trans-Chrysanthenyl acetate

Formula: C₁₂H₁₈O₂
Molecular weight: 194.2701
IUPAC Standard InChI: InChI=1S/C12H18O2/c1-7-5-6-9-11(14-8(2)13)10(7)12(9,3)4/h5,9-11H,6H2,1-4H3
IUPAC Standard InChIKey: UASZOTVHPVEMQR-UHFFFAOYSA-N
CAS Registry Number: 54324-99-1
Chemical structure:
This structure is also available as a 2d Mol file
Species with the same structure:
- Bicyclo[3.1.1]hept-2-en-6-ol, 2,7,7-trimethyl-, acetate, [1S-(1α,5α,6β)]-
- (1R,5S,6R)-2,7,7-Trimethylbicyclo[3.1.1]hept-2-en-6-yl acetate
Stereoisomers:
- cis-Chrysanthenyl acetate
- Chrysanthenyl acetate
Other names: (E)-Chrysanthenyl acetate; trans -Crysanthenyl acetate
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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	DB-5	1235.	Adams and Nguyen, 2005	30. m/0.26 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 246. C
Capillary	DB-5	1235.	Adams, 2000	30. m/0.26 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 240. C
Capillary	DB-5	1235.	Adams, 2000, 2	30. m/0.26 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 246. C

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

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DB-5MS	1228.	Tuberoso, Kowalczyk, et al., 2005	30. m/0.25 mm/0.25 μm, He; Program: 60C(5min) => 2C/min => 140C= 5C/min => 250C(5min)
Capillary	OV-1	1219.	El-Shazly, Dorai, et al., 2002	30. m/0.25 mm/0.25 μm, He; Program: 44C(4min) => 3C/min => 74C => 6C/min => 134C => 12C/min => 312C
Capillary	DB-5	1235.	Adams, 1998	30. m/0.26 mm/0.25 μm; Program: not specified

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

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	HP-5	1237.	Flamini, Luigi Cioni, et al., 2005	30. m/0.25 mm/0.25 μm, N2, 60. C @ 10. min, 5. K/min; T_end: 220. C
Capillary	HP-1	1231.	Fernández-Ocaña, Gómez-Rodríguez, et al., 2004	25. m/0.32 mm/0.17 μm, He, 3. K/min; T_start: 50. C; T_end: 200. C
Capillary	HP-5	1238.	Flamini, Luigi Cioni, et al., 2003	30. m/0.25 mm/0.25 μm, N2, 60. C @ 10. min, 5. K/min; T_end: 220. C

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

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	BPX-5	1246.	Cardeal, da Silva, et al., 2006	30. m/0.25 mm/0.25 μm; Program: 35C(5min) => 3C/min => 210C => 40C/min => 240C (4min)
Capillary	HP-5MS	1238.	Akpulat, Tepe, et al., 2005	30. m/0.25 mm/0.25 μm, He; Program: 50C (3min) => 3C/min => 200C => 6C/min => 240C

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

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	HP-20M	1559.	Jerkovic, Mastelic, et al., 2003	50. m/0.2 mm/0.2 μm, He, 70. C @ 4. min, 4. K/min, 180. C @ 10. min
Capillary	HP-Innowax	1534.	Christensen, Jakobsen, et al., 1999	He, 32. C @ 1. min, 2. K/min, 220. C @ 40. min; Column length: 60. m; Column diameter: 0.25 mm

