cis-Verbenol

Formula: C₁₀H₁₆O
Molecular weight: 152.2334
IUPAC Standard InChI: InChI=1S/C10H16O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-9,11H,5H2,1-3H3
IUPAC Standard InChIKey: WONIGEXYPVIKFS-UHFFFAOYSA-N
CAS Registry Number: 1845-30-3
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.
Stereoisomers:
Other names: Bicyclo[3.1.1]hept-3-en-2-ol, 4,6,6-trimethyl-, (1α,2β,5α)-; Bicyclo(3.1.1)hept-3-en-2-ol, 4,6,6-trimethyl-, (1R,2R,5R)-rel-; (.+/-.)-cis-Verbenol; cis-2-Pinen-4-ol; (Z)-Verbenol; (S)-cis-verbenol; δ-Verbenol
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Information on this page:
Other data available:
- Gas Chromatography
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Normal alkane RI, non-polar column, temperature ramp

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

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	5 % Phenyl methyl siloxane	HP-5	HP-5 MS	HP-5 MS	SPB-1
Column length (m)	60.	30.	30.	30.	30.
Carrier gas	Helium	N2	Helium	Helium	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.25	0.2
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.2
T_start (C)	90.	60.	50.	50.	70.
T_end (C)	225.	220.	240.	230.	220.
Heat rate (K/min)	3.	5.	3.	3.	3.
Initial hold (min)		10.		10.
Final hold (min)	3.			10.	15.
I	1142.	1144.	1129.	1141.	1118.
Reference	Retta, Gattuso, et al., 2009	Flamini, Tebano, et al., 2008	Sarikurkcu, Tepe, et al., 2008	Adams, Beauchamp, et al., 2007	Pinto, Salgueiro, et al., 2007
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5	SPB-1	HP-5MS	HP-5MS	RTX-1
Column length (m)	30.	30.	30.	30.	30.
Carrier gas	He	Helium	He	He	He
Substrate
Column diameter (mm)	0.25	0.20	0.25	0.25	0.32
Phase thickness (μm)	0.25	0.20	0.25	0.25	0.25
T_start (C)	50.	70.	50.	50.	60.
T_end (C)	240.	220.	250.	280.	300.
Heat rate (K/min)	4.	3.	2.	5.	4.
Initial hold (min)				4.
Final hold (min)		15.		10.
I	1140.	1122.	1140.	1152.	1130.
Reference	Sefidkon, Abbasi, et al., 2007	Cavaleiro, Pinto, et al., 2006	Farah, Afifi, et al., 2006	Kim, Abd El-Aty, et al., 2006	Kula, Izydorczyk, et al., 2006
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-5 MS	HP-5	DB-5	NB-30	HP-5MS
Column length (m)	30.	30.	30.	30.	30.
Carrier gas	Nitrogen	N2	He	He	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.2	0.25
Phase thickness (μm)	0.25	0.52	0.25	0.25	0.25
T_start (C)	50.	50.	60.	50.	40.
T_end (C)	280.	280.	220.	250.	260.
Heat rate (K/min)	5.	5.	4.	2.	4.
Initial hold (min)			5.
Final hold (min)	5.	5.
I	1128.	1128.	1143.	1132.	1143.
Reference	Marzouk, Mansour, et al., 2006	Marzouk, Neffati, et al., 2006	Morteza-Semnani K., Saeedi M., et al., 2006	Orav, Raal, 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	DB-5	HP-5MS	DB-1	DB-5	DB-5
Column length (m)	30.	30.	30.	30.	30.
