9,12-Octadecadienoic acid (Z,Z)-
- Formula: C18H32O2
- Molecular weight: 280.4455
- IUPAC Standard InChI: InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-
- IUPAC Standard InChIKey: OYHQOLUKZRVURQ-HZJYTTRNSA-N
- CAS Registry Number: 60-33-3
- 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: cis-9,cis-12-Octadecadienoic acid; cis,cis-Linoleic acid; Grape seed oil; Linoleic; Linoleic acid; Linolic acid; Polylin No. 515; Telfairic acid; Unifac 6550; 9,12-Octadecadienoic acid, cis,cis-; Leinoleic acid; 9,12-Linoleic acid; cis,cis-9,12-Octadecadienoic acid; Emersol 310; Emersol 315; Vespula pensylvanica b708568k063; 9-(Z), 12-(Z)-Octadecadienoic acid; Acide linoleique; Octadeca-9,12-dienoic acid, (cis,cis)-; (Z,Z)-9,12-Octadecadienoic acid; (Z,Z)-Octadeca-9, 12-dienoic acid; 9,12-Octadecadienoic acid (9Z,12Z)-; 9-cis,12-cis-Linoleic acid; 9Z,12Z-Linoleic acid; all-cis-9,12-Octadecadienoic acid; cis-Δ9,12-Octadecadienoic acid; Extra Linoleic 90; Polylin 515; 9,12-Octadecadienoic acid; Pamolyn 125 (Salt/Mix)
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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 | HP-5 MS | DB-5 MS | HP-5 MS |
| Column length (m) | 25. | 30. | 30. | 30. | 30. |
| Carrier gas | Helium | Helium | Helium | Helium | |
| Substrate | |||||
| Column diameter (mm) | 0.20 | 0.25 | 0.25 | 0.25 | 0.25 |
| Phase thickness (μm) | 0.30 | 0.25 | 0.25 | 0.25 | 0.25 |
| Tstart (C) | 40. | 60. | 40. | 70. | 70. |
| Tend (C) | 260. | 300. | 260. | 290. | 290. |
| Heat rate (K/min) | 10. | 15. | 4. | 5. | 5. |
| Initial hold (min) | 2. | 2. | |||
| Final hold (min) | 20. | 10. | 5. | 10. | 10. |
| I | 2179. | 2113. | 2147. | 2128. | 2136. |
| Reference | Sandoval-Montemayor, Garcia, et al., 2012 | Xu, Han, et al., 2012 | Miyazawa, Marumoto, et al., 2011 | Stojanovic, RAdulovic, et al., 2011 | Radulovic, Blagojevic, 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 | HP-5 MS | HP-5 MS |
| Column length (m) | 30. | 30. | 30. | 30. | 30. |
| Carrier gas | Helium | Helium | Helium | Helium | 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) | 70. | 50. | 35. | 70. | 60. |
| Tend (C) | 290. | 220. | 195. | 290. | 300. |
| Heat rate (K/min) | 5. | 4. | 2. | 5. | 15. |
| Initial hold (min) | 2. | 5. | 2. | ||
| Final hold (min) | 10. | 2. | 30. | 10. | 10. |
| I | 2133. | 2109. | 2135. | 2136. | 2113. |
| Reference | Radulovic, Dordevic, et al., 2010 | Xu, Tang, et al., 2010 | Kim and Chung, 2009 | Radulovic, Blagojevic, et al., 2009 | Xu, Han, et al., 2009 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | HP-5 MS | HP-101 | HP-101 | HP-5 MS | HP-5MS |
| Column length (m) | 30. | 25. | 25. | 30. | 30. |
| Carrier gas | Helium | Helium | Helium | Helium | He |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.20 | 0.20 | 0.25 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
| Tstart (C) | 50. | 70. | 70. | 60. | 60. |
| Tend (C) | 280. | 200. | 200. | 280. | 250. |
| Heat rate (K/min) | 4. | 3. | 3. | 10. | 2. |
| Initial hold (min) | 2. | 2. | 1. | 8. | |
| Final hold (min) | 7. | 15. | |||
| I | 2154. | 2111. | 2130. | 2146. | 2144. |
| Reference | Zhao, Zeng, et al., 2009 | Blazevic and Mastelic, 2008 | Blazevic and Mastelic, 2008 | Szarka, Hethelyi, et al., 2008 | Ferhat, Meklati, 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 | HP-5 | HP-5 | HP-5 MS | SPB-5 |
| Column length (m) | 30. | 30. | 30. | 30. | 30. |
| Carrier gas | He | Helium | Helium | Helium | He |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.25 | 0.32 | 0.25 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
| Tstart (C) | 60. | 40. | 40. | 60. | 60. |
| Tend (C) | 250. | 260. | 240. | 250. | 250. |
| Heat rate (K/min) | 2. | 4. | 4. | 2. | 4. |
| Initial hold (min) | 8. | 8. | 2. | ||
| Final hold (min) | 15. | 5. | 15. | 20. | |
| I | 2156. | 2136. | 2122. | 2156. | 2132. |
