Methyl jasmonate
- Formula: C13H20O3
- Molecular weight: 224.2961
- IUPAC Standard InChI: InChI=1S/C13H20O3/c1-3-4-5-6-11-10(7-8-12(11)14)9-13(15)16-2/h4-5,10-11H,3,6-9H2,1-2H3/b5-4+/t10-,11-/m0/s1
- IUPAC Standard InChIKey: GEWDNTWNSAZUDX-NNOMMRTBSA-N
- CAS Registry Number: 1211-29-6
- 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. - Stereoisomers:
- methyl epijasmonate
- Cyclopentaneacetic acid, 3-oxo-2-(2-pentenyl)-, methyl ester, [1α,2α(Z)]-
- (+)-Jasmonic acid, methyl ester (cis)
- (-)-Jasmonic acid, methyl ester (trans)
- (+)-(Z)-Methyl epijasmonate
- Methyl (Z)-epi-jasmonate
- cis-Methyl jasmonate
- (E)-methyl jasmonate
- Methyl epi-jasmonate
- (Z)-Methyl epi-jasmonate
- Other names: Cyclopentaneacetic acid, 3-oxo-2-(2-pentenyl)-, methyl ester, [1R-[1α,2β(Z)]]-; Cyclopentaneacetic acid, 3-oxo-2-(2Z)-2-penten-1-yl-, methyl ester, (1R,2R)-; Cyclopentaneacetic acid, 3-oxo-trans-2-(cis-2-pentenyl), methyl ester; Z-Methyl jasmonoate; Methyl cis-jasmonate; Methyl 2-((1R,2R)-3-oxo-2-((Z)-pent-2-en-1-yl)cyclopentyl)acetate; Methyl (3-oxo-2-[(2Z)-2-pentenyl]cyclopentyl)acetate; 17627-54-2; 54595-01-6; methyl [1R-[1α,2β(Z)]]-3-oxo-2-(pent-2-enyl)cyclopentaneacetate
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Options:
Gas Chromatography
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
Van Den Dool and Kratz RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | HP-5MS | 1655.4 | 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) |
| Capillary | CP Sil 5 CB | 1629. | Blake, Taylor, et al., 2002 | 25. m/0.25 mm/0.25 μm, He; Program: 60C (1min) => 20C/min => 170C => 4C/min => 290C |
| Capillary | CP Sil 5 CB | 1629. | Blake, Taylor, et al., 2002 | 25. m/0.25 mm/0.25 μm, He; Program: 60C (1min) => 20C/min => 170C => 4C/min => 290C |
Van Den Dool and Kratz RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | DB-Wax | 2338. | Shimoda, Shigematsu, et al., 1995 | 60. m/0.25 mm/0.25 μm, 2. K/min; Tstart: 50. C; Tend: 230. C |
| Capillary | DB-Wax | 2338. | Shimoda, Shigematsu, et al., 1995, 2 | 60. m/0.25 mm/0.25 μm, He, 2. K/min; Tstart: 50. C; Tend: 230. C |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | OV-1 | 1606. | Nibret and Wink, 2009 | 30. m/0.25 mm/0.25 μm, Helium, 40. C @ 2. min, 4. K/min, 300. C @ 10. min |
| Capillary | HP-5 MS | 1644. | Zaibunnisa, Norashikin, et al., 2009 | 30. m/0.25 mm/0.25 μm, Helium, 60. C @ 6. min, 10. K/min, 325. C @ 10. min |
| Capillary | HP-5 | 1615. | Bousaada, Ammar, et al., 2008 | 30. m/0.25 mm/0.25 μm, Nitrogen, 50. C @ 1. min, 5. K/min, 280. C @ 1. min |
| Capillary | DBP-5 | 1611. | Heravi and Sereshti, 2007 | 25. m/0.25 mm/0.22 μm, Helium, 40. C @ 1. min, 3. K/min, 250. C @ 10. min |
| Capillary | DBP-5 | 1611. | Sereshti and Samadi, 2007 | 25. m/0.25 mm/0.22 μm, Helium, 40. C @ 1. min, 3. K/min, 250. C @ 10. min |
| Capillary | DB-5 | 1652. | Rout, Naik, et al., 2006 | 30. m/0.25 mm/0.25 μm, He, 2. K/min, 200. C @ 60. min; Tstart: 60. C |
| Capillary | CP Sil 5 CB | 1607. | Tesso, König, et al., 2006 | H2, 3. K/min; Column length: 25. m; Column diameter: 0.25 mm; Tstart: 50. C; Tend: 230. C |
| Capillary | DB-5 | 1638. | Rouseff, Jella, et al., 2001 | 30. m/0.32 mm/0.5 μm, 6. K/min; Tstart: 35. C; Tend: 275. C |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | CP Sil 5 CB | 1612. | Weyerstahl, Marschall, et al., 1997 | N2; Column length: 30. m; Column diameter: 0.25 mm; Program: not specified |
Normal alkane RI, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | CP-Wax | 2303. | Ka, Choi, et al., 2005 | 30. m/0.32 mm/0.25 μm, He, 40. C @ 2. min, 5. K/min; Tend: 180. C |
| Capillary | DB-Wax | 2332. | Lee, Umano, et al., 2005 | 30. m/0.25 mm/0.25 μm, He, 3. K/min, 180. C @ 40. min; Tstart: 50. C |
| Capillary | DB-Wax | 2345. | Ito, Sugimoto, et al., 2002 | 60. C @ 4. min, 3. K/min; Column length: 60. m; Column diameter: 0.25 mm; Tend: 180. C |
References
Go To: Top, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Andriamaharavo, 2014
Andriamaharavo, N.R.,
Retention Data. NIST Mass Spectrometry Data Center., NIST Mass Spectrometry Data Center, 2014. [all data]
Blake, Taylor, et al., 2002
Blake, P.S.; Taylor, J.M.; Finch-Savage, W.E.,
