(2E,4S,7E)-4-Isopropyl-1,7-dimethylcyclodeca-2,7-dienol

Formula: C₁₅H₂₆O
Molecular weight: 222.3663
IUPAC Standard InChI: InChI=1S/C15H26O/c1-12(2)14-8-7-13(3)6-5-10-15(4,16)11-9-14/h6,9,11-12,14,16H,5,7-8,10H2,1-4H3/b11-9+,13-6+
IUPAC Standard InChIKey: RHCTXHCNRLCYBN-BMCYRRRCSA-N
CAS Registry Number: 198991-79-6
Chemical structure:
This structure is also available as a 2d Mol file
Species with the same structure:
- Unknown Black Pepper Gremacrene-D-4-ol isomer RI 1627
Stereoisomers:
Other names: Germacrene D-4-ol; 2,7-Cyclodecadien-1-ol, 1,7-dimethyl-4-(1-methylethyl)-, (2E,4S,7E)-; Germacren D-4-ol; Germacrene-δ-4-ol; D-Germacren-4-ol
Information on this page:
Other data available:
- Gas Chromatography
Options:
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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	HP-5 MS	HP-5 MS	DB-5	HP-5 MS	HP-5
Column length (m)	30.	30.	30.	30.	30.
Carrier gas	Helium	Hydrogen	Nitrogen	Helium	Helium
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.25	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	60.	30.	40.	50.	50.
T_end (C)	220.	230.	230.	280.	300.
Heat rate (K/min)	5.	8.	2.	4.	3.
Initial hold (min)	10.	5.
Final hold (min)		10.			30.
I	1575.	1595.	1576.	1579.	1571.
Reference	Ogunwande, Flamini, et al., 2010	Karlsson, Birgersson, et al., 2009	Scrivanti, Anton, et al., 2009	Zhao, Zeng, et al., 2009	Isidorov, Lech, et al., 2008
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	SLB-5 MS	RTX-1	HP-5MS	HP-5	HP-5MS
Column length (m)	30.	60.	30.	30.	30.
Carrier gas	Helium	He	He	N2	He
Substrate
Column diameter (mm)	0.25	0.22	0.25	0.25	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	50.	60.	60.	50.	60.
T_end (C)	250.	230.	240.	240.	250.
Heat rate (K/min)	3.	2.	3.	5.	2.
Initial hold (min)	2.			1.	8.
Final hold (min)	10.	35.		4.	15.
I	1579.	1573.	1597.	1574.	1567.
Reference	Lo Presti, Sciarrone, et al., 2008	Paolini, Tomi, et al., 2008	Argyropoulou, Daferera, et al., 2007	Cheraif, Ben Jannet, et al., 2007	Ferhat, Meklati, et al., 2007
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-5MS	Col-Elite 5MS	DB-1	Elite-5MS	HP-5
Column length (m)	30.	30.	50.	30.	30.
Carrier gas	He	He	He	He	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.32	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.5	0.25
T_start (C)	60.	30.	95.	40.	50.
T_end (C)	250.	246.	240.	280.	300.
Heat rate (K/min)	2.	3.	4.	4.	5.
Initial hold (min)	8.			5.	5.
Final hold (min)	15.			10.	5.
I	1572.	1597.	1578.	1578.	1579.
Reference	Ferhat, Tigrine-Kordjani, et al., 2007	Gudaityte and Venskutonis R.P., 2007	Pala-Paul, Brophy, et al., 2007	Tava, Pecetti, et al., 2007	Figuérédo, Cabassu, 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	CP Sil 5 CB	DB-5	DB-1	DB-1
Column length (m)	30.	30.	30.	50.	50.
Carrier gas		N2	He	N2	N2
Substrate
Column diameter (mm)	0.25	0.32	0.25	0.25	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	40.	50.	60.	95.	90.
T_end (C)	210.	300.	220.	240.	240.
Heat rate (K/min)	2.	4.	4.	4.	4.
Initial hold (min)	2.
Final hold (min)	33.
