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
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Options:
Normal alkane RI, non-polar column, temperature ramp
Go To: Top, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | HP-5 MS | HP-5 | SPB-1 | HP-5 MS | ZB-5 |
| Column length (m) | 30. | 30. | 30. | 30. | 30. |
| Carrier gas | Helium | Helium | Helium | Helium | Helium |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.25 | 0.20 | 0.25 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.20 | 0.25 | 0.25 |
| Tstart (C) | 60. | 50. | 70. | 70. | 50. |
| Tend (C) | 230. | 240. | 220. | 290. | 240. |
| Heat rate (K/min) | 3. | 3. | 3. | 5. | 3. |
| Initial hold (min) | 5. | ||||
| Final hold (min) | 15. | 10. | 1. | ||
| I | 1994. | 2011. | 1967. | 2003. | 2012. |
| Reference | Pripdeevech and Saansoomchai, 2013 | Monsef-Esfahani, Miri, et al., 2010 | Neves, Rosa, et al., 2010 | Radulovic, Blagojevic, et al., 2010 | Gardini, Beletti, et al., 2009 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | SLB-5 MS | HP-5 MS | CP Sil 5 CB | SE-30 | HP-5 |
| Column length (m) | 30. | 30. | 30. | 30. | 30. |
| Carrier gas | Helium | Helium | N2 | He | He |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.25 | 0.32 | 0.25 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
| Tstart (C) | 50. | 50. | 60. | 40. | 40. |
| Tend (C) | 250. | 230. | 300. | 250. | 250. |
| Heat rate (K/min) | 3. | 3. | 4. | 5. | 5. |
| Initial hold (min) | 2. | 10. | 5. | 5. | |
| Final hold (min) | 10. | 10. | 10. | 10. | |
| I | 2002. | 1989. | 1990. | 1989. | 1993. |
| Reference | Lo Presti, Sciarrone, et al., 2008 | Adams, Beauchamp, et al., 2007 | Baran, von Reuss, et al., 2007 | Loizzo, Tundis, et al., 2007 | Loizzo, Tundis, et al., 2007 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | AT-5 | SPB-1 | HP-5 | DB-5 | HP-5MS |
| Column length (m) | 60. | 30. | 30. | 30. | 30. |
| Carrier gas | He | Helium | He | He | He |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.20 | 0.25 | 0.25 | 0.25 |
| Phase thickness (μm) | 0.25 | 0.20 | 0.25 | 0.25 | 0.25 |
| Tstart (C) | 60. | 70. | 100. | 60. | 40. |
| Tend (C) | 200. | 220. | 240. | 220. | 260. |
| Heat rate (K/min) | 4. | 3. | 5. | 4. | 4. |
| Initial hold (min) | 2. | ||||
| Final hold (min) | 20. | 15. | 5. | ||
| I | 1988. | 1964. | 1989. | 1998. | 2000. |
| Reference | Borges, Rojas, et al., 2006 | Cavaleiro, Pinto, et al., 2006 | Lago, Soares, et al., 2006 | Morteza-Semnani, Akbarzadeh, et al., 2006 | Petrovic, Ristic, et al., 2006 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | HP-5MS | HP-5 | HP-5MS | DB-5 | HP-5MS |
| Column length (m) | 30. | 25. | 30. | 30. | 30. |
| Carrier gas | He | H2 | He | He | |
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.32 | 0.25 | 0.25 | 0.2 |
| Phase thickness (μm) | 0.25 | 0.52 | 0.25 | 0.25 | |
| Tstart (C) | 60. | 50. | 60. | 60. | 60. |
| Tend (C) | 280. | 280. | 280. | 220. | 280. |
| Heat rate (K/min) | 3. | 2.5 | 3. | 4. | 3. |
| Initial hold (min) | 5. | 4. | |||
| Final hold (min) | |||||
| I | 1978. | 2000. | 1980. | 1999. | 1989. |
| Reference | Pitarokili, Tzakou, et al., 2006 | Wang, Kong, et al., 2006 | Basta, Tzakou, et al., 2005 | Morteza-Semnani and Saeedi, 2005 | Petrakis, Roussis, et al., 2005 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary | Capillary | Capillary |
|---|---|---|---|---|---|
