Geranyl isovalerate

Formula: C₁₅H₂₆O₂
Molecular weight: 238.3657
IUPAC Standard InChI: InChI=1S/C15H26O2/c1-12(2)7-6-8-14(5)9-10-17-15(16)11-13(3)4/h7,9,13H,6,8,10-11H2,1-5H3/b14-9+
IUPAC Standard InChIKey: SOUKTGNMIRUIQN-NTEUORMPSA-N
CAS Registry Number: 109-20-6
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.
Species with the same structure:
- (E)-3,7-Dimethylocta-2,6-dien-1-yl 3-methylbutanoate
Stereoisomers:
- Butanoic acid, 3-methyl-, 3,7-dimethyl-2,6-octadienyl ester, (Z)-
Other names: Butanoic acid, 3-methyl-, 3,7-dimethyl-2,6-octadienyl ester, (E)-; 2,6-Octadien-1-ol, 3,7-dimethyl-, isovalerate, (E)-; Butyric acid, 3-methyl-, 3,7-dimethyl-2,6-octadienyl ester, (E)-; trans-3,7-Dimethyl-2,6-octadienyl isopentanoate; Isovaleric acid, 3,7-dimethyl-2,6-octadienyl ester, (E)-; Geranyl 3-methylbutanoate; Geranyl isopentanoate; (2E)-3,7-Dimethyl-2,6-octadienyl 3-methylbutanoate
Information on this page:
Other data available:
- Mass spectrum (electron ionization)
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Gas Chromatography

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

Kovats' RI, non-polar column, temperature ramp

Column type	Active phase	I	Reference	Comment
Capillary	HP-5MS	1604.	Asuming, Beauchamp, et al., 2005	30. m/0.25 mm/0.25 μm, He, 50. C @ 10. min, 3. K/min, 250. C @ 5. min
Capillary	BP-1	1582.	Rajeswara Rao, Kaul, et al., 2005	30. m/0.32 mm/0.25 μm, 5. K/min, 245. C @ 10. min; T_start: 60. C
Capillary	BP-1	1582.	Rao, Kaul, et al., 2005	30. m/0.32 mm/0.25 μm, 5. K/min, 245. C @ 10. min; T_start: 60. C
Capillary	Cross-Linked Methylsilicone	1585.	Rajeswara Rao, Kaul, et al., 2002	50. m/0.2 mm/0.25 μm, He, 4. K/min; T_start: 100. C; T_end: 280. C
Capillary	BP-1	1579.	Jain, Aggarwal, et al., 2001	25. m/0.55 mm/0.25 μm, N2, 5. K/min, 220. C @ 15. min; T_start: 60. C
Capillary	BP-1	1583.	Rao, Sastry, et al., 2000	25. m/0.50 mm/0.25 μm, N2, 5. K/min, 220. C @ 10. min; T_start: 60. C
Capillary	BP-1	1578.	Kulkarni, Mallavarapu, et al., 1998	N2, 5. K/min; Column length: 25. m; Column diameter: 0.25 mm; T_start: 60. C; T_end: 220. C
Capillary	Methyl Silicone	1580.	Mallavarapu, Rao, et al., 1998	N2, 5. K/min; Column length: 25. m; Column diameter: 0.5 mm; T_start: 60. C; T_end: 220. C

Kovats' RI, polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	Carbowax 20M	1880.	Kulkarni, Mallavarapu, et al., 1998	N2, 5. K/min; Column length: 25. m; Column diameter: 0.25 mm; T_start: 60. C; T_end: 200. C
Capillary	Carbowax 20M	1923.	Mallavarapu, Rao, et al., 1998	N2, 5. K/min; Column length: 25. m; Column diameter: 0.5 mm; T_start: 60. C; T_end: 200. C
Capillary	Carbowax 20M	1913.	Randriamiharisoa and Gaydou, 1987	He, 2. K/min; Column length: 50. m; Column diameter: 0.3 mm; T_start: 70. C; T_end: 210. C

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

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Column type	Active phase	I	Reference	Comment
Capillary	SPB-1	1573.	Blagojevic, Radulovic, et al., 2006	30. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 5. K/min, 250. C @ 15. min
Capillary	DB-5	1582.	Blagojevic, Radulovic, et al., 2006	30. m/0.2 mm/0.25 μm, He, 50. C @ 3. min, 5. K/min, 250. C @ 15. min
Capillary	HP-5MS	1597.	Saroglou, Dorizas, et al., 2006	30. m/0.25 mm/0.25 μm, He, 60. C @ 5. min, 4. K/min; T_end: 280. C
Capillary	Methyl Silicone	1605.	Píry, Príbela, et al., 1995	25. m/0.2 mm/0.3 μm, He, 2. K/min; T_start: 40. C; T_end: 200. 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-5MS	1610.7	Andriamaharavo, 2014	30. m/0.25 mm/0.25 μm, He; Program: 60C (1 min) => 5 C/min => 210C => 10 C/min => 280C (15 min)

