Methyl cis-cinnamate

Formula: C₁₀H₁₀O₂
Molecular weight: 162.1852
IUPAC Standard InChI: InChI=1S/C10H10O2/c1-12-10(11)8-7-9-5-3-2-4-6-9/h2-8H,1H3/b8-7-
IUPAC Standard InChIKey: CCRCUPLGCSFEDV-FPLPWBNLSA-N
CAS Registry Number: 19713-73-6
Chemical structure:
This structure is also available as a 2d Mol file
Stereoisomers:
- 2-Propenoic acid, 3-phenyl-, methyl ester
- 2-Propenoic acid, 3-phenyl-, methyl ester, (E)-
Other names: 2-Propenoic acid, 3-phenyl-, methyl ester, (2Z)-; Cinnamic acid, methyl ester, (Z); Cinnamic acid, methyl ester, cis-; (Z)-3-Phenyl-2-propenoic acid methyl ester; (Z)-Methyl 3-phenylacrylate; Methyl (Z)-cinnamate; Methyl cis-3-phenylacrylate; cis-Methyl 3-phenyl-2-propenoate; (Z)-Methyl cinnamate; Methyl cinnamate, (Z)
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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-5	1321.	Bouzouita, Kachouri, et al., 2003	30. m/0.25 mm/1. μm, He, 40. C @ 1. min, 5. K/min; T_end: 250. C
Capillary	DB-5	1301.	Viña and Murillo, 2003	30. m/0.25 mm/0.25 μm, He, 50. C @ 5. min, 0.5 K/min, 250. C @ 10. min
Capillary	BP-1	1343.	Jain, Srivastava, et al., 2001	25. m/0.55 mm/0.25 μm, N2, 5. K/min, 220. C @ 15. min; T_start: 60. C

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

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Column type	Active phase	I	Reference	Comment
Capillary	HP-101	1281.	Politeo, Jukic, et al., 2007	25. m/0.2 mm/0.2 μm, He, 70. C @ 2. min, 3. K/min, 200. C @ 15. min
Capillary	DB-5	1300.	bin Jantan, Yalvema, et al., 2005	25. m/0.25 mm/0.25 μm, N2, 75. C @ 10. min, 3. K/min, 210. C @ 1. min
Capillary	BPX-5	1300.	bin Ahmad and bin Jantan, 2003	30. m/0.25 mm/0.25 μm, N2, 75. C @ 10. min, 3. K/min, 210. C @ 1. min

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

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Column type	Active phase	I	Reference	Comment
Capillary	HP-5MS	1308.2	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)

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	BPX-5	1292.	Fons, Rapior, et al., 2006	25. m/0.20 mm/0.13 μm, Helium, 50. C @ 2. min, 3. K/min; T_end: 230. C
Capillary	RSL-200	1348.	Jirovetz, Buchbauer, et al., 2003	30. m/0.32 mm/0.25 μm, H2, 40. C @ 5. min, 6. K/min, 280. C @ 5. min
Capillary	RSL-200	1320.	Jirovetz, Buchbauer, et al., 2003, 2	30. m/0.32 mm/0.25 μm, H2, 40. C @ 5. min, 6. K/min, 280. C @ 5. min
Capillary	BP-1	1321.	Mallavarapu, Kulkarni, et al., 1999	25. m/0.50 mm/0.25 μm, N2, 5. K/min, 220. C @ 10. min; T_start: 60. C
Capillary	DB-5MS	1301.	Zoghbi, Andrade, et al., 1999	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 240. C

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

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	SLB-5 MS	1303.	Costa, De Fina, et al., 2008	30. m/0.25 mm/0.25 μm, Helium; Program: 50 0C 3 0C/min -> 250 0C (1 min) 10 0C/min -> 300 0C (5 min)
Capillary	SLB-5 MS	1299.	Costa, De Fina, et al., 2008	30. m/0.25 mm/0.25 μm, Helium; Program: not specified
Capillary	CP Sil 8 CB	1306.	Meekijjaroenroj, Bessière, et al., 2007	30. m/0.25 mm/0.25 μm, He; Program: 50C(3min) => 3C/min => 100C => 2.7C/min => 140C => 2.4C/min => 180C => 6C/min => 250C
Capillary	DB-1	1300.	Cavalcanti, de Morais, et al., 2004	He; Column length: 30. m; Column diameter: 0.25 mm; Program: 35C => 4C/min => 180C => 10C/min => 250C
Capillary	DB-1	1306.	Silva, Santos, et al., 2003	30. m/0.25 mm/0.1 μm, He; Program: 35C => 4C/min => 180C => 10C/min => 250C

References

Go To: Top, Gas Chromatography, Notes

Bouzouita, Kachouri, et al., 2003
Bouzouita, N.; Kachouri, F.; Hamdi, M.; Chaabouni, M.M., Antimicrobial activity of essential oils from Tunisian aromatic plants, Flavour Fragr. J., 2003, 18, 5, 380-383, https://doi.org/10.1002/ffj.1200 . [all data]