| Active phase | DB-1 | RTX-5Sil | DB-5 | DB-5 | HP-5 |
| Column length (m) | 50. | 30. | 30. | 30. | 30. |
| Carrier gas | He | He | He | ||
| Substrate | |||||
| Column diameter (mm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.32 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.25 | 0.25 | 0.25 |
| Tstart (C) | 60. | 70. | 60. | 35. | 100. |
| Tend (C) | 240. | 200. | 280. | 280. | 240. |
| Heat rate (K/min) | 3. | 4. | 3. | 3. | 5. |
| Initial hold (min) | 2. | 2. | |||
| Final hold (min) | 10. | 30. | 15. | 5. | |
| I | 1965. | 2004. | 1971. | 2009. | 1957. |
| Reference | Velasco-Negueruela, Pérez-Alonso, et al., 2005 | Dudai, Larkov, et al., 2003 | Marongiu, Porcedda, et al., 2003 | Krauze-Baranowska, Mardarowicz, et al., 2002 | Lago, Reis, et al., 2002 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI | MSDC-RI |
| Column type | Capillary | Capillary | Capillary |
|---|---|---|---|
| Active phase | DB-1 | DB-5 | HP-1 |
| Column length (m) | 50. | 30. | 23. |
| Carrier gas | N2 | He | He |
| Substrate | |||
| Column diameter (mm) | 0.25 | 0.25 | 0.32 |
| Phase thickness (μm) | 0.25 | 0.25 | 0.17 |
| Tstart (C) | 60. | 60. | 60. |
| Tend (C) | 240. | 240. | 250. |
| Heat rate (K/min) | 3. | 3. | 5. |
| Initial hold (min) | 3. | ||
| Final hold (min) | 30. | ||
| I | 1965. | 1995. | 1985. |
| Reference | Velasco-Negueruela, Pérez-Alonso, et al., 2002 | Zoghbi, Andrade, et al., 1999 | Ayedoun, Adeoti, et al., 1996 |
| Comment | MSDC-RI | MSDC-RI | MSDC-RI |
References
Go To: Top, Normal alkane RI, non-polar column, temperature ramp, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Pripdeevech and Saansoomchai, 2013
Pripdeevech, P.; Saansoomchai, J.,
Antibacterial activity and chemical composition of essential oil and various extracts of Fagraea fragrans Roxb. flowers,
Chiang Mai J. Sci., 2013, 40, 2, 214-223. [all data]
Monsef-Esfahani, Miri, et al., 2010
Monsef-Esfahani, H.R.; Miri, A.; Amini, M.; Amanzadeh, Y.; Hadjiakhoondi, A.; Hajiaghaee, R.; Ajani, Y.,
Seasonal variations in the chemical composition, antioxidant activity and total phenolic content of Teucrium persicum Boiss. essential oils,
Res. J. Biol. Sci., 2010, 5, 7, 492-498, https://doi.org/10.3923/rjbsci.2010.492.498
. [all data]
Neves, Rosa, et al., 2010
Neves, A.; Rosa, S.; Goncalves, J.; Rufino, A.; Judas, F.; Salgueiro, L.; Lopes, M.C.; Cavaleiro, C.; Mendes, A.F.,
Screening of five essential oils for identification of potential inhibitors of IL-1-unduced Nf-kB activation and NO production in human clondrocytes: characterization of the inhibitory activity of alpha-pinene,
Plante Med., 2010, 76, 03, 303-308, https://doi.org/10.1055/s-0029-1186085
. [all data]
Radulovic, Blagojevic, et al., 2010
Radulovic, N.; Blagojevic, P.; Palic, R.,
Comparative study of the leaf volatiles of Arctostaphylos uva-ursi (L.) Spreng. and Vaccinium vitis-idaea L. (Ericaceae),
Molecules, 2010, 15, 9, 6168-6185, https://doi.org/10.3390/molecules15096168
. [all data]
Gardini, Beletti, et al., 2009
Gardini, F.; Beletti, N.; Ndagikimana, M.; Guerzoni, M.E.; Tchoumbougnang, F.; Zollo, P.H.A.; Micci, C.; Lanciotti, R.; Kamdem, S.L.S.,
Composition of four essential oils obtained from plants from Cameroon, and their bactericidal and bacteriostatic activity against Listeria Monocytogenes, Salmonella enteritidis and Staphyllococcus aureus,
