Acetic acid, cinnamyl ester

Formula: C₁₁H₁₂O₂
Molecular weight: 176.2118
IUPAC Standard InChI: InChI=1S/C11H12O2/c1-10(12)13-9-5-8-11-6-3-2-4-7-11/h2-8H,9H2,1H3
IUPAC Standard InChIKey: WJSDHUCWMSHDCR-UHFFFAOYSA-N
CAS Registry Number: 103-54-8
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:
- 2-Propen-1-ol, 3-phenyl-, acetate, (E)-
- (Z)-Cinnamyl acetate
Other names: 2-Propen-1-ol, 3-phenyl-, acetate; Cinnamyl alcohol, acetate; γ-Phenylallyl acetate; Cinnamyl acetate; 3-Phenyl-2-propenyl acetate; 3-Phenyl-2-propen-1-yl acetate; 3-Phenyl-2-propen-1-ol acetate; 1-Acetoxy-3-phenyl-2-propene; 2-Propen-1-ol, 3-phenyl-, 1-acetate; 3-Phenylallyl acetate; NSC 46109
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Gas Chromatography

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

Kovats' RI, non-polar column, isothermal

Column type	Active phase	Temperature (C)	I	Reference	Comment
Capillary	SE-30	150.	1413.	Tudor and Moldovan, 1999
Capillary	SE-30	100.	1413.2	Tudor, 1997	40. m/0.35 mm/0.35 μm

Kovats' RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	Methyl Silicone	1440.	Jayaprakasha, Rao, et al., 2000	30. m/0.32 mm/0.25 μm, He, 60. C @ 2. min, 2. K/min, 225. C @ 5. min
Capillary	OV-101	1419.	Gaydou, Randriamiharisoa, et al., 1986	100. m/0.3 mm/0.15 μm, H2, 2. K/min; T_start: 90. C; T_end: 220. C

Kovats' RI, non-polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	HP-5	1445.	Sibanda, Chigwada, et al., 2004	30. m/0.25 mm/0.25 μm, He; Program: 40C(10min) => 3C/min => 200C => 2C/min => 220C

Kovats' RI, polar column, isothermal

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Column type	Active phase	Temperature (C)	I	Reference	Comment
Capillary	Carbowax 20M	180.	2176.	Tudor, Moldovan, et al., 1999	Phase thickness: 0.45 μm

Kovats' RI, polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	Carbowax 20M	2100.	Nishimura, Yamaguchi, et al., 1989	2. K/min; Column length: 50. m; Column diameter: 0.22 mm; T_start: 80. C; T_end: 200. C
Capillary	Carbowax 20M	2100.	Gaydou, Randriamiharisoa, et al., 1986	50. m/0.3 mm/0.15 μm, H2, 2. K/min; 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	BP-1	1408.	Gonny, Cavaleiro, et al., 2006	50. m/0.22 mm/0.25 μm, He, 2. K/min, 220. C @ 20. min; T_start: 60. C
Capillary	HP-1	1408.	Nath, Baruah, et al., 2006	25. m/0.2 mm/0.33 μm, He, 60. C @ 3. min, 5. K/min, 300. C @ 30. min
Capillary	HP-5	1455.	Shalit, Katzir, et al., 2001	He, 50. C @ 1. min, 4. K/min; Column length: 30. m; Column diameter: 0.25 mm; T_end: 200. C
Capillary	DB-1	1430.	Stashenko, Prada, et al., 1996	60. m/0.25 mm/0.25 μm, He, 50. C @ 5. min, 3.5 K/min; T_end: 250. C
Capillary	DB-5	1440.	Vahirua-Lechat, Menut, et al., 1996	He, 2. K/min, 200. C @ 30. min; Column length: 30. m; Column diameter: 0.32 mm; T_start: 80. C
Packed	SE-30	1422.	van den Dool and Kratz, 1963	Celite; T_start: 75. C; T_end: 228. C

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

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Column type	Active phase	I	Reference	Comment
Capillary	VF-5MS	1439.	Carasek and Pawliszyn, 2006	30. m/0.25 mm/0.25 μm, He; Program: 40C(2min) => 5C/min => 200C (2min) => 30C/min => 260C
Capillary	SE-52	1446.	Sacchetti, Guerrini, et al., 2006	30. m/0.32 mm/0.15 μm, He; Program: 45C => 1C/min => 100C => 5C/min => 250C(10min)