Van Den Dool and Kratz RI, polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	Carbowax 20M	1898.	Píry, Príbela, et al., 1995	50. m/0.2 mm/0.2 μm, He, 30. C @ 2. min, 4. K/min, 170. C @ 20. min

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	SPB-5	1605.	Raal, Orav, et al., 2007	30. m/0.25 mm/0.25 μm, He, 2. K/min; T_start: 50. C; T_end: 250. C
Capillary	DB-1	1585.	Sonboli, Kanani, et al., 2007	60. m/0.25 mm/0.25 μm, Nitrogen, 5. K/min, 250. C @ 10. min; T_start: 60. C
Capillary	NB-30	1585.	Orav, Raal, et al., 2006	30. m/0.2 mm/0.25 μm, He, 2. K/min; T_start: 50. C; T_end: 250. C
Capillary	NB-30	1590.	Orav, Raal, et al., 2006	30. m/0.2 mm/0.25 μm, He, 2. K/min; T_start: 50. C; T_end: 250. C
Capillary	SPB-1	1590.	Hamilton, Hall, et al., 2005	30. m/0.25 mm/0.2 μm, 60. C @ 2. min, 6. K/min; T_end: 250. C
Capillary	HP-5	1606.	Ghannadi, Sajjadi, et al., 2002	30. m/0.25 mm/0.25 μm, He, 4. K/min; T_start: 60. C; T_end: 275. C
Capillary	OV-101	1605.	Kuiate, Bessière, et al., 2002	He, 5. K/min; Column length: 25. m; Column diameter: 0.32 mm; T_start: 50. C; T_end: 200. C
Capillary	BP-1	1588.	Gupta, Mallavarapu, et al., 2001	30. m/0.25 mm/0.25 μm, N2, 5. K/min; T_start: 60. C; T_end: 220. C
Capillary	DB-1	1600.	Stashenko, Puertas, et al., 1996	60. m/0.25 mm/0.25 μm, He, 50. C @ 5. min, 2.5 K/min; T_end: 250. C

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

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	HP-5 MS	1606.	Sharopov, Sulaimonova, et al., 2012	30. m/0.25 mm/0.25 μm, Helium; Program: 40 0C (10 min) 3 0C/min -> 200 0C 2 0C/min -> 220 0C
Capillary	DB-1	1591.	Delort and Jaquier, 2009	60. m/0.25 mm/0.25 μm, Helium; Program: 50 0C (5 min) 3 0C/min -> 120 0C 5 0C/min -> 250 0C (3 min) 15 0C/min -> 300 0C (20 min)
Capillary	HP-5	1613.	Zhao, Li, et al., 2008	30. m/0.25 mm/0.25 μm; Program: 40 0C (2 min) 5 0C/min -> 80 0C 7 oC/min -> 160 0C 9 0C/min -> 200 0C 20 0C/min -> 280 0C (10 min)
Capillary	HP-5	1588.	Yasar, Üçüncü, et al., 2005	30. m/0.25 mm/0.25 μm, He; Program: 60C(5min) => 3C/min => 120C (2min) => 2C/min => 200C (2min) => 3C/min => 320C
Capillary	DB-1	1590.	Miguel, Simões, et al., 2004	30. m/0.25 mm/0.25 μm, He; Program: 45C => 3C/min => 175C => 15C/min => 300C (10min)
Capillary	SE-30	1593.	Vinogradov, 2004	Program: not specified

