1H-Naphtho[2,1-b]pyran, 3-ethenyldodecahydro-3,4a,7,7,10a-pentamethyl-, [3R-(3α,4aβ,6aα,10aβ,10bα)]-

Formula: C₂₀H₃₄O
Molecular weight: 290.4834
IUPAC Standard InChI: InChI=1S/C20H34O/c1-7-18(4)13-9-16-19(5)12-8-11-17(2,3)15(19)10-14-20(16,6)21-18/h7,15-16H,1,8-14H2,2-6H3/t15?,16?,18-,19+,20-/m1/s1
IUPAC Standard InChIKey: IGGWKHQYMAJOHK-DBYSVDLZSA-N
CAS Registry Number: 596-84-9
Chemical structure:
This structure is also available as a 2d Mol file
Stereoisomers:
Other names: Labd-14-ene, 8,13-epoxy-, (13R)-; Manoyl oxide; 8α,13-Epoxylabd-14-ene; Manool oxide; (3R,4aR,6aS,10aS,10bR)-3,4a,7,7,10a-Pentamethyl-3-vinyldodecahydro-1H-benzo[f]chromene; 3,4a,7,7,10a-Pentamethyl-3-vinyldodecahydro-1H-benzo[f]chromene
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Information on this page:
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

Kovats' RI, non-polar column, temperature ramp

Column type	Active phase	I	Reference	Comment
Capillary	HP-1	1998.	Meccia G., Rosquete C., et al., 2006	60. m/0.25 mm/0.25 μm, He, 60. C @ 5. min, 4. K/min, 200. C @ 25. min
Capillary	DB-5	1998.	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	DB-5	2017.	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	HP-5MS	1989.	Salido, Altarejos, et al., 2002	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 50. C; T_end: 250. C
Capillary	SE-54	1989.	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	1989.	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	1989.	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	1989.	Adams, 2000, 4	30. m/0.26 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 246. C
Capillary	DB-5	1989.	Adams, 1999	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-5	1989.	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	1994.	Benzo, Gilardoni, et al., 2007	30. m/0.25 mm/0.25 μm, He, 40. C @ 1. min, 5. K/min, 250. C @ 10. min
Capillary	BP-1	1992.	Duquesnoy, Castola, et al., 2007	50. m/0.22 mm/0.25 μm, He, 2. K/min, 220. C @ 20. min; T_start: 60. C
Capillary	DB-5	1989.	Martins, Santos, et al., 2007	30. m/0.22 mm/0.25 μm, 60. C @ 2. min, 3. K/min; T_end: 240. C
Capillary	RTX-1	1996.	Paolini, Muselli, et al., 2007	60. m/0.22 mm/0.25 μm, He, 2. K/min, 230. C @ 35. min; T_start: 60. C
Capillary	SPB-1	1998.	Radulovic, Lazarevic, et al., 2007	30. m/0.25 mm/0.25 μm, He, 50. C @ 3. min, 5. K/min, 250. C @ 15. min
Capillary	HP-5MS	2007.	Radulovic, Lazarevic, et al., 2007	30. m/0.25 mm/0.25 μm, He, 60. C @ 5. min, 4. K/min; T_end: 280. C
Capillary	BP-1	1985.	Boti, Bighelli, 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-5	1979.	Dob, Dahmane, et al., 2006	30. m/0.32 mm/0.25 μm, N2, 60. C @ 3. min, 3. K/min, 240. C @ 5. min
Capillary	BP-1	1990.	Duquesnoy, Dinh, 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	1978.	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-5MS	1990.	Saroglou, Dorizas, et al., 2006	30. m/0.25 mm/0.25 μm, He, 60. C @ 5. min, 4. K/min; T_end: 280. C
Capillary	HP-5	1992.	Celik, Gokturk, et al., 2005	30. m/0.25 mm/0.25 μm, N2, 60. C @ 10. min, 5. K/min; T_end: 220. C
Capillary	DB-1	1989.	Dob, Berramdane, et al., 2005	30. m/0.32 mm/0.25 μm, N2, 50. C @ 3. min, 2. K/min, 260. C @ 5. min
Capillary	HP-5	1996.	Javidnia, Miri, et al., 2005	He, 3. K/min; Column length: 30. m; Column diameter: 0.25 mm; T_start: 60. C; T_end: 260. C
