9,12-Octadecadienoic acid (Z,Z)-, methyl ester
- Formula: C19H34O2
- Molecular weight: 294.4721
- 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,
Chiang Mai J. Sci., 2013, 40, 2, 214-223. [all data]
Vedernikov, Shabanova, et al., 2011
Vedernikov, D.N.; Shabanova, N.Yu.; Roshchin, V.I.,
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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Dib, Bendahou, et al., 2010
Dib, M.A.; Bendahou, M.; Bendiabdellah, A.; Djabou, N.; Allali, H.; Tabti, B.; Paolini, J.; Costa, J.,
Partial chemical composition and antimicrobial activity of Daucus crinitus Desf. extracts,
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Radulovic, Dordevic, et al., 2010
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Volatile constituents of Glechoma Hirsuta Waldst. Kit. and G. Hederacea L. (Lamiaceae),
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Silva, Pott, et al., 2010
Silva, D.B.; Pott, A.; Oliveira, D.C.R.,
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
Vedernikov, D.N.; Roschin, V.I.,
Extractive compounds of Birch Buds (Betula pendula Roth.): I. Composition of fatty acids, hydrocarbons , and esters,
Rus. J. Bioorg. Chem., 2010, 36, 7, 894-898, https://doi.org/10.1134/S1068162010070174
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Xu, Tang, et al., 2010
Xu, X.; Tang, Z.; Liang, Y.,
Comparative analysis of plant essential oils by GC-MS coupled with integrated chemometric resolution methods,
Anal. Methods, 2010, 2, 4, 359-367, https://doi.org/10.1039/b9ay00213h
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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,
Biochem. Systematics Ecol., 2009, 37, 3, 206-213, https://doi.org/10.1016/j.bse.2009.03.009
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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,
J. Sep. Sci., 2009, 32, 4, 660-670, https://doi.org/10.1002/jssc.200800484
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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,
Flav. Fragr. J., 2008, 23, 6, 426-433, https://doi.org/10.1002/ffj.1901
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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,
Eur. Food Res. Technol., 2007, https://doi.org/10.1007/s00217-007-0623-y
. [all data]
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,
Biochem. Syst. Ecol., 2007, 35, 2, 99-113, https://doi.org/10.1016/j.bse.2006.09.012
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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,
J. Supercrit. Fluids, 2007, 43, 2, 249-258, https://doi.org/10.1016/j.supflu.2007.05.007
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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,
Flavour Fragr. J., 2006, 21, 3, 556-558, https://doi.org/10.1002/ffj.1666
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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,
Flavour Fragr. J., 2005, 20, 4, 442-444, https://doi.org/10.1002/ffj.1466
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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,
DARU, 2005, 13, 1, 34-36. [all data]
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,
J. Oleo Sci., 2004, 53, 10, 511-513, https://doi.org/10.5650/jos.53.511
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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,
J. Oleo Sci., 2004, 53, 11, 511-513, https://doi.org/10.5650/jos.53.511
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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),
Flavour Fragr. J., 2003, 18, 3, 195-197, https://doi.org/10.1002/ffj.1180
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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
in International Symposium on Loquat, April 11-13, 2002 (CIHEAM-IAMZ, 2003, p. 191-193), Llácer,G.; Badenes,M.L., ed(s)., Centre International de Hautes Etudes Agronomiques Mediterranean, Valencia, Spain, 2002, 191-193. [all data]
Pino, Marbot, et al., 2002
Pino, J.A.; Marbot, R.; Vazquez, C.,
Characterization of volatiles in Loquat fruit (Eriobotrya japonica Lindl.),
Revista CENIC Ciencias Quimicas, 2002, 33, 3, 115-119. [all data]
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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