Normal alkane RI, polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	Supelcowax-10	1910.	Raal, Orav, et al., 2007	30. m/0.25 mm/0.25 μm, He, 2. K/min; T_start: 50. C; T_end: 250. C
Capillary	NB-20M	1877.	Orav, Raal, et al., 2006	30. m/0.2 mm/0.25 μm, He, 2. K/min; T_start: 50. C; T_end: 250. C
Capillary	DB-Wax	1925.	Hamilton, Hall, et al., 2005	30. m/0.25 mm/0.2 μm, 60. C @ 2. min, 6. K/min; T_end: 250. C
Capillary	Innowax	1893.	Suleimenov, Atazharova, et al., 2003	He, 60. C @ 10. min, 4. K/min, 220. C @ 10. min; Column length: 60. m; Column diameter: 0.25 mm
Capillary	Innowax	1904.	Kaya, Baser, et al., 1999	60. m/0.25 mm/0.25 μm, He, 60. C @ 10. min; T_end: 220. C
Capillary	HP-Innowax	1904.	Kaya, Baser, et al., 1999, 2	60. m/0.25 mm/0.25 μm, He, 60. C @ 10. min; T_end: 220. C
Capillary	DB-Wax	1919.	Stashenko, Puertas, et al., 1996	60. m/0.25 mm/0.25 μm, He, 50. C @ 5. min, 2.5 K/min; T_end: 180. C

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	HP Innowax FSP	1893.	Tabanca N., Demirci B., et al., 2007	60. m/0.25 mm/0.25 μm, N2; Program: 60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C
Capillary	HP-Innowax FSC	1924.	Suleimenov Y.M., Atazhanova G.A., et al., 2006	60. m/0.25 mm/0.25 μm, He; Program: 60(10min) => 4C/min => 220C(10min) => 1C/min => 240C
Capillary	Carbowax 20M	1895.	Vinogradov, 2004	Program: not specified

References

Go To: Top, Gas Chromatography, Notes

Asuming, Beauchamp, et al., 2005
Asuming, W.A.; Beauchamp, P.S.; Descalzo, J.T.; Dev, B.C.; Dev, V.; Frost, S.; Ma, C.W., Essential oil composition of four Lomatium Raf. species and their chemotaxonomy, Biochem. Syst. Ecol., 2005, 33, 1, 17-26, https://doi.org/10.1016/j.bse.2004.06.005 . [all data]

Rajeswara Rao, Kaul, et al., 2005
Rajeswara Rao, B.R.; Kaul, P.N.; Syamasundar, K.V.; Ramesh, S., Chemical profiles of primary and secondary essential oils of palmarosa (Cymbopogon martinii (Roxb.) Wats var. motia Burk.), Ind. Crops Prod., 2005, 21, 1, 121-127, https://doi.org/10.1016/j.indcrop.2004.02.002 . [all data]

Rao, Kaul, et al., 2005
Rao, B.R.R.; Kaul, P.N.; Syamasundar, K.V.; Ramesh, S., Chemical profiles of primary and secondary essential oils of palmarosa (Cymbopogon martinii (Roxb.) Wats var. motia Burk.), Ind. Crops Prod., 2005, 21, 1, 121-127, https://doi.org/10.1016/j.indcrop.2004.02.002 . [all data]

Rajeswara Rao, Kaul, et al., 2002
Rajeswara Rao, B.R.; Kaul, P.N.; Syamasundar, K.V.; Ramesh, S., Water soluble fractions of rose scented geranium (Pelargonium species) essential oil, Bioresour. Technol., 2002, 84, 3, 243-246, https://doi.org/10.1016/S0960-8524(02)00057-3 . [all data]

Jain, Aggarwal, et al., 2001
Jain, N.; Aggarwal, K.K.; Syamasundar, K.V.; Srivastava, S.K.; Kumar, S., Essential oil composition of geranium (Pelargonium sp.) from the plains of Northern India, Flavour Fragr. J., 2001, 16, 1, 44-46, https://doi.org/10.1002/1099-1026(200101/02)16:1<44::AID-FFJ943>3.0.CO;2-X . [all data]

Rao, Sastry, et al., 2000
Rao, B.R.R.; Sastry, K.P.; Saleem, S.M.; Rao, E.V.S.P.; Syamasundar, K.V.; Ramesh, S., Volatile flower oils of three genotypes of rose-scented geranium (Pelargonium sp.), Flavour Fragr. J., 2000, 15, 2, 105-107, https://doi.org/10.1002/(SICI)1099-1026(200003/04)15:2<105::AID-FFJ875>3.0.CO;2-G . [all data]

Kulkarni, Mallavarapu, et al., 1998
Kulkarni, R.N.; Mallavarapu, G.R.; Baskaran, K.; Ramesch, S.; Kumar, S., Composition of the essential oils of two isomenthone-rich variants of geranium (Pelargonium sp.), Flavour Fragr. J., 1998, 13, 6, 389-392, https://doi.org/10.1002/(SICI)1099-1026(199811/12)13:6<389::AID-FFJ757>3.0.CO;2-2 . [all data]

