Geranyl tiglate
- Formula: C15H24O2
- Molecular weight: 236.3499
- IUPAC Standard InChI: InChI=1S/C15H24O2/c1-6-14(5)15(16)17-11-10-13(4)9-7-8-12(2)3/h6,8,10H,7,9,11H2,1-5H3/b13-10+,14-6+
- IUPAC Standard InChIKey: OGHBUHJLMHQMHS-KRDNBFTESA-N
- CAS Registry Number: 7785-33-3
- 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: 2-Butenoic acid, 2-methyl-, 3,7-dimethyl-2,6-octadienyl ester, (E,E)-; 2,6-Octadien-1-ol, 3,7-dimethyl-, 2-methyl-2-butenoate, (E,E)--; cis-α,β-Dimethyl acrylic acid, geraniol ester; trans-3,7-Dimethyl-2,6-octadien-1-yl cis-α,β-dimethyl acrylate; Tiglic acid, geraniol ester; (2E)-3,7-Dimethyl-2,6-octadienyl (2E)-2-methyl-2-butenoate; (E)-(E)-3,7-Dimethylocta-2,6-dien-1-yl 2-methylbut-2-enoate; (E)-3,7-Dimethylocta-2,6-dienyl (E)-2-methylbut-2-enoate; Gernyl tiglate; Geranyl (E)-2-methyl-2-butenoate; (E)-3,7-dimethyl-2,6-octadienyl 2-methylcrotonate
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Mass spectrum (electron ionization)
Go To: Top, Gas Chromatography, 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
Spectrum
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Additional Data
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| Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
|---|---|
| Origin | NIST Mass Spectrometry Data Center, 2010 |
| NIST MS number | 373714 |
Gas Chromatography
Go To: Top, Mass spectrum (electron ionization), 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
Kovats' RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | HP-5MS | 1704. | Jalali-Heravi, Zekavat, et al., 2006 | 60. m/0.25 mm/0.25 μm, He, 40. C @ 1. min, 3. K/min, 250. C @ 20. min |
| Capillary | Cross-Linked Methylsilicone | 1675. | Rajeswara Rao, Kaul, et al., 2002 | 50. m/0.2 mm/0.25 μm, He, 4. K/min; Tstart: 100. C; Tend: 280. C |
| Capillary | BP-1 | 1675. | Rajeswara Rao, 2002 | 25. m/0.5 mm/0.25 μm, N2, 5. K/min, 220. C @ 10. min; Tstart: 60. C |
| Capillary | BP-1 | 1675. | Rao B.R.R., 2002 | 25. m/0.5 mm/0.25 μm, 5. K/min, 220. C @ 10. min; Tstart: 60. C |
| Capillary | BP-1 | 1671. | Jain, Aggarwal, et al., 2001 | 25. m/0.55 mm/0.25 μm, N2, 5. K/min, 220. C @ 15. min; Tstart: 60. C |
| Capillary | BP-1 | 1675. | Rao, Kaul, et al., 2000 | N2, 5. K/min, 220. C @ 10. min; Column length: 25. m; Column diameter: 0.5 mm; Tstart: 60. C |
| Capillary | BP-1 | 1675. | Rao, Sastry, et al., 2000 | 25. m/0.50 mm/0.25 μm, N2, 5. K/min, 220. C @ 10. min; Tstart: 60. C |
| Capillary | BP-1 | 1672. | Kulkarni, Mallavarapu, et al., 1998 | N2, 5. K/min; Column length: 25. m; Column diameter: 0.25 mm; Tstart: 60. C; Tend: 220. C |
Kovats' RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | BP-1 | 1649. | Khan, Verma, et al., 2006 | 30. m/0.32 mm/0.25 μm, N2; Program: 60C => 5C/min => 220C (5min) => 3C/min => 245C(5min) |
| Capillary | BP-1 | 1688. | Raina, Srivastava, et al., 2003 | 25. m/0.32 mm/0.25 μm, N2; Program: 60C => 5C/min => 220C(5min) => 3C/min => 245C(5min) |
| Capillary | HP-5 | 1700. | Shellie and Marriott, 2003 | 30. m/0.25 mm/0.25 μm, He; Program: not specified |
Kovats' RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | HP-Wax | 2129. | Gauvin, Lecomte, et al., 2004 | 50. m/0.2 mm/0.4 μm, He, 4. K/min, 230. C @ 30. min; Tstart: 60. C |
| Capillary | Carbowax 20M | 2097. | Kulkarni, Mallavarapu, et al., 1998 | N2, 5. K/min; Column length: 25. m; Column diameter: 0.25 mm; Tstart: 60. C; Tend: 200. C |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | VF-5MS | 1703. | Liang, 2010 | 30. m/0.25 mm/0.25 μm, He; Tstart: 60. C; Tend: 270. C |
| Capillary | DB-5 | 1695. | Yu, Liao, et al., 2007 | 30. m/0.25 mm/0.25 μm, He, 3. K/min, 250. C @ 10. min; Tstart: 50. C |
| Capillary | HP-5 | 1705. | Shellie and Marriott, 2003 | 30. m/0.25 mm/0.25 μm, He, 3. K/min; Tstart: 40. C; Tend: 240. C |
| Capillary | HP-5MS | 1700. | Demetzos, Angelopoulou, et al., 2002 | 30. m/0.25 mm/0.25 μm, 50. C @ 5. min, 3. K/min; Tend: 280. C |