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

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Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax Etr	2153.	Aubert C. and Pitrat M., 2006	30. m/0.25 mm/0.25 μm, He, 40. C @ 3. min, 5. K/min, 250. C @ 15. min
Capillary	BP-20	2151.	Gonny, Cavaleiro, et al., 2006	50. m/0.22 mm/0.25 μm, He, 2. K/min, 220. C @ 20. min; T_start: 60. C
Capillary	DB-Wax	2150.	Brophy, Goldsack, et al., 2000	60. m/0.53 mm/1.0 μm, He, 3. K/min; T_start: 50. C; T_end: 220. C
Capillary	DB-Wax	2156.	Möllenbeck, König, et al., 1997	25. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 4. K/min; T_end: 240. C
Capillary	DB-Wax	2167.	Stashenko, Prada, et al., 1996	60. m/0.25 mm/0.25 μm, He, 50. C @ 5. min, 2.5 K/min; T_end: 180. C
Packed	Carbowax 20M	2125.	van den Dool and Kratz, 1963	Celite 545, 4.6 K/min; T_start: 75. C; T_end: 228. C

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	DB-5MS	1446.	Cheng, Liu, et al., 2008	30. m/0.25 mm/0.25 μm, He, 50. C @ 5. min, 2. K/min; T_end: 250. C
Capillary	FSOT-RSL-200	1444.	Schmidt, Jirovetz, et al., 2006	30. m/0.32 mm/0.25 μm, Hydrogen, 40. C @ 5. min, 6. K/min, 280. C @ 5. min
Capillary	DB-5	1440.	Chagonda and Chalchat, 2005	50. m/0.3 mm/0.25 μm, 2. K/min; T_start: 60. C; T_end: 240. C
Capillary	ZB-5	1454.	Dötterl, Wolfe, et al., 2005	60. m/0.25 mm/0.25 μm, He, 40. C @ 7. min, 6. K/min, 250. C @ 1. min
Capillary	HP-1	1406.	Fernandez, Lizzani-Cuvelier, et al., 2005	50. m/0.2 mm/0.25 μm, 60. C @ 60. min, 2. K/min; T_end: 250. C
Capillary	SPB-1	1411.	Wong, Lee, et al., 2005	50. m/0.2 mm/0.33 μm, He, 50. C @ 3. min, 4. K/min, 220. C @ 30. min
Capillary	CP Sil 8 CB	1453.	Wang, Guo, et al., 2004	30. m/0.32 mm/0.25 μm, 50. C @ 5. min, 5. K/min; T_end: 200. C
Capillary	DB-5	1441.	Caredda, Marongiu, et al., 2002	30. m/0.25 mm/0.25 μm, He, 3. K/min, 280. C @ 30. min; T_start: 60. C
Capillary	DB-1	1418.	Stashenko, Torres, et al., 1995	60. m/0.25 mm/0.25 μm, He, 50. C @ 5. min, 3.5 K/min; T_end: 250. C

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

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Column type	Active phase	I	Reference	Comment
Capillary	SE-30	1419.	Vinogradov, 2004	Program: not specified
Capillary	OV-101	1419.	Shibamoto, 1987	Program: not specified
Capillary	OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc.	1422.	Waggott and Davies, 1984	Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified

Normal alkane RI, polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	DB-FFAP	2142.	Osorio, Carriazo, et al., 2011	30. m/0.32 mm/0.25 μm, Helium, 50. C @ 4. min, 4. K/min, 250. C @ 5. min
Capillary	DB-Wax	2197.	Wei A. and Shibamoto T., 2007	60. m/0.25 mm/0.25 μm, He, 60. C @ 8. min, 3. K/min, 180. C @ 80. min
Capillary	Carbowax 20M	2098.	Fernandez, Lizzani-Cuvelier, et al., 2005	50. m/0.2 mm/0.25 μm, 60. C @ 60. min, 2. K/min; T_end: 250. C
Capillary	DB-Wax	2145.	Jiang and Kubota, 2004	He, 60. C @ 4. min, 2. K/min; Column length: 60. m; Column diameter: 0.25 mm; T_end: 220. C
Capillary	DB-Wax	2145.	Jiang and Kubota, 2004	He, 60. C @ 4. min, 2. K/min; Column length: 60. m; Column diameter: 0.25 mm; T_end: 220. C
Capillary	DB-Wax	2150.	Paniandy, Chane-Ming, et al., 2000	60. m/0.32 mm/0.25 μm, Helium, 50. C @ 2. min, 5. K/min; T_end: 230. C
Capillary	DB-Wax	2102.	Stashenko, Torres, et al., 1995	60. m/0.25 mm/0.25 μm, He, 50. C @ 5. min, 2.5 K/min; T_end: 180. C
Capillary	CP-Wax 52CB	2156.6	Chyau, Chen, et al., 1992	50. m/0.32 mm/0.22 μm, H2, 50. C @ 5. min, 2. K/min; T_end: 200. C