Carrier gas	Hydrogen	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
T_start (C)	70.	60.	50.	35.	40.
T_end (C)	280.	280.	265.	280.	250.
Heat rate (K/min)	4.	3.	2.5	4.	5.
Initial hold (min)	4.		1.	2.	0.5
Final hold (min)			30.		2.
I	1141.	1105.	1118.	1142.	1140.
Reference	Pino, Marbot, et al., 2006	Pitarokili, Tzakou, et al., 2006	Khalighi-Sigaroodi, Hadijiakhoondi, et al., 2005	Kowalski and Wolski, 2005	Özel, Gögüs, et al., 2005
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-5MS	DB-1	DB-1	DB-1	HP-5
Column length (m)	30.	60.	30.	60.	30.
Carrier gas	He	He	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
T_start (C)	60.	60.	50.	60.	60.
T_end (C)	280.	250.	265.	250.	260.
Heat rate (K/min)	4.	5.	2.5	5.	5.
Initial hold (min)			1.		2.
Final hold (min)		10.	20.	10.	13.
I	1140.	1111.	1120.	1106.	1135.
Reference	Sajjadi S.E. and Eskandari B., 2005	Salehi, Sonboli, et al., 2005	Sarkhail, Amin, et al., 2005	Sonboli, Salehi, et al., 2005	Yayli, Yasar, et al., 2005
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	ZB-5	RTX-1	NB-30	RSL-200	DB-1
Column length (m)	60.	30.	50.	30.	60.
Carrier gas	He	N2	He	H2	He
Substrate
Column diameter (mm)	0.25	0.25	0.20	0.32	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	40.	60.	50.	40.	40.
T_end (C)	260.	300.	250.	280.	260.
Heat rate (K/min)	6.	4.	2.	6.	4.
Initial hold (min)	4.6			5.	5.
Final hold (min)	1.			5.
I	1146.	1130.	1132.	1165.	1123.
Reference	Jürgens and Dötterl, 2004	Kalemba and Thiem, 2004	Raal, Paaver, et al., 2004	Jirovetz, Buchbauer, et al., 2003	Sefidkon, Naderi Nik, et al., 2003
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-5	HP-5	SPB-5	DB-1	DB-5
Column length (m)	30.	30.	60.	60.	30.
Carrier gas	He	He	He	He	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.25	0.25
Phase thickness (μm)	0.32	0.25	0.25	0.25	0.25
T_start (C)	60.	60.	50.	40.	60.
T_end (C)	250.	275.	240.	280.	240.
Heat rate (K/min)	5.	4.	5.	4.	3.
Initial hold (min)	30.		3.	5.
Final hold (min)			10.
I	1146.	1138.	1117.	1126.	1143.
Reference	Yassa, Akhani, et al., 2003	Ghannadi, Sajjadi, et al., 2002	Kim and Lee, 2002	Sefidkon, Jalili, et al., 2002	Zoghbi, Andrade, et al., 2002
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary
Active phase	HP-5	RTX-1	RTX-1	PONA
Column length (m)	30.	30.	30.	50.
Carrier gas	N2	N2	N2	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.2
Phase thickness (μm)	0.25	0.25	0.25	0.5
T_start (C)	60.	60.	60.	40.
T_end (C)	220.	300.	300.	250.
Heat rate (K/min)	5.	4.	4.	6.
Initial hold (min)	10.			5.
Final hold (min)
I	1141.	1130.	1129.	1140.
Reference	Gallori, Flamini, et al., 2001	Kalemba, Marschall, et al., 2001	Kalemba, 1999	Ramalho, de Freitas, et al., 1999
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

