trans-Pinocarvyl acetate

Formula: C₁₂H₁₈O₂
Molecular weight: 194.2701
IUPAC Standard InChI: InChI=1S/C12H18O2/c1-7-10-5-9(12(10,3)4)6-11(7)14-8(2)13/h9-11H,1,5-6H2,2-4H3
IUPAC Standard InChIKey: UDBAGFUFASPUFS-UHFFFAOYSA-N
CAS Registry Number: 1686-15-3
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.
Species with the same structure:
- Pinocarvyl acetate
Stereoisomers:
Other names: (1R,3S,5R)-6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptan-3-yl acetate; Bicyclo[3.1.1]heptan-3-ol, 6,6-dimethyl-2-methylene-, acetate, (1R,3S,5R)-; trans-Pinocarveyl acetate; trans-Pinocarveol, acetate; (E)-Pinocarvyl acetate
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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
Packed	Apiezon L	150.	1258.	ter Heide, 1968	N2, Embacel; Column length: 2.5 m

Kovats' RI, non-polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	DB-5	1298.	Adams, Morris, et al., 2005	30. m/0.26 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 246. C
Capillary	HP-5MS	1300.	Asuming, Beauchamp, et al., 2005	30. m/0.25 mm/0.25 μm, He, 50. C @ 10. min, 3. K/min, 250. C @ 5. min
Capillary	SE-54	1297.	Adams, 2000	30. m/0.26 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 246. C
Capillary	DB-5	1297.	Adams, 2000, 2	30. m/0.26 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 240. C
Capillary	SE-54	1297.	Adams, 2000, 3	30. m/0.26 mm/0.25 μm, 3. K/min; T_start: 60. C; T_end: 246. C
Capillary	DB-5	1297.	Adams, 2000, 4	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	HP-5	1295.	de Marchese, de Heluani, et al., 2007	He; Program: 60C(5min) => 3C/min => 100C => 1C/min => 160C => 10C/min => 240C(10min)
Capillary	DB-5	1297.	Adams, 1998	30. m/0.26 mm/0.25 μm; Program: not specified

Kovats' RI, polar column, isothermal

View large format table.

Column type	Active phase	Temperature (C)	I	Reference	Comment
Packed	Carbowax 20M	150.	1682.	ter Heide, 1968	N2, Embacel; Column length: 2.5 m

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

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Column type	Active phase	I	Reference	Comment
Capillary	RTX-1	1281.	Paolini J., Costa J., et al., 2007	60. m/0.22 mm/0.25 μm, He, 2. K/min, 230. C @ 35. min; T_start: 60. C
Capillary	HP-5	1298.	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-5	1298.	Ceccarini, Macchia, et al., 2004	30. m/0.25 mm/0.25 μm, 60. C @ 10. min, 5. K/min; T_end: 220. C
Capillary	DB-5	1298.	Flamini, Cioni, et al., 2004	30. m/0.25 mm/0.25 μm, N2, 3. K/min; T_start: 60. C; T_end: 240. C
Capillary	HP-5	1297.	Macchioni, Cioni, et al., 2003	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 240. C
Capillary	RTX-5	1328.	Mondello, Zappia, et al., 2002	30. m/0.25 mm/0.25 μm, He, 45. C @ 6. min, 3. K/min, 300. C @ 10. min
Capillary	HP-5MS	1297.	Skaltsa, Mavrommati, et al., 2001	30. m/0.25 mm/0.25 μm, He, 60. C @ 5. min, 4. K/min; T_end: 280. 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	HP-5MS	1302.3	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)

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

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Column type	Active phase	I	Reference	Comment
Capillary	RTX-Wax	1641.	Paolini J., Costa J., et al., 2007	60. m/0.22 mm/0.25 μm, He, 2. K/min, 230. C @ 35. min; T_start: 60. C
Capillary	RTX-Wax	1662.	Mondello, Zappia, et al., 2002	30. m/0.25 mm/0.25 μm, He, 45. C @ 6. min, 3. K/min, 250. C @ 10. min