Capillary	HP-5	2002.	Javidnia, Miri, et al., 2005, 2	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 260. C
Capillary	HP-5MS	1994.	Grujic-Jovanovic, Skaltsa, et al., 2004	30. m/0.25 mm/0.25 μm, He, 60. C @ 5. min, 4. K/min; T_end: 280. C
Capillary	HP-5MS	2001.	Karioti, Hadjipavlou-Litina, et al., 2004	30. m/0.25 mm/0.25 μm, He, 60. C @ 5. min, 4. K/min; T_end: 280. C
Capillary	DB-5MS	1995.	Yu, Kim, et al., 2004	30. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 4. K/min, 200. C @ 20. min
Capillary	SPB-1	1964.	Cavaleiro, Salgueiro, et al., 2003	30. m/0.2 mm/0.2 μm, He, 3. K/min, 220. C @ 15. min; T_start: 70. C
Capillary	HP-5	1990.	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
Capillary	HP-5	1991.	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	HP-5MS	2015.	Couladis, Chinou, et al., 2002	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 300. C
Capillary	HP-5MS	1989.	Demetzos, Angelopoulou, et al., 2002	30. m/0.25 mm/0.25 μm, 50. C @ 5. min, 3. K/min; T_end: 280. C
Capillary	DB-5	1989.	Javidnia, Miri, et al., 2002	He, 4. K/min; Column length: 25. m; Column diameter: 0.25 mm; T_start: 70. C; T_end: 275. C
Capillary	HP-5	1986.	Pitarokili, Couladis, et al., 2002	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 280. C
Capillary	HP-5	2010.	Aligiannis, Kalpoutzakis, et al., 2001	30. m/0.25 mm/0.25 μm, He, 60. C @ 5. min, 3. K/min; T_end: 280. C
Capillary	BP-1	1993.	Rezzi, Bighelli, et al., 2001	50. m/0.22 mm/0.25 μm, He, 2. K/min, 220. C @ 20. min; T_start: 60. C
Capillary	BP-1	1996.	Rezzi, Cavaleiro, et al., 2001	50. m/0.22 mm/0.25 μm, 2. K/min, 220. C @ 20. min; T_start: 60. C
Capillary	HP-5MS	1991.	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
Capillary	HP-5	1991.	Lazari, Skaltsa, et al., 2000	30. m/0.25 mm/0.25 μm, He, 50. C @ 5. min, 4. K/min; T_end: 280. C
Capillary	HP-101	1956.	Milos and Radonic, 2000	25. m/0.2 mm/0.2 μm, He, 70. C @ 2. min, 3. K/min, 200. C @ 10. min
Capillary	BP-1	1996.	Mariotti, Costa, et al., 1997	50. m/0.22 mm/0.25 μm, He, 2. K/min, 230. C @ 35. min; T_start: 60. C
Capillary	DB-5	1989.	Tzakou, Roussis, et al., 1997	He, 50. C @ 3. min, 5. K/min; Column length: 60. m; Column diameter: 0.24 mm; 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	1999.9	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	HP-5	1990.	Isidorov, Krajewska, et al., 2000	30. m/0.25 mm/0.25 μm; Program: 40C(1min) => 3C/min => 120C => 5C/min => 280C

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

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	BP-20	2346.	Duquesnoy, Castola, et al., 2007	50. m/0.22 mm/0.25 μm, He, 2. K/min, 220. C @ 20. min; T_start: 60. C
Capillary	RTX-Wax	2335.	Paolini, Muselli, et al., 2007	60. m/0.22 mm/0.25 μm, He, 2. K/min, 230. C @ 35. min; T_start: 60. C
Capillary	BP-20	2347.	Boti, Bighelli, et al., 2006	50. m/0.22 mm/0.25 μm, He, 2. K/min, 220. C @ 20. min; T_start: 60. C
Capillary	BP-20	2348.	Duquesnoy, Dinh, et al., 2006	50. m/0.22 mm/0.25 μm, He, 2. K/min, 220. C @ 20. min; T_start: 60. C
Capillary	BP-20	2341.	Rezzi, Bighelli, et al., 2001	50. m/0.22 mm/0.25 μm, He, 2. K/min, 220. C @ 20. min; T_start: 60. C
Capillary	BP-20	2345.	Mariotti, Costa, et al., 1997	50. m/0.22 mm/0.25 μm, He, 2. K/min, 230. C @ 35. min; T_start: 60. C

