Germacrene D

Formula: C₁₅H₂₄
Molecular weight: 204.3511
IUPAC Standard InChI: InChI=1S/C15H24/c1-12(2)15-10-8-13(3)6-5-7-14(4)9-11-15/h7-8,10,12,15H,3,5-6,9,11H2,1-2,4H3/b10-8-,14-7-
IUPAC Standard InChIKey: GAIBLDCXCZKKJE-BZXLUOIMSA-N
CAS Registry Number: 23986-74-5
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: (S,1Z,6Z)-8-Isopropyl-1-methyl-5-methylenecyclodeca-1,6-diene; D-Germacrene; 1(10),4(14),5-Germacratriene; (-)-Germacrene D; 1,6-Cyclodecadiene, 1-methyl-5-methylene-8-(1-methylethyl)-, [s-(E,E)]-
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Information on this page:
Other data available:
- Mass spectrum (electron ionization)
- Gas Chromatography
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Kovats' 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	DB-5	DB-5MS	HP-5MS	HP-5MS	DB-5MS
Column length (m)	30.	30.	30.	60.	30.
Carrier gas	He	He	He	He	He
Substrate
Column diameter (mm)	0.26	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.	60.	60.	40.	60.
T_end (C)	246.	180.	280.	250.	280.
Heat rate (K/min)	3.	3.	2.	3.	3.
Initial hold (min)			8.	1.
Final hold (min)		15.	30.	20.	30.
I	1480.	1474.	1480.	1503.	1451.
Reference	Adams, González Elizondo, et al., 2006	Angioni, Barra, et al., 2006	Hazzit, Baaliouamer, et al., 2006	Jalali-Heravi, Zekavat, et al., 2006	Marongiu, Porcedda, et al., 2006
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-1	HP-5	BP-1	DB-5	HP-5MS
Column length (m)	25.	25.	25.	30.	30.
Carrier gas	He		N2		He
Substrate
Column diameter (mm)	0.2	0.2	0.32	0.25	0.25
Phase thickness (μm)		0.33	0.25	0.25	0.25
T_start (C)	60.	60.	60.	40.	50.
T_end (C)	220.	240.	220.	210.	240.
Heat rate (K/min)	3.	3.	5.	2.	3.
Initial hold (min)	3.			2.
Final hold (min)			13.	33.
I	1486.	1481.	1473.	1482.	1519.
Reference	Mevy, Bessiere, et al., 2006	Oliveira, Leitao, et al., 2006	Raina, Verma, et al., 2006	Sylvestre, Pichette, et al., 2006	Tepe, Askin Akpulat, et al., 2006
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	SPB-1	DB-5	DB-5	HP-5MS	DB-5MS
Column length (m)	30.	30.	30.	30.	30.
Carrier gas	He	He	He	He	He
Substrate
Column diameter (mm)	0.32	0.26	0.26	0.25	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	60.	60.	60.	50.	60.
T_end (C)	240.	246.	246.	250.	240.
Heat rate (K/min)	4.	3.	3.	3.	3.
Initial hold (min)	4.			10.
Final hold (min)	2.			5.
I	1485.	1485.	1480.	1485.	1482.
Reference	Walde, Jyothirmayi, et al., 2006	Adams, Morris, et al., 2005	Adams and Nguyen, 2005	Asuming, Beauchamp, et al., 2005	Maia, Andrade, et al., 2005
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5	HP-5MS	SPB-5	HP-5	DB-5
Column length (m)	30.	30.	60.	30.	25.
Carrier gas	Helium	He	He	He	He
Substrate
Column diameter (mm)	0.25	0.25	0.32	0.25	0.25
Phase thickness (μm)	0.25	0.25	1.	0.25	0.25
T_start (C)	60.	50.	60.	50.	60.