| Reference | Ferhat, Tigrine-Kordjani, et al., 2007 | Ristic, Krivokuca-Dokic, et al., 2007 | Miyazawa and Kawata, 2006 | Tigrine-Kordiani, Meklati, et al., 2006 | Pino, Marbot, et al., 2005 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | HP-5 | SPB-1 | HP-5 | HP-5 | HP-5 |
| Column length (m) | 30. | 50. | 30. | 30. | 30. |
| Carrier gas | He | He | Helium | Helium | Helium |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.2 | 0.32 | 0.32 | 0.32 |
| Phase thickness (μm) | 0.33 | 0.25 | 0.25 | 0.25 | |
| Tstart (C) | 60. | 50. | 40. | 40. | 40. |
| Tend (C) | 240. | 220. | 250. | 250. | 250. |
| Heat rate (K/min) | 5. | 4. | 5. | 5. | 5. |
| Initial hold (min) | 3. | 2. | 2. | 2. | |
| Final hold (min) | 30. | 5. | 5. | 5. | |
| I | 2150. | 2107. | 2128. | 2130. | 2131. |
| Reference | Saeidnia, Gohari, et al., 2005 | Wong and Tan, 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 | HP-1 |
| Column length (m) | 30. | 30. | 50. | 30. | 25. |
| Carrier gas | Helium | Helium | Helium | He | H2 |
| Substrate | |||||
| Column diameter (mm) | 0.32 | 0.25 | 0.25 | 0.25 | 0.32 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.17 | ||
| Tstart (C) | 40. | 60. | 60. | 40. | 40. |
| Tend (C) | 250. | 240. | 240. | 250. | 260. |
| Heat rate (K/min) | 5. | 2. | 2. | 2. | 3. |
| Initial hold (min) | 2. | 5. | 5. | ||
| Final hold (min) | 5. | 999. | 999. | 20. | |
| I | 2140. | 2123. | 2123. | 2119. | 2107. |
| Reference | N/A | Miyazawa, Fuhita, et al., 2004 | Miyazawa, Fujita, et al., 2004 | Senatore, Rigano, et al., 2004 | Lopes, Koketsu, et al., 1999 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary |
|---|---|---|
| Active phase | OV-101 | OV-101 |
| Column length (m) | 50. | 50. |
| Carrier gas | Nitrogen | Nitrogen |
| Substrate | ||
| Column diameter (mm) | 0.25 | 0.25 |
| Phase thickness (μm) | ||
| Tstart (C) | 70. | 80. |
| Tend (C) | 200. | 200. |
| Heat rate (K/min) | 2. | 2. |
| Initial hold (min) | ||
| Final hold (min) | ||
| I | 2125. | 2125. |
| Reference | Sugisawa, Nakamura, et al., 1990 | Sugisawa, Nakamura, et al., 1990 |
| Comment | MSDC-RI | 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.
Sandoval-Montemayor, Garcia, et al., 2012
Sandoval-Montemayor, N.E.; Garcia, A.; Elizondo-Trevino, E.; Garza-Gonzales, E.; Alvarez, L.; Camacho-Corona, M. delR.,
Chemical composition of hexane extract of Citrus aurantifolia and anti-mycobacterium tuberculosis activity of some of its constituents,
Molecules, 2012, 17, 12, 11173-11184, https://doi.org/10.3390/molecules170911173
. [all data]
Xu, Han, et al., 2012
Xu, L.-L.; Han, T.; Wu, J.-Z.; Zhang, Q.-Y.; Zhang, H.; Huang, B.-K.; Rahman, K.,
Comparative research of chemical constituents, antifungal and antitumor properties of ether extracts of Panax ginseng and its endophytic fungus, 2012, retrieved from http://www.thefreelibrary.com/Comparative .... [all data]
Miyazawa, Marumoto, et al., 2011
Miyazawa, M.; Marumoto, S.; Kobayashi, T.; Yoshida, S.; Utsumi, Y.,
Determination of characteristic components in essential oils from Wisteria braphybotrys using gas chromatography - olfactometry incremental dilution technique,
Rec. Nat. Prod., 2011, 5, 3, 221-227. [all data]
Stojanovic, RAdulovic, et al., 2011
Stojanovic, I.Z.; RAdulovic, N.S.; Mitrovic, Y.L.J.; Stamenkovic, S.M.; Stojanovic, G.S.,
Volatile constituents of selected Parmeliaceae lichens,
J. Serb. Chem. Soc., 2011, 76, 7, 987-994, https://doi.org/10.2298/JSC101004087S
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Radulovic, Blagojevic, et al., 2010
Radulovic, N.; Blagojevic, P.; Palic, R.,
Comparative study of the leaf volatiles of Arctostaphylos uva-ursi (L.) Spreng. and Vaccinium vitis-idaea L. (Ericaceae),
Molecules, 2010, 15, 9, 6168-6185, https://doi.org/10.3390/molecules15096168
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Radulovic, Dordevic, et al., 2010
Radulovic, N.; Dordevic, N.; Markovic, M.; Palic, R.,
Volatile constituents of Glechoma Hirsuta Waldst. Kit. and G. Hederacea L. (Lamiaceae),
Bull. Chem. Soc. Ethiop., 2010, 24, 1, 67-76, https://doi.org/10.4314/bcse.v24i1.52962