References

Go To: Top, Normal alkane RI, non-polar column, temperature ramp, Notes

Retta, Gattuso, et al., 2009
Retta, D.; Gattuso, M.; Gattuso, S.; Lira, P. Di Leo; van Baren, C.; Ferraro, G.; Bandoni A., Essential oil composition of Achyrocline flaccida (Weinm.) DC. (Asteraceae) from different locations of Argentina, Biochem. Systematics Ecol., 2009, 36, 12, 877-881, https://doi.org/10.1016/j.bse.2008.11.001 . [all data]

Flamini, Tebano, et al., 2008
Flamini, G.; Tebano, M.; Cioni, P.L., Composition of the essential oils from leafy parts of the shoots, flowers and fruits of Eryngium amethystinum from Amiata Mount (Tuscany, Italy), Food Chem., 2008, 107, 2, 671-674, https://doi.org/10.1016/j.foodchem.2007.08.064 . [all data]

Sarikurkcu, Tepe, et al., 2008
Sarikurkcu, C.; Tepe, B.; Daferera, D.; Polissiou, M.; Harmandar, M., Studies on the anioxidant activity of the essential oil and methanol extract of Marrubium globosum subsp. globosum (lamiaceae) by three different chemical assays, Bioresource Technol., 2008, 99, 10, 4239-4246, https://doi.org/10.1016/j.biortech.2007.08.058 . [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]

Pinto, Salgueiro, et al., 2007
Pinto, E.; Salgueiro, L.R.; Cavaleiro, C.; Palmeira, A.; Goncalves, M.J., In vitro susceptibility of some species of yeasts and filamentous fungi to essential oils of Salvia of?cinalis, Ind. Crops Prod., 2007, 26, 2, 135-141, https://doi.org/10.1016/j.indcrop.2007.02.004 . [all data]

Sefidkon, Abbasi, et al., 2007
Sefidkon, F.; Abbasi, K.; Jamzad, Z.; Ahmadi, S., The effect of distillation methods and stage of plant growth on the essential oil content and composition of Satureja rechingeri Jamzad, Food Chem., 2007, 100, 3, 1054-1058, https://doi.org/10.1016/j.foodchem.2005.11.016 . [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]

Farah, Afifi, et al., 2006
Farah, A.; Afifi, A.; Fechtal, M.; Chhen, A.; Satrani, B.; Talbi, M.; Chaouch, A., Fractional distillation effect on the chemical composition of Moroccan myrtle (Myrtus communis L.) essential oils, Flavour Fragr. J., 2006, 21, 2, 351-354, https://doi.org/10.1002/ffj.1651 . [all data]

Kim, Abd El-Aty, et al., 2006
Kim, M.R.; Abd El-Aty, A.M.; Kim, I.S.; Shim, J.H., Determination of volatile flavor components in danggui cultivars by solvent free injection and hydrodistillation followed by gas chromatographic-mass spectrometric analysis, J. Chromatogr. A, 2006, 1116, 1-2, 259-264, https://doi.org/10.1016/j.chroma.2006.03.060 . [all data]

Kula, Izydorczyk, et al., 2006
Kula, J.; Izydorczyk, K.; Czajkowska, A.; Bonikowski, R., Chemical composition of carrot umbel oils from Daucus carota L. ssp. sativus cultivated in Poland, Flavour Fragr. J., 2006, 21, 4, 667-669, https://doi.org/10.1002/ffj.1646 . [all data]

Marzouk, Mansour, et al., 2006
Marzouk, Z.; Mansour, H.B.; Chraief, I.; Mosrati, R.; Cheriaa, J.; Neffati, A.; Marzouk, B.; Sfari, M.; Boukef, K.; Barillies, D.; Ghedira, L.C., Chemical composition, antibacterial and antimutagenic activities of four populations of Rosmarinus officinalis L. oils from Tunisia, J. Food Agriculture Environment, 2006, 4, 2, 89-94. [all data]

Marzouk, Neffati, et al., 2006
Marzouk, Z.; Neffati, A.; Marzouk, B.; Chraief, I.; Fathia, K.; Ghedira, L.C.; Boukef, K., Chemical composition and antibacterial and antimutagenic activity of Tunisian Rosmarinus officinalis L. oil from Kasrine, Journal of Food, Agriculture Environment, 2006, 4, 34, 61-65. [all data]

Morteza-Semnani K., Saeedi M., et al., 2006
Morteza-Semnani K.; Saeedi M.; Changizi S., The essential oil composition of Hypericum scabrum L. from Iran, Flavour Fragr. J., 2006, 21, 3, 513-515, https://doi.org/10.1002/ffj.1614 . [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]

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]

Pino, Marbot, et al., 2006
Pino, J.A.; Marbot, R.; Payo, A.; Chao, D.; Herrera, P., Aromatic Plants from Western Cuba VII. Composition of the Leaf Oil of Psidium wrightii KRug et Urb., Lantana involucrata L., Cinnamonum montanum (Sw.) Berchtold et J. Persl. and Caesalpinia violacea (Mill.) Standley, J. Essent. Oil. Res., 2006, 18, 2, 170-174, https://doi.org/10.1080/10412905.2006.9699058 . [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]