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	HP-5 MS	1994.	Pripdeevech and Saansoomchai, 2013	30. m/0.25 mm/0.25 μm, Helium, 3. K/min; T_start: 60. C; T_end: 230. C
Capillary	HP-5	2011.	Monsef-Esfahani, Miri, et al., 2010	30. m/0.25 mm/0.25 μm, Helium, 50. C @ 5. min, 3. K/min; T_end: 240. C
Capillary	SPB-1	1967.	Neves, Rosa, et al., 2010	30. m/0.20 mm/0.20 μm, Helium, 3. K/min, 220. C @ 15. min; T_start: 70. C
Capillary	HP-5 MS	2003.	Radulovic, Blagojevic, et al., 2010	30. m/0.25 mm/0.25 μm, Helium, 5. K/min, 290. C @ 10. min; T_start: 70. C
Capillary	ZB-5	2012.	Gardini, Beletti, et al., 2009	30. m/0.25 mm/0.25 μm, Helium, 3. K/min, 240. C @ 1. min; T_start: 50. C
Capillary	SLB-5 MS	2002.	Lo Presti, Sciarrone, et al., 2008	30. m/0.25 mm/0.25 μm, Helium, 50. C @ 2. min, 3. K/min, 250. C @ 10. min
Capillary	HP-5 MS	1989.	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	CP Sil 5 CB	1990.	Baran, von Reuss, et al., 2007	30. m/0.32 mm/0.25 μm, N2, 4. K/min; T_start: 60. C; T_end: 300. C
Capillary	SE-30	1989.	Loizzo, Tundis, et al., 2007	30. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 5. K/min, 250. C @ 10. min
Capillary	HP-5	1993.	Loizzo, Tundis, et al., 2007	30. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 5. K/min, 250. C @ 10. min
Capillary	AT-5	1988.	Borges, Rojas, et al., 2006	60. m/0.25 mm/0.25 μm, He, 4. K/min, 200. C @ 20. min; T_start: 60. C
Capillary	SPB-1	1964.	Cavaleiro, Pinto, et al., 2006	30. m/0.20 mm/0.20 μm, Helium, 3. K/min, 220. C @ 15. min; T_start: 70. C
Capillary	HP-5	1989.	Lago, Soares, et al., 2006	30. m/0.25 mm/0.25 μm, He, 100. C @ 2. min, 5. K/min, 240. C @ 5. min
Capillary	DB-5	1998.	Morteza-Semnani, Akbarzadeh, et al., 2006	30. m/0.25 mm/0.25 μm, He, 4. K/min; T_start: 60. C; T_end: 220. C
Capillary	HP-5MS	2000.	Petrovic, Ristic, et al., 2006	30. m/0.25 mm/0.25 μm, He, 4. K/min; T_start: 40. C; T_end: 260. C
Capillary	HP-5MS	1978.	Pitarokili, Tzakou, et al., 2006	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 280. C
Capillary	HP-5	2000.	Wang, Kong, et al., 2006	25. m/0.32 mm/0.52 μm, H2, 50. C @ 5. min, 2.5 K/min; T_end: 280. C
Capillary	HP-5MS	1980.	Basta, Tzakou, et al., 2005	30. m/0.25 mm/0.25 μm, He, 3. K/min; T_start: 60. C; T_end: 280. C
Capillary	DB-5	1999.	Morteza-Semnani and Saeedi, 2005	30. m/0.25 mm/0.25 μm, He, 60. C @ 4. min, 4. K/min; T_end: 220. C
Capillary	HP-5MS	1989.	Petrakis, Roussis, et al., 2005	3. K/min; Column length: 30. m; Column diameter: 0.2 mm; T_start: 60. C; T_end: 280. C
Capillary	DB-1	1965.	Velasco-Negueruela, Pérez-Alonso, et al., 2005	50. m/0.25 mm/0.25 μm, 3. K/min; T_start: 60. C; T_end: 240. C
Capillary	RTX-5Sil	2004.	Dudai, Larkov, et al., 2003	30. m/0.25 mm/0.25 μm, He, 4. K/min, 200. C @ 10. min; T_start: 70. C
Capillary	DB-5	1971.	Marongiu, Porcedda, et al., 2003	30. m/0.25 mm/0.25 μm, He, 3. K/min, 280. C @ 30. min; T_start: 60. C
Capillary	DB-5	2009.	Krauze-Baranowska, Mardarowicz, et al., 2002	30. m/0.25 mm/0.25 μm, He, 35. C @ 2. min, 3. K/min, 280. C @ 15. min
Capillary	HP-5	1957.	Lago, Reis, et al., 2002	30. m/0.32 mm/0.25 μm, 100. C @ 2. min, 5. K/min, 240. C @ 5. min
Capillary	DB-1	1965.	Velasco-Negueruela, Pérez-Alonso, et al., 2002	50. m/0.25 mm/0.25 μm, N2, 3. K/min; T_start: 60. C; T_end: 240. C
Capillary	DB-5	1995.	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
Capillary	HP-1	1985.	Ayedoun, Adeoti, et al., 1996	23. m/0.32 mm/0.17 μm, He, 60. C @ 3. min, 5. K/min, 250. C @ 30. min

