (min) | 0.5 |
| Final hold (min) | |
| I | 2073. |
| Reference | Ehrhardt, Osterroht, et al., 1980 |
| Comment | MSDC-RI |
References
Go To: Top, Normal alkane RI, non-polar column, temperature ramp, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Pripdeevech and Saansoomchai, 2013
Pripdeevech, P.; Saansoomchai, J.,
Antibacterial activity and chemical composition of essential oil and various extracts of Fagraea fragrans Roxb. flowers,
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Change in the chemical composition of the crust and inner bark of the Betula pendula Roth. Birch (Betulaceae) with tree height,
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Partial chemical composition and antimicrobial activity of Daucus crinitus Desf. extracts,
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Volatile constituents of Glechoma Hirsuta Waldst. Kit. and G. Hederacea L. (Lamiaceae),
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Analyses of the headspace volatile constituents of aerial parts (leaves and stems), flowers and fruits of Bidens gardneri Bak. and Bidens sulphurea (Cav.) Sch. Bip. using solid-phase microextraction,
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Vedernikov and Roschin, 2010
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Extractive compounds of Birch Buds (Betula pendula Roth.): I. Composition of fatty acids, hydrocarbons , and esters,
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Xu, Tang, et al., 2010
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Comparative analysis of plant essential oils by GC-MS coupled with integrated chemometric resolution methods,
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Kim and Chung, 2009
Kim, J.-S.; Chung, H.Y.,
GC-MS analysis of the volatile components in dried boxthorn (Lycium chimensis) Fruit,
J. Korean Soc. Appl. Biol. Chem., 2009, 52, 5, 516-524, https://doi.org/10.3839/jksabc.2009.088
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Scrivanti, Anton, et al., 2009
Scrivanti, L.R.; Anton, A.M.; Zygadlo, J.A.,
Essential oil conposition of Bothriochloa Kuntze (Poaceae) from South America and their chemotaxonomy,
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Zhao, Zeng, et al., 2009
Zhao, C.; Zeng, Y.; Wan, M.; Li, R.; Liang, Y.; Li, C.; Zeng, Z.; Chau, F.-T.,
Comparative analysis of essential oils from eight herbal medicines with pungent flavor and cool nature by GC-MS and chemometric resolution methods,
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Kowalski, 2008
Kowalski, R.,
Antimicrobial activity of essential oils and extracts of rosinweed (Silphoum trifoliatum and Silphium integrifolium) plants used by the American Indians,
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Noudogbessi, Yedomonhan, et al., 2008
Noudogbessi, J.-P.; Yedomonhan, P.; Sohounhloue, D.C.K.; Chalchat, J.-C.; Figueredo, G.,
Chemical composition of essential oil of syzygium guineense (Willd.) DC. var. guineense (Myrtaceae) from Benin,
Rec. Nat. Prod., 2008, 33-38. [all data]
Edris, Chizzola, et al., 2007
Edris, A.E.; Chizzola, R.; Franz, C.,
Isolation and characterization of the volatile aroma compounds from the concrete headspace and the absolute of Jasminum sambac (L.) Ait. (Oleaceae) flowers grown in Egypt,
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Ferhat, Tigrine-Kordjani, et al., 2007
Ferhat, M.A.; Tigrine-Kordjani, N.; Chemat, S.; Meklati, B.Y.; Chemat, F.,
Rapid Extraction of Volatile Compounds Using a New Simultaneous Microwave Distillation: Solvent Extraction Device,
Chromatographia, 2007, 65, 3-4, 217-222, https://doi.org/10.1365/s10337-006-0130-5
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Smelcerovic, Spiteller, et al., 2007
Smelcerovic, A.; Spiteller, M.; Ligon, A.P.; Smelcerovic, Z.; Raabe, N.,
Essential oil composition of Hypericum L. species from Southeastern Serbia and their chemotaxonomy,
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Zizovic, Stamenic, et al., 2007
Zizovic, I.; Stamenic, M.; Ivanovic, J.; Orlovic, A.; Ristic, M.; Djordjevic, S.; Petrovic, S.D.; Skala, D.,
Supercritical carbon dioxide extraction of sesquiterpenes from valerian root,
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Maronigiu, Piras, et al., 2006
Maronigiu, B.; Piras, A.; Porcedda, S.; Tuveri, E.,
Extraction of Santalum album and Boswellia carterii Birdw. volatile oil by supercritical carbon dioxide: influence of some process parameters,
Flavour Fragr. J., 2006, 21, 4, 718-724, https://doi.org/10.1002/ffj.1718
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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.,
Flavour Fragr. J., 2006, 21, 6, 906-911, https://doi.org/10.1002/ffj.1742
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Shen X., Gao Y., et al., 2006
Shen X.; Gao Y.; Su Q.D.,
Constituents of the essential oil of Rhizoma polygonati,
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Khanavi, Ghasemian, et al., 2005
Khanavi, M.; Ghasemian, L.; Motlagh, E.H.; Hadjiakhoondi, A.; Shafiee, A.,
Chemical composition of the essential oils of Marrubium parviflorum Fisch. C.A. Mey. and Marrubium vulgare L. from Iran,
Flavour Fragr. J., 2005, 20, 3, 324-326, https://doi.org/10.1002/ffj.1425
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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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Saeidnia, Gohari, et al., 2005
Saeidnia, S.; Gohari, A.R.; Yassa, N.; Shafiee, A.,
Composition of the volatile oil of Achillea conferta DC. from Iran,
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Miyazawa, Fuhita, et al., 2004
Miyazawa, M.; Fuhita, T.; Yamafuji, C.; Matsui, M.; Kasahara, N.; Takagi, Y.; Ishikawa, Y.,
Chemical composition of volatile oil from the roots of Periploca sepium,
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Miyazawa, Fujita, et al., 2004
Miyazawa, M.; Fujita, T.; Yamafuji, C.; Matsui, M.; Kasahara, N.; Takagi, Y.; Ishikawa, Y.,
Chemical composition of volatile oil from the roots of Periploca sepium,
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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,
Flavour Fragr. J., 2004, 19, 2, 149-152, https://doi.org/10.1002/ffj.1285
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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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Merle, Blázquez, et al., 2002
Merle, H.; Blázquez, M.A.; Boira, H.,
Chemical composition of the essential oil of Eriobotrya japonica (Thunb.) Lindl. flowers in the western Mediterranean area
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Pino, Marbot, et al., 2002
Pino, J.A.; Marbot, R.; Vazquez, C.,
Characterization of volatiles in Loquat fruit (Eriobotrya japonica Lindl.),
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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.),
Phytochemistry, 2002, 61, 2, 149-155, https://doi.org/10.1016/S0031-9422(02)00208-X
. [all data]
Palmeira, Conserva, et al., 2001
Palmeira, S.F., Jr.; Conserva, L.M.; Andrade, E.H.A.; Guilhon, G.M.S.P.,
Analysis by GC-MS of the hexane extract of the aerial parts of Aristolochia acutifolia Duchtr.,
Flavour Fragr. J., 2001, 16, 2, 85-88, https://doi.org/10.1002/1099-1026(200103/04)16:2<85::AID-FFJ948>3.0.CO;2-2
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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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. [all data]
Notes
Go To: Top, Normal alkane RI, non-polar column, temperature ramp, References
- Symbols used in this document:
Tend Final temperature Tstart Initial temperature - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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