Van Den Dool and Kratz RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-Wax | 2105. | Möllenbeck, König, et al., 1997 | 25. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 4. K/min; Tend: 240. C |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-5 | 1703. | Boukhris, Bouaziz, et al., 2012 | 30. m/0.25 mm/0.25 μm, Helium, 100. C @ 1. min, 10. K/min, 260. C @ 10. min |
| Capillary | HP-5 MS | 1712. | Zarai, Kadri, et al., 2011 | 30. m/0.25 mm/0.25 μm, Helium, 30. C @ 3. min, 5. K/min, 250. C @ 10. min |
| Capillary | FSOT-RSL-200 | 1696. | Jirovetz, Eller, et al., 2006 | 30. m/0.32 mm/0.25 μm, Hydrogen, 40. C @ 5. min, 6. K/min, 280. C @ 5. min |
| Capillary | BP-1 | 1672. | Gupta, Mallavarapu, et al., 2001 | 30. m/0.25 mm/0.25 μm, N2, 5. K/min; Tstart: 60. C; Tend: 220. C |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | HP-5 MS | 1700. | Bai, Liu, et al., 2011 | 30. m/0.25 mm/0.25 μm, Helium; Program: 60 0C (1 min) 10 0C/min -> 180 0C (1 min) 20 0C/min -> 280 0C (15 min) |
| Capillary | DB-1 | 1673. | 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 | SE-30 | 1659. | Vinogradov, 2004 | Program: not specified |
Normal alkane RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Carbowax PEG CB | 2109. | Adams and Dev, 2010 | 30. m/0.25 mm/0.25 μm, Helium, 3. K/min; Tstart: 60. C; Tend: 246. C |
| Capillary | PE-Wax | 2096. | Ram, Kumar, et al., 2005 | 50. m/0.32 mm/0.25 μm, H2, 4. K/min, 220. C @ 2. min; Tstart: 60. C |
References
Go To: Top, Mass spectrum (electron ionization), Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Jalali-Heravi, Zekavat, et al., 2006
Jalali-Heravi, M.; Zekavat, B.; Sereshti, H.,
Characterization of essential oil components of Iranian geranium oil using gas chromatography-mass spectrometry combined with chemometric resolution techniques,
J. Chromatogr. A, 2006, 1114, 1, 154-163, https://doi.org/10.1016/j.chroma.2006.02.034
. [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]
Rajeswara Rao, 2002
Rajeswara Rao, B.R.,
Biomass yield, essential oil yield and essential oil composition of rose-scented geranium (Pelargonium species) as influenced by row spacings and intercropping with cornmint (Mentha arvensis L.f. piperascens Malinv. ex Holmes),
Ind. Crops Prod., 2002, 16, 2, 133-144, https://doi.org/10.1016/S0926-6690(02)00038-9
. [all data]
Rao B.R.R., 2002
Rao B.R.R.,
Biomass yield, essential oil yield and essential oil composition of rose-scented geranium (Pelargonium species) as influenced by row spacings and intercropping with cornmint (Mentha arvensis L.f. piperascens Malinv. ex Holmes),
Industrial Crops and Products, 2002, 16, 2, 133-144, https://doi.org/10.1016/S0926-6690(02)00038-9
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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, Kaul, et al., 2000
Rao, B.R.R.; Kaul, P.N.; Mallavarapu, G.R.; Ramesh, S.,
First observation of little leaf disease and its impact on the yield and composition of the essential oil of rose-scented geranium (Pelargonium sp.),
Flavour Fragr. J., 2000, 15, 3, 137-140, https://doi.org/10.1002/1099-1026(200005/06)15:3<137::AID-FFJ880>3.0.CO;2-A
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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
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Khan, Verma, et al., 2006
Khan, M.; Verma, S.C.; Srivastava, S.K.; Shawl, A.S.; Syamsundar, K.V.; Khanuja, S.P.S.; Kumar, T.,
Essential oil composition of Taxus wallichiana Zucc. from the Northern Himalayan region of India,
Flavour Fragr. J., 2006, 21, 5, 772-775, https://doi.org/10.1002/ffj.1682
. [all data]
Raina, Srivastava, et al., 2003
Raina, V.K.; Srivastava, S.K.; Aggarwal, K.K.; Syamasunder, K.V.; Khanuja, S.P.S.,
Essential oil composition of Cymbopogon martinii from different places in India,
Flavour Fragr. J., 2003, 18, 4, 312-315, https://doi.org/10.1002/ffj.1222
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Shellie and Marriott, 2003
Shellie, R.A.; Marriott, P.J.,