African J. Microbiol. Res., 2009, 3, 5, 264-271. [all data]
Lo Presti, Sciarrone, et al., 2008
Lo Presti, M.; Sciarrone, D.; Crupi, M.C.; Costa, R.; Ragusa, S.; Dugo, G.; Mondello, L.,
Evaliation of the volatile and chiral composition in Pistacia lentiscus L. essential oil,
Flavour Fragr. J., 2008, 23, 4, 249-257, https://doi.org/10.1002/ffj.1878
. [all data]
Adams, Beauchamp, et al., 2007
Adams, R.P.; Beauchamp, P.S.; Dev, V.; Dutz, S.M.,
New Natural Products Isolated from One-Seeded Juniperus of the Southwestern United States: Isolation and Occurence of 2-Ethenyl-3-methyl Phanol and Its Derivatives,
J. Essent. Oil Res., 2007, 19, 2, 146-152, https://doi.org/10.1080/10412905.2007.9699247
. [all data]
Baran, von Reuss, et al., 2007
Baran, S.; von Reuss, S.H.; König, W.A.; Kalemba, D.,
Composition of the essential oil of Abies koreana Wils.,
Flavour Fragr. J., 2007, 22, 1, 78-83, https://doi.org/10.1002/ffj.1762
. [all data]
Loizzo, Tundis, et al., 2007
Loizzo, M.R.; Tundis, R.; Conforti, F.; Saab, A.M.; Statti, G.A.; Menichini, F.,
Comparative chemical composition, antioxidant and hypoglycaemic activities of Juniperus oxycedrus ssp. oxycedrus L. berry and wood oils from Lebanon,
Food Chem., 2007, 105, 2, 572-578, https://doi.org/10.1016/j.foodchem.2007.04.015
. [all data]
Borges, Rojas, et al., 2006
Borges, R.; Rojas, L.B.; Cegarra, J.A.; Usubillaga, A.,
Study of the essential oils from the leaves and flowers of Lepechinia conferta (Benth) Epl.,
Flavour Fragr. J., 2006, 21, 1, 155-157, https://doi.org/10.1002/ffj.1550
. [all data]
Cavaleiro, Pinto, et al., 2006
Cavaleiro, C.; Pinto, E.; Gonsales, M.J.; Salguero, L.,
Antifungal activity of Juniperus essential oils agains dermatophyte, Asrgillus and Candida strains,
J. Appl. Microbiol., 2006, 100, 6, 1333-1338, https://doi.org/10.1111/j.1365-2672.2006.02862.x
. [all data]
Lago, Soares, et al., 2006
Lago, J.H.G.; Soares, M.G.; Batista-Pereira, L.G.; Silva, M.F.G.F.; Corrêa, A.G.; Fernandes, J.B.; Vieira, P.C.; Roque, N.F.,
Volatile oil from Guarea macrophylla ssp. tuberculata: seasonal variation and electroantennographic detection by Hypsipyla grandella,
Phytochemistry, 2006, 67, 6, 589-594, https://doi.org/10.1016/j.phytochem.2005.12.018
. [all data]
Morteza-Semnani, Akbarzadeh, et al., 2006
Morteza-Semnani, K.; Akbarzadeh, M.; Changizi, S.,
Essential oils composition of Stachys byzantina, S. inflata, S. lavandulifolia and S. laxa from Iran,
Flavour Fragr. J., 2006, 21, 2, 300-303, https://doi.org/10.1002/ffj.1594
. [all data]
Petrovic, Ristic, et al., 2006
Petrovic, S.; Ristic, M.; Milenkovic, M.; Kukic, J.; Antic-Stankovic, J.; Niketic, M.,
Composition and antimicrobial activity of essential oil of Stachys plumosa Griseb.,
Flavour Fragr. J., 2006, 21, 2, 250-252, https://doi.org/10.1002/ffj.1570
. [all data]
Pitarokili, Tzakou, et al., 2006
Pitarokili, D.; Tzakou, O.; Loukis, A.,
Essential oil composition of Salvia verticillata, S. verbenaca, S. glutinosa and S. candidissima growing wild in Greece,
Flavour Fragr. J., 2006, 21, 4, 670-673, https://doi.org/10.1002/ffj.1647
. [all data]
Wang, Kong, et al., 2006
Wang, P.; Kong, C.H.; Zhang, C.X.,
Chemical Composition and Antimicrobial Activity of the Essential Oil from Ambrosia trifida L.,
Molecules, 2006, 11, 7, 549-555, https://doi.org/10.3390/11070549
. [all data]
Basta, Tzakou, et al., 2005
Basta, A.; Tzakou, O.; Couladis, M.,