Khalighi-Sigaroodi, Hadijiakhoondi, et al., 2005
Khalighi-Sigaroodi, F.; Hadijiakhoondi, A.; Shahverdi, A.R.; Mozaffarian, V.-A.; Shafiee, A., Chemical composition and antimicrobial activity of the essential oil of Ferulago Bernardii Tomk. and M.Pimen., DARU, 2005, 13, 3, 100-104. [all data]

Kowalski and Wolski, 2005
Kowalski, R.; Wolski, T., The chemical composition of essential oils of Silphium perfoliatum L., Flavour Fragr. J., 2005, 20, 3, 306-310, https://doi.org/10.1002/ffj.1418 . [all data]

Özel, Gögüs, et al., 2005
Özel, M.Z.; Gögüs, F.; Hamilton, J.F.; Lewis, A.C., Analysis of volatile components from Ziziphora taurica subsp. taurica by steam distillation, superheated-water extraction, and direct thermal desorption with GC×GC-TOFMS, Anal. Bioanal. Chem., 2005, 382, 1, 115-119, https://doi.org/10.1007/s00216-005-3156-x . [all data]

Sajjadi S.E. and Eskandari B., 2005
Sajjadi S.E.; Eskandari B., Chemical constituents of the essential oil of Nepeta oxyodonta, Chem. Nat. Compd. (Engl. Transl.), 2005, 41, 2, 175-177, https://doi.org/10.1007/s10600-005-0106-y . [all data]

Salehi, Sonboli, et al., 2005
Salehi, P.; Sonboli, A.; Eftekhar, F.; Nejad-Ebrahimi, S.; Yousefzadi, M., Essential Oil Composition, Antibacterial and Antioxidant Activity of the Oil and Various Extracts of Ziziphora clinopodioides subsp. rigida (BOISS.) RECH. f. from Iran, Biol. Pharm. Bull., 2005, 28, 10, 1892-1896, https://doi.org/10.1248/bpb.28.1892 . [all data]

Sarkhail, Amin, et al., 2005
Sarkhail, P.; Amin, G.; Surmaghi, M.H.S.; Shafiee, A., Composition of the volatile oils of Phlomis lanceolata Boiss. Hohen., Phlomis anisodonta Boiss. and Phlomis bruguieri Desf. from Iran, Flavour Fragr. J., 2005, 20, 3, 327-329, https://doi.org/10.1002/ffj.1427 . [all data]

Sonboli, Salehi, et al., 2005
Sonboli, A.; Salehi, P.; Allahyari, L., Essential oil composition of Nepeta involucrata from Iran, Chem. Nat. Compd. (Engl. Transl.), 2005, 41, 6, 683-685, https://doi.org/10.1007/s10600-006-0011-z . [all data]

Yayli, Yasar, et al., 2005
Yayli, N.; Yasar, A.; Gülec, C.; Usta, A.; Kolayli, S.; Coskuncelebi, K.; Karaoglu, S., Composition and antimicrobial activity of essential oils from Centaurea sessilis and Centaurea armena, Phytochemistry, 2005, 66, 14, 1741-1745, https://doi.org/10.1016/j.phytochem.2005.04.006 . [all data]

Jürgens and Dötterl, 2004
Jürgens, A.; Dötterl, S., Chemical composition of anther volatiles in Ranunculaceae: genera-specific profiles in Aemone, Aquilegia, Caltha, Pulsatilla, Ranunculus, and Trollius species, American Journal of Botany, 2004, 91, 12, 1969-1980, https://doi.org/10.3732/ajb.91.12.1969 . [all data]

Kalemba and Thiem, 2004
Kalemba, D.; Thiem, B., Constituents of the essential oils of four micropropagated Solidago species, Flavour Fragr. J., 2004, 19, 1, 40-43, https://doi.org/10.1002/ffj.1271 . [all data]

Raal, Paaver, et al., 2004
Raal, A.; Paaver, U.; Arak, E.; Orav, A., Content and composition of the essential oil of Thymus serpyllum L. growing wild in Estonia, Medicina (Kaunas), 2004, 40, 8, 795-800. [all data]