I	1573.	1560.	1577.	1597.	1559.
Reference	Garneau F.X., Collin G., et al., 2006	Lis and Milczarek, 2006	Morteza-Semnani, Akbarzadeh, et al., 2006	Pala-Paul J., Perez-Alonso M.J., et al., 2006	Velasco-Negueruela, Pérez-Alonso, 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	HP-5	DB-5	DB-1	HP-5MS
Column length (m)	25.	25.	30.	50.	30.
Carrier gas	He	H2	He	N2
Substrate
Column diameter (mm)	0.2	0.32	0.25	0.25	0.2
Phase thickness (μm)	0.33	0.52	0.25	0.25
T_start (C)	60.	40.	60.	95.	60.
T_end (C)	240.	240.	220.	240.	280.
Heat rate (K/min)	3.	4.	4.	4.	3.
Initial hold (min)			4.
Final hold (min)	7.
I	1569.	1560.	1578.	1578.	1576.
Reference	Duarte, Figueira, et al., 2005	Jovanovic, Kitic, et al., 2005	Morteza-Semnani and Saeedi, 2005	Pala-Paul, Perez-Alonso, et al., 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	HP-5MS	HP-5MS	RTX-5	DB-5	HP-5 MS
Column length (m)	30.	30.	30.	30.	30.
Carrier gas	He	He		He	Helium
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.32	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	60.	60.	60.	60.	60.
T_end (C)	280.	280.	220.	280.	240.
Heat rate (K/min)	4.	3.	3.	3.	3.
Initial hold (min)
Final hold (min)
I	1576.	1574.	1573.	1550.	1576.
Reference	Sajjadi S.E. and Eskandari B., 2005	Slavkovska, Couladis, et al., 2005	Szafranek, Chrapkowska, et al., 2005	Tzakou and Constantinidis, 2005	Urdampilleta, Amat, et al., 2005
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	CP Sil 5 CB	SE-54	NB-30	DB-5	RTX-5Sil
Column length (m)	30.	30.	50.	30.	30.
Carrier gas	N2	He	He	He	He
Substrate
Column diameter (mm)	0.25	0.25	0.20	0.25	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	50.	60.	50.	60.	70.
T_end (C)	200.	260.	250.	300.	200.
Heat rate (K/min)	5.	2.	2.	3.	4.
Initial hold (min)		5.
Final hold (min)					10.
I	1570.	1568.	1576.	1576.	1577.
Reference	Agnaniet, Menut, et al., 2004	Kilic, Hafizoglu, et al., 2004	Raal, Paaver, et al., 2004	Tirillini, Pellegrino, et al., 2004	Dudai, Larkov, 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	DB-5	DB-5	5 % Phenyl methyl siloxane	OV-101
Column length (m)	30.	30.	30.	30.	25.
Carrier gas	He		He	He	He
Substrate
Column diameter (mm)	0.25	0.25	0.249	0.25	0.32
Phase thickness (μm)	0.25	0.25	0.25	0.25
T_start (C)	60.	40.	60.	75.	50.
T_end (C)	280.	260.	300.	200.	200.
Heat rate (K/min)	4.	2.	3.	3.	5.
Initial hold (min)		5.		4.
Final hold (min)			5.	8.
I	1573.	1575.	1574.	1576.	1570.
Reference	Sajjadi and Mehregan, 2003	Senatore and Bruno, 2003	Bos, Koulman, et al., 2002	Cicció and Gómez-Laurito, 2002	Menut, Bessière, et al., 2002
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary
Active phase	Optima-5	OV-101	DB-1
Column length (m)	30.	25.	25.
Carrier gas	He	N2	He
Substrate
Column diameter (mm)	0.2	0.25	0.25
Phase thickness (μm)			0.25
T_start (C)	50.	50.	50.
T_end (C)	250.	200.	290.
Heat rate (K/min)	3.	5.	4.
Initial hold (min)	3.
Final hold (min)
I	1582.	1570.	1574.
Reference	Jacquemond-Collet, Bessière, et al., 2001	Ayedoun, Adéoti, et al., 1999	Koulman, 1999
Comment	MSDC-RI	MSDC-RI	MSDC-RI