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

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	TR-5 MS	2003.	Kurashov, Krylova, et al., 2013	15. m/0.25 mm/0.25 μm, Helium; Program: 35 0C (3 min) 2 0C/min -> 60 0C (3 min) 2 0C/min -> 80 0C (3 min) 4 0C/min -> 120 0C (3 min) 5 0C/min -> 150 0C (3 mion) 15 0C/min -> 240 0C (10 min)
Capillary	HP-5	1997.	Maggi, Bilek, et al., 2009	25. m/0.32 mm/0.17 μm, Helium; Program: 60 0C (5 min) 4 0C/min -> 220 0C 11 0C/min -> 280 0C
Capillary	CP Sil 8 CB	1988.	Kupcinskiene, Stikliene, et al., 2008	50. m/0.32 mm/0.25 μm, Helium; Program: not specified
Capillary	SLB-5 MS	1998.	Lo Presti, Sciarrone, et al., 2008	30. m/0.25 mm/0.25 μm, Helium; Program: not specified
Capillary	HP-5	1996.	Vichi, Aumatell, et al., 2008	30. m/0.25 mm/0.25 μm, Helium; Program: 130 0C 5 0C/min -> 240 0C 15 0C/min -> 320 0C (10 min)
Capillary	CP Sil 8 CB	1998.	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	CP Sil 8 CB	1989.	Mockute, Nivinskiene, et al., 2003	50. m/0.32 mm/0.25 μm, He; Program: 60C(1min) => 5C/min => 160C => 10C/min => 250C(5min)
Capillary	HP-5	1977.	Usubillaga, Aparicio, et al., 2001	30. m/0.25 mm/0.25 μm, He; Program: 50 0C 3 K/min -> 200 0C 8 K/min -> 280 0C
Capillary	DB-1	1977.	da Silva, Pedro, et al., 2000	30. m/0.25 mm/0.25 μm, H2; Program: 40 0C 3 K/min -> 175 0C 15 K/min -> 240 0C (10 min)
Capillary	DB-5	1982.	Pichette, Garneau, et al., 1998	Column length: 30. m; Column diameter: 0.25 mm; Program: 60 0C (2 min) 2 0C/min -> 140 0C 1 0C/min -> 190 0C 2 0C/min -> 210 0C (28 min)
Capillary	CP Sil 5 CB	1983.	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	TC-FFAP	2340.	Kurose, Okamura, et al., 2007	He, 3. K/min, 220. C @ 30. min; Column diameter: 0.25 mm; Phase thickness: 0.25 μm; T_start: 60. C
Capillary	Supelcowax 10	2339.	Cavaleiro, Pinto, et al., 2006	30. m/0.20 mm/0.20 μm, Helium, 3. K/min, 220. C @ 15. min; T_start: 70. C
Capillary	HP-20M	2358.	Mastelic and Jerkovic, 2003	50. m/0.2 mm/0.2 μm, He, 70. C @ 4. min, 4. K/min, 180. C @ 10. min
Capillary	HP Innowax FSP	2376.	Kaya, Baser, et al., 1999	60. m/0.25 mm/0.25 μm, He, 60. C @ 10. min, 220. C @ 10. min
Capillary	Innowax	2376.	Kaya, Baser, et al., 1999, 2	60. m/0.25 mm/0.25 μm, He, 60. C @ 10. min; T_end: 220. C
Capillary	HP-Innowax	2376.	Kaya, Baser, et al., 1999, 3	60. m/0.25 mm/0.25 μm, He, 60. C @ 10. min; T_end: 220. C