Jirovetz, Buchbauer, et al., 2003
Jirovetz, L.; Buchbauer, G.; Shafi, M.P.; Kaniampady, M.M., Chemotaxonomical analysis of the essential oil aroma compounds of four different Ocimumspecies from southern India, Eur. Food Res. Technol., 2003, 217, 2, 120-124, https://doi.org/10.1007/s00217-003-0708-1 . [all data]

Sefidkon, Naderi Nik, et al., 2003
Sefidkon, F.; Naderi Nik, A.; Bagaii, P.; Javidtash, I., Analysis of the essential oil of Stachys ixodes Boiss. Hausskn. ex Boiss. from Iran, Flavour Fragr. J., 2003, 18, 4, 301-302, https://doi.org/10.1002/ffj.1170 . [all data]

Yassa, Akhani, et al., 2003
Yassa, N.; Akhani, H.; Aqaahmadi, M.; Salimian, M., Essential oils from two endemic species of Apiaceae from Iran, Z. Naturforsch. C:, 2003, 58, 459-463. [all data]

Ghannadi, Sajjadi, et al., 2002
Ghannadi, A.; Sajjadi, S.E.; Beigihasan, A., Composition of the essential oil of Ferula ovina (Boiss.) Boiss. from Iran, DARU, 2002, 10, 4, 165-167, retrieved from http://www1.tums.ac.ir/daru/Daru4%202002/Ghannadi.PDF. [all data]

Kim and Lee, 2002
Kim, N.-S.; Lee, D.-S., Comparison of different extraction methods for the analysis of fragrances from Lavandula species by gas chromatography-mass spectrometry, J. Chromatogr. A, 2002, 982, 1, 31-47, https://doi.org/10.1016/S0021-9673(02)01445-0 . [all data]

Sefidkon, Jalili, et al., 2002
Sefidkon, F.; Jalili, A.; Mirhaji, T., Essential oil composition of three Artemisia spp. from Iran, Flavour Fragr. J., 2002, 17, 2, 150-152, https://doi.org/10.1002/ffj.1063 . [all data]

Zoghbi, Andrade, et al., 2002
Zoghbi, M.G.B.; Andrade, E.H.A.; da Silva, M.H.; Maia, J.G.S.; Luz, A.I.R.; da Silva, J.D., Chemical variation in the essential oils of Hyptis crenata Pohl ex Benth., Flavour Fragr. J., 2002, 17, 1, 5-8, https://doi.org/10.1002/ffj.1031 . [all data]

Gallori, Flamini, et al., 2001
Gallori, S.; Flamini, G.; Bilia, A.R.; Morelli, I.; Landini, A.; Vincieri, F.F., Chemical composition of some traditional herbal drug preparations: essential oil and aromatic water of costmary (Balsamita suaveolens Pers.), J. Agric. Food Chem., 2001, 49, 12, 5907-5910, https://doi.org/10.1021/jf0107656 . [all data]

Kalemba, Marschall, et al., 2001
Kalemba, D.; Marschall, H.; Bradesi, P., Constituents of the essential oil of Solidago gigantea Ait. (giant goldenrod), Flavour Fragr. J., 2001, 16, 1, 19-26, https://doi.org/10.1002/1099-1026(200101/02)16:1<19::AID-FFJ940>3.0.CO;2-U . [all data]

Kalemba, 1999
Kalemba, D., Constituents of the essential oil of Artemisia asiatica Nakai, Flavour Fragr. J., 1999, 14, 3, 173-176, https://doi.org/10.1002/(SICI)1099-1026(199905/06)14:3<173::AID-FFJ805>3.0.CO;2-Q . [all data]

Ramalho, de Freitas, et al., 1999
Ramalho, P.S.; de Freitas, V.A.P.; Macedo, A.; Silva, G.; Silva, A.M.S., Volatile components of Cistus ladanifer leaves, Flavour Fragr. J., 1999, 14, 5, 300-302, https://doi.org/10.1002/(SICI)1099-1026(199909/10)14:5<300::AID-FFJ830>3.0.CO;2-X . [all data]

Notes

Go To: Top, Normal alkane RI, non-polar column, temperature ramp, References

Symbols used in this document:

T_end Final temperature

T_start Initial temperature
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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