References

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

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]

Karlsson, Birgersson, et al., 2009
Karlsson, M.F.; Birgersson, G.; Prado, A.M.C.; Bosa, F.; Bengtsson, M.; Witzgall, P., Plant Odor Analysis of Potato: Responce of Guatemalan Moth to Above- and Background Potato Volatiles, J. Agric. Food Chem., 2009, 57, 13, 5903-5909, https://doi.org/10.1021/jf803730h . [all data]

Scrivanti, Anton, et al., 2009
Scrivanti, L.R.; Anton, A.M.; Zygadlo, J.A., Essential oil conposition of Bothriochloa Kuntze (Poaceae) from South America and their chemotaxonomy, Biochem. Systematics Ecol., 2009, 37, 3, 206-213, https://doi.org/10.1016/j.bse.2009.03.009 . [all data]

Zhao, Zeng, et al., 2009
Zhao, C.; Zeng, Y.; Wan, M.; Li, R.; Liang, Y.; Li, C.; Zeng, Z.; Chau, F.-T., Comparative analysis of essential oils from eight herbal medicines with pungent flavor and cool nature by GC-MS and chemometric resolution methods, J. Sep. Sci., 2009, 32, 4, 660-670, https://doi.org/10.1002/jssc.200800484 . [all data]

Isidorov, Lech, et al., 2008
Isidorov, V.A.; Lech, P.; Zolciak, A.; Rusak, N.; Szczepaniak, L., Gas Chromatographic - nass spectrometric investigation of metabolites from the needles and roots of pine seedlings at early stages of pathogenic fungi Armillaria ostoyae attack, Trees, 2008, 22, 4, 531-542, https://doi.org/10.1007/s00468-008-0213-z . [all data]

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Paolini, J.; Tomi, P.; Bernardini, A.-F.; Bradesi, P.; Casanova, J.; Kaloustian, J., Detailed analysis of the essential oil from Cistus albidus L. by combination of GC/RI, GC/MS and 13C-NMR spectroscopy, N.Z. J. Agric. Res., 2008, 22, 14, 1270-1278. [all data]

Argyropoulou, Daferera, et al., 2007
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Cheraif, Ben Jannet, et al., 2007
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Ferhat, Meklati, et al., 2007
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Ferhat, Tigrine-Kordjani, et al., 2007
Ferhat, M.A.; Tigrine-Kordjani, N.; Chemat, S.; Meklati, B.Y.; Chemat, F., Rapid Extraction of Volatile Compounds Using a New Simultaneous Microwave Distillation: Solvent Extraction Device, Chromatographia, 2007, 65, 3-4, 217-222, https://doi.org/10.1365/s10337-006-0130-5 . [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]

Pala-Paul, Brophy, et al., 2007
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Tava, Pecetti, et al., 2007
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Figuérédo, Cabassu, et al., 2006
Figuérédo, G.; Cabassu, P.; Chalchat, J.-C.; Pasquier, B., Studies of Mediterranean oregano populations. VIII. Chemical composition of essential oils of oreganos of various origins, Flavour Fragr. J., 2006, 21, 1, 134-139, https://doi.org/10.1002/ffj.1543 . [all data]

Garneau F.X., Collin G., et al., 2006
Garneau F.X.; Collin G.; Gagnon H.; Jean F.I.; Strobl H.; Pichette A., The essential oil composition of Devil's Club, Oplopanax horridus J. E. Smith Miq., Flavour Fragr. J., 2006, 21, 5, 792-794, https://doi.org/10.1002/ffj.1716 . [all data]