Viña and Murillo, 2003
Viña, A.; Murillo, E., Essential oil composition from twelve varieties of basil (Ocimum spp) grown in Columbia, J. Braz. Chem. Soc., 2003, 14, 5, 744-749, https://doi.org/10.1590/S0103-50532003000500008 . [all data]

Jain, Srivastava, et al., 2001
Jain, N.; Srivastava, S.K.; Aggarwal, K.K.; Ramesh, S.; Kumar, S., Essential oil composition of Zanthoxylum alatum seeds from northern India, Flavour Fragr. J., 2001, 16, 6, 408-410, https://doi.org/10.1002/ffj.1024 . [all data]

Politeo, Jukic, et al., 2007
Politeo, O.; Jukic, M.; Milos, M., Chemical composition and antioxidant capacity of free volatile aglycones from basil (Ocimum basilicum L.) compared with its essential oil, Food Chem., 2007, 101, 1, 379-385, https://doi.org/10.1016/j.foodchem.2006.01.045 . [all data]

bin Jantan, Yalvema, et al., 2005
bin Jantan, I.; Yalvema, M.F.; Ayop, N.; Ahmad, A.S., Constituents of the essential oils of Cinnamomum sintoc Blume from a mountain forest of Peninsular Malaysia, Flavour Fragr. J., 2005, 20, 6, 601-604, https://doi.org/10.1002/ffj.1495 . [all data]

bin Ahmad and bin Jantan, 2003
bin Ahmad, F.; bin Jantan, I., The essential oils of Boesenbergia stenophylla R. M. Sm. as natural sources of methyl (E)-cinnamate, Flavour Fragr. J., 2003, 18, 6, 485-486, https://doi.org/10.1002/ffj.1227 . [all data]

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

Fons, Rapior, et al., 2006
Fons, F.; Rapior, S.; Fruchier, A., Volatile composition of Clitocybe amoenolens, Tricholoma caligatum and Hebeloma radicosum, Cryptogamie, Mycologie, 2006, 27, 1, 45-55. [all data]

Jirovetz, Buchbauer, et al., 2003
Jirovetz, L.; Buchbauer, G.; Shafi, M.P.; Kaniampady, M.M., Chemotaxonomical analysis of the essential oil aroma compounds of four different Ocimumspecies from southern India, Eur. Food Res. Technol., 2003, 217, 2, 120-124, https://doi.org/10.1007/s00217-003-0708-1 . [all data]

Jirovetz, Buchbauer, et al., 2003, 2
Jirovetz, L.; Buchbauer, G.; Shafi, M.P.; Leela, N.K., Analysis of the essential oils of the leaves, stems, rhizomes and roots of the medicinal plant Alpinia galanga from southern India, Acta Pharm. Hung., 2003, 53, 73-81. [all data]

Mallavarapu, Kulkarni, et al., 1999
Mallavarapu, G.R.; Kulkarni, R.N.; Baskaran, K.; Rao, L.; Ramesh, S., Influence of plant growth stage on the essential oil content and composition in Davana (Artemisia pallens Wall.), J. Agric. Food Chem., 1999, 47, 1, 254-258, https://doi.org/10.1021/jf980624c . [all data]

Zoghbi, Andrade, et al., 1999
Zoghbi, M.G.B.; Andrade, E.H.A.; Maia, J.G.S., Volatile constituents from leaves and flowers of Alpinia speciosa K. Schum. and A. purpurata (Viell.) Schum., Flavour Fragr. J., 1999, 14, 6, 411-414, https://doi.org/10.1002/(SICI)1099-1026(199911/12)14:6<411::AID-FFJ854>3.0.CO;2-U . [all data]

Costa, De Fina, et al., 2008
Costa, R.; De Fina, M.R.; Valentino, M.R.; Rustaiyan, A.; Dugo, P.; Dugo, G.; Mondello, L., An investigation on the volatile composition of some Artemisia species from Iran, Flavour Fragr. J., 2008, 24, 2, 75-82, https://doi.org/10.1002/ffj.1919 . [all data]

Meekijjaroenroj, Bessière, et al., 2007
Meekijjaroenroj, A.; Bessière, J.-M.; Anstett, M.-C., Chemistry of floral scents in four Licuala species (Arecaceae), Flavour Fragr. J., 2007, 22, 4, 300-310, https://doi.org/10.1002/ffj.1797 . [all data]

Cavalcanti, de Morais, et al., 2004
Cavalcanti, E.S.B.; de Morais, S.M.; Lima, M.A.A.; Santana, E.W.P., Larvicidal activity of essential oils from Brazilian plants against Aedes aegypti L., Mem. Inst. Oswaldo Cruz., 2004, 99, 5, 541-544, https://doi.org/10.1590/S0074-02762004000500015 . [all data]

Silva, Santos, et al., 2003
Silva, M.G.V.; Santos, R.N.D.; Matos, F.J.A.; Machado, M.I.L., Volatile constituents from leaf, inflorescence and root oils of Ocimum americanum L. grown in north-eastern Brazil, Flavour Fragr. J., 2003, 18, 4, 303-304, https://doi.org/10.1002/ffj.1217 . [all data]

Notes

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Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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