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	HP-5 MS	1239.	Miyazawa, Marumoto, et al., 2011	30. m/0.25 mm/0.25 μm, Helium, 4. K/min, 260. C @ 5. min; T_start: 40. C
Capillary	HP-5MS	1233.	Basta, Pavlovic, et al., 2007	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 280. C
Capillary	Col-Elite 5MS	1219.	Gudaityte and Venskutonis R.P., 2007	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 30. C; T_end: 246. C
Capillary	DB-5	1230.	Pontes, de Olivera, et al., 2007	30. m/0.25 mm/0.25 μm, Hydrogen, 4. K/min; T_start: 50. C; T_end: 250. C
Capillary	NB-30	1220.	Orav, Raal, et al., 2006	30. m/0.2 mm/0.25 μm, He, 2. K/min; T_start: 50. C; T_end: 250. C
Capillary	DB-1	1223.	Palá-Paúl, García-Jiménez, et al., 2004	50. m/0.22 mm/0.25 μm, He, 4. K/min; T_start: 70. C; T_end: 220. C
Capillary	DB-5	1238.	Rohloff, Mordal, et al., 2004	30. m/0.25 mm/0.25 μm, He, 2.5 K/min, 220. C @ 6. min; T_start: 35. C
Capillary	DB-5	1236.	Senatore, Rigano, et al., 2004	30. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 2. K/min, 250. C @ 20. min
Capillary	DB-1	1214.	Perez-Alonso, Velasco-Negueruela, et al., 2003	50. m/0.25 mm/0.25 μm, N2, 4. K/min; T_start: 95. 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	HP-5	1245.	Veres, Csupor-Loffler, et al., 2012	30. m/0.35 mm/0.25 μm, Nitrogen; Program: 60 0C 3 0C/min -> 210 0C 5 0C/min -> 250 0C (2 min)
Capillary	DB-5	1235.	Nezhadali and Parsa, 2010	30. m/0.20 mm/0.32 μm, Helium; Program: 60 0C (1 min) 3 0C/min -> 140 0C 50 0C/min -> 250 0C (3 min)
Capillary	CBP-5	1236.	Cheriti, Saad, et al., 2007	30. m/0.25 mm/0.25 μm, He; Program: 60C(2min) => 3C/min => 240C => 10C/min => 300C
Capillary	DB-5	1235.	Pontes, de Olivera, et al., 2007	30. m/0.25 mm/0.25 μm, Hydrogen; Program: not specified
Capillary	BPX-5	1203.	Salamci, Kordali, et al., 2007	30. m/0.25 mm/0.25 μm, He; Program: 50C => 3C/min => 150C(10min) => 10C/min => 250C
Capillary	CP Sil 8 CB	1238.	Butkienë, Nivinskienë, et al., 2005	50. m/0.32 mm/0.25 μm, He; Program: 50C(5min) => 2C/min => 90C => 15C/min => 240C(4min)
Capillary	BPX-5	1238.	Judzentiene and Mockute, 2005	30. m/0.25 mm/0.25 μm; Program: 60C(0.2min) => 3K/min => 186C => 10C/min => 240C (5min)
Capillary	CP Sil 8 CB	1235.	Judpentienë and Mockutë, 2004	50. m/0.32 mm/0.25 μm, He; Program: 60C(2min) => 5C/min => 160C(1min) => 10C/min => 250C (5min)
Capillary	SE-30	1221.	Vinogradov, 2004	Program: not specified
Capillary	Methyl Silicone	1221.	Zenkevich, 1999	Program: not specified
Capillary	OV-101	1219.	De Pooter, Vermeesch, et al., 1989	Program: not specified
Capillary	OV-101	1219.	De Pooter, Vermeesch, et al., 1989	Program: not specified

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	Innowax FSC	1538.	Polatoglu, Demirci, et al., 2010	60. m/0.25 mm/0.25 μm, Helium; Program: 60 0C (10 min) 4 0C/min -> 220 0C (10 min) 1 0C/min -> 240 0C
Capillary	Carbowax 20M	1568.	Vinogradov, 2004	Program: not specified
Capillary	Innowax FSC	1582.	Baser, Demirei, et al., 2002	60. m/0.25 mm/0.25 μm, He; Program: 60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C
Capillary	HP-Innowax	1582.	Baser, Demirci, et al., 2001	60. m/0.25 mm/0.25 μm, He; Program: 60 0C (10 min) 10 K/min -> 220 0C (10 min) 1K/min -> 240 0C

References

Go To: Top, Gas Chromatography, Notes

Adams and Nguyen, 2005
Adams, R.P.; Nguyen, S., Infra-specific variation in Juniperus deppeana and F. Sperryi in the Davis Mountains of Texas: variation in leaf essential oils and random amplified polymorphic DNAS (RAPDS), Phytologia, 2005, 87, 2, 96-108. [all data]

Adams, 2000
Adams, R.P., Systematics of Juniperus section Juniperus based on leaf essential oils and random amplified polymorphic DNAs (RAPDs), Biochem. Syst. Ecol., 2000, 28, 6, 515-528, https://doi.org/10.1016/S0305-1978(99)00089-7 . [all data]