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	ZB-5	1299.	Vazquez, Demmel, et al., 2011	30. m/0.25 mm/0.25 μm, Nitrogen, 40. C @ 5. min, 5. K/min, 200. C @ 5. min
Capillary	HP-5 MS	1299.	Ogunwande, Flamini, et al., 2010	30. m/0.25 mm/0.25 μm, Helium, 60. C @ 10. min, 5. K/min; T_end: 220. C
Capillary	SPB-5	1305.	Gauvin-Bialecki and Marodon, 2009	60. m/0.35 mm/0.25 μm, Nitrogen, 4. K/min, 230. C @ 40. min; T_start: 60. C
Capillary	HP-5	1295.	Yassa and Akhani, 2008	30. m/0.25 mm/0.32 μm, Helium, 60. C @ 30. min, 5. K/min; T_end: 250. C
Capillary	HP-5 MS	1297.	Adams, Beauchamp, et al., 2007	30. m/0.25 mm/0.25 μm, Helium, 50. C @ 10. min, 3. K/min, 230. C @ 10. min
Capillary	SPB-5	1293.	Raal, Orav, et al., 2007	30. m/0.25 mm/0.25 μm, He, 2. K/min; T_start: 50. C; T_end: 250. C
Capillary	HP-5	1295.	Yassa and Akhani, 2007	30. m/0.25 mm/0.32 μm, He, 60. C @ 30. min, 5. K/min; T_end: 250. C
Capillary	HP-5MS	1296.3	Zizovic, Stamenic, et al., 2007	30. m/0.25 mm/0.25 μm, He, 4. K/min; T_start: 40. C; T_end: 260. C
Capillary	DB-5	1266.	Damjanovic, Skala, et al., 2006	30. m/0.32 mm/0.25 μm, 3. K/min, 230. C @ 15. min; T_start: 60. C
Capillary	DB-1	1273.	Cégiéla-Carlioz, Bessière, et al., 2005	25. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 3. K/min; T_end: 250. C
Capillary	DB-1	1273.	Khalighi-Sigaroodi, Hadijiakhoondi, et al., 2005	30. m/0.25 mm/0.25 μm, He, 50. C @ 1. min, 2.5 K/min, 265. C @ 30. min
Capillary	CP Sil 5 CB	1296.	Agnaniet, Menut, et al., 2004	30. m/0.25 mm/0.25 μm, N2, 5. K/min; T_start: 50. C; T_end: 200. C
Capillary	SE-54	1297.	Kilic, Hafizoglu, et al., 2004	30. m/0.25 mm/0.25 μm, He, 60. C @ 5. min, 2. K/min; T_end: 260. C
Capillary	DB-5	1297.	da Silva, Luz, et al., 2003	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 240. C
Capillary	DB-5	1297.	Tellez, Canel, 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	Polydimethyl siloxane with 5 % Ph groups	1324.	da Silva, de Souza, et al., 2012	30. m/0.25 mm/0.25 μm, Helium; Program: 50 0C 4 0C/min -> 200 0C (5 min) 20 0C/min -> 280 0C
Capillary	ZB-5	1298.	Vazquez, Demmel, et al., 2011	30. m/0.25 mm/0.25 μm, Nitrogen; Program: not specified
Capillary	DB-1	1278.	Mendes, Trindade, et al., 2009	30. m/0.25 mm/0.25 μm, Hydrogen; Program: 45 0C 3 0C/min -> 175 0C 15 0C/min -> 300 0C (10 min)
Capillary	HP-5 MS	1297.	Zellner, Amorim, et al., 2009	30. m/0.25 mm/0.25 μm, Helium; Program: 32 0C (1 min) 50 0C/min -> 115 0C 1.5 0C/min -> 145 0C 12 0C/min -> 240 0C (10 min)
Capillary	HP-5MS	1297.	Senatore, Apostolides Arnold, et al., 2006	30. m/0.25 mm/0.25 μm, He; Program: 40C(5min) => 2C/min => 250C (15min) => 10C/min => 270C
Capillary	CP Sil 8 CB	1298.	Butkienë, Nivinskienë, et al., 2004	50. m/0.32 mm/0.25 μm, He; Program: 50C(5min) => 2C/min => 90C => 15C/min => 240C(4min)
Capillary	SE-30	1307.	Vinogradov, 2004	Program: not specified
Capillary	Methyl Silicone	1307.	Zenkevich, 1999	Program: not specified
Capillary	CP Sil 5 CB	1291.	Weyerstahl, Marschall, et al., 1998	He; Column length: 25. m; Phase thickness: 0.39 μm; Program: not specified