T_end (C)	255.	240.	200.	280.	180.
Heat rate (K/min)	3.	3.	4.	3.	5.
Initial hold (min)				5.	6.
Final hold (min)			30.	25.	15.
I	1485.	1519.	1508.	1468.	1481.
Reference	Medina, Lucero, et al., 2005	Tepe, Sokmen, et al., 2005	Gauvin, Lecomte, et al., 2004	Mahmood, Kaul, et al., 2004	Merle, Morón, et al., 2004
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5	DB-5MS	CP Sil 8 CB	HP-5MS	HP-5MS
Column length (m)	30.	30.	30.	30.	30.
Carrier gas	He	He	H2	He	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.32	0.32
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	60.	60.	50.	70.	70.
T_end (C)	220.	240.	220.	250.	250.
Heat rate (K/min)	4.	3.	3.	3.	3.
Initial hold (min)	4.		2.	5.	5.
Final hold (min)
I	1480.	1480.	1476.	1472.	1487.
Reference	Morteza-Semnani, Azadbakht, et al., 2004	Palmeira, Moura, et al., 2004	Schwob, Bessiere, et al., 2004	Siani, Garrido, et al., 2004	Siani, Garrido, et al., 2004
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-1	SPB-1	DB-5	DB-5	HP-5MS
Column length (m)	50.	30.	25.	50.	30.
Carrier gas	N2	He	He	He	He
Substrate
Column diameter (mm)	0.25	0.32	0.25	0.32	0.25
Phase thickness (μm)	0.25	0.25		0.25	0.25
T_start (C)	95.	50.	40.	50.	50.
T_end (C)	240.	250.	280.	280.	280.
Heat rate (K/min)	4.	2.	3.	5.	4.
Initial hold (min)		2.	5.	2.	2.
Final hold (min)		5.	5.	10.	10.
I	1477.	1461.	1470.	1496.	1496.
Reference	Velasco-Negueruela, Sanz, et al., 2004	Yadav, Chauhan, et al., 2004	Amparo Blázquez, Pérez, et al., 2003	Baranauskiene, Venskutonis, et al., 2003	Baranauskiene, Venskutonis, et al., 2003, 2
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-5	HP-5MS	HP-5MS	CP Sil 5 CB	SPB-1
Column length (m)	30.	30.	30.	25.	30.
Carrier gas	He	He	He	H2	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.25	0.32
Phase thickness (μm)	1.	0.25	0.25	0.15	0.25
T_start (C)	40.	60.	60.	50.	60.
T_end (C)	250.	280.	280.	230.	225.
Heat rate (K/min)	5.	3.	3.	3.	2.
Initial hold (min)	1.				2.
Final hold (min)					5.
I	1508.	1461.	1464.	1478.	1455.
Reference	Bouzouita, Kachouri, et al., 2003	Couladis, Chinou, et al., 2003	Gkinis, Tzakou, et al., 2003	Ogunwande, Olawore, et al., 2003	Jayaprakasha, Rao, et al., 2002
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-5	Methyl Silicone	SE-30	BP-1	BP-1
Column length (m)	30.	50.	25.	60.	25.
Carrier gas	He	He	He	N2	N2
Substrate
Column diameter (mm)	0.25	0.25	0.22	0.32	0.55
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	60.	70.	70.	60.	60.
T_end (C)	200.	240.	220.	220.	220.
Heat rate (K/min)	4.	4.	4.	5.	5.
Initial hold (min)	1.
Final hold (min)	15.				15.
I	1482.	1493.	1481.	1476.	1461.
Reference	Juliani and Simon, 2002	Palá-Paúl, Pérez-Alonso, et al., 2002	Palá-Paúl, Velasco-Negueruela, et al., 2002	Raina, Lal, et al., 2002	Raina, Srivastava, et al., 2002