Adams, 2000, 2
Adams, R.P., The serrate leaf margined Juniperus (Section Sabina) of the western hemisphere: systematics and evolution based on leaf essential oils and Random Amplified Polymorphic DNAs (RAPDs), Biochem. Syst. Ecol., 2000, 28, 10, 975-989, https://doi.org/10.1016/S0305-1978(00)00022-3 . [all data]

Tuberoso, Kowalczyk, et al., 2005
Tuberoso, C.I.G.; Kowalczyk, A.; Coroneo, V.; Russo, M.T.; Dessì, S.; Cabras, P., Chemical Composition and Antioxidant, Antimicrobial, and Antifungal Activities of the Essential Oil of Achillea ligustica All., J. Agric. Food Chem., 2005, 53, 26, 10148-10153, https://doi.org/10.1021/jf0518913 . [all data]

El-Shazly, Dorai, et al., 2002
El-Shazly, A.; Dorai, G.; Wink, M., Composition and antimicrobial activity of essential oil and hexane-ether extract of Tanacetum santolinoides (DC.) Feinbr. and Fertig, Z. Naturforsch., 2002, 57c, 620-623. [all data]

Adams, 1998
Adams, R.P., The essential oils and chemotaxonomy of Juniperus sect. Juniperus, Biochem. Syst. Ecol., 1998, 26, 6, 637-645, https://doi.org/10.1016/S0305-1978(98)00020-9 . [all data]

Flamini, Luigi Cioni, et al., 2005
Flamini, G.; Luigi Cioni, P.; Morelli, I., Composition of the essential oils and in vivo emission of volatiles of four Lamium species from Italy: L. purpureum, L. hybridum, L. bifidum and L. amplexicaule, Food Chem., 2005, 91, 1, 63-68, https://doi.org/10.1016/j.foodchem.2004.05.047 . [all data]

Fernández-Ocaña, Gómez-Rodríguez, et al., 2004
Fernández-Ocaña, A.M.; Gómez-Rodríguez, M.V.; Velasco-Negueruela, A.; Camacho-Simarro, A.M.; Fernández-López, C.; Altarejos, J., In vivo antifungal activity of the essential oil of Bupleurum gibraltarium against plasmopara halstedii in sunflower, J. Agric. Food Chem., 2004, 52, 21, 6414-6417, https://doi.org/10.1021/jf040219n . [all data]

Flamini, Luigi Cioni, et al., 2003
Flamini, G.; Luigi Cioni, P.; Morelli, I., Differences in the fragrances of pollen, leaves, and floral parts of garland (Chrysanthemum coronarium) and composition of the essential oils from flowerheads and leaves, J. Agric. Food Chem., 2003, 51, 8, 2267-2271, https://doi.org/10.1021/jf021050l . [all data]

Cardeal, da Silva, et al., 2006
Cardeal, Z.L.; da Silva, M.D.R.G.; Marriott, P.J., Comprehensive two-dimensional gas chromatography/mass spectrometric analysis of pepper volatiles, Rapid Commun. Mass Spectrom., 2006, 20, 19, 2823-2836, https://doi.org/10.1002/rcm.2665 . [all data]

Akpulat, Tepe, et al., 2005
Akpulat, H.A.; Tepe, B.; Sokmen, A.; Daferera, D.; Polissiou, M., Composition of the essential oils of Tanacetum argyrophyllum (C. Koch) Tvzel. var. argyrophyllum and Tanacetum parthenium (L.) Schultz Bip. (Asteraceae) from Turkey, Biochem. Syst. Ecol., 2005, 33, 5, 511-516, https://doi.org/10.1016/j.bse.2004.10.006 . [all data]

Jerkovic, Mastelic, et al., 2003
Jerkovic, I.; Mastelic, J.; Milos, M.; Juteau, F.; Masotti, V.; Viano, J., Chemical variability of Artemisia vulgaris L. essential oils originated from the Mediterranean area of France and Croatia, Flavour Fragr. J., 2003, 18, 5, 436-440, https://doi.org/10.1002/ffj.1246 . [all data]