Normal alkane RI, polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	Supelcowax	1657.	Gauvin-Bialecki and Marodon, 2009	60. m/0.35 mm/0.25 μm, Nitrogen, 4. K/min, 230. C @ 40. min; T_start: 60. C

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	HP-Innowax	1661.	Senatore, Apostolides Arnold, et al., 2006	50. m/0.2 mm/0.2 μm, He; Program: 40C(5min) => 2C/min => 250C (15min) => 10C/min => 270C
Capillary	HP-Innowax FSC	1661.	Suleimenov Y.M., Atazhanova G.A., et al., 2006	60. m/0.25 mm/0.25 μm, He; Program: 60(10min) => 4C/min => 220C(10min) => 1C/min => 240C
Capillary	Innowax FSC	1661.	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	Innowax	1661.	Baser, Kürkcüoglu, et al., 1998	60. m/0.25 mm/0.25 μm; Program: 60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C
Capillary	DB-Wax	1671.	Weyerstahl, Marschall, et al., 1998	N2; Column length: 60. m; Phase thickness: 0.25 μm; Program: not specified

References

Go To: Top, Gas Chromatography, Notes

ter Heide, 1968
ter Heide, R., Studies on terpenes. II. Characterization of monoterpene esters by gas and thin-layer chromatography, Z. Anal. Chem., 1968, 236, 215-227. [all data]

Adams, Morris, et al., 2005
Adams, R.P.; Morris, J.A.; Pandey, R.N.; Schwarzbach, A.E., Cryptic speciation between Juniperus deltoides and Juniperus oxycedrus (Cupressaceae) in the Mediterranean, Biochem. Syst. Ecol., 2005, 33, 8, 771-787, https://doi.org/10.1016/j.bse.2005.01.001 . [all data]

Asuming, Beauchamp, et al., 2005
Asuming, W.A.; Beauchamp, P.S.; Descalzo, J.T.; Dev, B.C.; Dev, V.; Frost, S.; Ma, C.W., Essential oil composition of four Lomatium Raf. species and their chemotaxonomy, Biochem. Syst. Ecol., 2005, 33, 1, 17-26, https://doi.org/10.1016/j.bse.2004.06.005 . [all data]

Adams, 2000
Adams, R.P., Systematics of smooth leaf margin Juniperus of the western hemisphere based on leaf essential oils and RAPD DNA fingerprinting, Biochem. Syst. Ecol., 2000, 28, 2, 149-162, https://doi.org/10.1016/S0305-1978(99)00047-2 . [all data]

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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]

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Adams, R.P., Systematics of the one seeded Juniperus of the eastern hemisphere based on leaf essential oils and random amplified polymorphic DNAs (RAPDs), Biochem. Syst. Ecol., 2000, 28, 6, 529-543, https://doi.org/10.1016/S0305-1978(99)00096-4 . [all data]

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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]

de Marchese, de Heluani, et al., 2007
de Marchese, M.J.A.; de Heluani, C.S.; Catalán, C.A.N.; Griffin, C.A.; Vaughn, J.B., Jr.; Herz, W., Incisol, an alcohol with a novel sesquiterpene skeleton from Xenophyllum incisum, Biochem. Syst. Ecol., 2007, 35, 3, 169-175, https://doi.org/10.1016/j.bse.2006.10.006 . [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]