Lis and Milczarek, 2006
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Morteza-Semnani, Akbarzadeh, et al., 2006
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Pala-Paul J., Perez-Alonso M.J., et al., 2006
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Velasco-Negueruela, Pérez-Alonso, et al., 2006
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Duarte, M.C.T.; Figueira, G.M.; Sartoratto, A.; Rehder, V.L.G.; Delarmelina, C., Anti-Candida activity of Brazilian medicinal plants, J. Ethnopharmacol., 2005, 97, 2, 305-311, https://doi.org/10.1016/j.jep.2004.11.016 . [all data]

Jovanovic, Kitic, et al., 2005
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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]

Pala-Paul, Perez-Alonso, et al., 2005
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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]

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]

Slavkovska, Couladis, et al., 2005
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Agnaniet, Menut, et al., 2004
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Kilic, Hafizoglu, et al., 2004
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Raal, Paaver, et al., 2004
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Tirillini, Pellegrino, et al., 2004
Tirillini, B.; Pellegrino, R.; Bini, L.M., Essential oil composition of Stachys sylvatica L. from Italy, Flavour Fragr. J., 2004, 19, 4, 330-332, https://doi.org/10.1002/ffj.1308 . [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]

Sajjadi and Mehregan, 2003
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Senatore and Bruno, 2003
Senatore, F.; Bruno, M., Composition of the essential oil of Pallenis spinosa (L.) Cass. (Asteraceae), Flavour Fragr. J., 2003, 18, 3, 195-197, https://doi.org/10.1002/ffj.1180 . [all data]

Bos, Koulman, et al., 2002
Bos, R.; Koulman, A.; Woerdenbag, H.J.; Quax, W.J.; Pras, N., Volatile components from Anthriscus sylvestris (L.) Hoffm., J. Chromatogr. A, 2002, 966, 1-2, 233-238, https://doi.org/10.1016/S0021-9673(02)00704-5 . [all data]

Cicció and Gómez-Laurito, 2002
Cicció, J.F.; Gómez-Laurito, J., Volatile constituents of the leaves of Siparuna thecaphora (Siparunaceae) from Turrialba, Costa Rica, Rev. Biol. Trop., 2002, 50, 3/4, 963-967. [all data]

Menut, Bessière, et al., 2002
Menut, C.; Bessière, J.M.; Hassani, M.S.; Buchbauer, G.; Schopper, B., Chemical and biological studies of Ocotea comoriensis bark essential oil, Flavour Fragr. J., 2002, 17, 6, 459-461, https://doi.org/10.1002/ffj.1130 . [all data]

Jacquemond-Collet, Bessière, et al., 2001
Jacquemond-Collet, I.; Bessière, J.-M.; Hannedouche, S.; Bertrand, C.; Fourasté, I.; Moulis, C., Identification of the alkaloids of Galipea officinalis by gas chromatography-mass spectrometry, Phytochem. Anal., 2001, 12, 5, 312-319, https://doi.org/10.1002/pca.594 . [all data]

Ayedoun, Adéoti, et al., 1999
Ayedoun, M.A.; Adéoti, B.S.; Setondji, J.; Tchoumbougnang, F.; Kuiaté, J.R.; Zollo, P.H.A.; Menut, C.; Lamaty, G.; Bessière, J.M., Aromatic plants of tropical West Africa. XII. Essential oil of Hoslundia opposita Vahl. growing in Benin and Cameroon, Flavour Fragr. J., 1999, 14, 5, 319-321, https://doi.org/10.1002/(SICI)1099-1026(199909/10)14:5<319::AID-FFJ836>3.0.CO;2-O . [all data]

Koulman, 1999
Koulman, A., Podophyllotoxin: a study of biosynthesis, evolution, function, and use of podophyllotoxin and related lignans, University Library Groningen, Nederlands, 1999, 188, retrieved from http://www.ub.rug.nl/eldoc/dis/science/a.koulman/. [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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