Composition of the leaves essential oil of Melissa officinalis s. l. from Greece,
Flavour Fragr. J., 2005, 20, 6, 642-644, https://doi.org/10.1002/ffj.1518
. [all data]
Morteza-Semnani and Saeedi, 2005
Morteza-Semnani, K.; Saeedi, M.,
The essential oil composition of Phlomis bruguieri Desf. from Iran,
Flavour Fragr. J., 2005, 20, 3, 344-346, https://doi.org/10.1002/ffj.1459
. [all data]
Petrakis, Roussis, et al., 2005
Petrakis, P.V.; Roussis, V.; Papadimitriou, D.; Vagias, C.; Tsitsimpikou, C.,
The effect of terpenoid extracts from 15 pine species on the feeding behavioural sequence of the late instars of the pine processionary caterpillar Thaumetopoea pityocampa,
Behav. Processes, 2005, 69, 3, 303-322, https://doi.org/10.1016/j.beproc.2004.12.008
. [all data]
Velasco-Negueruela, Pérez-Alonso, et al., 2005
Velasco-Negueruela, A.; Pérez-Alonso, M.J.; Palá-Paúl, J.; Iñigo, A.; López, G.,
The volatile oil composition of the berries of Juniperus macrocarpa Sibth. and Sm., gathered in Spain,
J. Essent. Oil Res., 2005, 17, 1, 61-63, https://doi.org/10.1080/10412905.2005.9698831
. [all data]
Dudai, Larkov, et al., 2003
Dudai, N.; Larkov, O.; Chaimovitsh, D.; Lewinsohn, E.; Freiman, L.; Ravid, U.,
Essential oil compounds of Origanum dayi Post,
Flavour Fragr. J., 2003, 18, 4, 334-337, https://doi.org/10.1002/ffj.1237
. [all data]
Marongiu, Porcedda, et al., 2003
Marongiu, B.; Porcedda, S.; Caredda, A.; de Gioannis, B.; Vargiu, L.; la Colla, P.,
Extraction of Juniperus oxycedrus ssp. Oxycedrus essential oil by supercritical carbon dioxide: influence of some process parameters and biological activity,
Flavour Fragr. J., 2003, 18, 5, 390-397, https://doi.org/10.1002/ffj.1224
. [all data]
Krauze-Baranowska, Mardarowicz, et al., 2002
Krauze-Baranowska, M.; Mardarowicz, M.; Wiwart, M.; Poblocka, L.; Dynowska, M.,
Antifungal activity of the essential oils from some species of the genus Pinus,
Z. Naturforsch., 2002, 57c, 478-482. [all data]
Lago, Reis, et al., 2002
Lago, J.H.G.; Reis, A.A.; Roque, N.F.,
Chemical composition from volatile oil of the stem bark of Guarea macrophylla Vahl. ssp. tuberculata Vellozo (Meliaceae),
Flavour Fragr. J., 2002, 17, 4, 255-257, https://doi.org/10.1002/ffj.1091
. [all data]
Velasco-Negueruela, Pérez-Alonso, et al., 2002
Velasco-Negueruela, A.; Pérez-Alonso, M.J.; Palá-Paúl, J.; Íñigo, A.; López, G.,
Leaf essential oils analysis of Juniperus navicularis Gandoger,
Botanica Complutensis, 2002, 26, 85-91. [all data]
Zoghbi, Andrade, et al., 1999
Zoghbi, M.G.B.; Andrade, E.H.A.; Maia, J.G.S.,
The essential oil of Vitex angus-castus L. growing in the Amazon region,
Flavour Fragr. J., 1999, 14, 4, 211-213, https://doi.org/10.1002/(SICI)1099-1026(199907/08)14:4<211::AID-FFJ812>3.0.CO;2-W
. [all data]
Ayedoun, Adeoti, et al., 1996
Ayedoun, A.M.; Adeoti, B.S.; Sossou, P.V.; Leclerq, P.A.,
Influence of fruit conservation methods on the essential oil composition of xylopia aethiopica (Dunal) A. Richard from Benin,
Flavour Fragr. J., 1996, 11, 4, 245-250, https://doi.org/10.1002/(SICI)1099-1026(199607)11:4<245::AID-FFJ583>3.0.CO;2-K
. [all data]
Notes
Go To: Top, Normal alkane RI, non-polar column, temperature ramp, References
- Symbols used in this document:
Tend Final temperature Tstart Initial temperature - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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