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	Cross-Linked Methylsilicone	BP-1	BP-1	HP-5MS	BP-1
Column length (m)	50.	25.	25.	30.	30.
Carrier gas	He	N2		He	N2
Substrate
Column diameter (mm)	0.2	0.5	0.5	0.25	0.32
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	100.	60.	60.	50.	60.
T_end (C)	280.	220.	220.	250.	220.
Heat rate (K/min)	4.	5.	5.	3.	5.
Initial hold (min)
Final hold (min)		10.	10.		13.
I	1479.	1480.	1480.	1480.	1473.
Reference	Rajeswara Rao, Kaul, et al., 2002	Rajeswara Rao, 2002	Rao B.R.R., 2002	Salido, Altarejos, et al., 2002	Shawl, Srivastava, et al., 2002
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-5	PTE-5	BP-1	BP-1	HP-5
Column length (m)	50.	60.	25.	25.	25.
Carrier gas	He	H2	N2	N2	H2
Substrate
Column diameter (mm)	0.25	0.32	0.55	0.55	0.32
Phase thickness (μm)	0.25	0.39	0.25	0.25	0.52
T_start (C)	50.	60.	60.	60.	40.
T_end (C)	250.	285.	220.	220.	240.
Heat rate (K/min)	2.5	4.3	5.	5.	4.
Initial hold (min)	5.
Final hold (min)			15.	15.
I	1485.	1481.	1478.	1478.	1480.
Reference	Yáñez, Pinzón, et al., 2002	Gudzic, Dordevic, et al., 2001	Jain, Aggarwal, et al., 2001	Jain, Srivastava, et al., 2001	Kitic, Palic, et al., 2001
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5	DB-1	DB-1	HP-5	SE-54
Column length (m)	30.	28.	50.	30.	30.
Carrier gas	H2	He	N2	He	He
Substrate
Column diameter (mm)	0.20	0.25	0.25	0.25	0.26
Phase thickness (μm)		0.25	0.25	0.25	0.25
T_start (C)	60.	50.	80.	60.	60.
T_end (C)	240.	270.	225.	280.	246.
Heat rate (K/min)	3.	4.5	4.	3.	3.
Initial hold (min)		1.
Final hold (min)
I	1477.	1480.	1467.	1479.	1480.
Reference	Moreira, Sousa, et al., 2001	Nagalakshmi, Thangadurai, et al., 2001	Palá-Paúl, Velasco-Negueruela, et al., 2001	Tzakou and Couladis, 2001	Adams, 2000
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5	SE-54	DB-5	SE-30	PTE-5
Column length (m)	30.	30.	30.	25.	60.
Carrier gas	He		He	He	H2
Substrate
Column diameter (mm)	0.26	0.26	0.26	0.22	0.32
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.3
T_start (C)	60.	60.	60.	70.	60.
T_end (C)	240.	246.	246.	220.	285.
Heat rate (K/min)	3.	3.	3.	5.	4.3
Initial hold (min)
Final hold (min)
I	1480.	1480.	1480.	1465.	1480.
Reference	Adams, 2000, 2	Adams, 2000, 3	Adams, 2000, 4	Kardali, Velasco-Negueruela, et al., 2000	Mitic and Dordevic, 2000
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	BP-1	BP-1	HP-5MS	DB-5	DB-5
Column length (m)	25.	25.	30.	30.	30.
Carrier gas	N2	N2	He		He
Substrate
Column diameter (mm)	0.5	0.50	0.25	0.32	0.26
Phase thickness (μm)		0.25	0.25		0.25
T_start (C)	60.	60.	60.	50.	60.
T_end (C)	220.	220.	280.	250.	246.
Heat rate (K/min)	5.	5.	3.	3.	3.
Initial hold (min)				5.
Final hold (min)	10.	10.
I	1481.	1481.	1480.	1480.	1480.
Reference	Rao, Kaul, et al., 2000	Rao, Sastry, et al., 2000	Roussis, Tsoukatou, et al., 2000	Tzakou, Harvala, et al., 2000	Adams, 1999
