Bicyclo[3.1.1]hept-2-ene-2-carboxaldehyde, 6,6-dimethyl-

Formula: C₁₀H₁₄O
Molecular weight: 150.2176
IUPAC Standard InChI: InChI=1S/C10H14O/c1-10(2)8-4-3-7(6-11)9(10)5-8/h3,6,8-9H,4-5H2,1-2H3
IUPAC Standard InChIKey: KMRMUZKLFIEVAO-UHFFFAOYSA-N
CAS Registry Number: 564-94-3
Chemical structure:
This structure is also available as a 2d Mol file
Species with the same structure:
- (1R)-(-)-Myrtenal
Stereoisomers:
- Bicyclo[3.1.1]hept-2-ene-2-carboxaldehyde, 6,6-dimethyl-, (1S)-
Other names: 2-Norpinene-2-carboxaldehyde, 6,6-dimethyl-; Myrtenal; Benihinal; 6,6-Dimethylbicyclo(3.1.1)hept-2-ene-2-carboxaldehyde; 2-Formyl-6,6-dimethylbicyclo(3.1.1)hept-2-ene; 6,6-Dimethyl-bicyclo[3,1,1]hept-2-ene-2-carboxaldehyde; 6,6-Dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde; (-)-Myrtenal; (+)-myrtenal; 6,6-dimethyl-bicyclo[3.1.1]hept-2-ene-2-carboxaldehyde (myrtenal); cis-Myrtenal; pin-2-ene-1-carbaldehyde
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Other data available:
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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-5MS	DB-1	HP-5	BP-1	DB-5
Column length (m)	30.	25.	25.	30.	30.
Carrier gas	He	He		N2	He
Substrate
Column diameter (mm)	0.25	0.2	0.2	0.32	0.26
Phase thickness (μm)	0.25		0.33	0.25	0.25
T_start (C)	60.	60.	60.	60.	60.
T_end (C)	180.	220.	240.	220.	246.
Heat rate (K/min)	3.	3.	3.	5.	3.
Initial hold (min)		3.
Final hold (min)	15.			3.
I	1195.	1188.	1196.	1168.	1196.
Reference	Angioni, Barra, et al., 2006	Mevy, Bessiere, et al., 2006	Oliveira, Leitao, et al., 2006	Srivastava, Srivastava, et al., 2006	Adams, Morris, 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-5MS	SPB-1	CP Sil 8 CB	DB-5
Column length (m)	30.	30.	30.	30.	25.
Carrier gas	He	He	He	H2	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
T_start (C)	50.	60.	50.	50.	40.
T_end (C)	250.	240.	250.	220.	280.
Heat rate (K/min)	3.	3.	2.	3.	3.
Initial hold (min)	10.		2.	2.	5.
Final hold (min)	5.		5.		5.
I	1197.	1196.	1173.	1181.	1192.
Reference	Asuming, Beauchamp, et al., 2005	Maia, Andrade, et al., 2005	Behera, Nagarajan, et al., 2004	Schwob, Bessiere, et al., 2004	Amparo Blázquez, Pérez, et al., 2003
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5	HP-5MS	CP Sil 5 CB	BP-1	HP-5MS
Column length (m)	50.	30.	25.	25.	30.
Carrier gas	He	He	He	N2	He
Substrate
Column diameter (mm)	0.32	0.25	0.25	0.55	0.25
Phase thickness (μm)	0.25	0.25		0.25	0.25
T_start (C)	50.	60.	50.	60.	50.
T_end (C)	280.	280.	230.	220.	250.
Heat rate (K/min)	5.	3.	3.	5.	3.
Initial hold (min)	2.
Final hold (min)	10.			15.
I	1215.	1176.	1173.	1173.	1194.
Reference	Baranauskiene, Venskutonis, et al., 2003	Gkinis, Tzakou, et al., 2003	Kasali, Adio, et al., 2002	Raina, Srivastava, et al., 2002	Salido, Altarejos, et al., 2002
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	BP-1	SSP-1	DB-1	SE-54	DB-5
Column length (m)	30.	30.	50.	30.	30.
Carrier gas	N2	He	N2	He	He
Substrate
Column diameter (mm)	0.32	0.32	0.25	0.26	0.26
Phase thickness (μm)	0.25	0.25	0.25	0.25	0.25
T_start (C)	60.	50.	80.	60.	60.
T_end (C)	220.	250.	225.	246.	240.
Heat rate (K/min)	5.	2.	4.	3.	3.
Initial hold (min)		2.
Final hold (min)	13.	5.
I	1169.	1155.	1169.	1191.	1193.
Reference	Shawl, Srivastava, et al., 2002	Nagarajan, Rao, et al., 2001	Palá-Paúl, Velasco-Negueruela, et al., 2001	Adams, 2000	Adams, 2000, 2
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	SE-54	DB-5	Methyl Silicone	DB-5	DB-5
Column length (m)	30.	30.	30.	30.	30.
Carrier gas		He	He	He
Substrate
Column diameter (mm)	0.26	0.26	0.32	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.25
T_start (C)	60.	60.	60.	40.	40.
T_end (C)	246.	246.	250.	250.	210.
Heat rate (K/min)	3.	3.	2.	2.	2.
Initial hold (min)			2.	5.	2.
Final hold (min)			5.	20.	120.
I	1193.	1193.	1169.	1151.	1189.
Reference	Adams, 2000, 3	Adams, 2000, 4	Adegoke, Rao, et al., 1998	Senatore, Urrunaga Soria, et al., 1997	Loayza, Abujder, et al., 1995
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