Normal alkane RI, polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	HP-Innowax FSC	2174.	Tabanca, Demirci, et al., 2006	60. m/0.25 mm/0.25 μm, N2; Program: 60C(10min) => 4C/min => 220C => (10min) => 1C/min => 240C
Capillary	Carbowax 20M	2103.	Vinogradov, 2004	Program: not specified
Capillary	Carbowax 20M	2103.	Shibamoto, 1987	Program: not specified

References

Go To: Top, Gas Chromatography, Notes

Tudor and Moldovan, 1999
Tudor, E.; Moldovan, D., Temperature Dependence of the Retention Index for Perfumery Compounds on a Se-30 Glass Capillary Column. II. The Hyperbolic Equation, J. Chromatogr., 1999, 848, 1-2, 215-227, https://doi.org/10.1016/S0021-9673(99)00412-4 . [all data]

Tudor, 1997
Tudor, E., Temperature dependence of the retention index for perfumery compounds on a SE-30 glass capillary column. I. Linear equations, J. Chromatogr. A, 1997, 779, 1-2, 287-297, https://doi.org/10.1016/S0021-9673(97)00453-6 . [all data]

Jayaprakasha, Rao, et al., 2000
Jayaprakasha, G.K.; Rao, L.J.M.; Sakariah, K.K., Chemical composition of the flower oil of Cinnamomum zeylanicum blume, J. Agric. Food Chem., 2000, 48, 9, 4294-4295, https://doi.org/10.1021/jf991395c . [all data]

Gaydou, Randriamiharisoa, et al., 1986
Gaydou, E.M.; Randriamiharisoa, R.; Bianchini, J.-P., Composition of the essential oil of ylang-ylang (Canaga odorata Hook Fil. et Thomson forma genuina) from Madagascar, J. Agric. Food Chem., 1986, 34, 3, 481-487, https://doi.org/10.1021/jf00069a028 . [all data]

Sibanda, Chigwada, et al., 2004
Sibanda, S.; Chigwada, G.; Poole, M.; Gwebu, E.T.; Noletto, J.A.; Schmidt, J.M.; Rea, A.I.; Setzer, W.N., Composition and bioactivity of the leaf essential oil of Heteropyxis dehniae from Zimbabwe, J. Ethnopharmacol., 2004, 92, 1, 107-111, https://doi.org/10.1016/j.jep.2004.02.010 . [all data]

Tudor, Moldovan, et al., 1999
Tudor, E.; Moldovan, D.; Zârna, N., Temperature dependence of the retention index for perfumery compounds on two carbowax-20M glass capillary columns with different film thickness. 2, Rev. Roum. Chim., 1999, 44, 7, 665-675. [all data]

Nishimura, Yamaguchi, et al., 1989
Nishimura, O.; Yamaguchi, K.; Mihara, S.; Shibamoto, T., Volatile Constituents of Guava Fruits (Psidium guajava L.) and Canned Puree, J. Agric. Food Chem., 1989, 37, 1, 139-142, https://doi.org/10.1021/jf00085a033 . [all data]

Gonny, Cavaleiro, et al., 2006
Gonny, M.; Cavaleiro, C.; Salgueiro, L.; Casanova, J., Analysis of Juniperus communis subsp. alpina needle, berry, wood and root oils by combination of GC, GC/MS and ¹³C-NMR, Flavour Fragr. J., 2006, 21, 1, 99-106, https://doi.org/10.1002/ffj.1527 . [all data]

Nath, Baruah, et al., 2006
Nath, S.C.; Baruah, A.; Kanjilal, P.B., Chemical composition of the leaf essential oil of Cinnamomum pauciflorum Nees, Flavour Fragr. J., 2006, 21, 3, 531-533, https://doi.org/10.1002/ffj.1688 . [all data]