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	CP Sil 5 CB	OV-101	DB-5	DB-5	HP-5MS
Column length (m)	25.	25.	30.	30.	30.
Carrier gas	He				He
Substrate
Column diameter (mm)	0.25	0.32	0.25	0.25	0.32
Phase thickness (μm)					0.25
T_start (C)	60.	50.	60.	60.	70.
T_end (C)	280.	200.	240.	240.	250.
Heat rate (K/min)	5.	5.	3.	3.	3.
Initial hold (min)					5.
Final hold (min)
I	1488.	1487.	1480.	1480.	1474.
Reference	Kaul, Gujral, et al., 1999	Kuiate, Zollo, et al., 1999	Lopes, Kato, et al., 1999	Lopes, Kato, et al., 1999	Siani, Ramos, et al., 1999
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5	DB-5	DB-1	BP-1	CP Sil 5 CB
Column length (m)	30.	30.	60.	25.	30.
Carrier gas	He	He	He	N2	Ar
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
T_start (C)	60.	60.	50.	60.	60.
T_end (C)	240.	240.	250.	220.	220.
Heat rate (K/min)	3.	4.	3.	5.	3.
Initial hold (min)			5.
Final hold (min)			10.
I	1480.	1480.	1473.	1480.	1471.
Reference	da Silva, Andrade, et al., 1999	da Silva, Zoghbi, et al., 1999	Bylaite, Venskutonis, et al., 1998	Kulkarni, Mallavarapu, et al., 1998	Szafranek, Malinski, et al., 1998
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	CP Sil 8 CB	DB-5	DB-1	BPX-5	SPB-1
Column length (m)	25.	30.	30.	50.	30.
Carrier gas	Ar	He	He	N2	He
Substrate
Column diameter (mm)	0.15	0.25	0.23	0.22	0.32
Phase thickness (μm)	0.12	0.25		0.25	0.25
T_start (C)	60.	60.	50.	60.	60.
T_end (C)	220.	240.	200.	185.	250.
Heat rate (K/min)	3.	4.	3.	2.	5.
Initial hold (min)				10.	2.
Final hold (min)					5.
I	1479.	1479.	1479.	1480.	1477.
Reference	Szafranek, Malinski, et al., 1998	Zoghbi, Andrade, et al., 1998	Fiorini, Fourasté, et al., 1997	Fournier, Hadjiakhoondi, et al., 1997	Jayaprakasha, Jaganmohan Rao, et al., 1997
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5	DB-5	DB-5	DB-5	OV-1
Column length (m)	30.	30.	30.	30.	23.
Carrier gas	He				H2
Substrate
Column diameter (mm)	0.25				0.32
Phase thickness (μm)	0.25				0.3
T_start (C)	60.	40.	40.	40.	50.
T_end (C)	240.	210.	210.	210.	200.
Heat rate (K/min)	3.	2.	2.	2.	3.
Initial hold (min)		2.	2.	2.
Final hold (min)		120.	120.	120.
I	1481.	1475.	1480.	1481.	1473.
Reference	Tellez, Estell, et al., 1997	Loayza, Abujder, et al., 1995	Loayza, Abujder, et al., 1995	Loayza, Abujder, et al., 1995	Bicchi, Frattini, et al., 1988
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary
Active phase	BP-1	OV-101
Column length (m)	50.	100.
Carrier gas	H2	H2
Substrate
Column diameter (mm)	0.33	0.3
Phase thickness (μm)		0.15
T_start (C)	65.	90.
T_end (C)	220.	220.
Heat rate (K/min)	5.	2.
Initial hold (min)	2.
Final hold (min)
I	1487.	1486.
Reference	Ekundayo, Laakso, et al., 1988	Gaydou, Randriamiharisoa, et al., 1986
Comment	MSDC-RI	MSDC-RI