Christensen, Jakobsen, et al., 1999
Christensen, L.P.; Jakobsen, H.B.; Paulsen, E.; Hodal, L.; Andersen, K.E., Airborne compositae dermatitis: monoterpenes and no parthenolide are released from flowering Tanacetum parthenium (feverfew) plants, Arch. Dermatol. Res., 1999, 291, 7-8, 425-431, https://doi.org/10.1007/s004030050433 . [all data]

Miyazawa, Marumoto, et al., 2011
Miyazawa, M.; Marumoto, S.; Kobayashi, T.; Yoshida, S.; Utsumi, Y., Determination of characteristic components in essential oils from Wisteria braphybotrys using gas chromatography - olfactometry incremental dilution technique, Rec. Nat. Prod., 2011, 5, 3, 221-227. [all data]

Basta, Pavlovic, et al., 2007
Basta, A.; Pavlovic, M.; Couladis, M.; Tzakou, O., Essential oil composition of the flowerheads of Chrysanthemum coronarium L. from Greece, Flavour Fragr. J., 2007, 22, 3, 197-200, https://doi.org/10.1002/ffj.1781 . [all data]

Gudaityte and Venskutonis R.P., 2007
Gudaityte, O.; Venskutonis R.P., Chemotypes of Achillea millefolium transferred from 14 different locations in Lithuania to the controlled environment, Biochem. Syst. Ecol., 2007, 35, 9, 582-592, https://doi.org/10.1016/j.bse.2007.03.016 . [all data]

Pontes, de Olivera, et al., 2007
Pontes, W.J.T.; de Olivera, J.C.G.; da Camara, C.A.G.; Lopes, A.C.H.R.; Gondim Jr.; de Olivera, J.V.; Barros, R.; Schwartz, M.O.E., Chemical composition and acaridical activity of the leaf and fruit essential oils of Protium heptaphyllum (Aubl.) Marchand (Burseraceae), Acta Amazonica, 2007, 37, 1, 103-110, https://doi.org/10.1590/S0044-59672007000100012 . [all data]

Orav, Raal, et al., 2006
Orav, A.; Raal, A.; Arak, E.; Müürisepp, M.; Kailas, T., Composition of the essential oil of Artemisia absinthium L. of different geographical origin, Proc. Est. Acad. Sci. Chem., 2006, 55, 3, 155-165. [all data]

Palá-Paúl, García-Jiménez, et al., 2004
Palá-Paúl, J.; García-Jiménez, R.; Pérez-Alonso, M.J.; Velasco-Negueruela, A.; Sanz, J., Essential oil composition of the leaves and stems of Meum athamanticum Jacq., from Spain, J. Chromatogr. A, 2004, 1036, 2, 245-247, https://doi.org/10.1016/j.chroma.2004.02.064 . [all data]

Rohloff, Mordal, et al., 2004
Rohloff, J.; Mordal, R.; Dragland, S., Chemotypical variation of tansy (Tanacetum vulgare L.) from 40 different locations in Norway, J. Agric. Food Chem., 2004, 52, 6, 1742-1748, https://doi.org/10.1021/jf0352430 . [all data]

Senatore, Rigano, et al., 2004
Senatore, F.; Rigano, D.; de Fusco, R.; Bruno, M., Composition of the essential oil from flowerheads of Chrysanthemum coronarium L. (Asteraceae) growing wild in Southern Italy, Flavour Fragr. J., 2004, 19, 2, 149-152, https://doi.org/10.1002/ffj.1285 . [all data]

Perez-Alonso, Velasco-Negueruela, et al., 2003
Perez-Alonso, M.J.; Velasco-Negueruela, A.; Palá-Paúl, J.; Sanz, J., Variations in the essential oil composition of Artemisia pedemontana gathered in Spain: chemotype camphor-1,8-cineole and chemotype davanone, Biochem. Syst. Ecol., 2003, 31, 1, 77-84, https://doi.org/10.1016/S0305-1978(02)00082-0 . [all data]

Veres, Csupor-Loffler, et al., 2012
Veres, K.; Csupor-Loffler, B.; Lazar, A.; Holmann, J., Antifungal activity and composition of essential oils of Conyza canadensis herbs and roots, The Sci. World. J., 2012, 2012, 1-5, https://doi.org/10.1100/2012/489646 . [all data]