References

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

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]

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]

Srivastava, Srivastava, et al., 2006
Srivastava, A.K.; Srivastava, S.K.; Syamsundar, K.V., Volatile composition of Curcuma angustifolia Roxb. rhizome from central and southern India, Flavour Fragr. J., 2006, 21, 3, 423-426, https://doi.org/10.1002/ffj.1680 . [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]

Asuming, Beauchamp, et al., 2005
Asuming, W.A.; Beauchamp, P.S.; Descalzo, J.T.; Dev, B.C.; Dev, V.; Frost, S.; Ma, C.W., Essential oil composition of four Lomatium Raf. species and their chemotaxonomy, Biochem. Syst. Ecol., 2005, 33, 1, 17-26, https://doi.org/10.1016/j.bse.2004.06.005 . [all data]

Maia, Andrade, et al., 2005
Maia, J.G.S.; Andrade, E.H.A.; da Silva, A.C.M.; Oliveira, J.; Carreira, L.M.M.; Araújo, J.S., Leaf volatile oils from four Brazilian Xylopia species, Flavour Fragr. J., 2005, 20, 5, 474-477, https://doi.org/10.1002/ffj.1499 . [all data]

Behera, Nagarajan, et al., 2004
Behera, S.; Nagarajan, S.; Rao, L.J.M., Microwave heating and conventional roasting of cumin seeds (Cuminum cyminum L.) and effect on chemical composition of volatiles, Food Chem., 2004, 87, 1, 25-29, https://doi.org/10.1016/j.foodchem.2003.10.012 . [all data]

Schwob, Bessiere, et al., 2004
Schwob, I.; Bessiere, J.-M.; Masotti, V.; Viano, J., Changes in essential oil composition in Saint John's wort (Hypericum perforatum L.) aerial parts during its phenological cycle, Biochem. Syst. Ecol., 2004, 32, 8, 735-745, https://doi.org/10.1016/j.bse.2003.12.005 . [all data]

Amparo Blázquez, Pérez, et al., 2003
Amparo Blázquez, M.; Pérez, I.; Boira, H., Essential oil analysis of Teucrium libanitis and T. turredanum by GC and GC-MS, Flavour Fragr. J., 2003, 18, 6, 497-501, https://doi.org/10.1002/ffj.1256 . [all data]