References

Go To: Top, Kovats' RI, non-polar column, temperature ramp, Notes

Adams, González Elizondo, et al., 2006
Adams, R.P.; González Elizondo, M.S.; González Elizondo, M.; Slinkman, E., DNA fingerprinting and terpenoid analysis of Juniperus blancoi var. huehuentensis (Cupressaceae), a new subalpine variety from Durango, Mexico, Biochem. Syst. Ecol., 2006, 34, 3, 205-211, https://doi.org/10.1016/j.bse.2005.11.004 . [all data]

Angioni, Barra, et al., 2006
Angioni, A.; Barra, A.; Coroneo, V.; Dessi, S.; Cabras, P., Chemical composition, seasonal variability, and antifungal activity of Lavandula stoechas L. ssp. stoechas essential oils from stem/leaves and flowers, J. Agric. Food Chem., 2006, 54, 12, 4364-4370, https://doi.org/10.1021/jf0603329 . [all data]

Hazzit, Baaliouamer, et al., 2006
Hazzit, M.; Baaliouamer, A.; Faleiro, M.L.; Miguel, M.G., Composition of the Essential Oils of Thymus and Origanum Species from Algeria and Their Antioxidant and Antimicrobial Activities, J. Agric. Food Chem., 2006, 54, 17, 6314-6321, https://doi.org/10.1021/jf0606104 . [all data]

Jalali-Heravi, Zekavat, et al., 2006
Jalali-Heravi, M.; Zekavat, B.; Sereshti, H., Characterization of essential oil components of Iranian geranium oil using gas chromatography-mass spectrometry combined with chemometric resolution techniques, J. Chromatogr. A, 2006, 1114, 1, 154-163, https://doi.org/10.1016/j.chroma.2006.02.034 . [all data]

Marongiu, Porcedda, et al., 2006
Marongiu, B.; Porcedda, S.; Piras, A.; Sanna, G.; Murreddu, M.; Loddo, R., Extraction of Juniperus communis L. ssp. nana Willd. essential oil by supercritical carbon dioxide, Flavour Fragr. J., 2006, 21, 1, 148-154, https://doi.org/10.1002/ffj.1549 . [all data]

Mevy, Bessiere, et al., 2006
Mevy, J.P.; Bessiere, J.M.; Rabier, J.; Dherbomez, M.; Ruzzier, M.; Millogo, J.; Viano, J., Composition and antimicrobial activities of the essential oil of Triumfetta rhomboidea Jacq., Flavour Fragr. J., 2006, 21, 1, 80-83, https://doi.org/10.1002/ffj.1511 . [all data]

Oliveira, Leitao, et al., 2006
Oliveira, D.R.; Leitao, G.G.; Santos, S.S.; Bizzo, H.R.; Lopes, D.; Alviano, C.S.; Alviano, D.S.; Leitao, S.G., Ethnopharmacological study of two Lippia species from Oriximina, Brazil, J. Ethnopharmacol., 2006, 108, 1, 103-108, https://doi.org/10.1016/j.jep.2006.04.018 . [all data]

Raina, Verma, et al., 2006
Raina, V.K.; Verma, S.C.; Dhawan, S.; Khan, M.; Ramesh, S.; Singh, S.C.; Yadav, A.; Srivastava, S.K., Essential oil composition of Murraya exotica from the plains of northern India, Flavour Fragr. J., 2006, 21, 1, 140-142, https://doi.org/10.1002/ffj.1547 . [all data]

Sylvestre, Pichette, et al., 2006
Sylvestre, M.; Pichette, A.; Longtin, A.; Nagau, F.; Legault, J., Essential oil analysis and anticancer activity of leaf essential oil of Croton flavens L. from Guadeloupe, J. Ethnopharmacol., 2006, 103, 1, 99-102, https://doi.org/10.1016/j.jep.2005.07.011 . [all data]

Tepe, Askin Akpulat, et al., 2006
Tepe, B.; Askin Akpulat, H.; Sokmen, M.; Daferera, D.; Yumrutas, O.; Aydin, E.; Polissiou, M.; Sokmen, A., Screening of the antioxidative and antimicrobial properties of the essential oils of Pimpinella anisetum and Pimpinella flabellifolia from Turkey, Food Chem., 2006, 97, 4, 719-724, https://doi.org/10.1016/j.foodchem.2005.05.045 . [all data]

Walde, Jyothirmayi, et al., 2006
Walde, S.G.; Jyothirmayi, T.; Prabhakara Rao, P.G.; Srinivas, P., Flavour volatiles of flowers and stalks of Murraya koenigii L., Flavour Fragr. J., 2006, 21, 4, 581-584, https://doi.org/10.1002/ffj.1737 . [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
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Notes

Go To: Top, Kovats' 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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