Nezhadali and Parsa, 2010
Nezhadali, A.; Parsa, M., Study of the volatile compounds in Artemisia Sagebrush from Iran using HS/SPME/GC/MS, Int. J. Environ. Sci. Development, 2010, 1, 3, 287-289, https://doi.org/10.7763/IJESD.2010.V1.56 . [all data]

Cheriti, Saad, et al., 2007
Cheriti, A.; Saad, A.; Belboukhari, N.; Ghezali, S., The essential oil composition of Bubonium graveolens (Forssk.) Maire from the algerian Sahara, Flavour Fragr. J., 2007, 22, 4, 286-288, https://doi.org/10.1002/ffj.1794 . [all data]

Salamci, Kordali, et al., 2007
Salamci, E.; Kordali, S.; Kotan, R.; Cakir, A.; Kaya, Y., Chemical compositions, antimicrobial and herbicidal effects of essential oils isolated from Turkish Tanacetum aucheranum and Tanacetum chiliophyllum var. chiliophyllum, Biochem. Syst. Ecol., 2007, 35, 9, 569-581, https://doi.org/10.1016/j.bse.2007.03.012 . [all data]

Butkienë, Nivinskienë, et al., 2005
Butkienë, R.; Nivinskienë, O.; Mockutë, D., α-Pinene chemotype of leaf (needle) essential oils of Juniperus communis L. growing wild in Vilnius district, Chemija, 2005, 16, 1, 53-60. [all data]

Judzentiene and Mockute, 2005
Judzentiene, A.; Mockute, D., The inflorescence and leaf essential oils of Tanacetum vulgare L. var. vulgare growing wild in Lithuania, Biochem. Syst. Ecol., 2005, 33, 5, 487-498, https://doi.org/10.1016/j.bse.2004.11.003 . [all data]

Judpentienë and Mockutë, 2004
Judpentienë, A.; Mockutë, D., Chemical composition of essential oils of Artemisia absinthium L. (wormwood) growing wild in Vilnius, Chemija, 2004, 15, 4, 64-68. [all data]

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

Zenkevich, 1999
Zenkevich, I.G., Analytical Parameters of Components of essential Oils for their Gas Chromatographic and Chromato-Mass-Spectral Identification. Acetates of Terpene Alcohols, Rastitelnye Resursy (Plant Resources), 1999, 35, 1, 30-37. [all data]

De Pooter, Vermeesch, et al., 1989
De Pooter, H.L.; Vermeesch, J.; Schamp, N.M., The Essential Oils of Tanacetum vulgare L. and Tanacetum parthenium (L.) Schultz-Bip, J. Essent. Oil Res., 1989, 1, 1, 9-13, https://doi.org/10.1080/10412905.1989.9699438 . [all data]

Polatoglu, Demirci, et al., 2010
Polatoglu, K.; Demirci, F.; Demirci, B.; Goren, N.; Baser, K.H.C., Antimicrobial activity and essential oil composition of a new T. argyrophyllum (C. Koch) Tvzel var. argyrophyllium chemotype, J. Oleo Sci., 2010, 59, 6, 307-313, https://doi.org/10.5650/jos.59.307 . [all data]

Baser, Demirei, et al., 2002
Baser, K.H.C.; Demirei, B.; Özek, T.; Akalin, E.; Özhatay, N., Micro-distilled volatile compounds from Ferulago species growing in Western Turkey, Pharm. Biol., 2002, 40, 6, 466-471, https://doi.org/10.1076/phbi.40.6.466.8439 . [all data]

Baser, Demirci, et al., 2001
Baser, K.H.C.; Demirci, B.; Tabanca, N.; Özek, T.; Gören, N., Composition of the essential oils of Tanacetum armenum (DC.) Schultz Bip., T. balsamita L., T. chiliophyllum (Fisch. Mey.) Schultz Bip. var. chiliophyllum and T. haradjani (Rech. fil.) Grierson and the enantiomeric distribution of camphor and carvone, Flavour Fragr. J., 2001, 16, 3, 195-200, https://doi.org/10.1002/ffj.977 . [all data]

Notes

Go To: Top, Gas Chromatography, References

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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