Baranauskiene, Venskutonis, et al., 2003
Baranauskiene, R.; Venskutonis, R.P.; Demyttenaere, J.C.R., Sensory and instrumental evaluation of catnip (Nepeta cataria L.) aroma, J. Agric. Food Chem., 2003, 51, 13, 3840-3848, https://doi.org/10.1021/jf021187b . [all data]

Gkinis, Tzakou, et al., 2003
Gkinis, G.; Tzakou, O.; Iliopoulou, D.; Roussis, V., Chemical Composition and Biological Activity of Nepeta parnassica Oils and Isolated Nepetalactones, Z. Naturforsch. C:, 2003, 58, 681-686. [all data]

Kasali, Adio, et al., 2002
Kasali, A.A.; Adio, A.M.; Oyedeji, A.O.; Eshilokun, A.O.; Adefenwa, M., Volatile constituents of Boswellia serrata Roxb. (Burseraceae) bark, Flavour Fragr. J., 2002, 17, 6, 462-464, https://doi.org/10.1002/ffj.1124 . [all data]

Raina, Srivastava, et al., 2002
Raina, V.K.; Srivastava, S.K.; Jain, N.; Ahmad, A.; Syamasundar, K.V.; Aggarwal, K.K., Essential oil composition of Curcuma longa L. cv. Roma from the plains of northern India, Flavour Fragr. J., 2002, 17, 2, 99-102, https://doi.org/10.1002/ffj.1053 . [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]

Shawl, Srivastava, et al., 2002
Shawl, A.S.; Srivastava, S.K.; Syamasundar, K.V.; Tripathi, S.; Raina, V.K., Essential oil composition of Achillea millefolium L. growing wild in Kashmir, India, Flavour Fragr. J., 2002, 17, 3, 165-168, https://doi.org/10.1002/ffj.1074 . [all data]

Nagarajan, Rao, et al., 2001
Nagarajan, S.; Rao, L.J.M.; Gurudutt, K.N., Chemical composition of the volatiles of Hemidesmus indicus R. Br., Flavour Fragr. J., 2001, 16, 3, 212-214, https://doi.org/10.1002/ffj.985 . [all data]

Palá-Paúl, Velasco-Negueruela, et al., 2001
Palá-Paúl, J.; Velasco-Negueruela, A.; Pérez-Alonso, M.J.; Sanz, J., Analysis of the volatile components of Argyranthemum adauctum (Link.) Humphries by gas chromatography-mass spectrometry, J. Chromatogr. A, 2001, 923, 1-2, 295-298, https://doi.org/10.1016/S0021-9673(01)01003-2 . [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]

Adegoke, Rao, et al., 1998
Adegoke, G.O.; Rao, L.J.M.; Shankaracharya, N.B., A comparison of the essential oils of Aframomum daniellii (Hook. f.) K. Schum. and Amomum subulatum Roxb, Flavour Fragr. J., 1998, 13, 5, 349-352, https://doi.org/10.1002/(SICI)1099-1026(1998090)13:5<349::AID-FFJ758>3.0.CO;2-O . [all data]

Senatore, Urrunaga Soria, et al., 1997
Senatore, F.; Urrunaga Soria, E.; Urrunaga Soria, R.; Porta, G.D.; Taddeo, R.; de Feo, V., Essential oil of Eremocharis triradiata (Wolff.) Johnston (Apiaceae) growing wild in Perú, Flavour Fragr. J., 1997, 12, 4, 257-259, https://doi.org/10.1002/(SICI)1099-1026(199707)12:4<257::AID-FFJ645>3.0.CO;2-4 . [all data]

Loayza, Abujder, et al., 1995
Loayza, I.; Abujder, D.; Aranda, R.; Jakupovic, J.; Collin, G.; Deslauriers, H.; Jean, F.-I., Essential oils of Baccharis salicifolia, B. latifolia and B. dracunculifolia, Phytochemistry, 1995, 38, 2, 381-389, https://doi.org/10.1016/0031-9422(94)00628-7 . [all data]

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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