Shalit, Katzir, et al., 2001
Shalit, M.; Katzir, N.; Tadmor, Y.; Larkov, O.; Burger, Y.; Shalekhet, F.; Lastochkin, E.; Ravid, U.; Amar, O.; Edelstein, M.; Karchi, Z.; Lewinsohn, E., Acetyl-CoA: alcohol acetyltransferase activity and aroma formation in ripening melon fruits, J. Agric. Food Chem., 2001, 49, 2, 794-799, https://doi.org/10.1021/jf001075p . [all data]

Stashenko, Prada, et al., 1996
Stashenko, E.E.; Prada, N.Q.; Martínez, J.R., HRGC/FID/NP and HRGC/MSD study of Colombian Ylang-Ylang (Cananga odorata) oils obtained by different extraction techniques, J. Hi. Res. Chromatogr., 1996, 19, 6, 353-358, https://doi.org/10.1002/jhrc.1240190609 . [all data]

Vahirua-Lechat, Menut, et al., 1996
Vahirua-Lechat, I.; Menut, C.; Roig, B.; Bessiere, J.M.; Lamaty, G., Isoprene related esters, significant components of Pandanus tectorius, Phytochemistry, 1996, 43, 6, 1277-1279, https://doi.org/10.1016/S0031-9422(96)00386-X . [all data]

van den Dool and Kratz, 1963
van den Dool, H.; Kratz, P. Dec., A generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography, J. Chromatogr., 1963, 11, 463-471, https://doi.org/10.1016/S0021-9673(01)80947-X . [all data]

Carasek and Pawliszyn, 2006
Carasek, E.; Pawliszyn, J., Screening of Tropical Fruit Volatile Compounds Using Solid-Phase Microextraction (SPME) Fibers and Internally Cooled SPME Fiber, J. Agric. Food Chem., 2006, 54, 23, 8688-8696, https://doi.org/10.1021/jf0613942 . [all data]

Sacchetti, Guerrini, et al., 2006
Sacchetti, G.; Guerrini, A.; Noriega, P.; Bianchi, A.; Bruni, R., Essential oil of wild Ocotea quixos (Lam.) Kosterm. (Lauraceae) leaves from Amazonian Ecuador, Flavour Fragr. J., 2006, 21, 4, 674-676, https://doi.org/10.1002/ffj.1648 . [all data]

Aubert C. and Pitrat M., 2006
Aubert C.; Pitrat M., Volatile compounds in the skin and pulp of Queen Anne's pocket melon, J. Agric. Food Chem., 2006, 54, 21, 8177-8182, https://doi.org/10.1021/jf061415s . [all data]

Brophy, Goldsack, et al., 2000
Brophy, J.J.; Goldsack, R.J.; Punruckvong, A.; Bean, A.R.; Forster, P.I.; Lepschi, B.J.; Doran, J.C.; Rozefelds, A.C., Leaf essential oils of the genus Leptospermum (Myrtaceae) in eastern Australia. Part 7. Leptospermum petersonii, L. liversidgei and allies, Flavour Fragr. J., 2000, 15, 5, 342-351, https://doi.org/10.1002/1099-1026(200009/10)15:5<342::AID-FFJ924>3.0.CO;2-V . [all data]

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]

Cheng, Liu, et al., 2008
Cheng, S.-S.; Liu, J.-Y.; Lin, C.-Y.; Hsui, Y.-R.; Lu, M.-C.; Wu, W.-J.; Chang, S.-T., Terminating red imported fire ants using Cinnamomum osmophloeum leaf essential oil, Bioresour. Technol., 2008, 99, 4, 889-893, https://doi.org/10.1016/j.biortech.2007.01.039 . [all data]

Schmidt, Jirovetz, et al., 2006
Schmidt, E.; Jirovetz, L.; Buchbauer, G.; Eller, G.A.; Stoilova, I.; Krastanov, A.; Stoyanova, A.; Geisseler, M., Composition and antioxidant activities of the essential oil of cinnamon (Cinnamomum zeylanicum Blume) leaves from Sri Lanka, Jeobp, 2006, 9, 2, 170-182. [all data]

Chagonda and Chalchat, 2005
Chagonda, L.S.; Chalchat, J.-C., The essential oil of wild and cultivated Hoslundia opposita Vahl. from Zimbabwe, Flavour Fragr. J., 2005, 20, 2, 193-195, https://doi.org/10.1002/ffj.1402 . [all data]

Dötterl, Wolfe, et al., 2005
Dötterl, S.; Wolfe, L.M.; Jürgens, A., Qualitative and quantitative analyses of flower scent in Silene latifolia, Phytochemistry, 2005, 66, 2, 203-213, https://doi.org/10.1016/j.phytochem.2004.12.002 . [all data]