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Paolini J.; Costa J.; Bernardini A.F., Analysis of the essential oil from the roots of Eupatorium cannabinum subsp corsicum (L.) by GC, GC-MS and C-13-NMR, Phytochem. Anal., 2007, 18, 3, 235-244, https://doi.org/10.1002/pca.977 . [all data]

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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]

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Ceccarini, L.; Macchia, M.; Flamini, G.; Cioni, P.L.; Caponi, C.; Morelli, I., Essential oil composition of Helianthus annuus L. leaves and heads of two cultivated hybride Carlos and Florom 350, Ind. Crops Prod., 2004, 19, 1, 13-17, https://doi.org/10.1016/S0926-6690(03)00076-1 . [all data]

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Flamini, G.; Cioni, P.L.; Morelli, I.; Maccioni, S.; Baldini, R., Phytochemical typologies in some populations of Myrtus communis L. on Caprione Promontory (East Liguria, Italy), Food Chem., 2004, 85, 4, 599-604, https://doi.org/10.1016/j.foodchem.2003.08.005 . [all data]

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Macchioni, F.; Cioni, P.L.; Flamini, G.; Morelli, I.; Maccioni, S.; Ansaldi, M., Chemical composition of essential oils from needles, branches and cones of Pinus pinea, P. halepensis, P. pinaster and P. nigra from central Italy, Flavour Fragr. J., 2003, 18, 2, 139-143, https://doi.org/10.1002/ffj.1178 . [all data]

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Mondello, L.; Zappia, G.; Cotroneo, A.; Bonaccorsi, I.; Chowdhury, J.U.; Yusuf, M.; Dugo, G., Studies on the essential oil-bearing plants of Bangladesh. Part VIII. Composition of some Ocimum oils O. basilicum L. var. purpurascens; O. sanctum L. green; O. sanctum L. purple; O. americanum L., citral type; O. americanum L., camphor type, Flavour Fragr. J., 2002, 17, 5, 335-340, https://doi.org/10.1002/ffj.1108 . [all data]

Skaltsa, Mavrommati, et al., 2001
Skaltsa, H.D.; Mavrommati, A.; Constantinidis, T., A chemotaxonomic investigation of volatile constituents in Stachys subsect. Swainsonianeae (Labiatae), Phytochemistry, 2001, 57, 2, 235-244, https://doi.org/10.1016/S0031-9422(01)00003-6 . [all data]

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Vazquez, Demmel, et al., 2011
Vazquez, A.M.; Demmel, G.I.; Criado, S.G.; Aimar, M.L.; Cantero, J.; Rossi, L.I.; Velasco, M.I., Phytochemistry of TAgetes minuta L. (Asteraceae) from Cordoba, Argentina: comparative study between essential oil and HS-SPME analyses, Boletin Latinoamericano y del Caribe Plantas Medicinales y Aromaticas, 2011, 10, 4, 351-362. [all data]

Ogunwande, Flamini, et al., 2010
Ogunwande, I.A.; Flamini, G.; Cioni, P.L.; Omikorede, O.; Azeez, R.A.; Ayodele, A.A.; Kamil, Y.O., Aromatic plants growing in Nigeria: essential oil constituents of Cassia alata (Linn.) Roxb. and Helianthus annuus L., Rec. Nat. Prod., 2010, 4, 4, 211-217. [all data]

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Gauvin-Bialecki, A.; Marodon, C., Essential oil of Ayapana triplinervis from Reunion island: a good natural source of thymohydroquinone dimethyl ether, Biochem. Systematics Ecol., 2009, 36, 11, 853-858, https://doi.org/10.1016/j.bse.2008.09.006 . [all data]

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Cégiéla-Carlioz, Bessière, et al., 2005
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Khalighi-Sigaroodi, Hadijiakhoondi, et al., 2005
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Kilic, A.; Hafizoglu, H.; Kollmannsberger, H.; Nitz, S., Volatile constituents and key odorants in leaves, buds, flowers, and fruits of Laurus nobilis L., J. Agric. Food Chem., 2004, 52, 6, 1601-1606, https://doi.org/10.1021/jf0306237 . [all data]

da Silva, Luz, et al., 2003
da Silva, J.D.; Luz, A.I.R.; da Silva, M.H.L.; Andrade, E.H.A.; Soghbi, M.G.B.; Maia, J.G.S., Essential oils of the leaves and stems of four Psidium spp., Flavour Fragr. J., 2003, 18, 3, 240-243, https://doi.org/10.1002/ffj.1219 . [all data]