Identification of abscisic acid, indole-3-acetic acid, jasmonic acid, indole-3-acetonitrile, methyl jasmonate and gibberellins in developing, dormant and startified seeds of ash (Fraxinus excelsior),
Plant Growth Regul., 2002, 37, 2, 119-125, https://doi.org/10.1023/A:1020504610172
. [all data]
Shimoda, Shigematsu, et al., 1995
Shimoda, M.; Shigematsu, H.; Shiratsuchi, H.; Osajima, Y.,
Comparison of the odor concentrates by SDE and adsorptive column method from green tea infusion,
J. Agric. Food Chem., 1995, 43, 6, 1616-1620, https://doi.org/10.1021/jf00054a037
. [all data]
Shimoda, Shigematsu, et al., 1995, 2
Shimoda, M.; Shigematsu, H.; Shiratsuchi, H.; Osajima, Y.,
Comparison of volatile compounds among different grades of green tea and their relations to odor attributes,
J. Agric. Food Chem., 1995, 43, 6, 1621-1625, https://doi.org/10.1021/jf00054a038
. [all data]
Nibret and Wink, 2009
Nibret, E.; Wink, M.,
Volatile components of four Ethiopian Artemisia species extracts and their in vitro antipatrypanosomal and cytotoxic activities,
Phytomedicine, 2009, 00, 0, 000-000. [all data]
Zaibunnisa, Norashikin, et al., 2009
Zaibunnisa, A.H.; Norashikin, S.; Mamot, S.; Osman, H.,
An experimental design approach for the extraction of volatile compounds from turmeric leaves (Curcuma domestica) using pressurised liquid extraction (PLE),
LWT-Food Sci. Technol., 2009, 42, 1, 233-238, https://doi.org/10.1016/j.lwt.2008.03.015
. [all data]
Bousaada, Ammar, et al., 2008
Bousaada, O.; Ammar, S.; Saidana, D.; Chriaa, J.; Chraif, I.; Daami, M.; Helal, A.N.; Mighri, Z.,
Chemical composition and antimicrobial activity of volatile components from capitula and aerial parts of Rhaponticum acaule DC growing wild in Tunisia,
Microbiol. Res., 2008, 163, 1, 87-95, https://doi.org/10.1016/j.micres.2007.02.010
. [all data]
Heravi and Sereshti, 2007
Heravi, M.J.; Sereshti, H.,
Determination of Essential Oil Components of Artemisia haussknechtii Boiss. using Simultaneous Hydrodistillation-Static Headspace Liquid Phase Microextraction - Gas Chromatography Mass Spectrometry,
J. Chromatogr. A, 2007, 1160, 1-2, 81-89, https://doi.org/10.1016/j.chroma.2007.05.096
. [all data]
Sereshti and Samadi, 2007
Sereshti, H.; Samadi, S.,
Comparison of hydrodistillation-headspace liquid phase microextraction techniques with hydrodistillation in determination of essential oils in Artemisia Haussknechtii Boiss,
JSUT, 2007, 33, 2, 7-17. [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]
Tesso, König, et al., 2006
Tesso, H.; König, W.A.; Son, P.T.; Giang, P.M.,
Composition of the essential oil of flowers of Chloranthus spicatus (Thunb.) Makino,
Flavour Fragr. J., 2006, 21, 4, 592-597, https://doi.org/10.1002/ffj.1528
. [all data]
Rouseff, Jella, et al., 2001
Rouseff, R.; Jella, P.; Bazemore, R.; Yang, J.-J.,
Aroma active internal standards for gas chromatography-olfactometry of grapefruit juices,
Am. Chem. Soc. Symp. Ser., 2001, 782, 73-87. [all data]
Weyerstahl, Marschall, et al., 1997
Weyerstahl, P.; Marschall, H.; Seelmann, I.; Rustaiyan, A.,
Constituents of the essential oil of Achillea eriophora DC,
Flavour Fragr. J., 1997, 12, 2, 71-78, https://doi.org/10.1002/(SICI)1099-1026(199703)12:2<71::AID-FFJ620>3.0.CO;2-E
. [all data]
Ka, Choi, et al., 2005
Ka, M.-H.; Choi, E.H.; Chun, H.-S.; Lee, K.-G.,
Antioxidative Activity of Volatile Extracts Isolated from Angelica tenuissimae Roots, Peppermint Leaves, Pine Needles, and Sweet Flag Leaves,
J. Agric. Food Chem., 2005, 53, 10, 4124-4129, https://doi.org/10.1021/jf047932x
. [all data]
Lee, Umano, et al., 2005
Lee, S.-J.; Umano, K.; Shibamoto, T.; Lee, K.-G.,
Identification of volatile components in basil (Ocimum basilicum L.) and thyme leaves (Thymus vulgaris L.) and their antioxidant properties,
Food Chem., 2005, 91, 1, 131-137, https://doi.org/10.1016/j.foodchem.2004.05.056
. [all data]
Ito, Sugimoto, et al., 2002
Ito, Y.; Sugimoto, A.; Kakuda, T.; Kubota, K.,
Identification of potent odorants in Chinese jasmine green tea scented with flowers of Jasminum sambac,
J. Agric. Food Chem., 2002, 50, 17, 4878-4884, https://doi.org/10.1021/jf020282h
. [all data]
Notes
Go To: Top, Gas Chromatography, References
- Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.