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type	Active phase	I	Reference	Comment
Capillary	HP-Innowax FSC	2376.	Sezik E., Kocakulak E., et al., 2005	60. m/0.25 mm/0.25 μm, He; Program: 60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C
Capillary	HP-Innowax FSC	2376.	Demirci, Paper, et al., 2004	60. m/0.25 mm/0.25 μm, He; Program: 60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C
Capillary	Innowax FSC	2376.	Tunalier, Kirimer, et al., 2002	60. m/0.25 mm/0.25 μm; Program: 60C(10min) => 4C/min => 220C(10min) => 1C/min => 240C

References

Go To: Top, Gas Chromatography, Notes

Meccia G., Rosquete C., et al., 2006
Meccia G.; Rosquete C.; Rojas L.B.; San Felician A., New labdane derivative from the essential oil of Acalypha plicata Mull.Arg., Flavour Fragr. J., 2006, 21, 3, 559-561, https://doi.org/10.1002/ffj.1679 . [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]

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]

Salido, Altarejos, et al., 2002
Salido, S.; Altarejos, J.; Nogueras, M.; Sánchez, A.; Pannecouque, C.; Witvrouw, M.; De Clercq, E., Chemical studies of essential oils of Juniperus oxycedrus ssp. badia, J. Ethnopharmacol., 2002, 81, 1, 129-134, https://doi.org/10.1016/S0378-8741(02)00045-4 . [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]

Adams, 2000, 2
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, 3
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]

Adams, 2000, 4
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]

Adams, 1999
Adams, R.P., Systematics of multi-seeded eastern hemisphere Juniperus based on leaf essential oils and RAPD DNA fingerprinting, Biochem. Syst. Ecol., 1999, 27, 7, 709-725, https://doi.org/10.1016/S0305-1978(99)00016-2 . [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]

Benzo, Gilardoni, et al., 2007
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Mastelic, J.; Jerkovic, I., Application of co-distillation with superheated pentane vapour to the isolation of unstable essential oils, Flavour Fragr. J., 2003, 18, 6, 521-526, https://doi.org/10.1002/ffj.1261 . [all data]

Kaya, Baser, et al., 1999
Kaya, A.; Baser, K.H.C.; Koca, F., Essential oils of Acinos troodi (Post) Leblebici subsp. vardaranus Leblebici and subsp. grandiflorus Hartvig Strid, Flavour Fragr. J., 1999, 14, 1, 50-54, https://doi.org/10.1002/(SICI)1099-1026(199901/02)14:1<50::AID-FFJ783>3.0.CO;2-7 . [all data]

Kaya, Baser, et al., 1999, 2
Kaya, A.; Baser, K.H.C.; Demirci, B.; Koca, F., The essential oil of Acinos alpinus (L.) Moench growing in Turkey, Flavour Fragr. J., 1999, 14, 1, 55-59, https://doi.org/10.1002/(SICI)1099-1026(199901/02)14:1<55::AID-FFJ784>3.0.CO;2-Q . [all data]

Kaya, Baser, et al., 1999, 3
Kaya, A.; Baser, K.H.C.; Tümen, G.; Koca, F., The essential oil of Acinos suaveolens (Sm.) G. Don fil. Acinos arvensis (Lam.) Dandy and Acinos rotundifolius Pers. growing wild in Turkey, Flavour Fragr. J., 1999, 14, 1, 60-64, https://doi.org/10.1002/(SICI)1099-1026(199901/02)14:1<60::AID-FFJ785>3.0.CO;2-0 . [all data]

Sezik E., Kocakulak E., et al., 2005
Sezik E.; Kocakulak E.; Baser K.H.C.; Ozek T., Composition of the essential oils of Juniperus oxycedrus subsp macrocarpa from Turkey, Chem. Nat. Compd. (Engl. Transl.), 2005, 41, 3, 352-354, https://doi.org/10.1007/s10600-005-0149-0 . [all data]

Demirci, Paper, et al., 2004
Demirci, F.; Paper, D.H.; Franz, G.; Hüsnü Can Baser, K., Investigation of the origanum onites L. essential oil using the Chorioallantoic Membrane (CAM) assay, J. Agric. Food Chem., 2004, 52, 2, 251-254, https://doi.org/10.1021/jf034850k . [all data]

Tunalier, Kirimer, et al., 2002
Tunalier, Z.; Kirimer, N.; Baser, K.H.C., The composition of essential oils from various parts of Juniperus foetidissima, Chem. Nat. Compd. (Engl. Transl.), 2002, 38, 1, 43-47, https://doi.org/10.1023/A:1015725630556 . [all data]

Notes

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Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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