Mallavarapu, Rao, et al., 1998
Mallavarapu, G.R.; Rao, B.R.R.; Kaul, P.N.; Ramesh, S.; Bhattacharya, A.K., Volatile constituents of the essential oils of the seeds and the herb of palmarosa (Cymbopogon martinii (Roxb.) Wats. var. motia Burk.), Flavour Fragr. J., 1998, 13, 3, 167-169, https://doi.org/10.1002/(SICI)1099-1026(199805/06)13:3<167::AID-FFJ719>3.0.CO;2-B . [all data]

Randriamiharisoa and Gaydou, 1987
Randriamiharisoa, R.P.; Gaydou, E.M., Composition of Palmarosa (Cymbopogon martinii) essential oil from Madagascar, J. Agric. Food Chem., 1987, 35, 1, 62-66, https://doi.org/10.1021/jf00073a015 . [all data]

Blagojevic, Radulovic, et al., 2006
Blagojevic, P.; Radulovic, N.; Palic, R.; Stojanovic, G., Chemical composition of the essential oils of Serbian wild-growing Srtemisia absinthium and Artemisia vulgaris, J. Agric. Food Chem., 2006, 54, 13, 4780-4789, https://doi.org/10.1021/jf060123o . [all data]

Saroglou, Dorizas, et al., 2006
Saroglou, V.; Dorizas, N.; Kypriotakis, Z.; Skaltsa, H.D., Analysis of the essential oil composition of eight Anthemis species from Greece, J. Chromatogr. A, 2006, 1104, 1-2, 313-322, https://doi.org/10.1016/j.chroma.2005.11.087 . [all data]

Píry, Príbela, et al., 1995
Píry, J.; Príbela, A.; Durcanská, J.; Farkas, P., Fractionation of volatiles from blackcurrant (Ribes nigrum L.) by different extractive methods, Food Chem., 1995, 54, 1, 73-77, https://doi.org/10.1016/0308-8146(95)92665-7 . [all data]

Andriamaharavo, 2014
Andriamaharavo, N.R., Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2014. [all data]

Raal, Orav, et al., 2007
Raal, A.; Orav, A.; Arak, E.; Kailas, T.; Müürisepp, M., Variation in the composition of the essential oil of Valeriana officinalis L. roots from Estonia, Proc. Est. Acad. Sci. Chem., 2007, 56, 2, 67-74. [all data]

Sonboli, Kanani, et al., 2007
Sonboli, A.; Kanani, M.R.; Yousefzadi, M.; Mojarrad, M., Biological activity and composition of the essential oil of Tetrataenium nephrophyllum (Apiaceae) from Iran, Natural Product Communications, 2007, 2, 12, 1249-1252. [all data]

Orav, Raal, et al., 2006
Orav, A.; Raal, A.; Arak, E.; Müürisepp, M.; Kailas, T., Composition of the essential oil of Artemisia absinthium L. of different geographical origin, Proc. Est. Acad. Sci. Chem., 2006, 55, 3, 155-165. [all data]

Hamilton, Hall, et al., 2005
Hamilton, J.G.C.; Hall, D.R.; Kirk, W.D.J., Identification of a male-produced aggregation pheromone in the western flower thrips, J. Chem. Ecol., 2005, 31, 6, 1369-1379, https://doi.org/10.1007/s10886-005-1351-z . [all data]

Ghannadi, Sajjadi, et al., 2002
Ghannadi, A.; Sajjadi, S.E.; Beigihasan, A., Composition of the essential oil of Ferula ovina (Boiss.) Boiss. from Iran, DARU, 2002, 10, 4, 165-167, retrieved from http://www1.tums.ac.ir/daru/Daru4%202002/Ghannadi.PDF. [all data]

Kuiate, Bessière, et al., 2002
Kuiate, J.-R.; Bessière, J.-M.; Zollo, P.-H.A., Composition of the essential oils from three Laggera Spp. from Cameroon, Flavour Fragr. J., 2002, 17, 2, 105-108, https://doi.org/10.1002/ffj.1057 . [all data]

Gupta, Mallavarapu, et al., 2001
Gupta, R.; Mallavarapu, G.R.; Banerjee, S.; Kumar, S., Characteristics of an isomenthone-rich somaclonal mutant isolated in a geraniol-rich rose-scented geranium accession of Pelargonium graveolens, Flavour Fragr. J., 2001, 16, 5, 319-324, https://doi.org/10.1002/ffj.1002 . [all data]