Comprehensive two-dimensional gas chromatography-mass spectrometry analysis of Pelargonium graveolens essential oil using rapid scanning quadrupole mass spectrometry,
Analyst, 2003, 128, 7, 879-883, https://doi.org/10.1039/b304371a
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Gauvin, Lecomte, et al., 2004
Gauvin, A.; Lecomte, H.; Smadja, J.,
Comparative investigations of the essential oils of two scented geranium (Pelargonium spp.) cultivars grown on Reunion Island,
Flavour Fragr. J., 2004, 19, 5, 455-460, https://doi.org/10.1002/ffj.1354
. [all data]
Liang, 2010
Liang, Y.,
Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2010. [all data]
Yu, Liao, et al., 2007
Yu, J.Q.; Liao, Z.X.; Cai, X.Q.; Lei, J.C.; Zou, G.L.,
Composition, antimicrobial activity and cytotoxicity of essential oils from Aristolochia mollissima,
Environmental Toxicology and Pharmacology, 2007, 23, 2, 162-167, https://doi.org/10.1016/j.etap.2006.08.004
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Demetzos, Angelopoulou, et al., 2002
Demetzos, C.; Angelopoulou, D.; Perdetzoglou, D.,
A comparative study of the essential oils of Cistus salviifolius in several populations of Crete (Greece),
Biochem. Syst. Ecol., 2002, 30, 7, 651-665, https://doi.org/10.1016/S0305-1978(01)00145-4
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Möllenbeck, König, et al., 1997
Möllenbeck, S.; König, T.; Schreier, P.; Schwab, W.; Rajaonarivony, J.; Ranarivelo, L.,
Chemical composition and analyses of enantiomers of essential oils from Madagascar,
Flavour Fragr. J., 1997, 12, 2, 63-69, https://doi.org/10.1002/(SICI)1099-1026(199703)12:2<63::AID-FFJ614>3.0.CO;2-Z
. [all data]
Boukhris, Bouaziz, et al., 2012
Boukhris, M.; Bouaziz, M.; Feki, I.; Jemai, H.; El Feki, A.; Sayadi, S.,
Hypoglycemic and antioxidant effects of leaf essential oil of Pelargonium graveolens L'Her. in alloxan induced diabetic rats,
Lipids in Health and Disease, 2012, 11, 1, 1-10, https://doi.org/10.1186/1476-511X-11-81
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Zarai, Kadri, et al., 2011
Zarai, Z.; Kadri, A.; Ben Chobba, I.; Ben Mansour, R.; Bekir, R.; Mejdoub, H.; Gharsallah, N.,
The in-vitro evaluation of antibacterial, antifungal and cytotoxic properties of Marrubium vulgare L. essential oil grown in Tunisia,
Lipids in Health and Disease, 2011, 10, 161, 1-8. [all data]
Jirovetz, Eller, et al., 2006
Jirovetz, L.; Eller, G.; Buchbauer, G.; Schmidt, E.; Denkova, Z.; Stoyanova, A.S.; Nikolova R.; Geissler, M.,
Chemical composition, antimicrobial activities and odor descriptions of some essential oils with characteristic floral-rosy scent and of their principal aroma compounds,
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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,
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Bai, Liu, et al., 2011
Bai, C.Q.; Liu, Z.L.; Liu, Q.Z.,
Nematicidal constituents from the essential oil of Chenopodium ambrosioides aerial parts,
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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
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Vinogradov, 2004
Vinogradov, B.A.,
Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]
Adams and Dev, 2010
Adams, R.P.; Dev, V.,
Synthesis and GC-MS analysis of angelates and tiglates as an aid to identification of these components in essential oils,
Flavour Fragr. J., 2010, 25, 2, 71-74, https://doi.org/10.1002/ffj.1968
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Ram, Kumar, et al., 2005
Ram, P.; Kumar, B.; Naqvi, A.A.; Verma, R.S.; Patra, N.K.,
Post-harvest storage effect on quantity and quality of rose-scented geranium (Pelargonium sp. cv. 'Bourbon') oil in Uttaranchal,
Flavour Fragr. J., 2005, 20, 6, 666-668, https://doi.org/10.1002/ffj.1544
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Notes
Go To: Top, Mass spectrum (electron ionization), Gas Chromatography, References
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