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Tellez, M.R.; Canel, C.; Rimando, A.M.; Duke, S.O., Differential accumulation of isoprenoids in glanded and glandless Artemisia annua L, Phytochemistry, 1999, 52, 6, 1035-1040, https://doi.org/10.1016/S0031-9422(99)00308-8 . [all data]

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da Silva, A.C.; de Souza, P.E.; Machado, J. daC.; da Silva, B.M.; Pinto, J.E.B.P., Effectiveness of essential oils in the treatment of Colletotrichum truncatum-infected soybean seeds, Tropical Plant Patology, 2012, 37, 5, 305-313, https://doi.org/10.1590/S1982-56762012000500001 . [all data]

Mendes, Trindade, et al., 2009
Mendes, M.D.; Trindade, H.; Figueiredo, A.C.; Barroso, J.G.; Fontinha, S.S.; Pedro, L.G., Volatile and molecular characterization of two Portuguese endemic species: Angelica lignescens and Melanoselinium decipiens, Biochen. Systematics Ecol., 2009, 37, 2, 98-105, https://doi.org/10.1016/j.bse.2008.12.006 . [all data]

Zellner, Amorim, et al., 2009
Zellner, B.D.; Amorim, A.C.L.; de Miranda A.L.P.; Alves, R.J.V.; Barbosa, J.P.; da Costa, G.L.; Rezende, C.M., Screening of the odor-activity and bioactiovity of the essential oils of leaves and flowers of Hyptis Passerina Mart. from the Brazilian Cerrado, J. Braz. Chem. Soc., 2009, 20, 2, 322-332, https://doi.org/10.1590/S0103-50532009000200018 . [all data]

Senatore, Apostolides Arnold, et al., 2006
Senatore, F.; Apostolides Arnold, N.; Piozzi, F.; Formisano, C., Chemical composition of the essential oil of Salvia microstegia Boiss. et Balansa growing wild in Lebanon, J. Chromatogr. A, 2006, 1108, 2, 276-278, https://doi.org/10.1016/j.chroma.2006.01.066 . [all data]

Butkienë, Nivinskienë, et al., 2004
Butkienë, R.; Nivinskienë, O.; Mockutë, D., Chemical composition of unripe and ripe berry essential oils of Juniperus communis L. growing wild in Vilnius district, Chemija, 2004, 15, 4, 57-63. [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]

Weyerstahl, Marschall, et al., 1998
Weyerstahl, P.; Marschall, H.; Weirauch, M.; Thefeld, K.; Surburg, H., Constituents of commercial Labdanum oil, Flavour Fragr. J., 1998, 13, 5, 295-318, https://doi.org/10.1002/(SICI)1099-1026(1998090)13:5<295::AID-FFJ751>3.0.CO;2-I . [all data]

Suleimenov Y.M., Atazhanova G.A., et al., 2006
Suleimenov Y.M.; Atazhanova G.A.; Ozek T.; Demirci B.; Kulyyasov A.T.; Adekenov S.M.; Baser K.H.C., Essential oil composition of three species of Achillea from Kazakhstan, Chem. Nat. Compd. (Engl. Transl.), 2006, 37, 5, 447-450, https://doi.org/10.1023/A:1014471326724 . [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, Kürkcüoglu, et al., 1998
Baser, K.H.C.; Kürkcüoglu, M.; Aytac, Z., Composition of the essential oil of Salvia euphratica Montbret ex Bentham var. euphratica from Turkey, Flavour Fragr. J., 1998, 13, 1, 63-64, https://doi.org/10.1002/(SICI)1099-1026(199801/02)13:1<63::AID-FFJ694>3.0.CO;2-Z . [all data]

Notes

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Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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