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:
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
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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

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

View large format table.

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; T_start: 50. C; T_end: 230. C
Capillary	DB-Wax	2338.	Shimoda, Shigematsu, et al., 1995, 2	60. m/0.25 mm/0.25 μm, He, 2. K/min; T_start: 50. C; T_end: 230. C

Normal alkane RI, non-polar column, temperature ramp

View large format table.

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; T_start: 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; T_start: 50. C; T_end: 230. C
Capillary	DB-5	1638.	Rouseff, Jella, et al., 2001	30. m/0.32 mm/0.5 μm, 6. K/min; T_start: 35. C; T_end: 275. C

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

View large format table.

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

View large format table.

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; T_end: 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; T_start: 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; T_end: 180. C

References

Go To: Top, Gas Chromatography, Notes

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

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Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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