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:
- 9,12,15-Octadecatrienoic acid, methyl ester
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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Gas Chromatography

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Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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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

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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; T_start: 60. C

Kovats' RI, polar column, isothermal

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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

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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; T_start: 60. C
Capillary	HP-5MS	2105.4	Zeng, Zhao, et al., 2007	30. m/0.25 mm/0.25 μm, He, 4. K/min; T_start: 80. C; T_end: 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; T_end: 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; T_start: 40. C

Van Den Dool and Kratz RI, non-polar column, custom temperature program

View large format table.

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

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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

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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; T_start: 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; T_start: 150. C
Capillary	HP-5 MS	2100.	Zhao, Zeng, et al., 2009	30. m/0.25 mm/0.25 μm, Helium, 4. K/min; T_start: 50. C; T_end: 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; T_end: 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; T_start: 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; T_start: 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; T_start: 50. C; T_end: 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; T_end: 260. C
Capillary	DB-5	2098.	Tellez, Khan, et al., 2002	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 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; T_end: 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; T_end: 270. C

Normal alkane RI, non-polar column, custom temperature program

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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

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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; T_end: 200. C

Normal alkane RI, polar column, custom temperature program

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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, Gas Chromatography, Notes

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 . [all data]

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 . [all data]

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 . [all data]

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, Flavour Fragr. J., 2006, 21, 1, 140-142, https://doi.org/10.1002/ffj.1547 . [all data]

Rout, Rao, et al., 2007
Rout, P.K.; Rao, Y.R.; Sree., A.; Naik, S.N., Composition of essential oil, concrete, absolute, wax and headspace volatiles of Murrarya paniculata (Linn.) Jack flowers, Flavour Fragr. J., 2007, 22, 5, 352-357, https://doi.org/10.1002/ffj.1804 . [all data]

Zeng, Zhao, et al., 2007
Zeng, Y.-X.; Zhao, C.-X.; Liang, Y.-Z.; Yang, H.; Fang, H.-Z.; Yi, L.-Z.; Zeng, Z.-D., Comparative analysis of volatile components from Clematis species growing in China, Anal. Chim. Acta., 2007, 595, 1-2, 328-339, https://doi.org/10.1016/j.aca.2006.12.022 . [all data]

Radulovic, Lazarevic, et al., 2006
Radulovic, N.; Lazarevic, J.; Stojanovic, G.; Palic, R., Chemotaxonomically significant 2-ethyl substituted fatty acids from Stachys milanii Petrovic (Lamiaceae), Biochem. Syst. Ecol., 2006, 34, 4, 341-344, https://doi.org/10.1016/j.bse.2005.10.008 . [all data]

Zhao, Wang X.Y., et al., 2006
Zhao, Y.P.; Wang X.Y.; Wang, Z.C.; Lu Y.; Fu, C.X.; Chen, S.Y., Essential oil of Actinidia macrosperma, a catnip response kiwi endemic to China, Journal of Zhejiang University SCIENCE B, 2006, 7, 9, 708-712, https://doi.org/10.1631/jzus.2006.B0708 . [all data]

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, Flavour Fragr. J., 2003, 18, 3, 248-251, https://doi.org/10.1002/ffj.1179 . [all data]

Tan, Wilkins, et al., 1989
Tan, S.T.; Wilkins, A.L.; Holland, P.T.; McGhie, T.K., Extractives from New Zealand unifloral honeys. 2. Degraded carotenoids and other substances from heather honey, J. Agric. Food Chem., 1989, 37, 5, 1217-1221, https://doi.org/10.1021/jf00089a004 . [all data]

Tan, Holland, et al., 1988
Tan, S.-T.; Holland, P.T.; Wilkins, A.L.; Molan, P.C., Extractives from New Zealand honeys. 1. White clovers, manuka, and kanuka unifloral honeys, J. Agric. Food Chem., 1988, 36, 3, 453-460, https://doi.org/10.1021/jf00081a012 . [all data]

Sing, Smadja, et al., 1992
Sing, A.S.C.; Smadja, J.; Brevard, H.; Maignial, L.; Chaintreau, A.; Marion, J.-P., Volatile constituents of faham (Jumellea fragrans (Thou.) Schltr.), J. Agric. Food Chem., 1992, 40, 4, 642-646, https://doi.org/10.1021/jf00016a024 . [all data]

Filho and Lancas, 1995
Filho, N.R.A.; Lancas, F.M., Identification of FAMEs using ECL values and a three-dimensional Kovats retention index system, J. High Resol. Chromatogr., 1995, 18, 3, 167-170, https://doi.org/10.1002/jhrc.1240180306 . [all data]

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, Grasas y Aceites, 2010, 61, 3, 271-278, https://doi.org/10.3989/gya.122609 . [all data]

Escalona-Arranz, Perez-Roses, et al., 2010
Escalona-Arranz, J.C.; Perez-Roses, R.; Jimenez, I.L.; Rodriguez-Amado, J.; Argota-Coello, H.; Canizares-Lay, J.; Morris-Quevedo, H.J.; Sierra-Gonzales, G., Chemical constituents of Tamarindus indica L. leaves, Rev. Cubana Quim., 2010, 22, 3, 65-71. [all data]

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, Molecules, 2010, 15, 5, 3683-3693, https://doi.org/10.3390/molecules15053683 . [all data]

Lazarevic, Palic, et al., 2010
Lazarevic, J.S.; Palic, R.V.M.; Radulovic, N.S.; Ristic, N.R.; Stojanovic, G.S., Chemical composition and screening of the antimicrobial and antioxidative acrivity of extracts of Stachys species, J. Serb. Chem. Soc., 2010, 75, 10, 1347-1359, https://doi.org/10.2298/JSC100601117L . [all data]

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 . [all data]

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 . [all data]

Calyecac-cortero, Cibrian-Tovar, et al., 2007
Calyecac-cortero, H.G.; Cibrian-Tovar, J.; Soto-Hernandez, M.; Garcia-Velasco, R., Aislamento e identificacion de volatiles de Physalis philadelphica LAM. (Isolation and identification of Physalis philadelphica LAM. volatiles), Agrociencia, 2007, 41, 337-346. [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]

Tava, Pecetti, et al., 2007
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, Flavour Fragr. J., 2007, 22, 5, 363-370, https://doi.org/10.1002/ffj.1806 . [all data]

Mastelic, Jerkovic, et al., 2006
Mastelic, J.; Jerkovic, I.; Mesic, M., Volatile constituents from flowers, leaves, bark and wood of Prunus mahaleb L., Flavour Fragr. J., 2006, 21, 2, 306-313, https://doi.org/10.1002/ffj.1596 . [all data]

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 . [all data]

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 . [all data]

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 . [all data]

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), Flavour Fragr. J., 2003, 18, 3, 195-197, https://doi.org/10.1002/ffj.1180 . [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]

Ehrhardt, Osterroht, et al., 1980
Ehrhardt, M.; Osterroht, C.; Petrick, G., Fatty-acid methyl esters dissolved in seawater and associated with suspended particulate material, Marine Chem., 1980, 10, 1, 67-76, https://doi.org/10.1016/0304-4203(80)90059-6 . [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, Acta Sci. Pol. Hortorum Cultus, 2011, 10, 2, 85-94. [all data]

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, Food Chem., 2009, 113, 1, 216-221, https://doi.org/10.1016/j.foodchem.2008.07.066 . [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

Go To: Top, Gas Chromatography, References

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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