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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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Radulovic, Blagojevic, et al., 2009
Radulovic, N.S.; Blagojevic, P.D.; Palic, R.M.; Zlatkovic, B.K.; Stevanovic, B.M.,
Volatiles from vegetative organs of the paleoendemic resurrection plants Ramonda serbica Panc. and Ramonda nathaliae Panc. at Petrov,
J. Serb. Chem. Soc., 2009, 74, 1, 35-44, https://doi.org/10.2298/JSC0901035R
. [all data]
Xu, Han, et al., 2009
Xu, L.-L.; Han, T.; Wu, J.-Z.; Zhang, Q.-Y.; Zhang, H.; Huang, B.-K.; Rahman, K.,
Comparative research of chemical constituents, antifungal and antitumor properties of ether extracts of Panax ginseng and its endophytic fungus,
Phytomedicine: Int. J. Phytotherapy Phytopharmacology, 2009, 16, 6-7, 609-616, https://doi.org/10.1016/j.phymed.2009.03.014
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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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Blazevic and Mastelic, 2008
Blazevic, I.; Mastelic, J.,
Free and bounded volatiles of rocket (Eruca sativa Mill.),
Fravour Fragr. J., 2008, 23, 4, 278-285, https://doi.org/10.1002/ffj.1883
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Szarka, Hethelyi, et al., 2008
Szarka, S.; Hethelyi, E.; Kuzovkina, I.N.; Lemberkovics, E.; Szoke, E.,
GC-MS method development for the analyses of thiophenes from solvent extracats of Tagetes patula L.,
Chromatographia Suppl., 2008, 68, S1, s63-s69, https://doi.org/10.1365/s10337-008-0668-5
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Ferhat, Meklati, et al., 2007
Ferhat, M.A.; Meklati, B.Y.; Chemat, F.,
Comparison of different isolation methods of essential oil from Citrus fruits: cold pressing, hydrodistillation and microwave dry distillation,
Flavour Fragr. J., 2007, 22, 6, 494-504, https://doi.org/10.1002/ffj.1829
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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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Ristic, Krivokuca-Dokic, et al., 2007
Ristic, M.; Krivokuca-Dokic, D.; Radanovic, D.; Nastovski, T.,
Etarsko ulje Arnica montata i Arnica chamissonis,
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Miyazawa and Kawata, 2006
Miyazawa, M.; Kawata, J.,
Identification of the Key Aroma Compounds in Dried Roots of Rubia cordifolia,
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Tigrine-Kordiani, Meklati, et al., 2006
Tigrine-Kordiani, N.; Meklati, B.Y.; Chemat, F.,
Abalysis by gas chromatography - mass spectrometry of the essential oil of Zygophyllum album L., an aromatic and medicinal plant growing in Algeria,
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Pino, Marbot, et al., 2005
Pino, J.A.; Marbot, R.; Rosado, A.; Vázquez, C.,
Volatile constituents of genipap (Genipa americana L.) fruit from Cuba,
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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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Wong and Tan, 2005
Wong, K.C.; Tan, C.H.,
Volatile constituents of the flowers of Clerodendron fragrans (Vent.) R. Br.,
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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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Lopes, Koketsu, et al., 1999
Lopes, D.; Koketsu, M.; Carauta, J.P.P.; de Oliveira, R.R.; Kaplan, M.A.C.,
Chemical composition of Pourouma guianensis Aublet essential oils,
Flavour Fragr. J., 1999, 14, 4, 233-236, https://doi.org/10.1002/(SICI)1099-1026(199907/08)14:4<233::AID-FFJ813>3.0.CO;2-L
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Sugisawa, Nakamura, et al., 1990
Sugisawa, H.; Nakamura, K.; Tamura, H.,
The aroma profile of the volatile in marine green algae (Ulva pertusa),
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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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