Stashenko, Puertas, et al., 1996
Stashenko, E.E.; Puertas, M.A.; Combariza, M.Y., Volatile secondary metabolites from Spilanthes americana obtained by simultaneous steam distillation--solvent extraction and supercritical fluid extraction, J. Chromatogr. A, 1996, 752, 1-2, 223-232, https://doi.org/10.1016/S0021-9673(96)00480-3 . [all data]

Sharopov, Sulaimonova, et al., 2012
Sharopov, F.S.; Sulaimonova, V.A.; Setzer, W.N., Composition of the essential oil of Ertemisia absinthium from Tajikistan, Rec. Nat. Prod., 2012, 6, 2, 127-134. [all data]

Delort and Jaquier, 2009
Delort, E.; Jaquier, A., Novel terpenyl esters from Australian finger lime (Citrus australasica) peel extract, Flav. Fragr. J., 2009, 24, 3, 123-132, https://doi.org/10.1002/ffj.1922 . [all data]

Zhao, Li, et al., 2008
Zhao, Y.; Li, J.; Xu, Y.; Duan, H.; Fan, W.; Zhao, G., EXtraction, preparation and identification of volatile compounds in Changyu XO brandy, Chinese J. Chromatogr., 2008, 26, 2, 212-222, https://doi.org/10.1016/S1872-2059(08)60014-0 . [all data]

Yasar, Üçüncü, et al., 2005
Yasar, A.; Üçüncü, O.; Güleç, C.; Inceer, H.; Ayaz, S.; Yayh, N., GC-MS analysis of chloroform extracts in flowers, stems, and roots of Tripleurospermum callosum, Pharm. Biol., 2005, 43, 2, 108-112, https://doi.org/10.1080/13880200590919384 . [all data]

Miguel, Simões, et al., 2004
Miguel, G.; Simões, M.; Figueiredo, A.C.; Barroso, J.G.; Pedro, L.G.; Carvalho, L., Composition and antioxidant activities of the essential oils of Thymus caespititius, Thymus camphoratus and Thymus mastichina, Food Chem., 2004, 86, 2, 183-188, https://doi.org/10.1016/j.foodchem.2003.08.031 . [all data]

Vinogradov, 2004
Vinogradov, B.A., Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]

Suleimenov, Atazharova, et al., 2003
Suleimenov, E.M.; Atazharova, G.A.; Demirchi, B.; Baser, K.H.C.; Adekenov, S.M., Essential oil composition of Artemisia Lercheana and A. Sieversiana of Kazakhstan flora in Recent problems of development of new medicines of natural origin, Proceedings of symposium, St.Petersburg - Pushkin, 2003, 382-385. [all data]

Kaya, Baser, et al., 1999
Kaya, A.; Baser, K.H.C.; Demirci, B.; Koca, F., The essential oil of Acinos alpinus (L.) Moench growing in Turkey, Flavour Fragr. J., 1999, 14, 1, 55-59, https://doi.org/10.1002/(SICI)1099-1026(199901/02)14:1<55::AID-FFJ784>3.0.CO;2-Q . [all data]

Kaya, Baser, et al., 1999, 2
Kaya, A.; Baser, K.H.C.; Tümen, G.; Koca, F., The essential oil of Acinos suaveolens (Sm.) G. Don fil. Acinos arvensis (Lam.) Dandy and Acinos rotundifolius Pers. growing wild in Turkey, Flavour Fragr. J., 1999, 14, 1, 60-64, https://doi.org/10.1002/(SICI)1099-1026(199901/02)14:1<60::AID-FFJ785>3.0.CO;2-0 . [all data]

Tabanca N., Demirci B., et al., 2007
Tabanca N.; Demirci B.; Crockett S.L.; Baser K.H.C.; Wedge D.E., Chemical composition and antifungal activity of Arnica longifolia, Aster hesperius, and Chrysothamnus nauseosus essential oils, J. Agric. Food Chem., 2007, 55, 21, 8430-8435, https://doi.org/10.1021/jf071379c . [all data]

Suleimenov Y.M., Atazhanova G.A., et al., 2006
Suleimenov Y.M.; Atazhanova G.A.; Ozek T.; Demirci B.; Kulyyasov A.T.; Adekenov S.M.; Baser K.H.C., Essential oil composition of three species of Achillea from Kazakhstan, Chem. Nat. Compd. (Engl. Transl.), 2006, 37, 5, 447-450, https://doi.org/10.1023/A:1014471326724 . [all data]

Notes

Go To: Top, Gas Chromatography, References

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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