Fernandez, Lizzani-Cuvelier, et al., 2005
Fernandez, X.; Lizzani-Cuvelier, L.; Loiseau, A.-M.; Perichet, C.; Delbecque, C.; Arnaudo, J.-F., Chemical composition of the essential oils from Turkish and Honduras Styrax, Flavour Fragr. J., 2005, 20, 1, 70-73, https://doi.org/10.1002/ffj.1370 . [all data]

Wong, Lee, et al., 2005
Wong, K.C.; Lee, B.C.; Lam, N.F.; Ibrahim, P., Essential oils of the rhizomes of Alpinia conchigera Griff. and Alpinia latilabris Ridl., Flavour Fragr. J., 2005, 20, 4, 431-433, https://doi.org/10.1002/ffj.1458 . [all data]

Wang, Guo, et al., 2004
Wang, H.; Guo, Y.; Zhang, Z.; An, D., Fast analysis of volatile compounds in natural essences by automatic Static-Headspace-GC-MS, J. Instrum. Anal. (Chinese), 2004, 23, 1, 9-13. [all data]

Caredda, Marongiu, et al., 2002
Caredda, A.; Marongiu, B.; Porcedda, S.; Soro, C., Supercritical carbon dioxide extraction and characterization of Laurus nobilis essential oil, J. Agric. Food Chem., 2002, 50, 6, 1492-1496, https://doi.org/10.1021/jf0108563 . [all data]

Stashenko, Torres, et al., 1995
Stashenko, E.E.; Torres, W.; Morales, J.R.M., A study of the compositional variation of the essential oil of ylang-ylang (Cananga odorata Hook Fil. et Thomson, forma genuina) during flower development, J. Hi. Res. Chromatogr., 1995, 18, 2, 101-104, https://doi.org/10.1002/jhrc.1240180206 . [all data]

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

Shibamoto, 1987
Shibamoto, T., Retention Indices in Essential Oil Analysis in Capillary Gas Chromatography in Essential Oil Analysis, Sandra, P.; Bicchi, C., ed(s)., Hutchig Verlag, Heidelberg, New York, 1987, 259-274. [all data]

Waggott and Davies, 1984
Waggott, A.; Davies, I.W., Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]

Osorio, Carriazo, et al., 2011
Osorio, C.; Carriazo, J.G.; Barbosa, H., Thermal and structural study of Guava (Psidium guajava L.) powders obtained by two dehydration methods, Quim. Nova, 2011, 34, 4, 636-640, https://doi.org/10.1590/S0100-40422011000400016 . [all data]

Wei A. and Shibamoto T., 2007
Wei A.; Shibamoto T., Antioxidant activities and volatile constituents of various essential oils, J. Agric. Food Chem., 2007, 55, 5, 1737-1742, https://doi.org/10.1021/jf062959x . [all data]

Jiang and Kubota, 2004
Jiang, L.; Kubota, K., Differences in the volatile components and their odor characteristics of green and ripe fruits and dried pericarp of Japanese pepper (Xanthoxylum piperitum DC.), J. Agric. Food Chem., 2004, 52, 13, 4197-4203, https://doi.org/10.1021/jf030663a . [all data]

Paniandy, Chane-Ming, et al., 2000
Paniandy, J.-C.; Chane-Ming, J.; Pierbattesti, J.-C., Chemical Composition of the Essential Oil and Headspace Solid-Phase Microextraction of the Guava Fruit (Psidium guajava L.), J. Essent. Oil Res., 2000, 12, 153-158. [all data]

Chyau, Chen, et al., 1992
Chyau, C.-C.; Chen, S.-Y.; Wu, C.-M., Differences of volatile and nonvolatile constituents between mature and ripe guave (Psidium guajava Linn) fruits, J. Agric. Food Chem., 1992, 40, 5, 846-849, https://doi.org/10.1021/jf00017a028 . [all data]

Tabanca, Demirci, et al., 2006
Tabanca, N.; Demirci, B.; Can Baser, K.H.; Aytac, Z.; Ekici, M.; Khan, S.I.; Jacob, M.R.; Wedge, D.E., Chemical Composition and Antifungal Activity of Salvia macrochlamys and Salvia recognita Essential Oils, J. Agric. Food Chem., 2006, 54, 18, 6593-6597, https://doi.org/10.1021/jf0608773 . [all data]

Notes

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Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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